Sailing Trips in Maui
Top 10 Best Maui Sailing Trips
Found 20 Sailing Trips activities in Maui. Sort by Popularity.Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harbor
Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your loved ones to experience a beautiful Snorkeling, Sailing Cruise, and Whale Watching (Dec-Apr) on our Small Charming Hawaiian Catamara... More

Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harb....
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Maui
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Superb137 reviews4.7
Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your lov....
Four Winds Molokini Snorkeling Tour from Maalaea Harbor
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in the warmth of paradise. From the experienced snorkeler to those... More

Four Winds Molokini Snorkeling Tour from Maalaea Harbor
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Maui
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Superb779 reviews4.7
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....
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 enjoy... More

Turtles & Tacos Luxury Catamaran Snorkel
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Maui
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Superb12 reviews5
As you step aboard the spacious catamaran, you're immediately greeted by the friendly crew, who are ....
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... More

Day's End Cocktail Sunset Sail
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Maui
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Superb19 reviews4.7
Bring the whole family along for this upscale evening of outstanding food and beverages. We set the ....
Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor
Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the Lahaina harbor wildfires, moored outside of the harbor breakwall. Now operating from Ma'alaea Harbor, we invite you to join our cap... More

Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor
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Maui
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Superb52 reviews4.7
Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the L....
Sunset Sail from Ma'alaea Harbor
Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing catamaran, Ocean Spirit. It’s the perfect way to ex... More

Sunset Sail from Ma'alaea Harbor
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Maui
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Superb205 reviews4.6
Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunse....
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 pro... More

Luxury Catamaran Whale Watch
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Maui
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Superb39 reviews5
Come join us to observe the playful habits of Maui's most consistent return visitor - the humpback w....
Hawaiian Canoe Sailing Experience in Maui
Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning Hawaiian history and culture. Cold water and snorkel gear are... More

Hawaiian Canoe Sailing Experience in Maui
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Maui
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Superb56 reviews4.8
Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour include....
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 c... More

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
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Maui
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Superb20 reviews4.8
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
Experience “Amore” a 42-foot Boston Whaler with unmatched state-of-the-art features make the flagship 420 Outrage a boat like no other. From the expansive bow with innovative seating galore, to the beautifully designed convert... More

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
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Maui
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Superb10 reviews4.9
Experience “Amore” a 42-foot Boston Whaler with unmatched state-of-the-art features make the fla....
Molokini Snorkel and Performance Sail from Ma'alaea Harbor
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, and is home to over 250 species of t... More

Molokini Snorkel and Performance Sail from Ma'alaea Harbor
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Maui
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Superb198 reviews4.9
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....
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 buff... More

Snorkel Sail Adventure off Ka'anapali Beach, Maui
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Maui
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Superb9 reviews4.9
While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You w....
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-u... More

4-Hour Koa Kai Molokini Adventure Snorkel
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Maui
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Superb10 reviews5
Join us on this 3-hour snorkel adventure at Maui's most iconic snorkeling location, Molokini Crater.....
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 th... More

Half-Day Deluxe Molokini Snorkel Excursion in Maui
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Maui
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Superb75 reviews4.9
Since 1978, we have been proudly sailing the seas of Maui, whisking guests away on exhilarating snor....
Coral Gardens Snorkel & Whale Watch
This sailing experience blends adventure and tranquility against a backdrop of Maui’s pristine landscapes. Arrive at Coral Gardens, a sheltered snorkeling haven with calm, crystal-clear waters teeming with vibrant coral reefs a... More

Coral Gardens Snorkel & Whale Watch
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Maui
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Superb39 reviews4.8
This sailing experience blends adventure and tranquility against a backdrop of Maui’s pristine lan....
Midday 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. ... More

Midday Sail with the Whales Ma'alaea
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Maui
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Superb100 reviews4.9
Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....
'Alihilani Sunset Sail from Ma'alaea Harbor
We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sails. Our spacious catamarans make for a luxurious experience, allowing for incredible views of Maui and the inter islands while wa... More

'Alihilani Sunset Sail from Ma'alaea Harbor
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Maui
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Superb74 reviews5
We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sa....
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. ... More

Morning Sail With the Whales Ma'alaea
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Maui
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Superb10 reviews5
Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....
Early Sail with the Whales from Ma'alaea Harbor
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. ... More

Early Sail with the Whales from Ma'alaea Harbor
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Maui
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Good3 reviews3.3
Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....
Private Charter Snorkel Sail Adventure off Kaanapali Beach
PRIVATE CHARTER - 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 ‘H... More
Private Tour

Private Charter Snorkel Sail Adventure off Kaanapali Beach
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Maui
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Good3 reviews3.3
PRIVATE CHARTER - While snorkeling along West Maui’s coastline, experience warm waters abundant wi....
Private Tour