Sailing Trips in Maui
Top 10 Best Maui Sailing Trips
Found 18 Sailing Trips activities in Maui. Sort by Popularity.Turtles & Tacos Luxury Catamaran Snorkel
Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island flavor. Cruise aboard our spacious 65’ catamaran and snorkel alongside Hawaiian green sea turtles and colorful tropical fish at ... More

Turtles & Tacos Luxury Catamaran Snorkel
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Maui
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Superb49 reviews4.7
Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island ....
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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Superb800 reviews4.7
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....
Day's End Cocktail Sunset Sail
Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. This isn’t a dinner cruise, it’s happy hour reimagined (a true ‘pau hana’ at sea) with handcrafted drin... More

Day's End Cocktail Sunset Sail
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Maui
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Superb41 reviews4.7
Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most sce....
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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Superb24 reviews4.9
While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You w....
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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Superb153 reviews4.7
Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your lov....
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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Superb66 reviews4.8
Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the L....
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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Superb202 reviews4.9
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....
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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Superb32 reviews4.8
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....
Half-Day Deluxe Molokini Snorkel Excursion in Maui
Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical fish and coral reefs. Your adventure continues with a second snorkel... More

Half-Day Deluxe Molokini Snorkel Excursion in Maui
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Maui
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Superb86 reviews4.9
Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-re....
Luxury Catamaran Whale Watch
From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way to witness the wonder than from the deck of our 65’ catamaran. This two-hour ex... More

Luxury Catamaran Whale Watch
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Maui
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Superb40 reviews5
From December through April, the waters off Maui come alive with the sights and sounds of the majest....
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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Superb15 reviews4.8
Experience “Amore” a 42-foot Boston Whaler with unmatched state-of-the-art features make the fla....
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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Superb212 reviews4.6
Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunse....
2 Hours Holo Holo Sunset Cocktail Sail with Open Bar
Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience offers breathtaking views of the sunset complemented by deligh... More

2 Hours Holo Holo Sunset Cocktail Sail with Open Bar
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Maui
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Superb212 reviews4.6
Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cockt....
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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Superb58 reviews4.8
Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour include....
Afternoon Catamaran Sail with Local Culture, Cocktails and Snacks
Set sail on a midday escape where cocktails meet culture aboard Maui’s most luxurious sailing catamaran. Explore the island through authentic storytelling, coastal beauty, and handcrafted island specialties, both sippable and sa... More

Afternoon Catamaran Sail with Local Culture, Cocktails and Snacks
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Maui
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Superb58 reviews4.8
Set sail on a midday escape where cocktails meet culture aboard Maui’s most luxurious sailing cata....
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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Superb58 reviews4.8
PRIVATE CHARTER - While snorkeling along West Maui’s coastline, experience warm waters abundant wi....
Private Tour
Lahaina Sailing and Snorkeling Adventure Tour
5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and an open bar. This is our award-winning snorkel tour that... More
Private Tour

Lahaina Sailing and Snorkeling Adventure Tour
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Maui
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Superb58 reviews4.8
5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest ....
Private Tour
Lana'i Coast Snorkel and Sail
Nobody knows the waters of Maui better than our crew. Let us host you on our Gold Coast catamaran as we explore and snorkel the incredible coastline of Maui. We'll check the conditions for the day and take off across the channel o... More
Private Tour

Lana'i Coast Snorkel and Sail
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Maui
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Superb58 reviews4.8
Nobody knows the waters of Maui better than our crew. Let us host you on our Gold Coast catamaran as....
Private Tour