catamaran sailing maui

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CALYPSO CATAMARAN, MAUI

Maui catamaran cruises from ma'alaea harbor, welcome aboard calypso maui.

You come to Maui to have epic experiences, right? Months before your arrival, you’ll spend time daydreaming of the island vibes and aquamarine waters – imagining yourself swimming, sunning, snorkeling, diving, feasting, and drinking in deep relaxation and happiness. One of the most unique places to make all this happen is aboard the brand-new Calypso Maui.

MOLOKINI CRATER SNORKELING TOUR

Dollar Starting at $185.95 Hour Glass 5.5 hours

A Molokini snorkeling adventure aboard Calypso is the most fun on Maui! This stable, high-speed, triple-decker catamaran will get you to two snorkel sites fast: Molokini Crater and Turtle Town, and with all the equipment you need and plenty of food on board, what more could you ask for? You’ll be welcomed aboard by our friendly crew and enjoy a delicious, hearty breakfast. After everyone is settled in, it’s off to the most popular underwater destination in Maui for some morning Molokini snorkeling! While you’re enjoying the feel of the ocean wind in your hair, from December through April, watch the horizon for the incredible humpback whales!

Book Now! Seats Will Sell Out Quickly.

OUR MOST POPULAR MAUI CATAMARAN TOURS

• most popular!

From Ma'alaea Harbor: Maui Sunset Dinner Cruise Aboard the Calypso

This relaxing, two-hour excursion gives you time to enjoy a delicious meal, explore the incredible craft, listen to great island-style music, and watch the sun go down from your place on top of the waves! Book your sunset dinner cruise in Maui online today!

• DEC - APRIL

From Ma'alaea Harbor: Maui Whale Watch Cruise Aboard the Calypso

The two-hour Calypso whale watching in Maui is one of the most thrilling family-friendly Hawaiian activities! From December 18th through April 15th, climb aboard our boat, and make your way to the top. Book your Maalaea whale watching excursion online today!

ABOUT CALYPSO MAUI

The Calypso Maui is ready to take you on exciting ocean excursions. The boat launches from Ma’alaea – the most easily reached, centralized harbor on the island . You can go on the morning Molokini Snorkeling Tour , the Sunset Dinner Cruise , the seasonal Whale Watch , and – for super special occasions — the Private Charter !

This motorized catamaran is built with three decks of fun, and is a wonderful vessel for landlubbers and ocean adventurers alike. The Calypso Maui operates like a spacious, floating amusement park, and her double hulls are built for stability . When the boat is moving forward, the twin hulls cut smartly through the water, leaving most of the craft to float high above the waves, and ride on top of the sea-surface winds. This leads to a comfortable, smooth catamaran snorkeling trip in Maui for you and your group, even when island trade-winds factor in.

The views from Calypso Maui are better than any other boat for miles, because she is the only vessel on the island that has three decks .  As a bonus, you’ll find glass panels on the bottom of the boa t, too!  Two of the cabins are completely covered from the sun, but both ends are open to the sea air. The huge tinted windows along both the port and starboard sides ensure that you always have a good view of the great Pacific beyond the railings.  Year round, it’s good to keep your eyes open for  flying fish , sea turtles, dolphins, false killer whales, and other fantastic marine animals who may be up near the surface. During whale season (mid-December through mid-April), come out to see the 45-ton humpback whales! Once you’ve seen a whale, nothing else can compare.

Our fun, dynamic, and experienced crew is there for you no matter what you need, and safety is paramount. If you come out with us to Molokini Crater, the captain and crew will teach you what you need to know in order to snorkel. Crew members will explain how to use the wide dive steps, two water slides, or the “leap of faith” jump-off point to enter the water, and they will entertain you with little-known facts about the islands that you are gliding past. The crew will also have delicious food and drinks at the ready, along with local insider tips, good humor, and  Aloha .

600+ 5-STAR REVIEWS FROM GUESTS!

We had a large group with small children. The crew was very accommodating and friendly! They made sure we had a spot together on the boat and were comfortable! They had all the right equipment to make snorkeling doable for all skill levels and ages including a viewing board to allow my 2 year old niece to see the ocean bottom. The food was great! The boat was clean and spacious! The family said it was a highlight of the trip! We would definitely do it again!

Great experience! Enjoyed the large boat. The crew were awesome, friendly and professional! The food was delicious! It was two fabulous snorkeling spots!

This trip was amazing. Having a big boat was worth it. Sure there were more people. But when there was a heavy surf we barely noticed. The food for both breakfast and lunch was great!!! Also on the ride back they gave out some little ice creams too! The photographer Marley is amazing at photographing and he has both go pros and nice camera to use in the water. This was 100% worth it.

We took our kids (6 & 11) and we had a blast! The highlight was swimming with a turtle for sure. Every just seeing the cool fish was amazing. The girls loved the slides off the boat and the food was good. Definitely would do it again

An absolute must do. This is an awesome adventure for the price. You get to stop at two locations and even if you only get out and snorkel at one it is way worth it for the cost. Molokini was incredible and clear. The crew on this boat makes everything even better the captain is funny, friendly, gives clear helpful instructions to snorkel newbies like myself and they have everything they can for sea sickness. Truly an amazing time with the Calypso.

Me and my friend got to go on the dinner cruise. The captain was great, the boat was very nice, we loved the live music(Alex is very talented), the crew was good and the food and views were amazing! Thanks for an unforgettable evening aboard the Calypso!

Premier Snorkel Sail

West Maui Adventure Snorkel Sail

TURTLE REEF AFTERNOON SNORKEL

Holo Holo Sunset Cocktail Sail

Ka'anapali Sunset Dinner Sail

4th of July Sail

Premium Whale Watch

Classic Whale Watch

Discount Whale Watch

DOLPHIN WATCH

KA'ANAPALI SURF CLUB

AQUALANI WATERSPORTS WAILEA

• Private Charters
• 808-661-7245
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• 808.661.SAIL (7245)

SUNSET SAILS

Our commitment to luxury goes beyond aesthetics, creating an environment of utmost comfort and enjoyment.

Our team of knowledgeable professionals shares their passion and expertise, enriching your journey with valuable insights.

Witness spinner dolphins, snorkel pristine reefs, and encounter humpback whales up close for truly unforgettable memories.

Each adventure is thoughtfully designed to showcase Maui's marine wonders, from snorkeling to whale watching.

OUR SUNSET SAILS

Holo holo sunset cocktail sail.

KA'ANAPALI SUNSET DINNER SAIL

4TH OF JULY SAIL

WHAT TO EXPECT

From our customers.

Hawaii Sailing Adventures, LLC

Private Charters in Maui, Oahu, Lanai, Kauai

Private Catamaran Sailing Charter Trips in Maui

Perfect for family trips, weddings, honeymoons and vacations..

1/2 day, one-day, sunset, dinner, multi-day to multi-week inter-island vacation, and trip options are available.

As Hawaii's second largest island, Maui boasts white sand, crystal clear water, black sand beaches, waterfalls & mountains. With Hawaii Sailing Adventures, you can sail Maui by booking a private sailboat charter and luxuriously exploring the white, black, and red beaches or many activities, including sailing, surfing, paddleboard, kayaking, snorkeling, scuba, biking, windsurfing, swimming, shopping, eating. Our boat routes are perfect for family trips, friends, weddings, honeymoons, birthdays, anniversaries, and vacations.

We offer the only private vacation sailing catamarans and the most extensive fleet of monohulls available on and inter-island to Maui from the neighboring island for just your family and friends.

Contact us today to talk about booking your Hawaiian vacation!

Explore Our Maui Fleet

Custom 49 catamaran

Fountaine Pajot Helia 44

Excess 12 – 39’

42 Catalina MK 11

Beneteau Oceanis 48

Nautor Swan 46

Ferretti 69

Chesapeake Bay 36

Visit one of the luxury spa resorts on kaanapali beach..

• See “tons” of frolicking Humpback whales.
• Snorkel, sunbathe, fish, surf, sail, swim, relax.
• Maui, Lanai and Molokai, short sails between islands.
• Fishing is great and we know the most amazing snorkel spots.
• Lahaina is a historic whaling town, beautiful art galleries, wonderful upscale restaurants.

Sailing Maui and Oahu is a weather friendly option for Winter.

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Get information on prices, itineraries, private daily or weekly charters & tours in Hawaii.

What our customers say...

Adventure Sunset Sail

Quick details.

• User Ages: All ages

Offered Monday  – Friday

Includes: Three-course appetizers, plated and served; Open Bar; Sparkling wine toast at sunset

Beach load at Maluaka Beach in Makena

Ages 13 and up

Soak in the golden hour on a wailea sunset cruise.

There’s nothing quite like a Maui sunset, with Molokini silhouetted on the horizon and the presence of friends and loved ones and the best crew on Maui taking care of your every need.

Kai Kanani’s Adventure Sunset Sail is a two-hour sail featuring live music, a stellar menu from Wailea’s own Spoon & Key Market , and an open bar full of local spirits such as Ocean Vodka and Kula Rum , as well as wine from Ulupalakua’s MauiWine . At sunset, we pour their sparkling wine for a sunset toast. 

As the only catamaran in South Maui, we sail alone with the ocean, our canvas, and the wind as the brush.* Our captain and crew are there to serve you and your friends and make the tour as comfortable as possible. Sit back and enjoy what we think will be the best evening of your Maui vacation.

We offer a shuttle service from Wailea Resorts to and from our check-in location at Maluaka Beach . Space is limited, so contact us to reserve your spot. We look forward to seeing you aboard!

* All tour locations are subject to weather and at the captain’s discretion. Safety is our top concern at Kai Kanani, and we apologize if there is any inconvenience due to weather-related cancellations or changes.

Explore the Enchanting Wailea: A Sunset Cruise Like No Other

Maui, a part of the Hawaiian archipelago, is synonymous with paradise, and for a good reason. Its enchanting landscapes, friendly locals, and diverse marine life make it a prime destination for travelers seeking both relaxation and adventure. However, among its various attractions, the Wailea sunset cruise is a jewel that offers a unique way to experience the island’s beauty.

Embarking on a Journey: The Wailea Sunset

The Wailea sunset is not just a visual feast; it’s an experience that touches every sense. The gentle lapping of the waves, the salty breeze, and the kaleidoscope of colors in the sky create a symphony of sensations, making every sunset cruise a journey to remember. Wailea, with its pristine beaches and luxury resorts, provides a tranquil setting to witness the day’s end, where the golden sun meets the azure sea, leaving a trail of amber and rose hues in the sky.

Whether you are a photographer looking to capture the perfect shot or a romantic soul yearning for a serene escape, the Wailea sunset cruise offers something for everyone. It’s a place where time seems to slow down, and the worries of the world fade away, leaving only the beauty of the moment.

The Wailea Sunset Cruise Experience

What sets the Wailea sunset cruise apart is not just the stunning views but also the exceptional service and attention to detail. The crew is dedicated to making every journey special, providing insights about the island’s history, flora, and fauna, and ensuring every guest’s comfort and enjoyment.

As the boat sails smoothly over the clear waters, guests can savor delicious local cuisine, sip on exotic cocktails, and immerse themselves in the panoramic beauty of the seascape. It’s a celebration of the senses, where every flavor, sound, and sight is amplified by the surrounding natural beauty.

Diversity of Marine Life

Maui’s rich waters are home to a diverse array of marine life. During the cruise, it’s common to encounter playful dolphins, majestic whales (during the migration season), and colorful schools of fish. The Wailea sunset cruise provides a unique opportunity to witness these creatures in their natural habitat, adding another layer to the enchanting experience.

The island’s coral reefs, teeming with life, are a testament to the richness of Maui’s marine ecosystem. The vibrant underwater world, with its myriad of colors and shapes, is a paradise for divers and snorkelers. Those interested in exploring this aquatic wonderland can opt for Maui snorkeling tours , where expert guides help uncover the secrets of the deep, introducing the fascinating inhabitants of the reef.

Other Enchanting Experiences in Maui

While the sunset cruise is a highlight, Maui offers a plethora of other experiences that cater to different interests and preferences. For those who prefer active adventures, sailing tours in Maui allow the exploration of the island’s diverse coastlines, discovering secluded beaches, hidden coves, and dramatic cliffs.

The sunrise snorkel in Maui is another must-try experience, where the early rays of the sun illuminate the underwater world, revealing the vibrant colors and intricate patterns of the coral reefs. It’s a refreshing start to the day, filled with wonder and discovery.

For those who seek relaxation, Maui’s spas and wellness centers offer traditional Hawaiian healing practices and massages, using local ingredients like volcanic clay and coconut oil to rejuvenate the body and soul. The island’s farm-to-table dining experiences are a feast for the palate, showcasing the rich flavors of locally sourced ingredients prepared with culinary finesse.

The Essence of Aloha: Conclusion

Maui encapsulates the spirit of Aloha, a philosophy that goes beyond a greeting to represent love, compassion, and kindness. It’s this spirit that permeates every experience on the island, making each moment special.

Whether it’s the warmth of the locals, the breathtaking landscapes, the diverse activities, or the enchanting Wailea sunset cruise , Maui invites everyone to embrace the Aloha spirit, to connect with nature and each other, and to create memories that last a lifetime.

So come, explore the enchanting Wailea, embark on a sunset cruise, and discover the myriad treasures of Maui. Let the island’s beauty and charm captivate your heart and soul, and experience the true essence of paradise.

Discover the Magic of a Wailea Sunset Cruise

Experience the breathtaking beauty of Maui’s coast with a Wailea sunset cruise , a must-do for any visitor to the island. As the sun dips below the horizon, the sky transforms into a canvas of fiery oranges, pinks, and purples mirrored by the crystal-clear waters of the Pacific. But a sunset cruise in Wailea is more than just a visual spectacle; it’s an immersive experience that combines relaxation, romance, and adventure into one unforgettable journey.

Why Choose a Sunset Cruise in Wailea?

Wailea, located on Maui’s south shore, is renowned for its stunning beaches, luxurious resorts, and, most notably, its incredible sunsets. Opting for a sunset cruise in Maui Wailea provides not only spectacular views but also the chance to see marine life, enjoy live music, and savor gourmet appetizers and cocktails. It’s an all-encompassing experience that highlights the best of Maui’s natural beauty and hospitable culture.

What to Expect on Your Journey

From the moment you step aboard, you’ll feel the magic of the Hawaiian islands. Each sunset sail in Maui is designed to offer a unique experience. You’ll be greeted with a traditional Hawaiian welcome, complete with lei and a smile from the friendly crew who will be your guides through this journey.

As you sail along Wailea’s coastline, keep your eyes peeled for playful dolphins, majestic humpback whales (during the winter months), and sea turtles gliding through the waters. The crew, knowledgeable about Maui’s marine life and culture, will share fascinating stories and facts, making this cruise not only enjoyable but also educational.

Customize Your Experience

No two sunset cruises are the same, and with options for customization for sunset cruise Wailea , you can make your trip truly unique. Whether you’re seeking a romantic outing with your partner, a fun evening with friends, or a private family gathering, there’s a package that fits your needs. From private charters to intimate group settings, the emphasis is on creating moments that will be cherished for a lifetime.

Memorable Moments Await

As the cruise returns to shore, the fading light of the day sets a serene backdrop for reflection and relaxation. It’s a moment to take in the beauty of the islands, the warmth of the people, and the joy of life’s simple pleasures. A sunset cruise in Maui is more than just an activity; it’s a highlight of any Hawaiian vacation, a story to be told, and an experience that will be remembered forever.

Ready to embark on this magical journey? Explore our options for a Wailea sunset cruise and book your adventure today. Let the beauty of Maui’s sunsets captivate your heart and create memories that will last a lifetime.

• Chevron down Food Menu

All Courses are plated and served to our guests.

First Course: Hummus and crudités, assorted cheese and charcuterie

Second Course: Seared ahi with chimichurri sauce (lemon, garlic, herbs)

Third Course: Baked Pasta (three cheese, marinara, and herbs), Caprese Salad  (tomatoes, mozzarella cheese, basil pesto, balsamic drizzle)

Dessert: Kai Kanani Signature chocolate cake with berry compote

• Variety of juices and soft drinks
• Cocktails, premium liquor, Maui Brewing on tap, MauiWine and Champagne, and a Lokélani Sparkling Rosé toast at sunset

* Menu items may be substituted based on availability

Related Activities

• Most Popular
• Hour Glass 3.5-4.25 Hours
• User All ages

Signature Deluxe Snorkel

Snorkel Molokini and enjoy up to 200 ft. of visibility on our classic Maui adventure. An open bar, Maui Brewing beers, and a full-service deli lunch in three courses complete the perfect day!

Sunrise Deluxe Snorkel

The most exclusive tour on Maui, snorkeling Molokini before any other snorkel boats arrive. Hot cinnamon rolls, a three-course breakfast, plus an open bar make this the best morning of your visit to Maui.

• Hour Glass 2-2.75 Hours

Adventure Whale Watch

Sail with our attentive crew and naturalists as we welcome Pacific humpback whales to their winter home. Our beach-loading location gets you on the water and in nature easily.

Maui Sunset Cruises and Catamaran Tours

Book your sunset catamaran cruise on maui today.

Hawaii offers one of the best island adventures in the world, and you can get more of it by experiencing it through a Maui sunset cruise and Catamaran Tours! You will surely love the front row seat of Maui’s magnificent sunsets. Enjoy it more with handcrafted cocktails and seafood cuisine prepared just for you. The splendid Hawaiian sunset will bring awe and will surely be one core memory you can share with your loved ones and friends.

During the tour, marvel over the beauty of the nearby islands of Molokai, Lanai, and Kahoolawe. While at the water, look for dolphins as they swim and jump offshore while enjoying unlimited drinks from a premium bar and refreshments. These Maui sunset cruises and Catamaran tours will be the perfect way to end a day on the island.

At Sea Maui, we know that Hawaii is a major destination for relaxation and fun times. That is why we offer a Maui sunset dinner cruise! This will allow you to loosen up and enjoy yourself while marveling at the wondrous Maui sea. You can dance to live music on board and sip on two free drinks from a full bar. Travel by boat and see the sights illuminated at night. Our guests can also choose from various dinner options prepared by our experienced and talented chef. Make it more amazing by picking from multiple cruise times to fit your schedule.  

Sea Maui Sunset Cruise and Catamaran Tours

Sea Maui Sunset Cruise tour packages offer options that can fit your style and budget. You can pick slots that will suit your time, and we will ensure every second of your tour is worth it. Here are the three Sea Maui sunset cruise options that you can choose from:

• Hour Glass Approx 2.5 hours
• Calendar Daily , Includes Live Music on Wednesdays and Saturdays!

Premium Maui Sunset Cruise with Dinner

Are you looking for a unique dining experience to leave behind the hustle and bustle of the land? Sea Maui’s Sunset Dinner Sail is our premium dining and sailing experience.

• Most Popular!
• Hour Glass Approx 2 hours
• Calendar Daily , Includes Live Music on Tuesday & Thursday!

Original Sunset Cocktail Cruise on Maui

Experience Sea Maui’s classic sunset charter as we depart from Ka’anapali Beach to enjoy a beautiful Hawaiian sunset with handcrafted cocktails in hand.

Premium Sunset Cruise with Dinner Tour on Maui

Sea Maui’s Sunset Dinner Sail is our premium dining and sailing experience. Leave the rush and bustle of land behind as we welcome you on board our newest vessel. The stunning Sea Maui III is a 65-foot luxury catamaran recently renovated. Feel the flow of the ocean beneath you as you sail with the tradewinds down Maui’s shore. Take in the majestic sunset views of Maui and its neighboring islands. Drink exquisitely handcrafted beverages and quality beers from the spacious cabin for a memorable dining experience. This cruise also includes a splendid dinner made by Cafe Jai’s. It is a specifically designed buffet-style menu just for you. Find out more about the inclusions of the Premium Sunset Cruise here .

Original Sunset Cocktail Cruise

One of the Ka’anapali classics is Sea Maui’s Original Sunset Cocktail cruise where you can witness the picturesque and breathtaking view of Maui’s sea sunsets. You shall get the best view of the spectacular pastel sunset colors as they change and extend across the horizon and slowly dissolve into the waters of Hawaii.

During the winter, Sea Maui’s Sunset Cruise also participates in some Maui whale watching! Nothing more incredible than spotting majestic humpback whales as the sun sets over the Pacific.

You can expect to take in stunning panoramic views of Molokai, Lanai, Maui, and Kahoolawe. Make sure your cameras are on the go because there will be amazing photo moments during the cruise! You can also savor the pupus meals prepared and served by Cafe Jai. As we sail across the calm seas, there will be handcrafted cocktails from our premium bar and local Maui breweries. With a drink in hand, everything in Maui is more enjoyable! 

Sunset Live Music Cruise

Sea Maui’s Sunset Live is created for guests looking for more excitement while on the water. Every Sunset Live is transformed into an absolutely unique event. The guests will be entertained by musicians, who are well-known local artists who play exclusively for the audience on board.

Aside from the live music and entertainment, you can also sip through amazing handcrafted cocktails and delectable food to liven up your evening. Finally, enjoy the magnificence of the pastel sky as the sun sets over the Pacific! The perfect way to unwind and end your day on Maui.

Sea Maui’s Sunset Cruise and Tours

Sea Maui started back in 2015 as the new guys on shore. Despite being a newbie in the field, we are not new to sailing in Hawaii. Many of our crew started working on boats on Waikiki Beach.

Over the years, Sea Maui has worked out to become a staple in Ka’anapali Beach. We make sure our guests get the best time and the magical experience Hawaii has to offer to its tourists. In addition, all the crew members are experienced, certified, and skilled sailors, working together in harmony to give you the best possible experience. 

Since Maui is home to some of the most incredible sunsets on the planet, we put together our Maui sunset cruise and Catamaran tours , so everyone can experience Maui’s beauty on another level. You can witness the grand sunset of the Pacific while having some crafted drinks and food catered by our partner and trusted Cafe Jai. You can also see the magnificent sea creatures of Hawaii with the open-air layout of the cruise. A 360-degree view of the open sea with the seasonal appearance of whales and dolphins as live music plays in the background. Sea Maui’s famous sunset sail options are simply the best evening tours Ka’anapali has to offer.

Sea Maui is more than just Maui sunset cruise and Catamaran tours , and your trusted Maui adventure buddy, we make sure that every moment with us is comfortable and memorable. Get to know more about the adventures you can enjoy while in Maui and get in touch with us here !

More About Sea Maui Sunset Trips

• Chevron down More Information:
• Easy-to-find check-in location at The Whaler’s Village Shopping Center and the only boat with a physical location/booth on the beach. Our “Ocean Activities” booth is located along the beach walk at Whaler’s Village between Leilani’s restaurant and The Westin Resort.
• The only boat with free parking validation, savings of $20 or more!
• Exceptional staff & service/certified naturalists for whale watches (seasonal)
• All crew members are lifeguard and CPR-certified.
• Food prepared by Cafe Jai. Can easily accommodate food allergies or dietary restrictions with 24-hour notice.
• Premium open bar on all trips.
• Complimentary juice, water, Coke, Diet Coke, Sprite, and lemonade on all sails.
• Kama’aina rate available with Hawaii ID, please call  (808) SEA-MAUI  to book.
• Private charters also available.

Gemini is now open for tours 7 days a week and currently in our famous whale season. We are running our regular Snorkel Sail Adventure as well as two Whale Watches (AM & PM) per day at reduced capacity to ensure proper social distancing. We are once again offering our delicious catering from the chefs of the Westin Ka’anapali Beach. Space is limited so please book your tour early. Click HERE to reserve your spot!

• About the Vessel

Morning Snorkel Adventure

Snorkel sail adventure.

• Maui’s Premier Sunset Dinner Sail

Morning Whale Watches

Afternoon whale watches.

• Exclusive Private Charters
• 4th of July Fireworks Cruise
• Private Charters
• FAQ’s

Check out our Availability!

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky an endangered Hawaiian Green Sea turtle ‘Honu’. A hot buffet lunch is served and our complimentary bar is open.

Now offering a new Morning Snorkel Adventure tour for the summer months! Click HERE for more information

Sailing With Gemini Charters

Begin your Maui Snorkel adventure with the sensation of your bare feet slipping into the warm sands at Ka‘anapali Beach, Maui. Walk down a few feet to meet Gemini, our luxurious 64’ catamaran and her friendly, professional crew who will be on the beach ready to welcome you aboard. With ample seating in sun or shade, exposed to the gentle elements or sheltered by the spacious cabin, prepare to relax and enjoy your most memorable Maui day.

Sunset Dinner Sail

Relax as Gemini’s crew set sail for two hours of smooth and exciting Tradewind sailing with phenomenal views of West Maui’s mountains, Molokai and Lanai. Sip a Mai Tai or a Maui Brewed Beer, and lounge on Gemini’s decks or trampolines, as the sun sets on another perfect day in paradise.

Whale Watching Highlights

With Snorkel Sailing Adventures and seasonal Sunset Sails and Whale Watches, Gemini and her crew will always show you the best of times. Enjoy delicious catering by Westin Maui Resort & Spa and an all-inclusive complimentary bar onboard, we will deliver you back to the warm sands of Ka‘anapali with a well fed body, mind and spirit … and we’ll look forward to your return! Reserve your Maui snorkel or other boat tour today!

Winter Whale Watches

From December 15 to April 15 Gemini offers two daily Whale Watches. A morning Whale watch and an Afternoon Whale Watch. Our Professional Marine Naturalists share intriguing information and up-to date facts about the Whales as our guests listen to ‘Whale Songs’ live on Gemini’s hydrophone.

Official Whale Watch Charter of The Sentry

Gemini tours, premier sunset dinner sail, exclusive private charters.

Gemini Sailing

Over 1200+ 5 star reviews and counting.

GEMINI HIGHLIGHTS

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• (808) 751-1230
• Toll Free Phone: 800-542-3483

• Private Charters
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Makani Sunset Sail

• ADDITIONAL INFORMATION

Waiver: All guests are required to fill out a waiver prior to boarding Alii Nui. Waivers may be completed using the link in your confirmation email from FareHarbor. They may also be completed Here: https://waiver.smartwaiver.com/v/aliiboat

The best sunset view on the island.

• Light gourmet bites for a little taste of the islands.
• Year round sunset timing guarantee.
• The perfect cocktail hour prior to your favorite dinner reservation.
• Premium open bar with top shelf spirits, craft cocktails, local beers, seltzers, fine wines and bubbles.

• JACKFRUIT 'CRAB' CAKES crispy garlic F • SPICY AHI POKE* big island ahi with sriracha aioli • Haleakala Beef Satay Skewer with Mango Plum Sauce

• Kula Greens Salad with Candied Macadamia Nuts, Cherry Tomatoes, Shaved Red Onion, and Feta Cheese with Champagne Vinaigrette and House Made Ranch Dressing • Braised Bok Choy with Lemon-infused Olive Oil • Purple Molokai Sweet Potato Puree with Coconut Milk and Ginger • Vegetable Fried Rice with Truffle and Pineapple • Huli Huli Chicken • Ginger Braised Short Rib with Ginger Sake Sauce • Chef's Fresh Catch Special

• Lilikoi Mousse with Whipped Cream • Chocolate Torte • Chocolate Covered Strawberries

• Coffee & Tea Bar • POG, Orange, Pineapple, and Cranberry Juice • Coca Cola Soda products and filtered water • Beer, Wine, Sparkling Wine, and Seltzers** • Open Premium Bar featuring rum, gin, vodka, tequila, and whisky cocktails** **alcoholic beverages for guests 21+ with valid state ID

Additional Information

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Note to women: If you are pregnant, or attempting to become pregnant, do not dive .

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Our Story is a tribute to the dreamers and visionaries: Though our family’s legacy began in the 1920’s, it wasn’t until 1969 that a fateful shipwreck in SE Alaska changed the course of our future. After the disaster, Captain Eldon Coon and his wife, Jeannette, sold everything they had and used the proceeds, with help from their children, Jim, Rand, and Pattie, to build a 50′ sailing…

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PRIVATE SAILING CHARTERS

Chart your own adventure, trip details.

Nobody knows the waters of Maui better than our personable and experienced crew, so let us be your hosts on a distinguished private charter for any occasion. Maui private sailing charters are available from Ma’alaea & Lahaina harbors.

Best Private Charters on Maui

There is so much about our team that really makes charters with us stand out. Our captain and crew are passionate about what they do, and their enthusiasm really is infectious. They are fun, knowledgeable about the island, the waters, current events, and sailing, and they love to share what they know. Above and beyond that, we offer some of the most competitive private charter rates on the island, and our vessels are in beautiful condition. Additionally, we are one of the few companies that really value sailing, and can offer the best sailing experience available.

Our Catamaran Sailing Vessels

Our twin Paragon and Paragon II catamaran sailing vessels have been operating on Maui for the past 25 years, while our brand-new 65′ Gold Coast sailing catamaran, ‘Alihilani, features a more spacious and modern layout with plenty of seating and a large galley with bar.

Make the Experience Your Own

Maui Sailing

Unique Maps • Best Charters • Sailing Tips

Maui Sailing Charters

Below are some of the finest Maui sailing charters available.  Most of them have realtime availability directly on our site.  Book today before we’re sold out!

Maluaka Beach, Makena, South Maui

The Kai Kanani is a sailing catamaran that sails from Makena in South Maui, Hawaii. They’re one of the only vessel allowed to pick up passengers from the beach in Maui! Enjoy sailing conveniently from Maluaka Beach  on this luxury catamaran.

Trilogy Excursions

Maʻalaea harbor.

PacWhale Eco-Adventures

Rooted in ocean protection, Pacific Whale Foundations seeks to use research, education, and conservation programs to keep our oceans healthy. From that, a fleet of vessels and a crew of conservationists allow you the opportunity not only to see the beauty of the ocean but to learn about how you can protect it.

Four Winds II

Maui Custom Charters

Enjoy a completely private sailing tour aboard the beautiful S/V Artemis, a 47′ Leopard sailing catamaran or the sleek S/V Nova, a 42-foot Catalina MKII sailing yacht. As a private tour, you have the freedom to customize your own adventure, whether it be a whale watch, snorkel tour, or a full-day sunrise to sunset charter.

Island Star Excursions

With a welcoming crew and scrumptious onboard menu, a private tour aboard the elegant Island Star is a first-class experience. Departing out of Ma’alaea Harbor, this 57-foot luxury sailing yacht offers private snorkeling and whale watch excursions for up to 18 people.

Onboard the Ocean Spirit, a new luxury sailing catamaran sailing from Lahaina Harbor, this is one of the most eco-friendly boats in Maui waters with loads of room. Whale watching in season, Honolua Bay and more await you!

Makena Coast Charters

Kaʻanapali Beach

Maui Sailing Activites

There’s more to do on the water than just sail! We suggest taking a sailboat to go snorkel at Molokini, scuba diving at Lanai’s Cathedrals, enjoying cocktails during sunset, or going whale watching in season. Sailing for the sake of sailing is worth the trip alone, but why not enjoy the island’s many great activities while sailing? And, if you’re looking for more, check out our 2-week Maui itinerary .

Maalaea Harbor Slip #56 65ft Catamaran

Gemini Charters

Kaanapali Beach Entry 64ft Catamaran

Maui Custom Charters Nova

Maalaea Harbor Slip #103 42 Ft Sailing Yacht

Teralani Sailing Adventures

Kaanapali Beach Entry 65 ft Catamaran

Where Should We Sail?

Maui is the second largest island in the Hawaiian Island chain. It encompasses over 700 square miles (1883.5 Km square) .

Maui County is composed of four islands of which Maui is the largest. Lana’i , Kaho’olawe , and Moloka’i surround the island of Maui, Hawaii. Kahoolawe is uninhabited. Lana’i is famous for scuba diving and plush Four Season’s Resorts. Molokai is known for its natural beauty and sea cliff waterfalls. Molokini Crater is a volcanic atoll, but not considered an island.

Sailing in Maui is one of the best ocean activities to do. Travel to one of the islands in Maui County and experience sailing the way it should be.