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

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

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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.

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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.

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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.

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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!

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Catamaran Sunset Cruise

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What to Expect

Our Snorkel, Whale Watching, and Sunset adventures depart right from Ka’anapali Beach in front of Whaler’s Village. Green sea turtles, Hawaiian spinner dolphins, and humpback whales (seasonal) are regularly seen on daily adventures. Sit back, relax, and enjoy great company, food, and drinks while sailing through beautiful blue Hawaiian waters.

West Maui Half Day Snorkel Adventure

  • Breakfast is Served, come hungry to enjoy a delicious breakfast served onboard to start the trip.
  • The Captain will determine the best site to visit that day based upon current water conditions
  • Masks and snorkels for all ages/sizes (Sea Maui does not provide prescription masks and/or masks to fit over glasses. Visit The Snorkel Store for rentals)
  • Once in the water you will experience beautiful tropical fish, honu (Hawaiian green sea turtles), vibrant reef, and hopefully some other wildlife surprises
  • Once back on board you will enjoy a sumptuous lunch prepared by Chef Joey
  • You will be offered access to our premium beers, hand crafted cocktails, and other libations as we take a leisurely site seeing cruise and whale watching (seasonal) back to Ka’anapali Beach
  • Just bring your towel, sunscreen, and sense of adventure! We provide the rest

Lanai Half Day Snorkel Adventure

  • Experience another Hawaiian island on this delightful sailing catamaran, and cruise across the ‘Au’au Channel in style
  • The Captain will determine the best site to visit that day based upon current water conditions, typically renowned Manele Bay or Club Lanai 
  • Just bring your towel, sunscreen, and sense of adventure! We provide the rest!

Sunset Live!

  • Step onboard and enjoy access to our premium beers, hand crafted cocktails, and other libations as we take a leisurely site seeing cruise and whale watching (seasonal) through the ‘Au’au Channel.
  • Light Pupu’s (apetizer) served onboard prepared by Executive Chef Joey.
  • Site Back, Relax with a cold beverage, and enjoy our LIVE musician onboard for a one-of-a-kind catamaran experience.  

Original Sunset Cocktail Cruise

  • Light Pupu’s (apetizer) served onboard prepared by Executive Chef Joey

Whale Watch (Seasonal)

  • Departs daily right from Ka’anapali Beach in front of Whaler’s Village.
  • Step onboard and enjoy access to our premium beers and hand crafted cocktails, as we take a leisurely site seeing cruise and whale watch through the ‘Au’au Channel.

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

JOIN OUR SPECIAL ‘IKE MAUI SUNSET DINNER SAIL THIS FRIDAY! INCLUDING LIVE MUSIC, HULA, & TRADITIONAL HAWAIIAN CUISINE. ALL PROCEEDS GO DIRECTLY TO MAUI WILDFIRE VICTIMS – CLICK HERE TO BOOK NOW! 

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West Maui Snorkel Half Day Adventure

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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.

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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

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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.

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Top 5 Maui Sunset Cruises

Top 5 Maui Sunset Cruises

Maui sunsets are as exceptional as the rumors suggest, ranging in colors from whisper pink to fiery red and reminding all who witness them that nature’s shows are the best. Savoring them from the island’s shores is a highlight for kamaʻaina and visitors alike, but watching them from the stern of a boat? Now that’s another story. Here are the top Maui sunset cruises.

Sunset cruises go down as one of the most popular activities on Maui for a reason: They provide beauty and romance in equal measure, as well as an ambiance seldom found on terra firma.

Here are the top 5 dusk-on-deck affairs—and why you should book a spot on one of them.

  • Sunset Dinner Cruise – Full Dinner
  • Adventure Sunset Sail – Most Luxurious
  • Sunset Cocktail Sail – Best Price
  • ‘Alihilani Sunset Sail – Best Value
  • Sunset Live Music Cruise – Local Musicians

Sunset Dinner Cruise

Top Maui Sunset Cruises Kaanapali

Maalaea Harbor serves as the point of departure for this two-hour trip around the Pacific, where guests are treated to a number of sensory pleasures. Enjoy your choice of delectable rosemary garlic roasted prime rib or locally caught island fish as you watch the sun slip behind the horizon. Vegetarian options are available and they can accommodate most food allergies. Add an open bar, complete with local beer and Maitais, and you’re in for a night you won’t soon forget.

Know Before You Go:

  • Vegan, vegetarian, or gluten-free? Not to distress: Just call ahead of time to hear about your dining options.
  • Bring a light jacket (or, ladies, a pareo to wrap around your shoulders): Evenings on the ocean tend to be chilly.
  • Keen on learning more about Maui and its marine life? Then this is the cruise for you: A Certified Marine Naturalist is always on board—and they’re always happy to answer your questions.
  • Check-in is located at the Pacific Whale Foundation Ocean Store in the Maalaea Harbor Shops.

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Adventure Sunset Sail

adventure sunset sail kai kanani

There are few beaches as glorious as Makena’s Maluaka—and only commercial vessel that departs from it. That catamaran—the luxe Kai Kanani—not only hosts excellent snorkeling trips but also splendid sails, taking guests out into the sea to witness a sunset with the volcanic caldera Molokini in the distance. Kai Kanani has been building its stellar reputation for three decades, and such perseverance—and such a love for island culture—is apparent in the cruise’s details: The crew is knowledgeable and friendly, the spirits are from Maui wineries, breweries, and distilleries, most of the organic fare is locally-sourced, and the live ukulele music is performed by the acclaimed Dwight Quenga. With eats ranging from seared ahi to charcuterie—and a captain that knows how to tell a fine joke—their Adventure Sunset Sail is one for the record books.

  • Staying in Wailea? No need to stress about driving or taking Uber: The Kai Kanani offers complimentary shuttle service to and from the enclave’s resorts.
  • Vegetarian options are available, including chickpea salad, hummus with crudité, a garden salad, and more.
  • While it may be a sunset dinner cruise, the Kai Kanani recommends donning swimwear underneath for boarding and disembarking the boat.

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Sunset Cocktail Cruise

Top Maui Sunset Cruises Cocktails

Prefer to have your dining experience on land? Then this is the sunset cruise for you. Launching from Maʻalaea Harbor aboard PacWhale’s this two-hour voyage includes first-rate pupu (or appetizers) and superb drinks (to say nothing of the epic views). And what appetizers they are: Furikaki crusted ahi crostini and bbq kalua pork quesadillas are just two examples from this well-chosen menu. Certified Marine Naturalists will join you on board to give you info on Maui’s history, culture, and environment, while chill, island-style music will enhance the serenity of the whole experience.

  • Traveling with your littles? Children 4 and under are free.
  • This cruise sets sail on Sundays at 4:30, but guests are expected to check in 45 minutes before departure. In other words, make sure you arrive to Ma’alaea Harbor in advance: Traffic around this time can be heavy.
  • Check-in is located at the Pacific Whale Foundation Ocean Store, Maʻalaea Harbor Shops, next to Maui Ocean Center.

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‘Alihilani Sunset Sail

Aulii Luau Water Sunset

‘Alihilani translates to “where the heavenly horizon meets the sea”—which is no better way to describe a sunset on Maui. The newest catamaran in Sail Maui’s fleet—a sleek, 65’ catamaran complete with trampolines for lounging—is an ideal vessel on which to watch one. As the sun goes down, Sail Maui’s affable staff will treat you to a selection of drinks (champagne, Mai Tais, wine, and locally brewed beer) and an array of hot and cold eats. With panoramic views and guests limited to 49 passengers (read: a lovely, intimate experience), the ‘Alihilani Sunset Sail underscores why Sail Maui has consistently received a Certificate of Excellence from TripAdvisor. Having serviced visitors and residents for over 25 years, the company has its excursions down pat, giving you, well, a heavenly experience.

  • While Sail Maui provides vegetarian, vegan, and gluten-free options through their catering services, those who have severe nut allergies or celiac disease should be aware that they cannot guarantee there has been no cross-contamination.
  • As with most cruises, Sail Maui suggests bringing a hat, sunglasses, a camera, and a light jacket.
  • Due to the Maui fires, this excursion is taking bookings starting in December, but the location of check-in has not been determined yet. 

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Sunset Live Music Cruise

Top Maui Sunset Cruises Music

It’s understood that cocktails and sunset go hand-in-hand.  Sitting down to a beautiful sunset on the beach with a fresh drink is a moment we forever chase. Add a boat and some live music to the equation, and we are really talking! Glide out onto the water, cocktail in hand, and relax while taking in a beautiful Maui sunset.  Let the live music soothe your soul as you consider if life can get any better than this moment.  That’s when it happens, a whale breaches the water on the horizon as the sun goes down.  That’s right, an added bonus to this cruise is from December 15 to April 15, there is a high probability that you will see whales along your journey, rounding out your perfect Maui moment.

  • Check-in is located on Kaʻanapali Beach between Lelani’s and Hula Grill at The Whaler’s Villiage Shopping Center.
  • One of the biggest draws of this cruise is that it departs from Ka’anapali Beach, quite convenient for those staying in West Maui.
  • This is a gliding party—if you will—complete with an open bar, appetizers, and local musicians.
  • Traveling during the winter months? Keep your eyes on the water: Guests of this sunset live music cruise—as well as the others listed here—might see a Humpback Whale or two. We did say Maui is no ka oi, didn’t we?

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Still can’t decide?

Get more in-depth information as well as even more options for your maui sunset cruise ., top maui luaus, grand wailea luau.

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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: http://www.smartwaiver.com/v/aliinui

Maui Sunset Cruise

A sunset sail fit for the entire family.

  • 2 hour luxury sunset cocktail & appetizer sail
  • Family-friendly, recommended for guests 12+
  • Full premium open bar
  • Charter limited to approximately half capacity to assure guest comfort
  • Upscale hot & cold appetizers
  • Best dining views on Maui
  • Easy access on dock
  • Two oversized clean bathrooms
  • Transportation available

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Beer & wine, cocktails & spirits, local flavors of maui.

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7 Best Maui Sunset Cruises For a Great Night Out

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I’ve traveled all over the world and one of the things I always look forward to doing in every location is watching the sunset (and now that I have young kids I’m usually also watching the sunrise ). 

While we’ve seen some great sunsets, none compare to Maui. The sunsets here are unbelievably spectacular. Pink, purple, ombre skies that sometimes you can’t even believe are real. And while you can certainly see these sunsets from land, there’s something very special about enjoying them from the water. 

If you’re looking for a Maui sunset cruise that really wows, we have a list of the best of the best, and what makes each one so special. Living on Maui for three years we were able to experience more than our fair share of these, so we’re happy to be able to share our advice with you!

Want to get right to it without reading all the details? Jump in and book these recommended tours: 1. This is the cruise to book if you want live music 2. Book this for a convenient Wailea departure 3. Getaway from the crowds with this small group sail 4. Luau or cruise? Get both with this sunset luau cruise 5. Enjoy a full dinner cruise with your sunset Need more time on (and in) the water? Make sure you check out our top snorkeling tours on Maui .

Best Maui Sunset Cruises

Sunset Live Music Cruise (Ka’anapali)

Head out onto the water with a drink in hand while being serenaded by an on-bard musician. This sunset live music cruise really knows how to have a good time. Offered every Tuesday and Thursday, you and approximately 47 other guests will board a 55’ catamaran for two hours of fun. 

Included is live music, an open bar (beer, wine, champagne, and mixed drinks), and pupus (light appetizers). 

They depart from Ka’anapali beach (how convenient!) and if you’re not staying in Ka’anapali you’ll get a 4 hour Whalers Village parking validation. Note that because of the convenient location and not needing to drive to a harbor, they do beach loading. That means you’ll be wading into the water up to your knees in order to board. Long dresses and pants aren’t ideal here. 

If you’re not interested in live music, or you can’t go on Tuesday or Thursday, they offer a regular sunset cruise (sans live music) all other days of the week. Learn more about their standard Ka’anapali sunset cocktail cruise .

Sunset Luau Cruise (Ma’alaea Harbor)

Can’t decide between going to a luau or enjoying a sunset cruise for an evening activity? Do both with this sunset luau cruise ! While this isn’t a true full luau, you’ll still get to experience traditional music and dance with Maui’s gorgeous sunset as a backdrop. 

You’ll board the maxi powered catamaran which leaves from Ma’alaea Harbor in central Maui (paid parking available). On board you’ll be treated to appetizers, a full dinner, and an open bar with beer, wine, and mixed drinks. During the cruise you’ll have the opportunity to enjoy Polynesian dance, which makes this experience part sunset cruise, part luau. 

The boat has a coast guard approved occupancy of 149 people, but they intentionally limit it to 60% of capacity so there’s extra space to stretch out. While this is the most expensive cruise on this list, you do get to see hula and a full dinner.

If you prefer to keep your luau and your sunset sail separate, we have a list of the best luaus on Maui.

sunset catamaran cruise maui

Catamaran Sunset Sail

Spend 2.5 hours aboard this 48 passenger, 65’ catamaran, with plenty of room to spread out. Excited for a little more adventure? Head up front to the trampolines (though you might get a bit wet). 

They have two different boat options, both leaving from Lahaina Harbor. The first is on a 65’ Catamaran, with capacity up to 48 passengers. The second cruise on the Paragon is limited to 25 passengers. 

On both, you can enjoy pupus as well as an open bar with cocktails, wine, and beer. 

Note: Due to the damage to Lahaina Harbor during the fires, Sail Maui is no longer operating from Lahaina Harbor. Book their Molokini Snorkel Tour from Ma’alaea Harbor in Central Maui to support their crew!

Adventure Sunset Sail

Staying in Wailea or Kihei? This is the sunset cruise you want to be on. This Adventure Sunset Sail departs from Maluaka Beach , a very convenient South Maui location. The adventure part of this sunset sail is that you get to enjoy a beach loading, which means you should expect to get wet! We happened to go out on an evening when the south swell was particularly large, so we were in for even more of an adventure! (You can see the video of our experience below). 

Once aboard the 65’ catamaran, you’ll enjoy two hours of sail time, 3 appetizer courses from The Market Maui (a great Wailea deli/restaurant), and an open bar featuring local brand like MauiWine and Ocean Vodka. 

If you haven’t rented a car or you don’t want to drive, they do offer shuttle service from Wailea hotels. But book early as this option tends to fill up! 

We loved this sunset cruise experience and we were able to go out for a great night in Wailea after it ended. Here’s a list of our favorite Wailea restaurants .

Lahaina, Ka’anapali, or Ma’alaea Sunset Sail

Another stellar option is this 2 hour sunset cruise which departs from three different locations on the island: Lahaina Harbor, Ma’alaea Harbor, or Ka’anapali (beach loading). 

A standout feature here is that they offer private tables for two, which makes this a great option for a romantic evening on the sea. They serve plated appetizers and there is a premium open bar with beer, wine, and cocktails. 

If you’ve taken the cruise from Lahaina Harbor, it’s just a short walk to their family-owned pizza restaurant, Kapena’s , which we highly recommend!

Champagne Sunset Sail

If you’re looking for a smaller group, this is the sunset sail for you. This is a sailing experience, not just a sunset cruise on their Santa Cruz 50 sailing yacht. With a capacity of only 22 people, this is a fun small group experience. 

While you won’t find as much food on this sail as you will on the others, you’ll enjoy champagne and chocolate. Guests must be 13 years or older to enjoy this experience. 

Best Maui sunset cruise

Premium Sunset Dinner Cruise

If you’re looking for something more than a cocktail and pupu cruise, consider a dinner cruise . Hop aboard this 65’ luxury catamaran for 2.5 hours, relax, and enjoy the spectacular scenery and service. 

You’ll depart from the beach in Ka’anapali — very convenient if you’re staying in Ka’anapali. But if you’re not, don’t worry! They give you a 4 hour parking validation for Whalers Village . Once aboard, you’ll have an open bar and a buffet dinner to enjoy. There’s something for nearly everyone when it comes to the food selection. 

Kids of all ages are welcome. But don’t wear long dresses or pants. This is a beach loading boat, which means you’ll get a bit wet while getting on and off. The convenience of this beach loading cruise can’t be beat. 

Maui Sunset Cruise FAQs

Can you see whales on a maui sunset cruise.

You sure can! While these aren’t whale watching tours, if they come across a whale during whale season, they will absolutely stop to watch them. Whale season runs December – April , and these sunset cruises all cruise in prime whale watching locations. So the odds of seeing whales during your cruise is pretty good! 

Best sunset sail Maui

What is the best place to watch the sunset on Maui?

Head to West or South Maui for spectacular sunset views. You’ll get amazing views both from land or from sea. What we love about a sunset cruise is that you not only get to appreciate the sunset over the water, you get to see the island lit up in the glow of the setting sun. 

What do you wear on a Maui sunset cruise?

Pretty much anything you want! Bring a light jacket or sweater, especially during the winter if you tend to get cold in the evening. There is usually a light wind and after a day of fun in the sun, it can feel a little cool. 

If you’re doing one of the beach loading tours, don’t wear long dresses or pants. Expect that your knees and below will get wet. But that’s part of the adventure of beach loading!

How long is a sunset sail on Maui?

Most sunset sails on Maui are two hours, though you will find some that run a bit longer, at 2.5 hours. But they are quick tours that will usually get you back in time for any dinner plans you have that evening.

Find a great place to stay on Maui: The 7 Best Vacation Rentals in Wailea and Makena The 12 Best Maui Beach Hotels (+ 5 awesome beachfront condos) Where to Stay in Hana Maui for One Night: 4 Great Options

There’s More to See Than Sunsets

Maui is a dream destination and there is so much to see and do. If you want to make your trip planning easy, our itineraries are here to help . With carefully thought-out excursion days, we take you around the island, seeing the best sights, stopping at the best beaches, and eating at the best restaurants. We’ve done the homework for you, now you get to download and enjoy!

My twin sister and I just returned from an amazing birthday in Maui.  I ordered your itinerary for Maui and we relied on it heavily. I just wanted you to know your itinerary was spot on and your recommendations were the best. Thank you so so much. Kate R.

sunset catamaran cruise maui

Maui Wayfinder Itinerary

Get the maui itinerary.

The step-by-step itinerary takes you to all the best beaches, snorkeling spots, restaurants, and sights. You’ll get six carefully planned excursion days to help you see the can’t miss stops no matter how limited your time is.

Get all the details on our itinerary and download it for a memorable and easily planned trip to Maui.

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I'm the co-founder, with my husband Jordan, of The Hawaii Vacation Guide. We have lived on Maui and Oahu and continue to travel, experience, and learn about the Hawaiian Islands. We travel with our kids, Henry and Edith. I am a planner! I love to plan trips from the mainland and island-hopping adventures, excursion days, and everything in-between. I spend a lot of my time in Hawai'i on a SUP and my favorite time of year in Hawai'i is whale season!

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Calypso Maui

CRUISES FROM MA'ALAEA HARBOR ON MAUI

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.

underwater view of a coral

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.

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CHOOSE A CRUISE!

  • Special Offer Pricing!
  • Hour Glass 5.5 hours

Molokini Crater Snorkeling Tour

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.

  • Due to Lahaina Wildfire Not Available at this time

Lanai Snorkeling & Dolphin Encounters (Aboard Quicksilver in Lahaina)

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.

  • most popular!
  • Hour Glass 2 hours

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!

Maui Whale Watch Cruise

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!

Thanksgiving Dinner Cruise

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!

July 4th Fireworks Cruise

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!

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 boat, 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!

sunset catamaran cruise maui

CAPTAIN'S SUNSET

Dinner sail.

sunset catamaran cruise maui

FIRST-CLASS DINING

Guest dine on a chef-prepared gourmet 4-course dinner at intimate two-top tables seated on deck. The courses are fixed with exception to your entree, which you must select when booking. We do not offer vegan/veg appetizers. 

Ala’e Sea Salt Breadsticks with lilikoi butter

Smoked Salmon on Crispy Pita with fresh dill

Cucumber Cup with Maui Onion Cream Cheese

Tataki-Style Beef Tenderloin Crostini

Caesar Salad with Blue Cheese Vinaigrette

ENTREE OPTIONS (ONE PER GUEST)

Seared Top Sirloin Steak with herb & garlic crust

Fire-Grilled Chicken with citrus & thyme

Fresh Island Fish, panko-crusted with lemon caper butter

Pasta Primavera with Portobello mushroom & sauteed vegetables in fresh marinara with basil

DESSERT TRIO

Lilikoi Cheesecake

Fresh Island Fruit

Dark Chocolate Truffle

sunset catamaran cruise maui

DRINKS & COCKTAILS

Feel the aloha vibes as our Crew serve up a wide variety of alcoholic and non-alcoholic beverages–a little tasty something for everyone on this Dinner Sail.

PREMIUM BAR

Maui Brew Co. -Sunshine Girl Golden Ale

Maui Brew Co. -Seasonal Seltzer

Matua Sauvignon Blanc

Josh Pinot Noir

La Marca Prosecco

Captain’s Mule –  Our thirst-quenching twist on the classic Moscow Mule… New Amsterdam Vodka, splash of soda mixed with Elixir G ginger syrup and lime.*Option to sub Vodka for Tequila or Bourbon

Lana’i Tai –  A Mai Tai done the Trilogy way – Mango Rum, Orgeat, Fresh lime, Elixir G ginger syrup, pineapple juice and a float of Potter’s Dark Rum.

Good Ol’ Fashioned – Redemption Bourbon, agave syrup, splash of water, Watkins bitters.

Lahaina Sunrise – Camarena Reposado Tequila, Ginger ale, POG juice, splash of Elixir G ginger syrup and lime.

808 Margarita – Camarena Reposado Tequila, agave syrup, pineapple juice and a dash of bitters.  (808 is the area code encompassing Hawaii.)

*NOTE: Guests must be 21+ to enjoy our bar beverages.

sunset catamaran cruise maui

DEPARTURE TIMES

  • Feb 1 – April 14 | 5:00pm – 7:30pm
  • April 15 – Aug 31 | 5:30pm – 8:00pm
  • Sept 1 – Oct 14 | 5:00pm – 7:30pm
  • Oct 15 – Jan 31 | 4:30pm – 7pm

Check-in time is 15 minutes prior to scheduled departure time, at the loading dock.

TOUR DURATION

  • Approximately 2.5 hours

DEPARTURE LOCATIONS

  • Ma’alaea Harbor | Wednesday, Friday, Sunday

The dinner sail departs from slip #62 at Ma’alaea Harbor on Wednesdays, Fridays, and Sundays . Slip #62 is located on the break-wall (ocean) side of the harbor.

The dinner sail departing from Lahaina Harbor is temporarily suspended due to the Lahaina Fires. 

MA’ALAEA PARKING

  • 11 Ma’alaea Harbor Rd
  • Wailuku, HI 96793

Parking is available within Ma’alaea Harbor for $1 per hr. Please pay via the digital parking kiosks (QR Code) for parking prior to checking in. Trilogy is not responsible for cars that are towed due to a parking error.

WHAT'S INCLUDED

Chef prepared & plated 4-course Dinner with Appetizers, Salad, Entree & Dessert

21+ yrs: Premium Bar

Sodas, Filtered Water, Juices, Mocktails

Sailing & Stargazing (post sunset)

Whale watching (Dec-April)

NOTE: This tour is only available for guests 18 and over

Vegan, Vegetarian, and GF options available. Please make a note in your reservation at check-out

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