catamarans maui

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!

Maui Catamaran Tours

Join us where the horizon meet the sea, current maui catamaran trips.

Our charter boats take you to the best of Maui. Join us for one of our Maui catamaran tours and let our crew take you on the incredible, clear waters of Maui. Book your tour today and experience the best of what this beautiful island has to offer.

Lahaina Sunset Sail

Molokini performance sail, west maui performance sail, ‘alihilani sunset sail, lunch performance sail, lahaina, sailing along.

Best Catamaran Tours on Maui

Sail aboard our performance catamaran vessels to experience the very best sights and sounds on Maui. Our seasoned crew will take you to the most picturesque locations, creating a once-in-a-lifetime opportunity to take in the unique and unbelievable settings only Maui can provide.

Catamaran Maui Tours

Our fast and powerful charter boats take you to the best of Maui. All three vessels are 43 feet long, with endless comfortable options for drinking, dining sightseeing, or snorkeling. Guest limits are always capped below the maximum for the most authentic Maui catamaran tours available.

The Sail Maui Difference

Whether your Sail Maui tours includes whale watching, sunset cruising or tropical snorkeling, join us for an experience that is second to none. Sit back and  relax – we’ll bring the sunscreen, snorkel gear and beverages!

Featured Crew

Home State: Oregon

Home State: Kansas

Home State: Hawaii

"I would recommend Sail Maui's Paragon II, which caps trips at 38 guests"

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

Private Charters

• Special Events

Luxury Maui Sailing Charters

A voyage like no other.

Exceptional Sailing Experiences

Elite maui excursions on ali’i class yachts.

Deluxe Snorkel Sail

• 5-hour upscale adventure with multiple world-class snorkel stops, expert staff & luxury amenities
• Gourmet buffet breakfast, lunch & open bar with local beer, wine, sparkling & seltzers
• Premium complimentary snorkeling gear, flotation devices, towels & reef-safe sunscreen

Sunset Dinner Sail

Sunset Cocktail Sail

• 1.5-hour sunset sail offering gourmet appetizers & specialty cocktails
• The perfect happy hour at sea, complete with an all-inclusive open bar to enjoy before your dinner reservations
• Family-friendly, great for couples & perfect for groups (recommended for guests 12+)

Champagne Brunch

• 2.5 hour specialty brunch highlighting our Chef's favorite flavors of paradise
• Bottomless bar with premium spirits, specialty brunch cocktails & our signature wine selection
• Select & Private seating upgrades available
• Adults only, must be 18+ to join

Snorkel Sail

Turtles & tacos.

• April 1 - December 14
• 2.5-hour luxury snorkeling excursion featuring fresh grilled tacos & guaranteed turtle sightings
• Full open bar with local beer wine, seltzers & spirits
• Great for families, couples & groups of friends

Small Group Adventure Cruises

Snorkel tour.

8+ YEARS OLD

Snorkel and Whale Watch

Whale watch, snorkel & sunset.

Award Winning Food & Beverage Offerings

Introducing Ali’i Kai

Upcoming events, locals nights, locals night.

Set sail in Hawaii with loved ones, enjoying a beautiful sunset over the ocean. Indulge in gourmet appetizers and an open bar on the Makani Sunset Sail, celebrating Maui’s beauty together. For our State ID holding locals, enjoy a 40% discount. Learn More

Bring the whole family along for an afternoon sail with Santa, paired with hot cocoa, tasty treats, and holiday stories. This special time of year also provides the chance for a whale encounter in the waters off of Maui. Learn More

Maui Songwriters Festival

Join Sony Music Publishing and TuneIn’s ‘The Big 615’ Host Storme Warren with ‘CMT Hot 20 Countdown’ filming crew for a one-of-a-kind snorkeling, whale watching, and sailing experience. Learn More

Valentine’s Day

Spend the most romantic day of the year aboard Maui’s most luxurious catamaran, as you bask in the Hawaiian sunset’s warm glow and dine like royalty. Learn More

Halloween Sunset Costume Cruise

Celebrate Halloween in style with a Sunset Costume Cruise and free admission to Da Playground's Monster Masquerade Halloween Concert featuring live local band Espresso. Learn More

Thanksgiving Royal Sunset Cruise

Set sail aboard Maui’s most luxurious catamaran for an unparalleled sunset sail and dinner cruise experience. Learn More

Why Choose Us

Elevated sailing experiences, gourmet dining.

Indulge in an immersive gourmet dining celebrating ‘ono (delicious) Hawaiian flavors. Our talented chefs create innovative dishes using local ingredients for an authentic and culturally accurate dining experience.

Eco-Friendly Practices

Showcasing a commitment to Mālama ka ‘aina (taking care of the land), our catamaran employs eco-friendly and sustainable practices to minimize our ecological footprint.

UNRIVALED COMFORT AND SERVICE

From plush seating and premium amenities to our attentive crew, we prioritize your comfort and satisfaction throughout your journey.

COMMITMENT TO AINA

We prioritize sustainability by sourcing local ingredients and partnering with local brands. Choosing our offerings supports the preservation of our island's natural resources and local economy.

Exclusive Luxury Experiences

Romance glows aboard the Alii Nui

The royal treatment for any occasion

Rated Excellent By Our Visitors

Island Activities

Experience maui, helicopter & air tours, stay connected, subscribe to our newsletter, request to book.

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Complete this questionnaire as a prerequisite to a recreational scuba diving or freediving course.

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

Step 1 of 17

Complete this questionnaire as a prerequisite to a recreational scuba diving or freediving course. Note to women:

Box a – i have/have had:, box b – i am over 45 years of age and:, box c – i have/have had:, box d – i have/have had:, box e – i have/have had:, box f – i have/have had:, box g – i have had:, you're clear to dive we look forward to having you out with us, to ensure a safe and enjoyable dive experience, please complete our diver medical | medical examiner’s evaluation form before your trip..

Thank you for prioritizing safety on your diving adventure with us!

Ali'i Nui Maui Activity Request

Hawaii Sailing Adventures, LLC

Private Charters in Maui, Oahu, Lanai, Kauai

Private Hawaiian Catamaran, Sailing and Yacht Charters

It's time for the vacation of your dreams.

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

Hawaii Sailing Adventures offers private boats, catamaran charters, and sailing trips on our luxury fleet. We provide charter options for Maui, Kaanapali , Kauai , Niihau, Lanai , Molokai , Honolulu, Waikiki, Oahu , Kaneohe Bay, and The Big Island.   Snorkel, whale watch and visit Napali Coast, Kaanapali & Kohala Coast, exploring the beautiful "unknown" Hawaii through our one of our luxury boat trips.

Contact us  to learn more about booking a private catamaran or boat charter where you'll create a memorable adventure for your family and friends. Enjoy extraordinary encounters with whales, dolphins, and sea turtles, swim and snorkel in tropical island waters and have the best sailing experience in your lifetime!

Explore Our Fleet

Custom 49 catamaran

Fountaine Pajot Helia 44

Excess 12 – 39’

42 Catalina MK 11

Beneteau Oceanis 48

Nautor Swan 46

Beneteau 42

Beneteau Oceanis 41

Beneteau 393

Beneteau 39

Ferretti 69

Ready to find out more.

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

Napali Coast, "The Forbidden Island", North Shore Molokai, Kanaapali, Manele Bay

Niihau, Kalalau Valley, lagoon, reefs and beaches, sea cliffs, waterfalls, snorkel, scuba, swim, sunbathe, kayak, paddleboard, surf, windsurf, fish, and dine ashore. Stay in the harbor as a pleasant, charming, quiet, relaxing home base with all the cooking and sleeping amenities, a more creative environment than a hotel or house, and explore on-island activities on a week or two sailing charter. Relax, work the sails, whale watch, extended inter-island trips, short sailing tours, sunset sail, and dinner cruise. Feel what it is like to offshore cruise in the most dramatically beautiful settings in the world. Our crewed sailing and luxury yacht charters and boat tour prices include skipper, food, fuel, gear, other vessel costs, Sail Blue Hawaii, and much more.

What our customers say...

"Thank you so much! We loved the day and the memories will be cherished. We hope to do it again some day."

The Ferrier Family

A dream wedding in hawaii.

Ask us about our tropical, romantic wedding and honeymoon packages. Then, let us arrange your marriage ceremony aboard your private yacht.

Catamaran and Monohull sailboats to; Maui , Lahaina, Molokai , Lanai , Oahu , Honolulu, Kauai , Niihau, Big Island Hawaii .

Maui Snorkeling, Sunset Sails, Whale Watching Tours & Surf Lessons

The best way to see maui, featured maui ocean adventures.

• Hour Glass 2.5 hours
• Calendar Daily / April 15th - Dec 14th

Xpress Snorkel Tour on Maui

This one-of-a-kind Maui snorkeling adventure is the perfect option for customers who want to get to the snorkeling quickly at one of the most unique spots around the island!

• Hour Glass 3.5 hours
• Calendar Daily

Afternoon West Maui Snorkel Tour

Not exactly a morning person? This is the snorkel trip for you. The perfect way to spend the afternoon and not have to wake up early or spend 5 hours on the boat!

• 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.

Choose Your Ocean Adventure on Maui

Maui snorkeling tours.

Learn More »

Maui Sunset Tours

Maui private charters, book your vacation adventures in maui today check our availability, introducing the all new sea maui iii, our 65 ft. luxury catamaran departing daily on maui catamaran tours.

The best way to SEE Maui is SEA Maui!

At Sea Maui, we like to do things just a little differently than the rest. For starters, we’re more like your extended family or new best friends once you’re on board. You’re here to have a good time, learn about the ocean, Maui, whales (seasonal) and all that good stuff. We’re not operated by the corporate suits; we’re a team of like-minded, fun-going, salty sailors that absolutely love our jobs and all the cool people we get to meet! When you come on a trip with us we promise to do everything in our power to make sure you have the time of your life out on the water.

Discover the Sea Maui Difference: Read Our Maui Snorkeling, Whale Watching and Sunset Cruise Reviews

Just returned from Maui. Family and I did a Friday night sunset cruise. Highly recommend this trip. Capt. Phil and crew are top notch. They work hard to make sure you have fun. Great food and drink, whale watching and great views. The crew was very careful loading and unloading passengers at the start and end of the trip. Overall a great time. If you want to sail with a competent and caring crew, then Sea Maui is the place to be.

This was my third catamaran snorkel trip and it was the best one yet! First and foremost the staff was amazing. Throughout the trip the entire crew stayed engaged in conversation, and not just with one person. Hands down best part of my week stay here in Maui! Lunch was fantastic-drinks were flowing-& we made it back in a timely manner! Thank you so much to the crew of Sea Maui for being the best part of my vacation!

I had the joy of going on a Sea Maui trip. The boat was large and the vibe the crew had was amazing. They served us breakfast and lunch with a smile, had great drinks and music, and made us laugh the whole time. I chose to do SNUBA, and it was worth every extra penny. If I went back today, I would use Sea Maui and I recommend them to all of my friends who are going.

The crew and management at Sea Maui always go above and beyond to make sure their patrons have the best experience possible. They serve good food and drinks and have a smaller amount of people they go out with and they offer something for everyone. They are def my go to when I’m looking to get out in the beautiful waters of Maui.