catamaran sailing in maui

02 Nov Teralani Sailing Adventures

Teralani offers sailing adventures throughout the year including snorkel cruises, sunset dinner sails and whale watching (seasonal availability). Each excursion features gourmet cuisine, beverages and an open bar for guests 21 and older. Private charters for weddings and corporate events are also available.

Teralani Sailing Adventures delivers impeccable service and in 2015, was inducted into Tripadvisor’s Certificate of Excellence Hall of Fame for consistently achieving great traveler reviews for five consecutive years. Also, voted #1 Best Water Activity on Maui by locals and visitors from 2010-2013. For more information and reservations, contact Teralani Sailing Adventures at 808-661-SAIL (7245) or online at www.teralani.net . Follow Teralani on Facebook , Twitter and Instagram .

WHALE WATCHING

Each year the Pacific Humpback Whales migrate from Alaska to the coastal waters off Maui. Being on board one of our spacious catamarans is the best way to experience these gentle giants and the surrounding beautiful West Maui scenery. Make this an exciting learning experience with a marine naturalist on board each trip. You will actually be able to listen to the whale songs live on our under water hydrophone. The whales are not the only return visitors you may see while on the Morning Whale Watch. There are many of our guests that return year after year, always being sure to include Teralani on their ‘must do’ list!

TRIP FEATURES:

• See the whales up close in their natural habitat
• Marine naturalist on board to educate and inform
• Watch for thrilling breaches and tail slapping

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 First Friday of Every Month
• Hour Glass 2.5 hours

‘Ike Maui Sunset Dinner Sail

Indulge in the extraordinary ‘Ike Maui Sunset Dinner Sail, set against the stunning backdrop of Ka’anapali & Lahaina. Join us for an unforgettable evening as we honor the rich heritage of Hawai’i and delve into its captivating culture through mele (music) and hula.

• 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.

Welcome To Teralani Sailing

Teralani Sailing offers a fun filled family experience but does so with the comforts of a luxury sailing catamaran. For almost 30 years we have been creating lifelong memories for visitors to Maui. We treat our customers like family and it brings us joy to see guests come out with us time and time again. We believe in doing what’s right no matter the cost and that’s why we built our fleet of boats right here in the United States. We are proud to have Maui’s premier American made sailing fleet and would love an opportunity to share this experience with you. Aloha!

Say hello to our American made luxurious premium sailing Fleet!

Our fleet of maui sail boats….

For almost 30 years we have been dedicated to providing Maui visitors the very best in sailing excursions. We are proud to say that when you sail with Teralani you ride in luxury aboard vessels made right here in the USA! Take a glimpse into our fleet of sailing catamarans!

Luxury Sailing Catamarans

Crew Members

Get in Touch

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

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.

• 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.

EXPLORE MAUI

Sail trilogy, explore our maui snorkeling tours.

LANA'I

Tours by activity.

SUNSET SAIL

DINNER SAILS

WHALE WATCH

CELEBRATING

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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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

Fountaine Pajot Bahia 46

Lagoon 440 Fly Bridge

Excess 12 – 39’

Beneteau Oceanis 50

Beneteau Oceanis 48

Nautor Swan 46

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.

Ready to find out more?

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

What our customers say...

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!

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.