yacht charters lake michigan

Lake Michigan yacht charters offering Great Lakes yacht rentals of a lifetime!

Escaping with one of our Lake Michigan yacht charters is awaiting for you aboard our luxury 68′ Chris Craft yacht named “Adeline’s Sea Moose” When you long for nothing more but an escape from it all… Adeline’s Sea Moose and her attentive crew come to the rescue to meet all your needs. You’re about to embark on a Great Lakes yacht rentals experience unlike any other… and best of all it’s absolutely fun-filled! Slipping out of your shoes and onto her deck, you’ll quickly realize there’s going to be something uniquely different about private Adeline’s Sea Moose Great Lakes yacht rentals. With the greeting and handshake of the Captain down to the warm smiles of the gracious crew, you’ll immediately start to know you’re in exceptional hands and headed for an incredible fun-filled time aboard your very own floating playground.

Chicago Lake Michigan   boat   rentals  for parties

Adeline’s Sea Moose Chicago Lake Michigan boat rentals for parties offer a 68-foot luxury Chris Craft yacht and her attentive crew. Adeline’s Sea Moose Chicago Lake Michigan boat rentals for parties also offer a combination of luxury and versatility. It is easy to understand the popularity of the delightful aft-deck salon with a wet bar, whether for open-air dining or merely for the possibility of solitude with a good book. Above, the flybridge offers an ample seating or lounging area. Here, guests can enjoy the sun and cool drinks or gather for a sunset cocktail as a prelude to dinner.

When it comes to Lake Michigan boat rentals, go for our Private Yacht Rental!

There are Lake Michigan boat rentals, and then there is our Adeline’s Sea Moose private yacht rental Our alternative to Lake Michigan boat rentals will truly offer you the best memorable experience in Chicago AND even more, value when you consider… with Adeline’s Sea Moose, can have your extended family and friends aboard “your very own” 68 foot private yacht for food, drink, merriment and what surely will be a unique activity for all. There’s plenty of room to roam for the family for all and when the gathering is over, you and your select guests can continue to enjoy all the amenities the yacht has to offer for the rest of your time aboard.

Best Lake Michigan  Chicago   boat   rental  for company events

Lake Michigan Chicago   boat   rental  for birthday party

Ready for an epic cruise on your special day? Then you’re ready for an Adeline’s Sea Moose Lake Michigan Chicago boat rental for a birthday party. Your Lake Michigan Chicago boat rental for birthday party awaits you at J-Dock in Burnham Harbor. With our Lake Michigan Chicago boat rental for birthday party cruises, you get to combine all of the best elements of other parties and ditch the things that aren’t as great, like the large crowds of intrusive strangers. Take the delicious food, fun drinks, and your friends and relatives and sail away!

(224) 601-0220

TEXT Only 312-500-7838

Docking Address: J-Dock Burnham Harbor 1559 South Lake Shore Drive Chicago , IL 60605 at the end of Waldron Drive. The first dock north of the Harbormaster’s office.

• Sailing School
• Featured Yachts
• Service & Management

2025 Early Season Charter Specials

• 25% Off All Boats in May
• Short-Term Charters of 2+ days
• Click the “Specials” button below for details!

CAPTAIN CHARTERS

For those times when you want to sit back, relax, and let someone else do the heavy lifting. We can help coordinate hiring a licensed USCG Captain for your trip.

CHARTER FLEET & RATES

“Getaway” Jeanneau NC 1095  

“Northern Lights” – Jeanneau 469 (3 cabin)

“Spirited Away” – 2023 Jeanneau 440 (3 cabin)

“Becca T” – 2024 Jeanneau 440 (3 cabin)

“Osprey” – 2020 Jeanneau 440 (3 cabin)

“O’Murchadha” 2022  Jeanneau 410 (3 cabin)

“Moonshiner”  2024 Jeanneau 410 (3 cabin)

“Emma Joy”  Jeanneau 419 (3 cabin)

“Ann Gale II” – Jeanneau 41DS

“Resfeber” – 2023 Jeanneau 380

“Water Bear” – 2024 Jeanneau 380

“Perception”  Hunter 38  (3-cabin)

“Themiscyra”  Catalina 385

“Meander” Jeanneau 379

Breezin’ 2016 Catalina 355

“Venteux” Jeanneau 349

“Tivoli” Catalina 320  

“Dark Horse” Marlow Hunter 31

“Hippocampus” Hunter 31

“Clara Mae” Hunter 31

Marlow Hunter 22

AM: 11AM – 3PM

PM: 4PM – 8PM

The fiberglass Marlow-Hunter 22 is the ultimate daysailer. This stable platform is rated for five persons and will keep the family safe and dry but will get up and go when you want to run. The large cockpit accommodates the entire crew in comfort.

The Marlow Hunter 22 can be reserved for ½ day or full day (7 hour) sails.

GREAT LAKES SAILING CO.

Since 1983 Great Lakes Sailing Co. has been providing yacht charters on Northern Lake Michigan.

It’s not only our business, it’s our passion.

We continue to provide the best sailing charter fleet on Lake Michigan to cruise the harbors of Grand Traverse Bays, Little Traverse Bay, The Straits of Mackinaw, The Manitou Islands, Beaver Island, the Les Cheneaux Islands and beyond!

CHARTER DISCOUNTS

May 1 – June 3

June 4 – 24

September 3-16

Sept 17 – End of Season

PUMP & FUEL

Rates include fuel & final pump-out on all sailboats.

ADD TIME TO YOUR CHARTER

Early start.

Board by 2pm. Get Briefing.

Up to 39′  $395

40′ and up $595

SLEEP ABOARD

Board at 8pm. Sleep on Boat.

Morning Briefing.

LATE DEPART

Sleep onboard after final day

of sailing. Depart by 10am.

CHARTER EXTRAS

Captain (up to 4 hrs) $175

Captain (up to 8 hrs) $275

Captain (overnight) $325

Linens $25/per person

Dinghy Outboard $40/day

Dinghy (No charge, but must be requested in advance)

Grill – $25 (includes propane)

CHARTER RESOURCES

Charter documents & booking info, standard yacht inventory, harbor reservations, destinations & itineraries.

12935 S West Bay Shore Dr

Traverse City, Mi 49684

Free Spirit Private Yacht Charters

Experience all-inclusive luxury and set sail across the crystal blue waters of lake michigan., lake michigan, chicago, il, welcome aboard, whether celebrating a birthday or entertaining corporate clients, we personalize every detail of your event to provide an extraordinary experience you’ll never forget. soak in the magic of the chicago skyline. sip on refreshing cocktails and indulge in an array of delicious food. we’re thrilled to have you on board.

• Free Spirit

Our spacious Free Spirit luxury yacht accommodates up to 120 people and is custom-designed for your relaxation and comfort, inside and out. Free Spirit is perfect for larger groups for business meetings, company outings, networking events, family celebrations, weddings or parties. Whatever the occasion, it’s more memorable when it’s a boat!

• Gypsy Spirit

Our Gypsy Spirit luxury charter yacht is perfect for an intimate gathering or a small company outing. The Gypsy accommodates up to 49 passengers, offering multi-level entertaining with a salon, galley, and aft deck lounge area. Sit back, relax and cruise Chicago River or Lake Michigan.

WHAT WE Offer

We make special occasions memorable!

At Free Spirit Yacht Cruise, we go above and beyond to guarantee your occasion is truly special. You can delight out-of-state visitors with breathtaking views of Chicago’s world-famous skyline. Host a casual breakfast cruise with sparkling mimosas.

Need to impress new business clients? Break out of the ordinary and stun clients with an elegant dinner on a cruise along Lake Michigan.

From our attentive staff to the luxurious ambiance, our gorgeous yachts offer the perfect venue for you to host your next event.

Ready to Start Planning Your Event?

Free Spirit Yacht Cruises

708-361-2220

[email protected]

Burnham Harbor, Chicago, IL

Interested in chartering a yacht with us? Contact Free Spirit Cruises at 708-361-2220 or complete our online form. Let’s see how we can help you today!

Have A Question? Contact Us Today!

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Chicago's Premier Yacht Charter Service

Experience Lake Michigan with the ultimate comfort and style through our tailored charter services.

An Elevated Experience

our services

Charters & Rates

Whatever the occasion, do it in style.

Private Charters

• Chicago River
• Lake Michigan
• Corporate events
• and more…

Day Charters

• Milwaukee, WI
• New Buffalo, MI
• Michigan City, IN

Night Charters

• Firework nights
• Casino, Hammond, IN

Sea Ray SLX 400 40ft

Winner of the NMMA Innovation Award, the SLX 400, coined “The Entertainer”, combines peak performance, superior comfort, incredible versatility and style, and state-of-the-art technology

• Wet bar, 2 grills, refrigerator, wine cooler, microwave, 3 TVs
• Fresh water washdown, deck shower
• Platform (launch pad) that lowers into water
• Bathroom with toilet and fresh water sink
• Seating for 15 people
• Sleeps 4 overnight
• Stereo in cabin & cockpit, with bluetooth connectivity
• Satellite radio & weather
• Dual inboard-outboard MerCruiser engines
• and much more...

Streamlined process

How it Works

To confirm your booking, simply agree to the quote, sign the contract, and submit the corresponding deposit.

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highly-skilled professionals

City-Centered, Accessible Luxury

a curated experience

Our Concierge Service

we strive to exceed expectations

Our Happy Clients

What a perfect day out on Lake Michigan! We felt like kings and queens and the boat was as classy as the service. Eleven out of ten experience. 

You won’t find more genuine hosts who want nothing less than the best experience for their guests. Whether it’s a slow cruise down the river or an anchored stay in the Play Pen, you’re sure to be charmed by the magic of the city. They think of everything so you don’t have to, a stress free experience. 10/10 would recommend.

We may be the Second City but Chi City Charters is second to none! Best boat on the lake, period!

We had the best time cruising along the Chicago River on Lock Leader. Our captain and crew were utter professionals and taught us a lot about Lake Michigan and Chicago. Highly recommended to see the city from a different view.

If you have any inquiries, please refer to our list of frequently asked questions (FAQs) provided below. In case you cannot find the answer you seek, please do not hesitate to reach out to us.

A bareboat charter, as defined by the United States Coast Guard (USCG), is an arrangement granting the Charterer (the individual renting the yacht) temporary ownership and use of a vessel for a specified duration. Under this agreement, the Charterer assumes responsibility for the vessel, their guests, hiring their own Crew, and providing their own food and beverages.

It is important to note that the Charterer may either operate the vessel themselves if they possess the required credentials or choose to hire their own Captain and Crew.

However, it is crucial to adhere to the maximum passenger limit of 12 individuals for a bareboat chartered vessel.

For bareboat charters, the maximum capacity is 12 passengers, excluding the Captain and Crew.

The hired Captain and Crew are not counted as passengers. So, to clarify, the Charterer can bring a maximum of 11 guests.

Please keep in mind that infants and children are included in the total capacity count. Your Captain will count as an additional person, and the Crew can range from 1 to 2 people, depending on your specific requirements.

Once your booking is confirmed, Chi City Charters will provide you with a selection of qualified and approved Captains who have extensive knowledge of the yacht.

Our Captains can offer valuable recommendations regarding the number of Crew members you may require, depending on your specific charter plan. They have a network of experienced Crew members who are familiar with the yacht, and they can enhance your charter experience by providing additional safety, assistance, and service throughout your journey.

Alternatively, Charterers are welcome to provide their own certified Captain. It’s important to note that Captains are independent contractors hired directly by the Charterer and are not affiliated with or employed by Chi City Charters.

The rate for Captains typically ranges from $80 to $250 per hour, depending on their skills, experience, and qualifications, and this does not include gratuity.

It is customary to show appreciation to your hired Captain and Crew by leaving a gratuity of 18-25% of the total charter price (excluding the Captain’s hourly rate). Payment and gratuity should be made directly to your hired Captain.

Captains usually accept cash or payment through peer-to-peer platforms such as ApplePay, Venmo, Zelle, and others.

At Chi City Charters, we accept all major credit cards, including ApplePay, Venmo, Zelle, direct deposit, and cash, providing you with flexible payment options.

However, please be aware that we are unable to accept payment on behalf of your hired Captain or Crew, as they are separate contractors hired directly by the Charterer.

We recommend discussing the preferred method of payment with your hired Captain to ensure a smooth transaction process that aligns with their payment preferences.

fun in the sun

Get ready for an unforgettable yacht experience on Lake Michigan! Use our booking app to find your desired date and time, and bring your perfect day in the sun to life.

• Diversey Harbor, 2601 N. Cannon Drive, Chicago, IL 60614
• 319-889-7170
• [email protected]

Send us a message

Please allow 1 business day for follow up.

TO OUR LITTLE SLICE OF PARADISE

At our family-owned sailboat charter, we're not just offering a boat — we're inviting you on an unforgettable journey. Picture yourself cruising under the vast Michigan sky, sails billowing in the cool lake breeze, surrounded by the stunning beauty of nature. Whether you're looking to pick up some handy sailing tips and tricks along the way, or just discovering the allure of the open water; our experienced captain is here to ensure your sailing adventure is nothing short of perfect. So come aboard the sailing vessel Julianna , feel the rhythm of the water beneath you, and let us create lifelong memories together on the shimmering blue of Lake Michigan. We can't wait to share our passion for sailing with you!

CANCELLATIONS & RESCHEDULING If you need to cancel your charter, please inform us at least 1 day (24 hours) in advanc e of your scheduled departure for a full refund. If you cancel within t he 24-hour window, we're unable to offer a refund due to the preparations made for your sail. We appreciate your understanding and cooperation with our policy.

INCLEMENT WEATHER CONDITIONS Safety and enjoyment are our top priorities. If the weather is forecasted to be unsafe for sailing, we will work with you to reschedule your trip to a more suitable date or issue a full refund.

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SUNSET SAIL

Max. 6 guests on board  

In compliance with U.S. Coast Guard regulations, individuals under the age of 13 are required to wear a life preserver. We encourage those who possess their own to kindly bring it for use. However, should it be necessary, we are prepared to provide one.  

Embark on our 3-hour+ sailboat charter, featuring a captivating 30-minute cruise down the channel to the lake and back, promising an unforgettable aquatic experience.  

**Additional time aboard may be permitted if there are no back-to-back bookings  -- $100/hr. Talk to Captain Tim once your journey begins!

Do children count towards the total number of passengers on board?

Yes, according to U.S. Coast Guard regulations, all individuals, regardless of age, are accounted for as souls on board.  

Are we permitted to bring our own food and beverages, including alcohol?

Certainly! We encourage you to bring along any drinks, snacks, or alcohol you'd like to enjoy once we have set sail.

What essentials should we pack for our sailboat charter trip? We recommend bringing closed-toed shoes for safety, layered clothing to accommodate changing weather conditions, sunglasses, sunscreen, towels, hats, and any snacks or drinks you might desire during the trip.

Is it possible to take a swimming break during our sailboat journey? Absolutely, your day is entirely customizable! We can drop anchor for a swimming break, as long as it fits within the allocated time for your charter.

Are there bathroom facilities available on board? Yes, our sailboat is equipped with a marine head, complete with a flushable toilet and sink for your convenience.

What are the safety measures onboard? We prioritize your safety above all. Our boat is equipped with life jackets, fire extinguishers, first aid kits, and other safety equipment. Furthermore, our captain is well-trained in safety procedures and emergency responses.

ABOARD JULIANNA

A day in the life aboard the sailing vessel julianna.

LYNDA WARNER Form Submission 2023

Loved talking about the history of the Douglas Saugatuck area. Was a great time looking forward to going again next year.

EDDIE HARTMANN Google Review 2023

We have sailed on Juliana several times and could not recommend it more, and we plan to stop by for a sail whenever we are in Douglas.

KRISTEN MENNEMEIER Facebook Rev iew 2023

The boat is beautiful and Tim was kind, knowledgeable, and very accommodating. He anchored to let our children swim and even let them sail the boat.

CLAIRE McCORMACK Google Review 2023

We learned so much about sailing during our adventure. We even got to steer the boat! Unforgettable memories were made.

ABOUT THE CAPTAIN

Captain tim.

Captain Tim's love for the water runs deep, beginning back in his teenage years in the quiet lakes and Forest Preserves of DuPage County, Illinois. Alongside his father, he learned to sail small boats such as Sunfishes, Hobie Cats, and sloop-rigged dinghies.

Their boating adventures took a leap when his father bought a larger 25-foot sailboat in the late '70s. It was then that Tim started his journey of sailing on Lake Michigan, spending most weekends with his family enjoying the

waters and the scenery of Chicago.

Fast forward to 2005, when Captain Tim and his wife Julie became the proud owners of "Julianna". With this vessel, they've explored much of Lake Michigan and Huron, taking their children on summer cruises for the last 18 seasons and logging thousands of miles on the water.

In 2012, the Julianna  began participating in the Chicago to Mackinaw race, a tradition Captain Tim plans to continue. Throughout the years, he's ensured the safety of his wife Julie and crew during many challenging passages on the race up the Lake.

In addition to "Julianna", Captain Tim has spent considerable time on other boats on Lake Michigan, serving as a Delivery Captain for several private owners. He's also expanded his sailing experiences to the Southern Atlantic Ocean and the Caribbean.

Captain Tim's passion for sailing is unmistakable. We are confident that his enthusiasm will be contagious during your journey on board the sailing vessel  Julianna , creating a memorable and enjoyable experience for you.

219 North Union Street

Douglas, MI 49406

Tel:  (269) 447-7000

HOURS OF OPERATION:

Tues - Sun: 10am - 10:30pm

(Closed Mondays)​​

Thanks for Your Message!

Deeplake Ventures is located on the eastern shore of Lake Michigan in Holland, Michigan and offers sailing charters, sailing instruction and captain services.

Deeplake Ventures is owned and operated by Captain Jeremy Smith, a USCG licensed 100-Ton Master of Motor and Auxiliary Sail Vessels.

Charters depart from Eldean Shipyard, just minutes by boat to Lake Michigan and centrally located on the West Michigan coast, to easily serve visitors to the region including the South Haven, Saugatuck, Grand Haven, Muskegon and Grand Rapids areas.

To learn more explore the site or simply contact Captain Jeremy:

Jeremy@ deeplakeventures.com, (616) 403-5491, customer feedback:.

"I cannot thank you enough for the wonderful evening you showed us.  Our children thought it was the highlight of the trip."

"Thank you again for sharing your boat with us, you made our vacation one to remember."  

"Jeremy was an awesome captain and tour guide!  This was the best part of our trip to Michigan by far.  Thank you!"  

"We really enjoyed our first time sailing.  Weather was great and Jeremy made it so enjoyable and we learned so much at the same time."  

"Everything was great!  My wife and I had a terrific time and would recommend this to our friends and family!!"

"We had a great time with Jeremy. It was a fun way to get out on Lake Michigan. He was very knowledgeable and personable. Would definitely recommend sailing with him!"

"Capt. Jeremy was great to work with! He was very accommodating, knowledgeable, and friendly. I would definitely recommend his services to anyone looking to get out on the lake!"

"What a great way to see Lake Michigan and Lake Macatawa!  Jeremy did a great job accommodating our family of 6 including two small children.  I high recommend this as a must do in Holland.  Jeremy is very knowledgeable of the area and very easy to get a long with."

• Schedule & Rates
• Captain & Vessel

​Sailing Charters & Captain Services

SAIL LAKE MICHIGAN WITH US!

Schedule & rates.

Improve your sailing skills and gain confidence, or have your boat moved to your next destination.

More > 

Contact Captain Jeremy to schedule your day on the water, sunset sail, or special occasion today.

Chartering is a convenient and relaxing way to experience sailing on the Great Lakes.

Choices Charters ​

Experience Chicago on the Water

Choices Charters Luxury Yacht Rentals

Experience elegance at its finest. .

The Choices Charters invites you to cruise with us along the beautiful blue waters of Lake Michigan and the Chicago River. Join us for private trips, spectacular views and unforgettable memories on a private yacht of your dreams! We are here to give you the very best boating experience possible by exceeding your expectations. 

ROMANTIC DINNER CRUISE FOR TWO

A private boat dinner is the epitome of romance and luxury combined into one perfect evening. Imagine dining on a private yacht with a perfectly painted Lake Michigan sunset as your backdrop, your favorite song playing in the background, and gourmet food prepared by our Signature Chef Kathryn’s Soul. Kathryn's Soul's Catering has a romantic all inclusive menu designed to suit your every taste and need, with the option to cater to special diets. Catering is sold separately.

Our Rental Experiences

Dockside Bed & Breaksfast

Dockside Rental

Romantic Dinner Cruise for Two

Iconic Lakefront Cruise

Wednesday Morning Sunrise Retreat

Signature Dining Experience

Lake Michigan Sunset Cruise

Navy Pier Firework Cruise

Just Chill'n

Captain Ed is a US Coast Guard Certified, Licensed Captain. He is a Navy Veteran (Viet Nam Era). He has been boating for over 15 Years. His love for being on the water has led him to desiring that others experience the beauty and serenity of the Sea. Choices Charters is the result of Choice. Captain Ed strongly believes that “The Choices we make, dictate the lives that we lead.”  thus, the name of his boat and his desire to expose others to the beauty of the boating lifestyle.

Kathryn’s Soul

Kathryn Miles, chef and owner of Kathryn’s Soul. Her love for cooking and baking started at the very young age of 10. Her father noticed that she had a gift for cooking, so he began to encourage it.

In 2019, Kathryn decided to take a chance and pursue her passion. Kathryn’s Soul, a restaurant that offers quality comfort food made with love was born.

"The choices we make, dictate the lives that we lead."

From the city to the shore.

TESTIMONIALS

GREG & MARIE

Every summer, I have the perfect  getaway on the Choices Charter! Sitting on the dockside is just enough for me to enjoy the Chicago Skyline and Lake Michigan.  

My first week in Chicago, I was able to set sail with my  friends for her birthday with Captain Ed. The combination of a relaxed atmosphere and impeccable service was perfect.

OTIS & CHANTI

We had the best time with Choices Charters! Captain Ed was very  accommodating ! This was our  first  time on a private  yacht.   We highly recommend!

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Now Booking Summer 2024!

Great Lakes Marine Charters

Sail Into Something New

Time To Escape Your “Normal” and Lean Into Adventure

Step aboard our intimate, active yacht experiences and discover pristine shorelines and horizons. Feel the gentle spray off the water, enjoy sun-soaked afternoons improving your mood and your health, and dive into new memories with the crew of the Athina. Find a new perspective along the stunning shores of Lake Huron and Lake Michigan.

Explore. Experience. Enjoy.

Our intimate trips aboard our catamaran “Athina” offer a distinct experience for everyone. From a pleasure cruise during the afternoon to corporate retreats, SUP excursions, kid’s activities or evening sunset cruises, we would love to be part of your memories. Find your adventure aboard the Athina, and allow yourself a little relaxation this season!

Planning Your Sail

Our crewed yacht charters have staff that will guide you through everything from booking to ensuring your trip is one of a lifetime. Whether you want to learn how to sail, enjoy a glass of local wine you bring onboard by the light of the setting sun, or create a unique adventure, you’ll find our customer service and attention to detail unmatched. If you want to step outside of the ordinary and find something truly refreshing, you’ve come to the right place.

Testimonials

-Augie & Dee

QUICK LINKS

Sailing Trips About the Athina Dock Locations Book Your Sail

810-858-0330 [email protected] Michigan, USA

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Best Chicago Boat Tours

Knock out charters.

2-5 Hour Private Charters

Take a cruise tailored to your preferences. Spend some time anchored, sunning or swimming! Let us customize the perfect cruise for you. I don’t think we have ever said no unless it was illegal.

Built to cruise the ocean, she plays on Lake Michigan with ease. With plenty of space, this boat has all the amenities and comforts of home. This boat is the pride of the Chicago Charter Boat fleet.

Special Chicago Boat Trips

Marriage Proposals

You waited your whole life to meet this person and to ask what probably will be the most important question you ask in your entire life. They waited their whole life for you to ask this question.

Casino Package

We depart Chicago and head South to The Horseshoe Casino in Hammond. We drop you off right at the parking deck for some casino fun. We can either wait for you or help you arrange a Limo back to the city.

Architecture Tour

Discover Chicago’s architectural marvels from the comfort of a private boat tour. Glide along the Chicago River, enjoying expert commentary on iconic skyscrapers, historic landmarks, and innovative designs.

Contact Us or Book Direct Online to Make a Reservation

Knock Out Charters is an award-winning company in Chicago. We want you to be as happy as we are to be enjoying Lake Michigan and the spectacular views of Chicago from both the Lake and The Chicago River...

The Captain

Licensed Master Captain Chris Connor has been boating for over 40 years on a myriad of both Power and Sail boats. He has been on Lake Michigan for over 20 years, and the passion has not waned one bit...

Chicago Boat Trip Photo Gallery

Contact info.

• Phone (312) 613-9799
• Email [email protected]
• Address DuSable Harbor 111 N. Lake Shore Drive Chicago IL, 60601

Book Direct

• Cancellations less than 24 hours in advance, deposit will not be refunded.
• Cancellations more than 24 hours, deposit will be refunded.
• In the case of weather-related cancellations by Knock Out Charters, customers will be offered opportunity to re-schedule or be refunded their deposit.

© 2019 - 2024 All Rights Reserved

Our 2024 season in South Haven is delayed — but our location in Saugatuck is open. See more details here.

Our 2023 season in South Haven is delayed. Availability will be released as soon as possible.

TWO HOUR PRIVATE SAILING CHARTERS IN SOUTH HAVEN

Free cancellation.

Private Charter

Best of the best

Ranked #1 tour in South Haven

360+ five-star reviews

Daily private sailing tours in South Haven for groups up to 6.

Set sail in South Haven. Private tours for groups up to 6 people.

2 hours long

Day Sailing Cruise

$350 + tax

See more details

Sunset Sailing Cruise

$395 + tax

Welcome aboard!

Set sail on the Margaret Ann, a cozy and welcoming sailboat from the scenic lakeside city of South Haven, Michigan. Our two-hour sailing charters offer an unforgettable experience for groups up to 6 people as we sail along the shore of Lake Michigan.

Whether you're a seasoned sailor or a first-timer, our commitment is to provide a relaxing and enjoyable trip that will create cherished memories for all who embark with us.

Private Charters Only

Our boat is your boat. You can even bring your own food and drinks on board.

Get directions

Simple Booking

Easily book online with a free and easy cancellation policy.

See more info

DNR Certified

Our Captains, crew and sailing vessels certified to provide a safe and fun sailing experience.

Another Option: Tall ship sailing in Saugatuck

Just 18 minutes away in Saugatuck, you can sail onour 65 foot tall ship, the Schooner Serenity.

Daily Public Sail in Saugatuck

Up to 24 guests, us coast guard certified.

Make your next private event or leisurely outing on the water an unforgettable experience by chartering Schooner Serenity. With room for up to 24 guests and our professional captain and crew, you'll have everything you need.

$56 / person

Starting at $1,288, some recent reviews.

"So much fun!"

"So peaceful and beautiful! Our first time sailing and it was amazing! The captain and crew were the best- full of info and a great sense of humor. The boat is perfect for a family of 6. We enjoyed it so much and highly recommend!"

September 2022

"Just the best!"

"We've done the larger sails out of South Haven, and they can be fun. But for a more intimate experience, we chose Sailing South Haven. Just my husband and I, and the captain and deck hand. The weather was perfect, and it was fun to get to pilot the sailboat for a bit. You can help as much (or as little) as you want. And of course, the BYOB is awesome. Definitely worth the price."

August 2022

"Must do in South Haven!"

"We had the absolute best time with Andy and Ann. They made us feel comfortable and safe and made sure we had an amazing tim. We kept saying this was the highlight of our weekend in South Haven - we will for sure be doing this again!!! Can't express enough how great this experience was - if you're thinking about booking, just DO IT!"

Jacqueline T.

"Amazing time sailing on Lake Michigan."

"My husband and I were in South Haven for our mini moon and decided to take a trip on Sailing South Haven for our last night and boy are we glad we did! It was such a wonderful experience, Captain Andy & Ann were awesome! They took us out and we had the most magical evening watching the sunset and enjoying the peace and quiet of Lake Michigan with champagne and snacks!"

$59 / all ages

$68 / all ages

Our 2023 season in South Haven is delayed — but our location in Saugatuck is open.

See more details here.

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Departure date

Trip duration, multiple days (less than 1 week), weekly trip show boats that have weekly prices. most weekly boats outside of the us are available only saturday to saturday., boat length: 5ft -, manufacturer, boat build year: -, weekly trip, price: $ - $.

In addition to the best offers we have for boat and yacht charters in Lake Michigan, see also options available for rent in these nearby locations:

• 22 boat rentals in Lombard, IL
• 22 boat rentals in Lake Forest, IL
• 22 boat rentals in Streeterville, Chicago, IL
• 22 boat rentals in Glencoe, IL
• 22 boat rentals in Park Ridge, IL
• 22 boat rentals in Glenview, IL
• 22 boat rentals in Edgewater, Chicago, IL
• 22 boat rentals in Englewood, Chicago, IL
• 22 boat rentals in Lincolnwood, IL
• 22 boat rentals in Elk Grove Village, IL

Discover Lake Michigan with Sailo - a gorgeous boating playground for you to enjoy!

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Luxury Yacht Charters

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Book a minimum of a 4 hour charter and get 10% off your charter package! Use code Entertainment2023!

We charter professionally crewed luxury yachts at the 31st Harbor in Chicago

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The best captain

So friendly just amazing to have captain T

Had a wonderful time!

The service was excellent. Fantastic views of the city and skyline.

Enjoyed a very relaxing and entertaining afternoon. Hosts were professional as well as caring. The ride was smooth and the weather was amazing. Thoroughly enjoyed this day on the water.

Everything was OUTSTANDING friendly and PROFESSIONAL!

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Clients say.

5 star experience!

Everything about this boat was a 10/10 experience. Erika the boat owner was incredibly responsive and super quick to answer any questions that I had. I mentioned that I wanted to rent a boat for my friend’s birthday and she had decorations set up inside the boat when we arrived. We had Captain Tay drive us for the day and he was so nice and made the experience so fun for all of us. We got to use the lilypad and lay out in the pay pen for the day. Would book with them again in a heartbeat!

The trip with Erika was very appreciated! The boat was clean, spacious for all guests, and Captain T was a great captain. All around 5 stars.

Erika’s boat was fantastic. Had a blast for my friends birthday gathering. She even decorated the boat for us. Highly recommend!

Luxury Yacht Charters

Welcome Aboard!

Now available for charters.

Zen is a fully crewed 76’ Lazzara motor yacht now available for private charter in the southern Lake Michigan area.  She is based in Michigan City, Indiana, but can be relocated for other embarkation preferences. 

She is currently available for many exciting events, such as local air shows, boat races (sail and power), fireworks displays, water sports like wakeboarding, water skiing, or tubing, or just for a relaxing day on the water to enjoy a beautiful Lake Michigan day and sunset.   Or, perhaps a wine tasting and special dinner is your preference?  Or a trip across Lake Michigan to Chicago, with its many great events, museums, and restaurants?  Charity rides are also possible by arrangement. 

We can host your small wedding, reception, anniversary or a special birthday party.  Our very reasonable rates begin at $2,500.00.  Book your private charter on Hot Tomolly today! 

Charter Dates Are Filling Up Fast!

We currently have many dates open for cruises during the fireworks displays, air shows, and the Great Lakes Grand Prix Boat Races, but they’re booking fast!

Call us at 219-763-3777 or email us at: [email protected] or [email protected] to discuss your private charter.

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• About Hot Tomolly
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Welcome Aboard...

Hot Tomolly is a fully crewed 76’ Lazzara motor yacht now available for private charter in the southern Lake Michigan area.  She is based in Michigan City, Indiana, but can be relocated for other embarkation preferences. 

She is currently available for many exciting events, such as local air shows, boat races (sail and power), fireworks displays, water sports like wakeboarding, water skiing, or tubing, or just for a relaxing day on the water to enjoy a beautiful Lake Michigan day and sunset.   Or, perhaps a wine tasting and special dinner is your preference?  Or a trip across Lake Michigan to Chicago, with its many great events, museums, and restaurants?  Charity rides are also possible by arrangement. 

We can host your small wedding, reception, anniversary or a special birthday party.  Our very reasonable rates begin at $2,500.00.  Book your private charter on Hot Tomolly today! 

2018 Charter Dates Are Filling Up Fast!

We currently have many dates open for cruises during the fireworks displays, air shows, and the Great Lakes Grand Prix Boat Races, but they’re booking fast!

Call us at 219-763-3777 or email us at: [email protected] or [email protected] to discuss your private charter.

Check out our specials!

2018 Cruising Rates

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