Sailing Trips in Maui
Top 10 Best Maui Sailing Trips
Found 28 Sailing Trips activities in Maui. Sort by Popularity.Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar
Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where our experienced crew selects the day’s best snorkel destination based on weather, tides, and ocean conditions. • Explore Lana... More
Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar
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Maui
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Superb81 reviews5
Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where ....
'Alihilani Lahaina Sunset Sail
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 from the... More
'Alihilani Lahaina Sunset Sail
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Maui
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Superb199 reviews4.9
We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sa....
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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Superb163 reviews4.7
Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island ....
Akialoa Mā’alaea Sunset Sail
Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sunset Sail offers a two-hour journey through the picturesque inter-island channel, showcasing the beauty of Maui, Lāna‘i, and Kah... More
Akialoa Mā’alaea Sunset Sail
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Maui
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Superb37 reviews4.9
Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sun....
Ka'anapali Luxury Sunset Cocktail Sail with Open Bar in Maui
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
Ka'anapali Luxury Sunset Cocktail Sail with Open Bar in Maui
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Maui
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Superb84 reviews4.6
Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cockt....
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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Superb857 reviews4.7
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....
Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar
Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury sailing catamaran? Perfect for families, couples, kids, first-time snorkelers, and ocean lovers, this Lahaina adventure combines a... More
Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar
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Maui
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Superb134 reviews4.9
Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury ....
Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali
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
Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali
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Maui
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Superb37 reviews4.9
5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest ....
Paragon Lahaina Sunset Sail
Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from Lahaina Harbor. Enjoy the afternoon hours at sea in the glassy, miraculous ‘au’au Channel is like floating inside an infinite ... More
Paragon Lahaina Sunset Sail
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Maui
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Superb35 reviews4.9
Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from L....
Happy Hour Sunset Sail on Maui's Luxury Catamaran
Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. Happy hour at sea with handcrafted drinks, vibrant music, and a relaxed-yet-refined vibe that turns every pour ... More
Happy Hour Sunset Sail on Maui's Luxury Catamaran
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Maui
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Superb98 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 in 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 in Maui
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Maui
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Superb49 reviews5
While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You w....
Molokini Crater Deluxe Snorkel and Sail - Half Day Excursion
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
Molokini Crater Deluxe Snorkel and Sail - Half Day Excursion
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Maui
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Superb134 reviews4.9
Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-re....
Luxury Catamaran Royal Sunset Dinner at Sea (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 at Sea (Adults-Only)
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Maui
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Superb61 reviews4.8
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....
Molokini Crater Snorkel, Sailing Adventure with Breakfast & Lunch
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 Crater Snorkel, Sailing Adventure with Breakfast & Lunch
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Maui
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Superb223 reviews4.8
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....
Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor
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Maui
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Exellent24 reviews4.5
Join us aboard the Malolo for drinks as we cruise gently along the Maui coastline. Sit back, relax, ....
Maui Premier Whale Watching Cruise - Luxury Catamaran Experience
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
Maui Premier Whale Watching Cruise - Luxury Catamaran Experience
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Maui
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Superb89 reviews4.9
From December through April, the waters off Maui come alive with the sights and sounds of the majest....
Honolua Snorkel Sail from Lahaina
Sail to the storied waters of Honolua Bay, long valued in Hawaiian culture and now protected as a Marine Life Conservation District. Along the way, watch for wild dolphins, then snorkel among Hawaiian green sea turtles in this vib... More
Honolua Snorkel Sail from Lahaina
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Maui
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Superb61 reviews4.9
Sail to the storied waters of Honolua Bay, long valued in Hawaiian culture and now protected as a Ma....
Midday Whale Watch: Mā’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
Midday Whale Watch: Mā’alaea Harbor
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Maui
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Superb104 reviews4.9
Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....
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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Superb63 reviews4.6
Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour include....
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experience Maui’s golden hour from the water. Departing from Ma‘alaea, this intimate evening cruise offers stunning views of the coast... More
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
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Maui
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Superb20 reviews4.9
Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experien....