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Sunset Sails and Cruises on Maui

Sunset Sails & Cruises on Maui

There are 41 products in this category that range in price from $19.98 to $3500.00.

Maui's coastline is lovely at any time of day, but even more beautiful during a Maui sunset sail.


From the deck of a Maui sailboat in the light sundown breeze, you will understand why sunset sails are so popular here on Maui.
The strong afternoon winds die down at sunset and are reduced to a gentle breeze. The heat of the day has been replaced with a hint of coolness. The bright wash of midday has turned to vivid pastels. The sun glows orange and red and drops quickly into the ocean, disappearing in an instant display of Maui's famous "green flash." The water is calm, a gentle swell lulls the quiet scene.
Looking back toward Maui, you find the West Maui Mountains or the slopes of Haleakala draped with rainbow colors and a halo of clouds turns from pink to purple to violet before your eyes. And then a twinkling, a glitter, as stars appearing above the Lahaina or Kihei lights reflect across the water. If you're lucky, as I was the first day I set foot on Maui many years ago, you may see the full moon rise out of an enchanted valley. It's a good omen: you'll be back again as Maui now has you under its spell.

Many vessels can take you on a sunset cruise.
Most sunset sails depart from Lahaina and Maalaea Harbors. Catamarans, sloops, schooners, and even power vessels are used for this purpose. No matter what boat you take, one thing is certain. It will be the beginning of an evening you will remember for a long time to come.


We sell tickets to 41 items in the category Sunset Sails & Cruises on Maui.

View the complete list below or use our Activity Finder to narrow down your options.

Displaying 41 of 41 Results

$69.00
(6 Reviews, 5 Stars)

Enjoy two hours of sailing off the majestic West Maui Coast, while enjoying one of our complimentary beverages-beer, wine, soft drink, or bottled water-while you sit back, relax and let us do all the work.…

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$54.90 - $64.90
(4 Reviews, 5 Stars)

Enjoy a wonderful sunset cruise on the brand new pirate-themed Queen's Treasure catamaran. Feasting, merrymaking, and relaxing are all done in a luxurious environment that any pirate would envy.

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$69.00
(3 Reviews, 5 Stars)

Experience a romantic sunset sail exploring the West Maui coastline surrounding Kaanapali. Enjoy Maui's legendary kamakani (wind) with Trilogy. They really put the sails up! This is a beach loading…

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$118.90
(2 Reviews, 5 Stars)

Alii Nui and her expert crew will treat you to a memorable evening! Go with them as they set the sails and chase the sun as it sets into the distant horizon into the Pacific Ocean. Enjoy a delicious array…

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$70.20
(2 Reviews, 5 Stars)

April marks the return of the best ocean view dining on Maui. The background music is a soothing compilation of Hawaiian and Island style tunes over a state of the art surround sound stereo system. You…

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$99.90
(2 Reviews, 5 Stars)

Enjoy a private sunset on the water or opt for a shared boat with other visiting guests. Shadowfax is a blue water sailer and you will enjoy a beautiful Maui sunset under sail. Hot and cold appetizers…

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$61.90 - $3500.00
(1 Review, 5 Stars)

This is a premier sailing experience. Sunsets at sea, viewed from Sea Maui are spectacular. Enjoy panoramic views of Molokai, Lanai, Maui and Kahoolawe while feasting on delicious pupus prepared by Chef…

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$750.00
(1 Review, 5 Stars)

Set sail in the calm leeward waters of Lahaina and discover the beauty of catching the wind. Relax and enjoy 360 degree views as the sun sets and lights up the islands of Maui, Molokai and Lanai. A private…

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$69.90
(1 Review, 5 Stars)

On this adults- only (21 and over) cruise, experience the essence of ho'okipa (hospitality) as we share with you the breathtaking beauty of Maui's sunset. Departing from historic Lahaina Harbor, you'll…

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$81.90
(1 Review, 5 Stars)

Come experience a traditional Hawaiian Outrigger Canoe Tour as you learn the art and sport of canoe paddling and information pertaining to the non-instrumental navigational techniques used by Polynesian…

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$61.90
(1 Review, 5 Stars)

Set out from Ka'anapali Beach aboard the 64' catamaran "Gemini". See the beautiful Hawaiian sunset as well as the tri-island view of Maui, Molokai and Lanai (and if you look to the South you can even see…

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$69.95 - $69.95
(5 Reviews, 4.8 Stars)

Enjoy live entertainment, sunset views of 5 islands, great food, great service and great fun. There is covered seating on the upper and lower deck of this smooth and stable high tech catamaran, excellent…

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$59.90
(5 Reviews, 4.8 Stars)

The peaceful sounds of the wind in our sails while viewing Maui's Western coastline offers a most relaxing experience. The crew will pamper you with complimentary hors d'oeuvres and beverages,…

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$58.90
(15 Reviews, 4.7 Stars)

Come and enjoy a wonderful two hour sunset sail with appetizers and an open bar, departing from West Maui's beautiful Ka'anapali area.

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$35.90
(10 Reviews, 4.6 Stars)

Enjoy beautiful sunset views of 5 islands, appetizers, two free drinks, great service and great fun on this smooth and stable high tech catamaran! This tour has a 48 hour cancellation policy. This means…

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$152.90
(12 Reviews, 4.6 Stars)

Come aboard the Ali'i Nui catamaran and experience a dinner like no other on Maui. The Royal Feast provides a unique dining experience while you relax in comfort and dine like royalty. This two and…

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$1200.00 - $1500.00
(2 Reviews, 4.5 Stars)

Design your own custom charter for you and your private group.

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$71.90
(28 Reviews, 4.4 Stars)

2.5 hour sunset dinner cruise on board Maui Princess offering topside dinner seating to enjoy the views. Fine dining on linen covered tables with full table side service by wait staff and featuring a live…

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$75.90
(7 Reviews, 4.4 Stars)

Enjoy two and a half hours on the ocean for a Maui sunset sail with dinner and an open bar.

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$64.90
(6 Reviews, 4.3 Stars)

Take a scenic cruise off the shores of Maui for sunset viewing, gourmet appetizers, open bar and great entertainment. Live entertainment is provided by master guitarist Joe Cano. He performs solo on Tuesday…

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$61.90
(3 Reviews, 4 Stars)

Enjoy a beautiful sunset on the water and live music by Marty Dread, Maui's reggae favorite. Join in for the most fun and exciting evening of your vacation, cruising the Maui coastline as you enjoy…

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$61.90
(1 Review, 4 Stars)

Experience the essence of ho'okipa (hospitality) as we share with you the breathtaking beauty of Maui's sunset. Departing from historic Lahaina Harbor, you'll experience the beauty of the Pacific Ocean…

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$55.90
(1 Review, 4 Stars)

Join Pacific Whale Foundation for a celestial stargazing cruise, featuring special guest astronomer Harriett Witt. Cruise beneath a starlit sky and learn about the stars, tides and cultural significance…

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$82.90 - $98.90
(2 Reviews, 3 Stars)

Enjoy a premier dining experience on the waters of Maui. All guests are offered outdoor seating, and indoor by request. Departing nightly from historic Lahaina Harbor, this cruise features a stunning sunset…

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$450.00 - $2250.00

This wonderful sailing power catamaran is ideal for small groups or a family searching for a moderately priced excursion with the luxury of a private charter. Go sailing, snorkeling, cruising the coastline…

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$900.00

Plunge into the most exclusive and romantic way to watch sunset in Maui! The unobstructed views of sunset paired with warm tropical air and world-class service provided by Sea Monkey Staff will insure…

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$129.00 - $129.00

Experience fine dining with an unbeatable view! Tables are set for intimacy and comfort. Your evening begins with cocktails and sailing along the pali sea cliffs. After mooring in a protected cove, your…

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$119.00

Enjoy a two hour sunset sail departing from a beautiful white sand beach in South Maui. Sample pupu's (appetizers) and sip on cocktails from the bar as you take in the sights and colors of the picturesque…

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$62.90

Enjoy cool 50's and 60's music under Maui's beautiful sunset. If you have fond memories of old time rock 'n' roll, or want to make some new ones, we invite you to shake, rattle, and…

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$56.90

Enjoy a full moon cruise with narration by international award winning astronomy writer and speaker Harriet Witt. A truly magical, memorable evening including pupus, desserts and drinks! Departing from…

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$61.90

Join Marty Dread, one of Maui's favorite entertainers, for a sunset cruise that includes dancing to reggae and island style music on an outdoor deck, watching whales as they breach and cavort in the ocean…

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$55.90

Enjoy a two hour cruise with Island Style Music for the most relaxing and romantic evening of your vacation. Cruise the south or west coastline of Maui as you enjoy hot and cold pupus, unlimited soft drinks…

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$77.90

Finally, something to do "after hours" on Maui! Alii Nui will be offering an option for visitors and locals alike for late night entertainment. Walk the "Red Carpet" as you come aboard Alii Nui, Maui's…

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$54.90 - $64.90

Enjoy a wonderful sunset cruise on the brand new pirate-themed Queen's Treasure catamaran. Sail, whale watch and explore Maui's beautiful west coast. Feasting, merrymaking, and relaxing are all…

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$70.20

This two and a half hour sunset dinner cruise offers whale watching with informal narration and hydraphones that are hooked up to the surround sound stereo system for your listening pleasure. Hula Girl…

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$19.98 - $35.90

Enjoy a beautiful sunset on the water and two hours of whale watching with expert narration by the captain and crew. We guarantee whale sightings from the middle of December to the middle of April.

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$43.90

This two hour sunset cocktail cruise and whale watching boat departs from the Lahaina Harbor and goes into the channel to take in the four-island views and sunset along the scenic West Maui coastline.…

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$58.50

The focus of this excursion will be high tech sailing in West Maui's tradewinds. Hula Girl is decked out with Spectra racing sails and will be sure to please even the most passionate sailor while offering…

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$58.50

Enjoy a sunset cruise and whale watching with informal narration and hydrophones that are hooked up to the surround sound stereo system. An extensive a la carte menu is available for purchase, featuring…

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$700.00

Your Private Charter is designed to fit your perfect Maui vacation experience. Aboard the Kaha Loa you can go snorkeling, go on the search for whales and dolphins, cast some fishing lines out for the area's…

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