Calypso Maui

MAUI CATAMARAN CRUISES

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! Book your catamaran cruise in Maui online today!

  • Special Offer Pricing!

From Ma’alaea Harbor: Molokini Crater Snorkeling Tour Aboard the Calypso

Cruise on this high-speed, triple-decker catamaran for an epic snorkeling adventure at two incredible locations: Molokini Crater and Turtle Town! Swim in pristine waters teeming with colorful marine life.

  • 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!

  • 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!

From Ma’alaea Harbor: Lanai Snorkel & Dolphin Encounter Aboard the Quicksilver

One of the most unique places you can snorkel on Maui is actually off Maui, on Lana’i! Just 8.8 miles across the channel is the Pineapple Isle – Maui’s closest neighbor island.

  • Hour Glass 2 hours

From Ma’alaea Harbor: Thanksgiving Dinner Cruise Aboard the Calypso

Enjoy the spectacular views of the West Maui Mountains and neighboring islands on Molokai and Lanai as our crew serves you table-side a Hawaiian-influenced Thanksgiving day feast with all the fixings!

From Ma’alaea Harbor: 4th of July Fireworks Cruise Aboard the Calypso

Meet us at Ma’alaea Harbor and join us for a July 4Th Cocktail Cruise aboard the Calypso! Enjoy fireworks, cocktails, appetizers, and more. Book a ticket for everyone in the family and in your party online!

logo-teralani

  • Premier Snorkel Sail

catamaran cruises in maui

  • West Maui Adventure Snorkel Sail

catamaran cruises in maui

TURTLE REEF AFTERNOON SNORKEL

catamaran cruises in maui

  • Holo Holo Sunset Cocktail Sail

Two couples smiling and relaxing on a Teralani Tours main holo-holo sailboat

  • Ka'anapali Sunset Dinner Sail

Two couples enjoying a scenic sail and dinner together

4th of July Sail

Two Teralani boats peacefully sailing on the open sea

  • Premium Whale Watch

Thrilling main mid-day whale watch adventure with breathtaking views of majestic whales in the ocean

  • Classic Whale Watch

An up-close encounter with magnificent whales at sea

  • Discount Whale Watch

incredible marine giants in their natural habitat.

DOLPHIN WATCH

the sunlight sparkles on the ocean waves, enhancing the dolphins' energetic performance

KA'ANAPALI SURF CLUB

A bright yellow kayak rests on the sandy shore beside the calm, blue sea

AQUALANI WATERSPORTS WAILEA

Two individuals are kayaking on the serene blue waters near Teralani.

Teralani Sailing Adventures

Maui’s best sailing cruises and tours, discover maui with luxury snorkel tours, sunset sails, & whale watch tours, sailing charters, sail in luxury.

When it comes to experiencing the beauty of Maui’s waters in true style, look no further than our luxury Teralani Charters. Whether you’re seeking adventure, relaxation, or an unforgettable wildlife encounter, our exclusive offerings ensure you’ll make cherished memories. Join us for our top-rated snorkel tours, sunset sails, whale watch tours, and more. Here’s a glimpse of what our best charters have to offer:

SNORKEL SAILS

Sunset sails.

  • Ka'anapali Wild Dolphin Sail

WHALE WATCH

Private sailing charters, your exclusive maui adventure.

Departing from the World Famous Ka’anapali Beach on Maui, Teralani’s fleet of state-of-the-art sailing catamarans is sure to exceed your expectations. Teralani Sailing is proud to offer exclusive private charters, designed to provide a luxurious experience and conform to your style of adventure.

  • Wedding rehearsals and receptions
  • Birthdays and Graduations
  • Family Reunions
  • Corporate and group events
  • Fundraising events
  • Company parties
  • Incentive trips
  • Ash scattering / Celebration of life

home-dinner

UNPARALLELED LUXURY

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

THOUGHTFULLY CURATED

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

KNOWLEDGEABLE TEAM

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

UNFORGETTABLE MOMENTS

Witness face to fin wildlife encounters, snorkel pristine reefs, and encounter humpback whales up close for truly unforgettable memories.

CULINARY EXCELLENCE

Indulge in culinary delights that perfectly complement the beauty of the surroundings.

TAILORED FOR YOU

Whether a private charter or group adventure, our experiences are tailored to your preferences.

TERALANI SAILING FLEET

  • Built in 2005
  • Luxury sailing catamaran
  • Trips depart from convenient Ka'anapali locations
  • Built in 2019
  • Built in 2020

Explore Teralani Sailing Gallery

#luxurysailing.

  • FOLLOW US ON

Proud Partner of REVO sunglasses

logo-teralani-white

thumbnail image

Mala Wharf, Lahaina HI

broken image

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:

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

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

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.

catamaran cruises in maui

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.

Maui Catamaran Charters

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

top view anchored

Custom 49 catamaran

2 boats

Fountaine Pajot Bahia 46

h45dssalon

Fountaine Pajot Helia 44

Catamaran Maui

Excess 12 – 39’

anchored

42 Catalina MK 11

Top view Waikiki (1)

Beneteau Oceanis 48

saling 3

Nautor Swan 46

Untitled-10

Beneteau 42

stern view

Beneteau Oceanis 41

side view group 1

Beneteau 393

OLYMPUS DIGITAL CAMERA

Beneteau 39

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 .

Facebook

SELECT YOUR SAILING CHARTER

Hula Girl Sailing Charters

High Performance Sailing Restaurant & Bar

ShangriLa Sailing Charters

Exclusive Private Charters

Kai Kanani

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
  • User All ages
  • Hour Glass 3.5-4.25 Hours

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 SAILING TOURS

Welcome the night with sails out, sail maui sunset tours, current sunset sail tours.

Experience what makes Sail Maui’s sunset tours so dynamic and memorable. We currently offer two unique sunset tours that depart daily from Lahaina Harbor. Choose your tour below or chart your own on a private sailing charter .

Experience what makes Sail Maui’s sunset tours so dynamic and memorable. We currently offer two unique sunset tours that depart daily from Lahaina Harbor. Choose your tour below or chart your own on a private sailing charter.

Paragon Sunset Sail

‘alihilani sunset catamaran sail, ‘alihilani sunset catamaran sail, what to expect on a sunset sail maui cruise.

Best Maui snorkeling

OUR CHARTER BOATS

Come aboard Maui’s fastest, high-performance sailing catamarans for a fun-filled, authentic experience. Our Paragon catamaran sailing vessel has been operating on Maui for over 25 years, while our brand new 65′ Gold Coast catamaran, ‘Alihilani, features a more spacious and modern layout. No matter which Sail Maui sunset tour you choose, we always cap guest limits below our boats’ maximum for the most intimate experience.

WHAT’S INCLUDED

Each Sail Maui sunset sail cruise not only provides amazing sights, but also offers complimentary drinks and hors d’oeuvres. Experience relaxation and fun with an open bar serving alcoholic beverages including mai tais, locally brewed beer, champagne, and wine. Nonalcoholic beverages are also available. If you’re joining us on a sunset sail, you may want to bring a light jacket for when the wind picks up.

Catamaran Maui snorkeling

THE SAIL MAUI DIFFERENCE

At Sail Maui, we love what we do. Our friendly and knowledgeable crew enjoys getting to know you while showing you the very best destinations of Maui. Your unique sunset cruising experience will be like no other as you bask in the beauty — we can’t wait to spend it with you!

From the Press

catamaran cruises in maui

catamaran cruises in maui

Our talented team of Trilogy Coordinators work with groups ranging in size from 2 to 200. Each event is unique and thoughtfully crafted to reflect your personality and vision. Whether it’s a wedding, family reunion, or incentive trip, when you’re multiple time zones away from your party destination, we know it can be challenging! We see it as an honor and privilege to be your “go-to” source, coordinating with vendors, offering our local expertise, and bringing the vision of your perfect day to life. No matter the occasion, we take the stress out of your planning.

This level of customer service and our clients’ word-of-mouth recommendations have won us the loyalty of our guests for the past 45 years, giving Trilogy the honor of being Maui’s #1 sailing company since 1973.

EXPLORE TRILOGY WEDDINGS

fire knife dancer at a luau at trilogy's hale o manele

REQUEST A QUOTE

Personal info.

  • 808-875-0333
  • Toll Free Phone: 800-542-3483

catamaran cruises in maui

Private Charters

  • Special Events

" * " indicates required fields

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/ansunset/

Your Dream Day in Paradise

Ready to set sail? Simply fill out the form with additional details, and our team will contact you. Customize your day, your way!

Unforgettable & Elevated Celebrations

The royal treatment for any occasion, why choose an ali’i class yacht, expert team.

Our dedicated professionals ensure every detail is attended to and executed.

Luxurious Experience

Our luxury yachts offer unparalleled comfort and elegance.

Stunning Backdrop

Enjoy panoramic views of Maui and all of its natural beauty.

Elevated Offerings

Gourmet food, an onboard photographer and a top-shelf bar are just the beginning.

Customizable Events

Tailor your celebration or event perfectly to your preferences.

Seating Options

catamaran cruises in maui

Premium Top Deck Seating

• Priority boarding by Captain

• Private server / crew member • Specialty boarding snack(s) & welcome lei • Elevated champagne & exclusive cocktails • Free to enjoy the entire vessel • Exclusive access only to Premium ticket holders (maximum 12)

catamaran cruises in maui

Select Outdoor

• Exceptional views with our outdoor seating • Dedicated service directly to your table

catamaran cruises in maui

Standard Cabin Seating

• Bench seating inside our spacious cabin

Request To Book

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

IMAGES

  1. A New Maui Catamaran Experience With Teralani Sailing Adventures

    catamaran cruises in maui

  2. Trilogy II 64' Catamaran Charter Vessel Built For Trilogy Excursions, Maui

    catamaran cruises in maui

  3. Kaanapali Sunset Cruise with Dinner & Open Bar

    catamaran cruises in maui

  4. 5 of the best Maui Catamaran Tours

    catamaran cruises in maui

  5. West Maui Snorkel Catamaran

    catamaran cruises in maui

  6. Alii Nui Catamaran Maui Private Sunset Sail Charter [Open Now] tours

    catamaran cruises in maui

COMMENTS

  1. THE TOP 10 Maui Catamaran Cruises (Prices from $60)

    The best Catamaran Cruises in Maui according to Viator travelers are: Premium Sunset Dinner Cruise from Ka'anapali Beach. Maui Sunset Luau Dinner Cruise from Ma'alaea Harbor aboard Pride of Maui. Four Winds Molokini Snorkeling Tour from Maalaea Harbor. Premium Dinner Cruise: Four Course Dining Experience - Ma'alaea.

  2. Maui Sailing Charters

    Elite Maui Excursions on Ali'i Class Yachts. Embark on an exceptional sailing charter aboard an Ali'i Class Yacht. Allow our dedicated crew to curate your unique experience infused with the warmth of aloha. Our luxury catamarans feature a shaded cabin, spacious deck areas, and two restrooms. Immerse yourself in a meticulously crafted ...

  3. 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 ...

  4. Maui Catamaran Tours

    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.

  5. Maui Catamaran Cruises from Ma'alaea Harbor

    Book your catamaran cruise in Maui online today! Special Offer Pricing! From $ 178.95. From Ma'alaea Harbor: Molokini Crater Snorkeling Tour Aboard the Calypso. Cruise on this high-speed, triple-decker catamaran for an epic snorkeling adventure at two incredible locations: Molokini Crater and Turtle Town! Swim in pristine waters teeming with ...

  6. Sea Maui

    Explore ocean adventures with Sea Maui! Choose from whale watching, snorkeling, and sunset cruises on Maui with a fun-loving crew! Book a tour today! ... Our 65 Ft. Luxury Catamaran Departing Daily on Maui Catamaran Tours. DCIM101GOPROGOPR1874. The best way to SEE Maui is SEA Maui!

  7. Deluxe Kaanapali Sunset Sail

    2605 Ka'anapali Pkwy. Lahaina,HI 9676. Parking is available at the Sheraton Maui for $15. Guests also have the option to park at Whalers Village. Trilogy will not validate your parking pass at Whalers. *On days when beach loading is not possible due to large surf, we will depart from Maalaea Harbor.

  8. Teralani Sailing Adventures

    Proud Partner of REVO sunglasses. All guests receive 20% off REVO sunglasses purchase at any Aqualani Kiosk on Ka'anapali Beach with a Teralani Sailing Adventures booking confirmation. Set sail on the waters of Maui from Ka'anapali Beach with Teralani Sailing Adventures. Enjoy snorkel tours, whale watching, and luxury catamaran cruises.

  9. Sea Monkey Luxury Private Charters

    With cutting-edge catamaran hull technology, SeaKeeper gyros and Zipwake technologies, our vessels offer an unmatched smooth and comfortable ride so that you can sit back, relax, and take in the breathtaking views of Maui's natural wonders. Our private tours allow you to fully immerse yourself in the local culture and enjoy a more intimate ...

  10. Sail Maui

    Sail Maui offers the most intimate and authentic catamaran sailing experience in Hawai'i. We offer performance sailing cruises, coastal snorkeling at various destinations, remarkable sunset sailing, and exclusive private charters. Set sail with us today, and discover the very best of Maui with our expert crew. We loved the boat and the crew.

  11. THE TOP 10 Maui Catamaran Cruises (w/Prices)

    The best Catamaran Cruises in Maui according to Viator travelers are: Original Sunset Cruise with Open Bar from Ka'anapali Beach. Maui Sunset Luau Dinner Cruise from Ma'alaea Harbor aboard Pride of Maui. Premium Sunset Dinner Cruise from Ka'anapali Beach. Ma'alaea Harbor: Sunset Prime Rib or Mahi Mahi Dinner Cruise.

  12. Kai Kanani

    View All Tours. The Kai Kanani II is the only commercial catamaran that lives in South Maui, moored off of Maluaka Beach in Makena. Seven days-a-week, she takes passengers on the short cruise out to Molokini Crater, just 3 miles away, to swim and play in the clearest water in all of Hawaii. Five nights-a-week, the Kai Kanani II raises her sails ...

  13. Maui Sunset Cruise and Catamaran Sail

    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 ...

  14. Elite Maui Excursions & Sailing Tours

    From sunset cruises to Maui sailing tours all around the island, your voyage is guaranteed an exceptional adventure. 808-875-0333; Toll Free Phone: 800-542-3483; CONTACT; ... If you are seeking the most luxurious catamaran experiences on Maui, your search ends here. Our excursions are renowned for their excellence, thanks to our dedicated crew ...

  15. Private Catamaran Charters in Maui & Oahu

    Featured in the Netflix series "The most Amazing Vacation Rentals" Episode 1, Season 9. 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.

  16. Hula Girl Sailing Charters │ Shangri La Sailing Charters │ Maui Sailing

    We are proud to introduce you to our yacht the Hula Girl, a state of the art 65 x 35 ft sailing catamaran and Shangri-La - where innovation meets with tradition aboard this 65' luxury sailing yacht

  17. Sunset Sail from Ma'alaea Harbor 2024

    Maui, Hawaii. Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor. 32. from $119.00. Likely to Sell Out. Maui, Hawaii. Maui Sunset Luau Dinner Cruise from Ma'alaea Harbor aboard Pride of Maui. 493. from $148.70.

  18. Sunset Sailing Tour

    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 ...

  19. Makani Sunset Sail

    PRICE. Starts at $179.00. Starts at $139.00. Starts at $259.00. Join us on board for one of the best Ali'i Nui Catamaran excursions - the Makani Sunset Sail. Enjoy Hawaiin appetizers and a premium open bar as you bask in the beauty of our famous sunset view!

  20. Maui Sunset Sail Tours and Cruises

    Our Paragon catamaran sailing vessel has been operating on Maui for over 25 years, while our brand new 65′ Gold Coast catamaran, 'Alihilani, features a more spacious and modern layout. No matter which Sail Maui sunset tour you choose, we always cap guest limits below our boats' maximum for the most intimate experience.

  21. Welcome to Trilogy Excursions

    51 YEARS. 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 ...

  22. Maui Private Charters

    For Private Charters & Weddings, call (808) 661-4743 ext. *7018 - or - REQUEST QUOTE. We had the best time of our lives. The whole experience was fabulous. Every single one of our wedding guests told us how amazing the wedding was and how great the service that Trilogy provided. - Mike & Kung (grooms) on.

  23. Private Sailing Charters

    Experience your dream day in paradise with our private sailing charters in Maui. Whether you are planning a wedding or corporate retreat, our team is ready to help you create incredible memories. 808-875-0333; Toll Free Phone: 800-542-3483 ... Our spacious catamarans and luxury yachts provide a unique and exclusive setting for your dream ...

  24. 2024 (Makawao) Maui Pineapple Farm Tour in Haliimaile

    She's a great representative of this wonderful industry. Tour is a must if you're in Maui. Pineapple is delicious! Read more. Written April 25, 2024. gerald n. 0 contributions ... Original Sunset Cruise with Open Bar from Ka'anapali Beach. 375. Catamaran Cruises . LIKELY TO SELL OUT* Haleakala Sunrise Best Self-Guided Bike Tour. 417 ...

  25. Private 90-Minute Amsterdam Canal Cruise (1 Hour 30 Minutes)

    Experience the unforgettable Private 90-Minute Amsterdam Canal Cruise in Amsterdam, Netherlands, and work with a Virtuoso travel Advisor to receive exclusive perks. ... The excursions were excellent with the Catamaran in MyKonos and the wine tour in Santorini. Our guide in Athens was a bit off - she could not find the tickets for 10 of us ...