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20 Best Small Sailboats for the Weekender

  • By Mark Pillsbury
  • Updated: May 24, 2024

In order to go cruising, most of us require a sailboat with a head, a galley, and bunks. The boat, likely a 30-footer and more often a 40-footer, will have electronics for navigation and entertainment, refrigeration if the trip is longer than a coastal hop, an engine for light wind, and, depending on our appetites for food and fun, perhaps a genset to power our toys and appliances.

To go sailing , however, all we really need is a hull, mast, rudder, and sail. To experience the pure joy of sheeting in and scooting off across a lake, bay, or even the open ocean, there’s nothing better than a small sailboat – we’re talking sailboats under 25 feet. You can literally reach out and touch the water as it flows past. You instantly feel every puff of breeze and sense every change in trim.

Some of the boats in this list are new designs, others are time-tested models from small sailboat manufacturers, but every one is easy to rig, simple to sail, and looks like a whole lot of fun either for a solo outing on a breezy afternoon or to keep family and friends entertained throughout your entire sailing season. This list is made up of all types of sailboats , and if you’re looking for a list of some of the best small sailboats for beginners, you’ll find exactly that here.

Any one of these popular boats could be labeled as a trailerable sailboat, daysailer, or even a weekender sailboat. And while most would be labeled as a one or two person sailboat, some could comfortably fit three or even four people.

– CHECK THE WEATHER – The weather changes all the time. Always check the forecast and prepare for the worst case. Safety Tip Provided by the U.S. Coast Guard

Marblehead 22 Daysailer

Marblehead 22 Daysailer

If you have an eye for elegant lines and your heart goes pitter-patter over just the right amount of overhang beneath a counter transom, the Marblehead 22 daysailer, designed by Doug Zurn and built by Samoset Boatworks in Boothbay, Maine, will definitely raise your pulse. Traditional-looking above the waterline and modern beneath, the cold-molded hull sports a deep bulb keel and a Hall Spars carbon-fiber mast with a wishbone rig and square-top main. The 11-foot-9-inch cockpit can seat a crowd, and a small cuddy forward will let you stow your friends’ gear for the day. samosetboatworks.com

Catalina 22 Sport

Catalina 22 Sport

Many a harbor plays host to an active fleet of Catalina 22s, one of the most popular small sailboats over the years, given its basic amenities and retractable keel, which allows it to be easily trailered. Recently, the company introduced the Catalina 22 Sport, an updated design that can compete with the older 22s. The boat features a retractable lead keel; a cabin that can sleep four, with a forward hatch for ventilation; and a fractional rig with a mainsail and a roller-furling jib. Lifelines, a swim ladder, and an engine are options, as are cloth cushions; vinyl cushions are standard. The large cockpit will seat a crowd or let a mom-and-pop crew stretch out and enjoy their sail. It’s clear why the Catalina 22 is one of the best sailboats under 25 feet. catalinayachts.com

Hunter 22

With its large, open-transom cockpit and sloop rig, the Hunter 22 makes a comfortable daysailer for family and friends. But with its cuddy cabin, twin bunks, optional electrical system, opening screened ports, and portable toilet, a parent and child or a couple could comfortably slip away for an overnight or weekend. Add in the optional performance package, which includes an asymmetric spinnaker, a pole, and a mainsheet traveler, and you could be off to the races. The boat features a laminated fiberglass hull and deck, molded-in nonskid, and a hydraulic lifting centerboard. Mount a small outboard on the stern bracket, and you’re set to go. marlow-hunter.com

the Daysailer

Not sure whether you want to race, cruise or just go out for an afternoon sail? Since 1958, sailors have been having a ball aboard the Uffa Fox/George O’Day-designed Daysailer. Fox, who in the 1950s was on the cutting edge of planning-dinghy design, collaborated with Fall River, Massachusetts boatbuilder O’Day Corp. to build the 16-foot Daysailer, a boat that features a slippery hull and a small cuddy cabin that covers the boat roughly from the mast forward. Thousands of Daysailers were built by various builders, and they can be found used for quite affordable prices. There are active racing fleets around the US, and new Daysailers are still in production today, built by Cape Cod Ship Building. capecodshipbuilding.com

BayRaider from Swallow Boats

BayRaider from Swallow Boats

Easy to rig and trailer, the BayRaider from England’s Swallow Yachts is a relative newcomer to the small-boat market in the United States. Nearly all of its 19 feet 9 inches is open cockpit, though a spray hood can be added to keep the forward sections dry. The BayRaider is ketch-rigged with a gunter-style mainmast. The topmast and mizzen are both carbon-fiber, which is an option for the mainmast as well. The BayRaider can be sailed with a dry hull in lighter conditions or with 300 pounds of water ballast to increase its stability. With the centerboard and hinged rudder raised, the boat can maneuver in even the thinnest water.

$28,900, (904) 234-8779, swallowyachts.com

12 1/2 foot Beetle Cat

Big fun can come in small packages, especially if your vessel of choice happens to be the 12 ½-foot Beetle Cat. Designed by John Beetle and first built in 1921, the wooden shallow draft sailboat is still in production today in Wareham, Massachusetts at the Beetle Boat Shop. With a draft of just 2 feet, the boat is well-suited for shallow bays, but equally at home in open coastal waters. The single gaff-rigged sail provides plenty of power in light air and can be quickly reefed down to handle a blow. In a word, sailing a Beetle Cat is fun. beetlecat.com

– LEARN THE NAVIGATION RULES – Know the “Rules of the Road” that govern all boat traffic. Be courteous and never assume other boaters can see you. Safety Tip Provided by the U.S. Coast Guard

West Wight Potter P 19

West Wight Potter P 19

With berths for four and a workable galley featuring a cooler, a sink, and a stove, West Wight Potter has packed a lot into its 19-foot-long P 19. First launched in 1971, this is a line of boats that’s attracted a true following among trailer-sailors. The P 19′s fully retractable keel means that you can pull up just about anywhere and go exploring. Closed-cell foam fore and aft makes the boat unsinkable, and thanks to its hard chine, the boat is reportedly quite stable under way. westwightpotter.com

NorseBoat 17.5

NorseBoat 17.5

Designed for rowing and sailing (a motor mount is optional), the Canadian-built NorseBoat 17.5—one of which was spotted by a CW editor making its way through the Northwest Passage with a two-man crew—features an open cockpit, a carbon-fiber mast, and a curved-gaff rig, with an optional furling headsail set on a sprit. The lapstrake hull is fiberglass; the interior is ply and epoxy. The boat comes standard with two rowing stations and one set of 9-foot oars. The boat is designed with positive flotation and offers good load-carrying capacity, which you could put to use if you added the available canvas work and camping tent. NorseBoats offers a smaller sibling, the 12.5, as well; both are available in kit form.

$19,000, (902) 659-2790, norseboat.com

Montgomery 17

Montgomery 17

Billed as a trailerable pocket cruiser, the Montgomery 17 is a stout-looking sloop designed by Lyle Hess and built out of fiberglass in Ontario, California, by Montgomery Boats. With a keel and centerboard, the boat draws just under 2 feet with the board up and can be easily beached when you’re gunkholing. In the cuddy cabin you’ll find sitting headroom, a pair of bunks, a portable toilet, optional shore and DC power, and an impressive amount of storage space. The deck-stepped mast can be easily raised using a four-part tackle. The builder reports taking his own boat on trips across the Golfo de California and on visits to California’s coastal islands. Montgomery makes 15-foot and 23-foot models, as well. If you’re in search of a small sailboat with a cabin, the Montgomery 17 has to be on your wish list.

CW Hood 32 Daysailer small sailboat

With long overhangs and shiny brightwork, the CW Hood 32 is on the larger end of the daysailer spectrum. Designers Chris Hood and Ben Stoddard made a conscious decision to forego a cabin and head in favor of an open cockpit big enough to bring 4 or 5 friends or family out for an afternoon on the water. The CW Hood 32 is sleek and graceful through the water and quick enough to do some racing, but keeps things simple with a self-tacking jib and controls that can be lead back to a single-handed skipper. A top-furling asymmetrical, electric sail drive and Torqeedo outboard are all optional. The CW Hood 32 makes for a great small family sailboat.  cwhoodyachts.com

Sun Cat from Com-Pac

Sun Cat from Com-Pac

Shallow U.S. East Coast bays and rock-strewn coasts have long been graced by cat boats, whose large, gaff-rigged mainsails proved simple and powerful both on the wind and, better yet, when reaching and running. The 17-foot-4-inch Sun Cat, built by Com-Pac Yachts, updates the classic wooden cat with its fiberglass hull and deck and the easy-to-step Mastender Rigging System, which incorporates a hinged tabernacle to make stepping the mast a one-person job. If you want a personal sailboat ideal for solo sailing, the Sun Can is a great choice. Belowdecks, the twin 6-foot-5-inch berths and many other features and amenities make this cat a willing weekender.

$19,800, (727) 443-4408, com-pacyachts.com

Catalina 16.5

Catalina 16.5

The Catalina 16.5 sits right in the middle of Catalina Yachts’ line of small sailboats, which range from the 12.5 to the 22 Capri and Sport, and it comes in both an easy-to-trailer centerboard model and a shoal-draft fixed-keel configuration. With the fiberglass board up, the 17-foot-2-inch boat draws just 5 inches of water; with the board down, the 4-foot-5-inch draft suggests good windward performance. Hull and deck are hand-laminated fiberglass. The roomy cockpit is self-bailing, and the bow harbors a good-sized storage area with a waterproof hatch. catalinayachts.com

Hobie 16

No roundup of best small sailboats (trailerable and fun too) would be complete without a mention of the venerable Hobie 16, which made its debut in Southern California way back in 1969. The company has introduced many other multihulls since, but more than 100,000 of the 16s have been launched, a remarkable figure. The Hobie’s asymmetric fiberglass-and-foam hulls eliminate the need for daggerboards, and with its kick-up rudders, the 16 can be sailed right up to the beach. Its large trampoline offers lots of space to move about or a good place to plant one’s feet when hanging off the double trapezes with a hull flying. The boat comes with a main and a jib; a spinnaker, douse kit, trailer, and beach dolly are optional features. hobiecat.com

Hunter 15

Novice sailors or old salts looking for simplicity could both enjoy sailing the Hunter 15. With a fiberglass hull and deck and foam flotation, the boat is sturdily built. The ample freeboard and wide beam provide stability under way, and the heavy-duty rubrail and kick-up rudder mean that you won’t have to worry when the dock looms or the going grows shallow. Both the 15 and its slightly larger 18-foot sibling come standard with roller-furling jibs.

$6,900/$9,500 (boat-show prices for the 15 and 18 includes trailers), (386) 462-3077, marlow-hunter.com

– CHECK THE FIT – Follow these guidelines to make sure your life jacket looks good, stays comfortable and works when you need it. Safety Tip Provided by the U.S. Coast Guard

Super Snark

Super Snark

Under various owners, the Snark brand of sailboats, now built by Meyers Boat Co., has been around since the early 1970s. The Super Snark, at 11 feet, is a simple, easily car-topped daysailer that’s fit out with a lateen rig and sail. Billed as unsinkable, the five boats in the company’s line are built with E.P.S. foam, with the external hull and deck vacuum-formed to the core using an A.B.S. polymer. The Super Snark weighs in at 50 pounds, and with a payload capacity of 310 pounds, the boat can carry two.

$970, (800) 247-6275, meyersboat.com

Norseboat 21.5

Norseboat 21.5

Built in Canada, the NorseBoat 21.5 is a rugged looking craft that comes in a couple of configurations: one with an open cockpit and small doghouse, and another with a smaller cockpit and cabin that houses a double berth for two adults and optional quarter berths for the kids. Both carry NorseBoat’s distinctive looking carbon fiber gaff-rigged mast with main and jib (a sprit-set drifter is optional), and come with a ballasted stub keel and centerboard. Because of its lightweight design, the boat can be rowed and is easily trailered.

$36,000 (starting), 902-659-2790, norseboat.com

Flying Scot

Flying Scot

Talk about time-tested, the 19-foot Flying Scot has been in production since 1957 and remains a popular design today. Sloop rigged, with a conventional spinnaker for downwind work, the boat is an easily sailed family boat as well as a competitive racer, with over 130 racing fleets across the U.S. Its roomy cockpit can seat six to eight, though the boat is often sailed by a pair or solo. Hull and deck are a fiberglass and balsa core sandwich. With the centerboard up, the boat draws only eight inches. Though intended to be a daysailer, owners have rigged boom tents and berths for overnight trips, and one adventurous Scot sailor cruised his along inland waterways from Philadelphia to New Orleans.

RS Venture

Known primarily for its line of racing dinghys, RS Sailing also builds the 16-foot, 4-inch Venture, which it describes as a cruising and training dinghy. The Venture features a large, self-draining cockpit that will accommodate a family or pack of kids. A furling jib and mainsail with slab reefing come standard with the boat; a gennaker and trapeze kit are options, as is an outboard motor mount and transom swim ladder. The deck and hull are laid up in a fiberglass and Coremat sandwich. The Venture’s designed to be both a good performer under sail, but also stable, making it a good boat for those learning the sport.

$14,900, 203-259-7808, rssailing.com

Topaz Taz

Topper makes a range of mono- and multihull rotomolded boats, but the model that caught one editor’s eye at Strictly Sail Chicago was the Topaz Taz. At 9 feet, 8 inches LOA and weighing in at 88 pounds, the Taz is not going to take the whole crowd out for the day. But, with the optional mainsail and jib package (main alone is for a single child), the Taz can carry two or three kids or an adult and one child, and would make a fun escape pod when tied behind the big boat and towed to some scenic harbor. The hull features Topper’s Trilam construction, a plastic and foam sandwich that creates a boat that’s stiff, light, and durable, and shouldn’t mind being dragged up on the beach when it’s time for a break.

$2,900 (includes main and jib), 410-286-1960, topazsailboats.com

WindRider WRTango

WindRider WRTango

WRTango, a fast, sturdy, 10-foot trimaran that’s easy to sail, is the newest portable craft from WindRider International. It joins a line that includes the WR16 and WR17 trimarans. The Tango features forward-facing seating, foot-pedal steering, and a low center of gravity that mimics the sensation of sitting in a kayak. It weighs 125 pounds (including the outriggers and carbon-fiber mast), is extremely stable, and has single-sheet sail control. The six-inch draft and kick-up rudder make it great for beaching, while the hull and outriggers are made of rotomolded polyethylene, so it can withstand running into docks and being dragged over rocks.

$3,000, 612-338-2170, windrider.com

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Average Cost of Buying & Owning a Sailboat (2022)

Here are the 2022 data for our research on the average cost of buying and owning a sailboat.

Examples of Popular Sailboats, and How Much They Cost

boat price class one-time cost monthly cost
Island Packet 26' medium $25,000 $470
Catalina 22' low budget $2,500 $115
Ocean cruiser 35' low budget $38,000 $450
Luxury yacht 40' expensive $166,000 $1,300

What Does it Cost to Buy a Sailboat?

The average price of a new sailboat per foot in USD:

  • under 30 ft: $2,400 per ft
  • 30 - 50 ft: $5,700 - $8,500 per ft
  • over 50 ft: $11,900 - $65,400 per ft

On average, second-hand sailboats go at 1/3 - 1/4 of the cost of a new boat:

  • under 30 ft: $815 per ft
  • 30 - 50 ft: $3,020 per ft
  • over 50 ft: $5,100 - $17,000 per ft

Price of new sailboats

I've looked at the prices of thousands of yachts (really) on one of the largest yacht marketplaces in the world (- not manually, don't worry: with the help of their search function). This is what I came up with:

Length Range Low Average High
15-19ft $22,000 $24,000 $27,000
20-24ft $41,000 $50,000 $71,000
25-29ft $71,000 $96,000 $133,000
30-34ft $155,000 $183,000 $260,000
35-39ft $191,000 $251,000 $420,000
40-44ft $245,000 $326,000 $522,000
45-49ft $348,000 $400,000 $526,000
50-60ft $563,000 $654,000 $902,000
80-100ft $5,677,000 $5,889,000 $6,518,000

Source: Yachtworld Q2 2022

The price of new sailboats ranges from roughly $1,412 - $65,433 per foot. I've used these numbers to calculate the following list:

Prices per foot in USD

Here's the detailed price per foot for all lengths from 20 to 100 feet:

Length Range Per Foot
15-19ft $1,412
20-24ft $2,273
25-29ft $3,556
30-34ft $5,719
35-39ft $6,784
40-44ft $7,762
45-49ft $8,511
50-60ft $11,891
80-100ft $65,433

Price of used sailboats

We did the same for used catamarans, comparing thousands of listings. Here are the complete data:

Length Range Low Average High
15-19ft $5,000 $8,000 $19,000
20-24ft $6,000 $19,000 $59,000
25-29ft $7,000 $30,000 $96,000
30-34ft $9,000 $66,000 $228,000
35-39ft $14,000 $111,000 $392,000
40-44ft $22,000 $150,000 $512,000
45-49ft $36,000 $162,000 $518,000
50-60ft $60,000 $281,000 $897,000
80-100ft $433,000 $1,534,000 $4,720,000
Length Range Per Foot
15-19ft $471
20-24ft $864
25-29ft $1,111
30-34ft $2,063
35-39ft $3,000
40-44ft $3,571
45-49ft $3,447
50-60ft $5,109
80-100ft $17,044

The price of used sailboats ranges from roughly $471-$17,044 per foot.

Prices on Craigslist

To get an average of the price of a used sailboat, I went over to Craigslist. I took the first 10 relevant search results for sailboats under, and over 30 feet.

Of course, the averages here are very speculative, as prices vary from day to day. But it gives a broad range of what to expect.

Over 50 feet, listings become meagre. I believe people tend to not place their 80-ft sailboats on Craigslist, but sell it through a broker instead.

Median Craigslist price of a used sailboat:

  • under 30 ft: $7,900
  • over 30 ft: $96,900

Average Craigslist price-per-foot of a used sailboat:

  • under 30 ft: $354 per ft
  • over 30 ft: $1,845 per ft

This is what I found on Craigslist under 30 feet:

Washington dc.

Boat Year Length (ft) Price (USD)
Columbia MK II 1975 26 $6,500
Newport 1979 17 $5,000
Catalina 1983 22 $4,950
Macgregor Venture 1977 22 $1,800

Source: Craigslist Washington DC Q2 2022

Los Angeles

Boat Year Length (ft) Price (USD)
Catalina 1998 25 $18,500
Catalina 1974 27 $13,999
Pacific Seacraft 25 1976 28 $11,500
Newport 1979 28 $10,500

Source: Craigslist Los Angeles Q2 2022

Boat Year Length (ft) Price (USD)
Catalina 1983 25 $7,900
Catalina 1985 22 $5,000
O'Day 1977 22 $3,800
Vagabond 1981 17 $3,750

Source: Craigslist Houston Q2 2022

South Florida

Boat Year Length (ft) Price (USD)
MacGregor 26X 2001 26 $13,999
Cape Dory 1979 25 $8,500
Precision 1990 23 $7,500
Dusky 1998 17 $7,000

Source: Craigslist Miami Q2 2022

Boat Year Length (ft) Price (USD)
C&C 1985 27 $12,000
O'Day 1987 27 $11,500
Impulse 1987 21 $8,500
Catalina Capri 1986 22 $7,900

Source: Craigslist New York Q2 2022

Here's what I found for 30 feet and up:

Boat Year Length (ft) Price (USD)
MeadowLark 1970 37 $43,000
Pearson 323 1983 33 $18,000
O'Day 1988 17 $3,300
Boat Year Length (ft) Price (USD)
Cheoy Lee 1984 48 $112,000
Hunter Legend 1996 43 $109,900
Vagabond Ketch 1984 47 $102,000
Marine Technologies Ketch 1979 48 $99,500
Boat Year Length (ft) Price (USD)
Trintella 1982 42 $105,000
Hunter 2001 46 $96,900
Hunter 1997 34 $59,000
Mason 1983 43 $49,999
Boat Year Length (ft) Price (USD)
Hunter 2005 38 $104,900
Endeavour 1989 51 $99,000
Beneteau 1998 40 $99,000
Hunter 2004 36 $94,500
Boat Year Length (ft) Price (USD)
Catalina Mark 2 1998 42 $97,900
X-119 1992 40 $84,000
Cape Dory 32#7 1986 33 $38,000
Irwin Citation 1984 31 $35,000

The Initial Purchase Cost

The most obvious cost involved in buying a sailboat is the initial purchase cost. The price of the boat will vary depending on a few factors such as the type of the boat, the size, whether it's new or used, its condition, and many more.

In most cases, buying a used boat is a lot cheaper than buying a brand new boat. Keep in mind that buying a brand new boat is almost comparable to buying a brand new car. You'll not only pay a huge premium but its value will depreciate immediately after you buy it. More importantly, you should first consider the types of activities you want to use the boat for and how often you'll be hitting the waters.

When buying a used boat , the rule of thumb is to prudently look for a 2 to 10-year-old boat. This is a great way of saving on the initial purchase cost. You should, however, check if it's in perfect condition. For example, you should get an expert to check the viability of the hull, drivetrain, and even the engine if it has any.

If you don't have enough cash to buy a sailboat outright, you can consider various financing options that are available out there. You can either choose to use your bank of a specialized marine lender. Keep in mind that factors such as your income, credit rating, and the value of the boat may be considered. These options can make boat ownership quite affordable, though you may have to pay some down payment.

Normally, brand new boats will come with warranties but this may not be the case when buying used boats, especially from an individual. You should, however, make sure that you get a warranty of some kind to cover you in case of anything negative. You should ask for maintenance logs and receipts for parts or repairs.

Buying a Brand New or a Used Sailboat

In addition to the typical costs of owning a boat such as maintenance and mooring, which we will discuss later, buying a brand new or a used sailboat come with potential hidden charges. They include:

Surveying or Inspection Cost - It's generally advisable that you have the boat inspected before purchasing it. This, of course, is crucial whether you're buying a brand new boat or a used boat. So in addition to the cost of buying the boat, you should also have inspection fees that could be around $1,500 for inspection fees and around $800 for the survey.

Buying a boat without proper inspection can be detrimental especially if it turns out that the boat is in bad condition. It would be really short-sighted on your part to buy a boat without proper inspection especially if you take into account the fact that marine mechanics are very complicated and costly. Normally, inspection should be carried out by a profession but here are some of the things to look at.

  • ‍Check the sails, batteries, and the engine
  • Pull out the dipstick and check the engine
  • Check the boat's hull
  • Make sure that the safety gears of the boat are in tip-top condition

Even though pre-purchase boat inspection can be grueling especially if you're looking at many different boats, it's of great importance if you do not want to waste your hard-earned money by purchasing a lemon. You should, therefore, always consider paying for a thorough and professional inspection even if it means you'll lose $1,500 and end up not buying the boat.

With that in mind, you should be prepared to pay for inspection whether or not you'll make the final decision to purchase the boat. For instance, you can carry out an inspection, get unsatisfied, and choose not to buy the boat. In such a scenario, you'll be short of $1,500 and still walk home without a boat.

Add-ons - Generally speaking, a boat should come with essential add-ons such as sails, anchors, life jackets, and rigs. But what if the particular boat that has captured your attention doesn't have this essential add-on? Well, you may have to go into your pocket and buy these add-ons. However, make sure that you use such add-ons to negotiate for a lowered price.

Depreciation - Needless to say, the cost of a brand new boat will depreciate immediately after you buy it. In other words, it's not possible to sell the boat at the same price at which you bought it.

Although it's generally said that the value of a boat depreciates quickly after purchase, it's quite difficult to predict the rate of such depreciation. Figures will, of course, vary depending on various factors such as the style and age of the boat. To give you a rough idea, new boats may lose around 40-50% of the initial purchasing cost in the first 8 or 10 years.

This depreciation rate will reduce about 5% annually after 10 years, though the condition of the boat may have a significant bearing on the value of the boat. You may have to replace things such as the sails, electronics, batteries, and canvas after every 5 years. But with proper care and maintenance, these parts can last longer and save you from unexpected expenditures.

Moorings and Storage of the Boat

The cost of mooring your boat may vary based on the nature of the marina, the facility, and the region. However, it's easy to quantify these costs, even though you'll have to do some considerable legwork if you want a budget-friendly option. You can easily find a mooring costing about $500 for a 30ft boat but the same space can cost well over $6,000 in prime locations.

In addition to working within a budget, the most important thing is to ensure that your boat is securely moored or stored, especially against pilings, banging, spillage, or breaking free. Without this, you could end up having to deal with avoidable repair costs.

Insurance, Registration, and Taxes

Insurance is not a major expense, particularly when compared to other costs. In fact, it's relatively cheaper and should be a problem. The cost of insuring a boat will depend directly on the value of the boat. Generally, the insurance cost maybe about 1.5% of the boat's value. For example, if the value of your boat is $30,000, the insurance cost may be about $450. Believe it or not, the insurance cost of your boat is a lot cheaper than the insurance cost of the car despite the significantly lower value of the car.

In terms of taxes, this may vary depending on your state. For example, South Carolina charges about 10.5% of the boat's yearly value while Rhode Island has no boat tax. The registration cost may also vary from state to state but may cost about $250.

Maintenance Costs and Repairs

Just like any automobile, owning a boat comes with monthly and yearly maintenance costs. The costs may, however, vary depending on the type of the boat, its size, the rate of use, and your geographical region (such as saltwater and freshwater).

Needless to say, a new boat will cost a lot less in terms of maintenance than a used boat. There are engine maintenance costs, hull maintenance, winterizing, rigging inspection, sail assessing, and many more. Generally, the yearly maintenance cost can be 10% of the boat's value. For example, maintaining a boat worth $30,000 would be $3,000 per year. You may also have to consider some unexpected repair costs in case there's unplanned damage on your boat.

Operating Expenses

There will, of course, be operating expenses every time you run your boat. For example, you'll have to fuel the boat if you aren't planning on using the free winds to sail. On top of the fuel costs, there are other costs but this may depend on the type of your boat. For example, you may have to buy fuel additives to eradicate ethanol problems if your boat has a carbureted engine. If your boat uses some sort of electricity, you may want to consider expenses such as electricity bills.

So how much should you budget for operating expenses? This may be difficult to say as it can vary greatly. It may depend on the amount of time you spend on the water and how often you go sailing. It's, however, advisable to budget beforehand to at least have an idea of what to expect.

15 Popular Sailboats and How Much They Cost

While there are a lot of great sailboats out there that can be quite affordable, others can be very expensive. But even with that, there are a lot of great boats that are affordable and can serve you well. Let's look at these 15 popular sailboats and how much they cost.

1) Catalina 30 ($18,000)

Depending on the year of production, a Catalina 30 can cost around $18,000. Having been around since 1972, the Catalina 30 is known for its great performance both when racing and cruising. This is a boat that will never let you down when sailing or racing. Well, that's because it brings forth a perfect blend of comfort, durability, and speed. If anything, buying a Catalina 30 would mean that you're the proud owner of one of the most popular sailboats of all time.

The Catalina 30 is very affordable and comes fairly equipped as a very basic but reliable boat, though you can significantly improve its functionality if you customize it. There are so many Catalina 30s in the globe that it shouldn't be a problem finding one that suits your budget in terms of the initial purchase cost and maintenance cost.

But like with any boat, you should be willing to compromise when it comes to certain features. However, you can significantly improve it if you spend some amount on improving it. All in all, a Catalina 30 is one of the most affordable and easy to maintain boats in the world.

2) Islander 36 ($22,000 and above)

Built from 1971 to 1985, the Islander 36 was and remains one of the longest-lived 36-footers in the U.S. market. With over 1,000 units built during that period, this was a sailboat that was designed by the widely revered Australian boat designer, Alan Gurney. It's possible to find a worthy Islander 36 for $22,000 or slightly above that. This is perhaps because it goes against the normal norm of using a balsa deck. Instead, the Islander 36 is designed with plywood, which increases weight and elegance but can be prone to rot.

In the past, the Islander 36 looked conservatively modern given that it had a flattish appearance. But by today's standards, the Islander 36's hull is very ideal for both racing and cruising. It has a moderate beam and perfectly carried aft so that it doesn't squat excessively even when the boat is fully loaded.

This is a boat that is easy to sail single-handedly, especially with an autopilot. It has superb speed and points well into the wind. It also offers plenty of space and the utmost fun when sailing in windy conditions. In terms of maintenance, the Islander 36 is made with very durable parts that make it a lot easier to maintain. It also has one of the best values, especially if you want it for coastal sailing.

3) Contessa 32 ($30,000-$50,000)

Designed in 1970 by David Sadler and Jeremy Rogers, the Contessa is a very capable and larger alternative of the Contessa 26. With over 750 units built, the Contessa 32 remains one of the most popular cruiser-racer sailboats of all time so it's not a surprise that its cost can be quite hefty.

This is a seaworthy vessel that's superb for offshore voyages even when the weather seems to be extreme. In other words, the Contessa 32 has become widely revered thanks to its ability to endure rough seas and harsh weather. That's not all; a Contessa 32 will never disappoint you in a race.

In essence, the Contessa 32 is a great boat that will give you the confidence of sailing far and wide even single-handed. This is an incredible upwind boat that's impeccably behaved and easy to maneuver, though it can be a bit difficult to handle when sailing downwind. If you own a Contessa 32, you'll never crave anything else as it's durable, easy to maintain, and will serve you across generations.

This is not just another fiberglass boat. It's a great boat that may seem expensive given its initial cost but has unmatched curricula vitae. This is a worthy sailboat that means that you'll be joining a cult of the few.

4) Pearson 34 ($14,000-$30,000)

Pearson is one of the well-known producers of sailboats in the world. Since the 1980s, the Pearson 34 has been magnificently sailing the blue waters thanks to its superb sails, electronics, and equipment.

This is, without a doubt, a real eye-catcher that's highly comfortable for day sailing, weekends, and extended voyages. In terms of pricing, the Pearson 34 is fairly priced though it may seem quite expensive when compared to most sailboats on this list. However, that may not be true especially if you consider the many features that come with the Pearson 34.

This is a sailboat that can be easily handled by two people, which is one of the main reasons that it remains competitive in the market today. This boat has plenty of room but has some shortcomings such as small tankage of 22 gallons. Its 6 foot daft can also be an issue but this isn't an issue in a keel version.

In short, the Pearson sails are great and are easy to handle though you'll have to make sure that it's perfectly maintained, which can be quite costly.

5) Nordic 40 ($130,000 and above)

Designed by Robert H. Perry, the Nordic 40 is thus far the biggest and the most expensive boat on our list. This is an excellent offshore sailboat that's willing to take on many challenges with a special aura.

In addition to being quite roomy, the Nordic 40 has a deep-draft fin keel that gives it a superior windward ability. It has large fuel tanks and fresh water tanks that will ensure that you're sufficiently fueled for your voyages.

This is a thoughtfully designed sailboat that should offer the utmost comfort for your bluewater escapades. It will allow you to confidently cruise through your chosen grounds with ease while turning heads. Given that it's a pretty large boat, you should be prepared for some hefty maintenance costs. All you have to do is make sure that you take good care of it if you're lucky enough to find one to purchase.

In short, the Nordic 40 should be in excellent condition at all times. Make sure that the sails are in top condition and upgraded at all times. If you want to enhance your sailing experience, make sure that the interior is also upgraded to modern standards. All in all, this is a gem that you'd be very lucky to call yours.

6) Peterson 44 ($73,500-$230,000)

Designed by Doug Peterson for Jack Kelly Yachts in 1976, the 44 is a dedicated cruiser that can sail perfectly in any type of wind. With only 200 units built, finding this unbeatable sailboat is quite difficult but not impossible. For those who have owned it, they have nothing but lots of praise for this moderate-displacement blue-water design.

With a low-profile center cockpit, the 44 remains an eye-catcher not just physically but also aesthetically. The long-fin keel with a cutaway forefoot and after-body is essential in reducing wetted surface. The 44 is easy on the helm with a servo-pendulum wind vane that makes handling quite controllable. It's even much better if you use autopilot with many owners reporting that heaving-to with a reefed main and staysail set is the best option, especially in heavy weather.

30 years since it debuted, the 44s still play the seas. Ask any owner of this beauty and he/she will tell that the boat's performance is impressive and among the best. Both Jack Kelly and Doug Peterson were from San Diego and many of these units were sold on the West Coast.

Today, this is a classic that many owners are very proud of. This is a fine sailboat that was designed for long voyages given its ample accommodation and comfort. It is also more solid and very dependable.

7) Nor'Sea 27 (Less than $30,000)

This 27-footer sailboat designed by Lyle Hess is one of the most ocean-capable and quite affordable sailboats that are still in production today. This is a very compact sailboat that can be moved safely and easily by trailer from one area to another or across any ocean.

Do not get duped by its small and compact size; this is a very solid sailboat that can withstand even the worst of weather conditions. In addition to a lapstrake fiberglass hull, this boat has sturdy bulwarks, a full keel, and a round stern that gives it the utmost seaworthiness.

The Nor'Sea should just be evaluated in terms of features. It should also be evaluated in terms of its sailing performance and comfort too. This is a versatile boat that is of high quality. It is a tight little boat that is spacious and can be easily transported. The cost of the used models may vary considerably but this may depend on the age of the boat, condition, and quality of finish. Given that this is one of the most transportable boats, it will be sold together with a trailer. As such, you shouldn't overlook the cost of replacing a trailer as it can cost as much as $9,000. So if you need an affordable and compact boat to circumnavigate the globe, the Nor'Sea 27 may be a good option.

8) Cal 34 ($19,000-$30,000)

Designed by Bill Lapworth, the Cal 34 is a beautifully balanced boat that will make sailing quite delightful. This is a very dependable boat that has a solid reputation not just for its rugged design but also for its incredible sailing characteristics.

Although Lapworth was not the inventor of light-displacement cruiser-racers, he puts his stamp on this design. This is one of the most successful sailboats that have had various configurations from 1966 to 1979. This model has an enviable reputation as one of the best-designed sailboats in the industry. Its performance is superb and can mix with the best racers even though it's typically a cruiser.

It has various extras that make it safe and comfortable. For example, this boat comes with a cockpit cushion, sound system, outboard, and superb ground tackle. This is, without a doubt, a worthy sailboat that will serve you well for many years to come as long as you maintain and service it properly.

According to owners, the Cal 34 requires a good breeze to get it moving. This is because it has a trapezoidal fin keel that brings a more wetted surface than most modern fin keelboats. It has a lot of efficient features such as better sail handling layout, efficient rig. Wheel steering, diesel engine, anchor locker, a more useful interior layout, and bigger water capacity.

When buying an older model, keep in mind that most parts are now obsolete and can be difficult to find. So if the boat is not properly maintained, you may find yourself a boat with hard-to-find parts.

9) Catalina 38 ($25,000-$75,000)

With its reputation, it is not surprising that the owners of the Catalina 38 agree that sailing windward is like sailing on rails while it does magnificently well in light air. Debuted in 1978, this racer-cruiser was designed by Sparkman & Stephens. Although it's currently out of production, there are about 365 units built from 1978 to 1990.

Down below, the Catalina 38 is designed molded hull liner and teak trims and veneers like the ones used in drawer facings, doors, and bulkheads. Like most boats designed as IOR warhorses, they tend to be unstable downwind and this is a major drawback that you should consider when buying the 38. To deal with this, you shouldn't overpower or sail it extremely hard given that it's unstable and can topple over.

As a recreational keelboat built mainly of fiberglass, the Catalina 38 has nurtured loyal following with many owners praising its design, quality, and performance. This is a classic boat that's rare and considered some sort of vintage, so you'll be very lucky to get your hand on it. All in all, the Catalina 38 will perform consistently and magnificently for many years to come provided that you're lucky to get your hands on one of them.

10) Hunter 33 ($55,000-$95,000)

Although the Hunter 33 originally debuted in 1977, there's a new model that was introduced in 2011. This new model doesn't have the old-fashion features of the original Hunter 33 but is selling quite well given that it's devoted to pursuing innovations. In addition to being quite modern, this is an affordable (by its standards) boat that combines ease of handling, comfort, and incredible performance. This is a model that seems determined to make sailing less complex and more fun.

Despite such an overall impressive quality and performance, you can purchase the Hunter 33 for less than $100,000. More importantly, the boat is solid on the water. The hull is solid and is strengthened to ensure that it doesn't suffer from any impact. Thanks to its upgraded quality construction, excellent design features, and comprehensive standard gear package, it's very likely that the Hunter 33 is on its way to becoming another bestseller from one of America's well-known boat brands.

11) Tayana 37 ($34,000)

The Tayana 37 has a real love story that may be so captivating to any boat lover. This boat was done in the 1970s by Robert Perry who is still considered as arguably one of the most prolific boat designers to ever grace the world. When designing the Tayana 37, Perry wanted it to be a cruising sailboat with a more traditional touch in terms of appearance and features.

The Tayana 37 was, therefore, designed with a moderately heavy displacement, a very efficient cutter rig with a modern touch, and a long waterline. Perry's main intention was to market the Tayana 37 as a boat with a double-ended hull that could keep the displacement moderate while performing efficiently.

In essence, Perry was inspired to design the Tayana 37 as a typical Taiwanese boat, so it's important to read much about the Tayana 37 before buying it. When compared to other boats of her size and type, and displacement, a well-equipped Tayana 37 stands well above the rest. You'll, of course, have to handle it properly and well-maintained. This will be a great retirement sailboat, especially if you're experienced and planning to sail as a couple.

12) Contessa 26 ($18,000)

Like her bigger sister that we discussed earlier, the Contessa 26 was designed by David Sadler and Jeremy Rodgers in the 1960s. This is a sailboat that goes against the norm by showing that a boat doesn't have to necessarily be fast or have a groundbreaking design to be considered legendary.

With a posse of young adventurers, Contessa 26 captured the hearts and minds of many sailors across the world. This not only made it legendary but ensured that it had a place in the memories of many sailors. That's not all; the Contessa 26 held its place as a strong and seaworthy boat. In addition to performing excellently well in transatlantic races of yesteryears, the Contessa 26 was good-looking. It has a narrow beam and a low freeboard but with a large cockpit for such a small boat.

Although its upwind performance is wanting, you won't require much wind to get it moving but will be guaranteed of surviving nearly any storm. As one of the most popular British sailboats, Contessa 26 remains one of the most affordable sailboats in the world. You can get a perfectly maintained Contessa 26 with as little as $18,000.

13) Bristol 40 ($29,000-$49,000)

Designed by Ted Hood in 1970, the Bristol 40 remains one of the best cruising sailboats of all time. This is a reliable and attractive passagemaker that can be summed as being an eloquently excellent offshore design that looks perfect but very slow.

But whatever it misses in terms of speed, the Bristol 40 compensates in its construction. With an excellent hull that is also bulletproof, it is perfect and very stable with a long keel that always receives high grades from owners.

The Bristol 40 may not be a modern design but you'll find it quite appealing if you like traditional sailboats. It has long overhangs, low freeboard, a lovely sheerline, an undistorted hull shape, a narrow cabin trunk, and a narrow beam that's typically associated with the gorgeous sailboat of the past.

This is an exceptionally gorgeous sailboat that's carefully refined and very popular with fantastic owners who are always willing to pay high prices just to be proud owners of a sailboat design that has been around for over 3 decades. This can be a great option if you like the traditional looks of past sailboats. It's perfect for coastal cruising but may let you down for offshore voyages.

14) Island Packet 31 ($35,000-$50,000)

If you've been looking for a gorgeous sailboat that's perfect for shallow water sailing, the Island Packet 31 is one of the best options. This is a boat that's designed with the kind of shoal-draft required to safely navigate shallow coastal waters.

Let's be very honest. The Island Packet 31 is not the fastest boat and surely not one of the fastest boats out there. Fortunately, this small-sized boat isn't designed to win races. Instead, it's designed for leisurely cruises around the coastal areas. That's why it delivers ultimate comfort and interior volume, as well as a smooth and soft motion when sailing.

It has a solid fiberglass hull that's finished with a high-end end-grain balsa core deck to prevent rot and delamination. We have to note that her seaworthy credentials aren't among the best but it can be a solid investment if you're looking for a good-looking boat that may serve you perfectly in shallow waters.

But before investing your hard-cash in buying this beauty, make sure that every gear is working perfectly. For instance, look at the wind indicators, the halyards, and every other part. You certainly do not want a gear that isn't working as this may cost you an additional $1,200.

15) Tartan 37 ($23,000 Upwards)

If you look at the gorgeously pleasing and modern lines of the Tartan 37, you'd find it quite hard to believe that this model was designed way back in 1976. Designed by Charlie Britton in collaboration with Sparkman & Stephens design team, Tartan 37 remains a beauty that is functional and reliable, especially for offshore cruising and racing.

The Tartan 37 remains a popular choice for several reasons. With a carefully hand-laid hull, this boat is molded as a single unit. Various high-stress areas such as the mast step, engine bed, thru-hulls, shroud terminals, and keel sections are cored with solid glass and end-grain balsa to make them extremely strong.

In terms of performance, this boat is a great performer in the off wind and will hold its own among the best. It has plenty of rudder contributions as well as incredible control especially when in full motion.

The Tartan has great value but this may depend on several factors such as condition, year of manufacture, and equipment such as electronics. So when buying a used Tartan 37, make sure that it's in a good and capable condition. All in all, the Tartan 37 is a reliable and proven sailboat that should fit the billBottom Line.

Bottom Line

Owning a sailboat is not an easy adventure but nobody said it's impossible. You certainly do not have to be a millionaire to own one! The most important thing when it comes to owning a boat is knowing the type of boat that you desire, how much it costs, and the many but affordable costs that revolve around owning a boat. If you plan appropriately and have a reasonable budget, then buying and owning a boat should be an enjoyable adventure.

As such, you shouldn't have the idea that owning a boat is a costly endeavor. They come at various prices, so you should go for something that you can afford. And whatever type of boat you own, it's important to have an idea of the costs of owning one. More importantly, make sure that these costs are kept in check.

Go out there and enjoy the winds!

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Daniel Wade

I've personally had thousands of questions about sailing and sailboats over the years. As I learn and experience sailing, and the community, I share the answers that work and make sense to me, here on Life of Sailing.

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One heck of a number that has continuously evolved these last twenty years and more, with a touch of insolence that has kept it young.  The First 20 has become more aggressive and stylish. Her look is more modern and in her class she offers the best balance between safety, performance and habitability. This classic small boat enjoys playing in the big league in all weather.

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Fun and a high-performer, this 6.50 m cruiser embraces a racing yet reassuring style. This unanimously acclaimed sailing yacht is small in size but has terrific qualities and she is loved because she is affordable and very easy to use.

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Whether for day-sailing or short cruises, the First 20 can adapt to all programmes, and all stretches of water. With her lifting keel and outboard engine, she can be beached and transported on a trailer. 

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1983 Pacific Seacraft Flicka

  • Bottom professionally sanded and freshly painted September 2022
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20 foot sailboat price

Average Sailboat Prices: 27 Helpful Examples (With Pictures)

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The average price of used sailboats is around $21,000, but new boats cost $60,000 on average and upwards. Some used boats can be purchased for less than $10,000, depending on their age, size, and condition. This is because pre-owned sailboats have about 80 percent of the market share.

You will find models from the early 1960s still racing across the Pacific and Atlantic like new. So what are your options?

Below, we provide a comprehensive list of enduring sailboat designs:

You can also check out our in-depth guide for more information on general boat average prices. In this guide, we have included a long list of boat types

Table of Contents

27 Good Examples When Looking At Sailboat Prices

1) tayana 37.

20 foot sailboat price

Marine designer Robert Perry is arguably one of the most prolific in the boatbuilding world.

His Tayana 37 is one of the most popular production sailboats of all time, with over 650 built.

The Tayana 37 features a sturdy fiberglass hull and a balsa-cored deck for smooth and comfortable circumnavigation.

It comes with a variety of customizations, including different rigs, decks, accommodation, and more.

However, the early boats have V-berths, a high-aspect-ration rig, and a luxurious teak-trimmed interior.

Measuring 36’8″ in length with a displacement of 24,000 pounds, the Tayana 37 is one of the best world cruisers ever made. While production stopped in 2016, you can get one for $34,000 to $65,000.

2) Catalina 22

20 foot sailboat price

Depending on the production year, the ubiquitous Catalina 22 can be as low as $4,000 or up to $15,000 for recent models.

This trailerable sailboat was first built in 1969 and enjoyed popularity thanks to its family-friendliness and compact design.

With over 10,000 boats commissioned, the Catalina 22 and its successors Catalina 27 and Catalina 30 are a permanent feature at lakes, rivers, and the high seas.

Despite its size, the Catalina 22 can hold its own in rough seas thanks to the hand-laid fiberglass hull. It is spacious below deck and comes with all the facilities you need to feel at home.

Whether you are a club racer or weekend cruiser, this dependable platform offers one of the best values for money when you want to spend quality time on the water.  If you get one with a trailer, that can save you a lot of money on marina and storage fees over time.

3) Hunter 356

20 foot sailboat price

Starting in 2000, Glenn Henderson’s Hunter 356 took the sailboat industry by storm.

500 boats later, the 356 is still one of the best high-performance sailboats in its class.

This boat features a solid and balanced hull, shoal draft, and exceptional sailing qualities.

It has a sleek design, a clutter-free cockpit, and is easy to handle.

Early production Hunter 356s are available for less than $60,000.

Hunter Marine no longer produces the 356, but the sailboat is still popular among sailors old and young.

4) Contessa 26

20 foot sailboat price

The compact Contessa 26 was designed by David Sadler and Jeremy Rodgers in the 1960s. It blew into the limelight when it helped Tanie Aebi complete her solo circumnavigation.

This fiberglass monohull is a sturdy and dependable vessel, and around 650 are voyaging across the oceans today.

She has a low freeboard, and the rudder is attached to the keel in a strong, traditional manner.

While you may have to bend a bit to access the cabin, there is plenty of space and amenities to deliver a home-away-from-home feel.

This is one of the most popular British sailboats and is most sought after by long-distance ocean sailors or just someone who wants a classic sailboat.

You can get a well-kept boat of this type for less than $10,000 or over $20,000.

The sister ship Contessa 32 is also a well-built model popular among sailors.

5) Island Packet 31

20 foot sailboat price

If you love sailing in shallow waters, the Island Packet 31 is designed for the shoal draft needed to safely navigate Florida waters.

Featuring a solid fiberglass hull, the 31 has an end-grain balsa core deck, which gives it a powerful and solid feeling.

The boat is roomy, comfortable, and is designed to be simple to use and maintain.

While her seagoing credentials might not be the best, the Island Packet 31 is a vintage liveaboard yacht with all the trappings of royalty.

This boat costs about $35,000 to $50,000.

6) Bristol 40

20 foot sailboat price

This Ted Hood design is one of the best cruising boat designs of all time.

Featuring a narrow beam and solid hull, the Bristol 40 has a low freeboard, large overhangs, and exceptional seaworthiness.

Its long keel carries an attached rudder for excellent tracking and stability.

The Bristol 40 has a relatively small interior with separate cabins , sea berths, and an enclosed head.

This boat was produced in keel or keel/centerboard configuration and came with the powerful Atomic 4 gas engine.  Many have been upgraded to diesel engines.

If you want a vintage racing sailboat that can deliver an impressive pace in the water, consider one of these.

The Bristol 40 was produced from 1966 to 1986, and you can get one for $29,000 to $49,000.

7) Cape Dory 30

20 foot sailboat price

This 30-footer introduced in 1976 is a popular sailboat for people on a budget.

It boasts a robust design with a solid single hull, balsa-cored deck, and extensive bronze and teak hardware in the interior and exterior.

Like the Bristol 40, this boat has its rudder attached to the keel for stable tracking and safety, but not as much overhang in the stern.  The space below the deck uses a traditional design. But this tried and tested design is still ruling the waves.

For more room and improved handling, you can check out the bigger Cape Dory MK11, which comes at over $50,000.

20 foot sailboat price

If you live on the West Coast of the United States, chances are you’ve seen one of these beauties.

Over 400 units of the Gulf 32 were produced, and the boat’s durable construction and beautiful design make it a good fit for many sailors.

It features a flush cambered deck, a sweeping sheer, and a low profile pilothouse, making it stand out on the water.

Specifications for the boat differ because it was built by two different boatyards. However, all Gulf 32 boats have a cavernous interior, comfortable wood finishes, and motorsailer dimensions.

Good samples of this model go for $24,000 to $39,000 but check the side decks for delamination.

9) Endeavour 37

20 foot sailboat price

The Endeavour 37 is the successor of the successful Endeavour 32.

It is available as a sloop and ketch and comes with a powerful Perkins 4-108 diesel to provide good power for its heavy design.

The Endeavour 37 can be slow going upwind because of its weight but offers comfortable and smooth rides.

The hull is single fiberglass, and the interior comes with plenty of plywood, although the craftsmanship is exceptional.

The boat could have two aft cabins with a convertible dinette forward or a single aft cabin with a V-berth forward.

It sells for $20,000-$49,000.

10) Tartan 37

20 foot sailboat price

The Tartan 37 is one of the three 37-footers Tartan Marine built over the years and the most popular.

This boat has a balsa-cored hull and deck and external lead ballast. The bulkheads are firmly tabbed to the deck to provide good structural strength.

With over 500 built, the Tartan 37 is a fast boat ideal for racing.

You can still find these boats for $23,000 and upward.

11) Islander 36

20 foot sailboat price

As the name suggests, the Islander 36 is a 36-footer sailboat designed by the Australian Alan Gurney for Islander Yachts.

It features a skeg-mounted rudder, fin keel and has a solid fiberglass hull.

Unlike most sailboats with end-grain balsa deck, the Islander 36 uses plywood, which increases weight and can be stronger, but it can also get wet from leaks in the deck and rot.

What the boat excels at is the interior space.

The boat’s wide beam allowed the builder to provide more accommodation, unlike other boats in its category.

Over 1,000 units of this boat were built, and you can buy one for $22,000 and above.

12) Hallberg-Rassy 35 Rasmus

20 foot sailboat price

This Olle Enderlein design features a center cockpit, a huge windscreen, and a full keel for improved stability and handling.

It has all the amenities of a small home, including a saloon, galley, main cabin, v-berth, and enclosed head.

The sailboat has a solid fiberglass construction and rides well in choppy waters.

A 75HP Volvo Pentad MD21 diesel supplements wind power, making this boat a reliable cruiser.

The boat sells for about $30,000.

13) Dufour Arpege 30

20 foot sailboat price

You might not hear of this boat builder often, but it was one of the most successful in France and beyond.

The Arpege 30 sports luxurious facilities include stylish sea berths, a large galley, and plenty of forepeak storage compartments.

This 30-footer was so popular over 1,500 were sold from 1966 onward.

If you need a classic sailboat with high-end performance and fittings, this weekend cruiser is it.

One of these beauties goes for around $18,000

14) Mason 43/44

20 foot sailboat price

The Taiwan-built Maison 43/44 from Al Mason is a fast, comfortable, and reliable oceangoing sailboat.

These boats were first introduced as the Mason 43 and upgraded to the Mason 44 in 1985.

The boat has a full keel and a cutter rig and rides well in the sea.

There are double-berth cabins fore and aft, a galley, and everything a small family or couple needs to cross any ocean in comfort.

These beautiful boats are still found in docks worldwide and go for $60,00 to over $120,000.

15) Nor’Sea 27

20 foot sailboat price

This 27-footer designed by Lyle Hess is one of the most affordable and ocean-capable sailboats still in production today.

Despite being compact enough to move by trailer from one boating hotspot to another, the Nor’Sea 27 can take you safely across any ocean.

Don’t be fooled by its small size; this is a solid boat that can withstand a heavy bashing at sea.

It has a lapstrake fiberglass hull, a full keel, sturdy bulwarks, and a round stern for exceptional seaworthiness.

The Nor’Sea 27 featured a bowsprit and extended anchor roller, giving it a traditional sailboat appearance.

If you need an affordable sailboat that can circumnavigate the world, the Nor’Sea 27 is a capable cruiser that won’t hurt your purse.

You can get a 1981 model for less than $30,000.

16) C&C Landfall 38

20 foot sailboat price

If you need a highly maneuverable sailboat, fast, and has exceptional cruising capabilities, one of the best examples is the Landfall 38.

This boat was produced in the shallow draft and deep fin configurations, and later versions gained 1700 pounds in weight.

However, this didn’t dampen the boat’s performance in bluewater environments.

The Landfall 38 was one of the first boats to feature a hull and deck with end-grain balsa coring, making it light and increasing stiffness.

There are a keel-stepped mast, through-bolted deck hardware, and a spade rudder, which provides improved control and sailing performance in all weather.

The interior is lavishly finished in teak, and the aft cabin has a double berth.

These boats were equipped with a venerable Yanmar diesel engine and sails upwind like a racer.

This boat costs around $33,000, and the last units were built in 1987.

17) Gulfstar 50

Gulfstar 50 is one of the most comfortable family-sized sailboats in the world.  Gulfstar also made versions from 36 feet to 60 feet.

Despite its luxurious trims and decent performance, the 50-footer from Gulfstar Yachts is affordable considering its features.

It features a center console cockpit, which provides for a spacious owner’s stateroom aft.

There is plenty of accommodation for a family or a small group because it was designed for charter. With its solid fiberglass hull and exquisite interior finishing, this boat continues to be one of the most preferred liveaboards for people who choose the sailing lifestyle.

A 1978 model goes for around $99,000.

18) Beneteau 423

20 foot sailboat price

This Groupe Finot-designed sailboat is one of the best from the French boatbuilder Beneteau.

It has a solid construction, exceptional speed and is easy to handle even in rough waters. The interior is clutter-free, comfortable, and spacious.

Plus, the 423 is a quality boat that delivers tremendous value for money considering the pedigree and quality.

You can get one for less than $100,000 to around $195,000, based on the year of production and condition.

19) Alberg 30

20 foot sailboat price

With over 750 of this boat built over 25 years, the Alberg 30 is one of the most beloved cruising-racing sailboats.

Featuring the wooden boats’ classy look, the Alberg 30 has a full keel, long overhangs, and a low freeboard.

Despite production stopping since 1984, these boats are going strong thanks to durable fiberglass construction and attention to detail.

The Alberg 30 is not the most accommodating by modern standards. But it has a sal0on, a V-berth forward, and an enclosed head aft.

There is also a small galley to starboard, and the design is clutter-free.

If you want to own one of these legendary club racers, you will be surprised they go for as low as $10,000 to $25,000. 

The price will often depend on whether the original Atomic 4 gas engine has been upgraded to a diesel engine.

20) Peterson 44

20 foot sailboat price

The Peterson 44 was designed by Doug Peterson of the Jack Kelly Yachts in 1975.

This fine boat was designed for long-distance cruising and its center-cockpit style provided ample accommodation and comfort.

You can still find these beautiful boats crisscrossing the oceans , and many of them have circumnavigated.

The Peterson 44 featured hand-laid fiberglass matt and polyester resin roving, making it a solid and dependable cruiser.

It has a three-cabin layout with V-berths, a dinette, and an enclosed head.

The boat is powered by a 62HP Perkins 4-152 Diesel, although a few have 80HP Ford Lehman’s, allowing it to run fast under power.

It is estimated that over 600 hulls of the Peterson 44 were built, and price ranges from around $73,500 to $230,000.

21) Hinckley Bermuda 40

20 foot sailboat price

Few sailboats hold their value, like the Bermuda 40 from Hinckley.

This elegant and capable boat was built to exacting specifications with its yawl rig, low freeboard, and sweeping overhangs.

Most used B 40s are still in mint shape because their proud owners well maintain them, many serviced by the boatbuilder.  So they retain most of their value even after thousands of miles on the high seas.

Despite its 40-foot length, the Bermuda 40 is limited in space, making it ideal for couples.

It has V-berths forward, which you can convert to a comfortable double bed.

There is plenty of storage space, and the head has a shower and a sink.

The deck is spacious, and the boat handles nimbly even in turbulent waters.

This boat is geared towards traditional sailors who want a top-end boat, as even a base model from 1975 goes for about$90,000.

22) Pacific Seacraft 37

20 foot sailboat price

Since its introduction in 1980, the Pacific Seacraft 37 has proven to be one of the best world cruising sailboats in its class.

This boat is fast, comfortable and solidly built for safe passages across the ocean.

It was offered in the cutter and yawl configurations, and its traditional stern style sits atop a modern skeg rudder underbody.

This boat has accommodation for six passengers and every amenity to ensure a comfortable time on the ocean.

She is a prominent feature at the Singlehanded Pacific Yacht Race and other top sail boating events.

This boat is still in production and goes new for around $450,000, so an older used model for less than $100,000 is a good deal.

23) Gemini 3000

20 foot sailboat price

A successor to the Gemini 31, the 3000 is the most popular American-built cruising cat on the market.

Featuring a simple design, this highly functional cat is affordable and fast.

Despite its narrow beam, the Gemini 3000 boasts a master stateroom with a queen-size double berth forward.

There are guest staterooms aft of both hulls with two small doubles.

It has a small saloon with a collapsible table with two settees and a galley, converting to a double berth.

This 30-footer can sleep three couples comfortably and will accommodate a family with several small children without issues.

The Gemini 3000 has deep pivoting centerboards for improved performance and directional stability.

Geminis are not considered suitable for bluewater cruising because they are not designed to withstand serious bashing.

However, these cats offer an affordable ticket for a family or group of friends to enjoy coastal cruising. This boat goes for around $35,000 to $65,000.

24) Gunboat 62 (catamaran)

20 foot sailboat price

The Gunboat 62 from the same name’s cat builder is one of the safest offshore sailing catamarans in its class. It’s also insanely expensive!

This high-performance cat is perfect for oceanic cruises.

Its innovative design opened up plenty of space for accommodation and recreation.

It features three private cabins, each with queen berths and 2 roomy heads with a separate shower in each hull.

There is a galley, a lounge, a folding dining table, and a full pantry below the deck.

The starboard bow has a crew head, and the port bow houses the crew quarters.

This cat comes with air conditioning, refrigerator, deep freezer, and dishwasher, among others.

The cockpit is lavished with teak, and every part of the boat oozes luxury.

This cat carries a premium price tag of over 2 million dollars.

25) Lagoon 380 (catamaran)

20 foot sailboat price

Lagoon 380 is a 4 cabin sailing cat built by Jeanneau.

This cat accommodates 10 passengers and is an excellent platform for cruising across the ocean or lounging on coastal waters.

With over 500 units cruising across the world, the Lagoon 380 has won the heart of many cat sailors as a comfortable and safe platform.

This workhorse comes with an exquisitely furnished interior at an affordable price.

It might not be the fastest catamaran, but the Lagoon 380 provides all the comfort and stability you need to have fun and memorable moments on the water.

These boats go for $400,000 or more, so they may still be out of many sailors’ reach.

26) Catana 50 Carbon (Catamaran)

20 foot sailboat price

If you need a light, fast and go-anywhere cat, the Catana 50 Carbon is one of the best on the market.

Using weight-saving carbon fiber, Catana reduced the weight, turning the boat into a racy oceangoing multi-hull.

With this vessel, you get a luxurious interior, ample deck space, superior performance, and easy handling.

This boat costs a whopping $1.3 million at a base price, making it a choice of select premium sailors.

27) Prout Snowgoose 37 (Catamaran)

20 foot sailboat price

With an estimated 500 units built, the Prout Snowgoose 37 from Prout boatyard is one of the most popular cats from the UK.

This catamaran features solid construction that allows it to sail across oceans, and many are reported to have completed circumnavigations.

The Prout 37 may not look like the newest designs, but it has a comfortable deck and interior.

Below deck, this boat has two large double cabins aft and a full queen berth forward.

There is a saloon with a large table and wraparound settees.

It has a changing station, a full-length bookshelf, and a large storage starboard hull. And the galley is well-equipped to keep a family well-fed on long voyages.

There are hundreds of Prout Snowgoose 37s plying the world’s ocean, and you can own one for less than $100,000.

2 Ways To Reduce the Cost of Buying a Sailboat

There are two main ways of saving cost when buying a sailboat or any boat. They include:

1) Buying Used Boats

If you’ve followed this article this far, you notice that the most affordable boats on this list are used.

Contrary to many novice sailors’ belief, you can buy sailboats for low prices as long as you do due diligence.

Many models from the last half of the 20th century are available for less than $30,000.

Because most serious sailors are passionate about their hobbies, they take exceptional care of their boats. This makes most sailboats on the market retain their value for many years.

In fact, you can get oceangoing boats of 26-32 feet in almost pristine conditions under $100,000.

The best part is most popular sailboats have a strong following worldwide, and sourcing spare parts won’t be a problem.

2) Partnerships

The other way to reduce the cost of a sailboat is to partner with someone.

Partners will share the purchase cost and other expenses related to the boat. However, this can be problematic.

Sometimes, a partner will not honor their commitment when it’s time to pay.

A partner may spend more time on the boat, and this can lead to conflict over responsibilities.

If you choose this route, it’s better to partner with a family or friend. And have a contractual agreement stipulating the rights and obligations of all the parties involved in the transaction.

Considering that most used sailboats are affordable and in good condition, you can save yourself the potential problems that come with co-owning a boat.

The best way to experience sailing life is to own your boat.

Final Words

Sailboats have come a long way since they became a serious pastime for people in the early part of the last century.

Because of the early sailboats’ quality construction, new sailors have myriad options to choose from without hurting their finances.

You can get a pre-owned offshore capable sailboat for less than $10,000 in many parts of the world.

However, very inexpensive used boats may need many repairs and upgrades, so it is often more inexpensive in the end, too, but a well-maintained and upgraded vessel. If you have a fat purse, you can go for newer, premium sailboats in the hundreds of thousands.

But whatever your budget and sailing dreams, there is a sailboat out there for everybody who dares to explore the oceans.

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2004 Seahunt Escape 200 - $21,000 (Conroe)

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2004 Seahunt Escape 200 - boats - by owner - marine sale - craigslist

For sale is a 20 ft 2004 Seahunt Escape 200 Yamaha 150 outboard engine and trailer. Boat comes with 9 inch Lowrance fishfinder and map. Boat is in excellent shape and is maintained and run regularly...

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