Maui Sailing

Top Maui Sailing Tours

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26 results

Best Seller
Whale Watching Cruise with Open Bar from Ka'anapali Beach
4.8
(571)

Whale Watching Cruise with Open Bar from Ka'anapali Beach

Set sail into one of the world’s most active winter whale playgrounds on a whale-watching tour from Maui’s Ka’anapali Beach. Head offshore directly from the beach and, with the help of a naturalist guide, look for pods of humpback whales making their winter home in Maui’s warm waters. Get comfortable aboard a spacious catamaran with plenty of seating—including bean bags on open nets that get you close to the action—and enjoy unlimited drinks from an open bar as you cruise alongside spectacular marine mammals.
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  • 2 hours
  • Free Cancellation
from
$103
2-Hour Oahu Whale Watch from Ala Wai Harbor, Waikiki
4.6
(1,675)

2-Hour Oahu Whale Watch from Ala Wai Harbor, Waikiki

Catch an exciting peek at the underwater world from Waikiki, Honolulu on Oahu. Our comfortable, spacious, vessel often attracts whales, led by our expert crew who will live narrate what you are seeing. Enjoy stunning views and photo opportunities while traveling along Oahu's exquisite coastline. Your family-friendly cruise comes with a guarantee that you spot a whale during your adventure. Our crew will explain these Humpback whales’ actions between breaches, flukes, tail slaps, movements in the water and more! Booking this tour, you are supporting a directly impacted Lahaina, Maui Wildfire tour company whose home harbor was Lahaina Harbor. The Humpback Whale migration is a must do adventure so join us on a once in a lifetime experience. -You are welcome to bring your own snacks and beverages! -We offer snacks, beverages, gifts & other retail items for purchase.
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  • 2 hours
  • Free Cancellation
from
$49
Eye-Level Whale Watching Eco-Raft Tour from Lahaina
4.9
(1,518)

Eye-Level Whale Watching Eco-Raft Tour from Lahaina

This tour departs from Lahaina, Maui to find the majestic humpback whales that frequent the waters surrounding Maui in the winter months. Traveling in a small raft creates an intimate whale watching experience not found on the larger vessels commonly used on whale watching tours. Plus, the raft travels quickly, letting you spend more time whale watching and less time in transit. -Enjoy a small group whale watching tour off the coast of Maui. -You can choose from a morning or afternoon tour so it doesn’t interfere with other plans -In the event of cancellation due to weather, you are offered an alternate outing or a full refund -Prepare for the chance to photograph whales in their natural habitat
... More
  • 2 hours
  • Free Cancellation
from
$79
Likely to Sell Out
Original Sunset Cruise with Open Bar from Ka’anapali Beach
4.8
(1,043)

Original Sunset Cruise with Open Bar from Ka’anapali Beach

Enjoy a ‘front-row seat’ for Maui’s epic sunset accompanied by cocktails and snacks during this sailing cruise from Ka’anapali Beach. Enjoy views of nearby Lanai, Molokai, and Kahoolawe from your boat, drink and food in hand, as the Hawaiian sky puts on its nightly display. Plus, keep your eyes peeled for local marine life, including whales from mid-December to mid-April. Snacks, unlimited alcoholic drinks, and non-alcoholic beverages are all included.
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  • 2 hours
  • Free Cancellation
from
$115
Sunset Sail from Ma'alaea Harbor
4.6
(193)

Sunset Sail from Ma'alaea Harbor

Eat, drink, and be merry on a sunset cruise aboard a luxury catamaran. Sail the waters off Maui as you experience the ho’okipa (hospitality) of the crew and panoramic views. Enjoy an array of premium appetizers and a full bar—three alcoholic drinks are included in the price. There’s also a marine biologist on board to comment on any wildlife you may encounter or answer questions about the local flora and fauna.
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  • 2 hours
  • Free Cancellation
from
$125
Four Winds Molokini Snorkeling Tour from Maalaea Harbor
4.7
(756)

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

Snorkeling in Molokini Crater is undeniably one of the best parts about visiting Maui. Here in this crescent, submerged volcano off Maui’s southern coastline, over 250 species of fish inhabit a world-class reef. Experience water so exceptionally clear you can see down 75 feet, and swim with schools of tropical fish while cruising the vibrant reef. You can also just sit and suntan on the deck, with sweeping views of Haleakala set just off the back of the boat.
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  • 5 hours
  • Free Cancellation
from
$192
Hawaiian Canoe Sailing Experience in Maui
4.8
(53)

Hawaiian Canoe Sailing Experience in Maui

Partake in a time-honored Hawaiian tradition during this private, outrigger canoe sailing experience along Maui's stunning Wailea coast. Learn about Hawaiian culture and history, including the ancient art of canoe construction, sailing, and navigation. Launch the boat from the beach using traditional methods. Spot sea turtles, reef fish, and seasonal humpback whales, with snorkeling equipment provided.
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  • 2 hours
  • Free Cancellation
from
$179
'Alihilani Sunset Sail from Ma'alaea Harbor
5.0
(68)

'Alihilani Sunset Sail from Ma'alaea Harbor

Sail along the coast of Maui and enjoy a stunning Hawaiian sunset during this evening cruise from Lahaina Harbor. Get comfortable on a spacious catamaran and enjoy the views while you enjoy complimentary hors d’oeuvres and non-alcoholic drinks. If you’re traveling between December and May, you may even spot humpback whales while you sail.
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  • 2 hours
  • Free Cancellation
from
$113
Luxury Catamaran Whale Watch
5.0
(16)

Luxury Catamaran Whale Watch

Come join us to observe the playful habits of Maui's most consistent return visitor - the humpback whale. The waters off West Maui have long been the favored vacation spot of these massive marine mammals. The Alii Class Yachts provide maximum space and comfort. There are plenty of areas to enjoy the "show" from our spacious, shaded cabin or deck areas. A Marine naturalist is always onboard with facts about these gentle giants. A hydrophone will allow you to listen to the amazing songs the humpback whales sing; Maui's best "Whale Karaoke." Our whale watch will run seven days a week from mid-December until the whales go home. Since 1978, Alii Nui Sailing Charters has been proudly sailing the seas of Maui, whisking guests away on exhilarating snorkeling trips, romantic sunset cruises, and everything in between. We’re honored to play a part in introducing our visitors to the island as well as its waters; as stewards of our proud culture, we take that responsibility seriously.
... More
  • 2 hours
  • Free Cancellation
from
$159
Likely to Sell Out
Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harbor
4.6
(127)

Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harbor

Maui's Olowalu reef and coral gardens which lies off the west coast of Maui, is home to hundreds of aquatic species and is an ideal place to snorkel. Enjoy your cruise to these beautiful snorkeling sites and begin exploring the volcanic gardens. Spend a good amount of time snorkeling and keep your eyes peeled for sea turtles, moray eels, and several fish species.
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  • 3 hours
  • Free Cancellation
from
$139
Day's End Cocktail Sunset Sail
4.6
(12)

Day's End Cocktail Sunset Sail

Bring the whole family along for this upscale evening of outstanding food and beverages. We set the sails and chase the sun as it sets into the distant horizon of the azure water of the South Pacific. This casual dining experience offers seating in the comfort of the cabin or enjoy your meal topside on our spacious deck. A variety of upscale hot and cold appetizers will be accompanied by a wide selection of domestic & craft beers, seltzers, premium red & white wines and champagne, and top tier liquors.
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  • 2 hours
  • Free Cancellation
from
$169
Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor
4.8
(44)

Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor

Escape the crowds and hop on a Hawaiian catamaran for an intimate sunset sail from Maalaea Harbor. Unlike the overpriced, tourist-packed boats, this vessel hosts a maximum of 40 passengers, ensuring personalized attention and ample space. Capture the moment when the sails unfurl against the Hawaiian sunset. Winona, a locally built and meticulously maintained catamaran, offers true Aloha hospitality, delicious Hawaiian snacks, and refreshing drinks.
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  • 2 hours
  • Free Cancellation
from
$119
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
4.7
(13)

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step aboard, you're greeted by the friendly crew who welcome you with warm aloha spirit. The catamaran, with its spacious deck and comfortable seating, offers unobstructed views of the surrounding ocean and the impending sunset. Once settled in, the catamaran sets sail, gliding effortlessly over the tranquil waters of the Pacific Ocean. You feel the soothing rhythm of the waves beneath you as you sip on a refreshing tropical drink, prepared with locally sourced ingredients. As the evening progresses, you're treated to a culinary journey that delights the senses. Each course is thoughtfully crafted to highlight the freshest local ingredients, from vibrant salads to succulent grilled meats and decadent desserts. Between courses, relax and soak in the beauty of the surroundings, the fiery orange and soft pink sky which Maui is famous for.
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  • 2 hours 30 minutes
  • Free Cancellation
from
$289
Half-Day Deluxe Molokini Snorkel Excursion in Maui
4.9
(65)

Half-Day Deluxe Molokini Snorkel Excursion in Maui

Since 1978, we have been proudly sailing the seas of Maui, whisking guests away on exhilarating snorkeling trips, romantic sunset cruises, and everything in between. We’re honored to play a part in introducing our visitors to the island as well as its waters; as stewards of our proud culture, we take that responsibility seriously. Our vessel is one of the widest and most stable on the island, ensuring a comfortable ride for everyone. We provide top of the line equipment, food, drinks, and customer service. Snorkeling demo is given to any individuals with all levels of experience. Included in the price of your charters is all snorkeling and flotation equipment, including premium silicon masks, snorkels, and fins, boogie boards, flotation belts, water noodles, wet suit tops, optical masks, and large terry beach towels. Once you have had your fill of snorkeling, enjoy a refreshing "rinse-off" shower with one of four heated fresh-water showers.
... More
  • 5 hours
  • Free Cancellation
from
$289
Molokini Snorkel and Performance Sail from Ma'alaea Harbor
4.9
(175)

Molokini Snorkel and Performance Sail from Ma'alaea Harbor

Sail aboard a catamaran to Molokini crater, one of Maui’s best snorkel sites. The volcanic atoll off the south coast is a natural marine preserve, home to 250 species of tropical fish. Join the crew at the helm of “Paragon II” as Maui’s afternoon trade winds get the boat to this top destination.
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  • 5 hours
  • Free Cancellation
from
$200
Snorkel Sail Adventure off Ka'anapali Beach, Maui
4.9
(7)

Snorkel Sail Adventure off Ka'anapali Beach, Maui

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, an endangered Hawaiian Green Sea turtle called a ‘Honu’. A hot buffet lunch is served and our complimentary bar is open after you are done snorkeling. We hoist the sails and return to Ka'anapali Beach while viewing the amazing coastline of Maui.
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  • 4 hours
  • Free Cancellation
from
$173
Midday Sail with the Whales Ma'alaea
4.9
(99)

Midday Sail with the Whales Ma'alaea

This sunset sail in Maui makes the perfect start or finish to your Hawaiian getaway. Not only does your guide know the perfect spot on the water to see the sunset, but you’ll also enjoy hors d’oeuvres, beer, wine, Champagne, and mai tais as you go. Unlike other cruises, this one sets off on a small boat, making it a more intimate experience for you and other cruise goers.
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  • 2 hours
  • Free Cancellation
from
$92
Morning Snorkel Sail from Lahaina Harbor
4.4
(36)

Morning Snorkel Sail from Lahaina Harbor

Start your day off with an exciting adventure aboard this snorkel tour from Lahaina. Join a small group and set out onto the seas for a sail along Maui's west coast. Your captain chooses a location for the day, depending on weather conditions, for the chance to see green sea turtles and other aquatic species that hang around the coral reefs.
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  • 4 hours
  • Free Cancellation
from
$144
Special Offer
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
4.8
(6)

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

Leave the chaos of the mainland behind when you embark on this sunset cruise in Maui. An exclusive experience for up to six guests, this trip takes you through multiple natural landscapes, from the Molokini Crater to the Kahalewai Mountains and Lanai Island. Take in views of the coastlines and island volcanoes and relax as you watch the sun setting with your chosen group. You even have the chance to catch a glimpse of the green flash phenomenon.
... More
  • 2 hours
  • Free Cancellation
from
$284
$213
1.5-Hour Koa Kai Adventure Whale Watch
5.0
(1)

1.5-Hour Koa Kai Adventure Whale Watch

Add some more outdoor adventure to your Maui itinerary with this Koa Kai whale watching trip at sunset. Get the chance to see humpback whales up close as they visit Maui to birth their young. Relax on deck, admire the natural scenery, and listen whale songs through the onboard hydrophone. Plus, you can enjoy alcoholic beverages and snacks throughout the journey.
... More
  • 1 hour 30 minutes
  • Free Cancellation
from
$109
Turtles & Tacos Luxury Catamaran Snorkel
5.0
(2)

Turtles & Tacos Luxury Catamaran Snorkel

As you step aboard the spacious catamaran, you're immediately greeted by the friendly crew, who are eager to guide you on an unforgettable journey. The vessel is equipped with all the amenities you need for a comfortable and enjoyable experience, including ample seating, shaded areas to escape the sun, and easy access to the water for snorkeling. After a leisurely sail, the captain anchors at a pristine snorkeling spot known for its abundant marine life. You eagerly don your snorkel gear and plunge into the cool, inviting waters below. Under the surface, you're greeted by a kaleidoscope of colors as you swim alongside schools of tropical fish darting through vibrant coral reefs. Keep your eyes peeled, for Maui's gentle giants—the majestic sea turtles—may gracefully glide by, offering an up-close encounter you'll never forget. After working up an appetite exploring the underwater wonderland, you resurface to find a tantalizing taco bar set up on the catamaran's deck.
... More
  • 3 hours
  • Free Cancellation
from
$169
Morning Sail With the Whales Ma'alaea
5.0
(8)

Morning Sail With the Whales Ma'alaea

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, the ‘Au ‘au channel off the coast of Maui boasts the greatest number. Our warm, relatively shallow and protected waters make an ideal location for the humpbacks to mate and give birth to their calves. These whales are known for their acrobatics, and are often seen fully breaching out of the ocean!
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  • 1 hour 30 minutes
  • Free Cancellation
from
$81
Likely to Sell Out
4-Hour Koa Kai Molokini Adventure Snorkel
5.0
(10)

4-Hour Koa Kai Molokini Adventure Snorkel

Join us on this 3-hour snorkel adventure at Maui's most iconic snorkeling location, Molokini Crater. You will be treated to exceptional service and premium equipment. Koa Kai is a multi-purpose raft that creates a unique close-up perspective when viewing Maui's natural inhabitants above water and below. With spacious seating, Koa Kai allows for optimum viewing for all participants. A snorkeling demo will be given to any individuals will all levels of experience.
... More
  • 4 hours
  • Free Cancellation
from
$169
Likely to Sell Out
Early Sail with the Whales from Ma'alaea Harbor
3.3
(3)

Early Sail with the Whales from Ma'alaea Harbor

The Au’au’ Channel is best known for its concentration of humpback whales. Hop on a boat in Maalaea Harbor to sip on a drink and spend time in the whales’ natural habitat. Your guide not only offers a trained whale-spotting eye but ensures you learn about the animals’ behavior and migration patterns. Don’t forget your camera: Lucky visitors get the chance to see the whales breaching in the open water.
... More
  • 1 hour 30 minutes
  • Free Cancellation
from
$92
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