Sailing Trips in Hawaii
Top 10 Best Hawaii Sailing Trips
Found 109 Sailing Trips activities in Hawaii. Sort by Popularity.Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure
There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way to experience a Hawaiian sunset than from the ocean, with the iconic Waikiki coastline as your backdrop. As the sun begins to se... More
Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure
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Hawaii
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Superb587 reviews4.7
There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way....
Waikiki: 2-hour Turtle Canyon Snorkeling Adventure
Join us for a 2-hour snorkeling adventure at Turtle Canyon, one of Oahu’s top snorkeling spots! Cruise along the stunning Waikiki coastline aboard our either 55-ft open-style catamaran or 50-ft double-decker power catamaran and ... More
Waikiki: 2-hour Turtle Canyon Snorkeling Adventure
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Hawaii
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Superb1,473 reviews4.7
Join us for a 2-hour snorkeling adventure at Turtle Canyon, one of Oahu’s top snorkeling spots! Cr....
Kona Signature Catamaran Sunset Sail
End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloha. Enjoy panoramic views of the ocean and coastline as the sky transforms with vibrant hues of orange, pink and gold. Relax on d... More
Kona Signature Catamaran Sunset Sail
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Hawaii
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Superb291 reviews4.8
End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloh....
Maui: Ka'anapali Luxury 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
Likely to Sell Out Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar
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Hawaii
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Exellent57 reviews4.5
Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cockt....
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed
Experience one Viator's 2025 Top 20 Best Excursions in the country. This Oahu Catamaran snorkel tour offers unbeatable value and family-friendly fun from Waikiki. Swim alongside Hawaiian green sea turtles and vibrant tropical fis... More
Likely to Sell Out Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed
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Hawaii
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Superb1,700 reviews4.9
Experience one Viator's 2025 Top 20 Best Excursions in the country. This Oahu Catamaran snorkel tour....
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
Likely to Sell Out Turtles & Tacos Luxury Catamaran Snorkel
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Hawaii
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Superb140 reviews4.7
Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island ....
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
Likely to Sell Out Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar
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Hawaii
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Superb55 reviews5
Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where ....
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
Likely to Sell Out Snorkel Sail Adventure off Ka'anapali Beach, Maui
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Hawaii
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Superb41 reviews5
While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You w....
Waikiki Turtle Snorkel and Sail on Hawea Catamaran
Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This popular Oahu tour blends marine exploration and island relaxation in one extraordinary outing. Swim among sea turtles and tropical fi... More
Likely to Sell Out Waikiki Turtle Snorkel and Sail on Hawea Catamaran
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Hawaii
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Superb1,740 reviews4.8
Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This pop....
Waikiki Sunset Boat Cruise
No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as we cruise the Waikiki coastline with views of Diamond head cra... More
Likely to Sell Out Waikiki Sunset Boat Cruise
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Hawaii
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Superb190 reviews4.9
No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed ....
Waikiki Sunset Cocktail Sail on the Moana Catamaran
All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Waikiki Sunset Cruise, an unmatched experience complete with premium drinks, indescribable views, and music. As we sail alongside Oa... More
Likely to Sell Out Waikiki Sunset Cocktail Sail on the Moana Catamaran
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Hawaii
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Superb2,356 reviews4.9
All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Wa....
Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed
Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and threats to the Hawaiian Sea Turtles "Honu" (Learning pr... More
Likely to Sell Out Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed
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Hawaii
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Superb2,123 reviews4.7
Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea ....
Kauai: Leila Na Pali Sunset Dinner Sail
Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjoy appetizers, craft beer, wine, and Koloa Rum Mai-Tais aboard our sleek and spacious sailing catamaran, Leila. Your captain will s... More
Likely to Sell Out Kauai: Leila Na Pali Sunset Dinner Sail
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Hawaii
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Superb578 reviews4.6
Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjo....
Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu
-Open bar fully included: beer, wine, cocktails, and more -21+ only on Fridays! -Direct beach boarding — no harbor shuttle, no bus, no wasted time -Spacious 45-foot catamaran with near 360 degree view -Families welcome: Keiki ra... More
Likely to Sell Out Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu
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Hawaii
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Superb584 reviews4.7
-Open bar fully included: beer, wine, cocktails, and more -21+ only on Fridays! -Direct beach boardi....
Waikiki Turtle Snorkeling Tour with Free Pickup
Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamaran. This all-in-one 6-in-1 ocean tour includes snorkeling, kayaking, stand-up paddleboarding (SUP), sea scooters, and more—offeri... More
Likely to Sell Out Waikiki Turtle Snorkeling Tour with Free Pickup
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Hawaii
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Superb228 reviews4.8
Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamara....
Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady
Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredible scenery topped off with a spectacular sunset. Look for dolphins, whales, and other marine critters as you sip a drink, snap som... More
Likely to Sell Out Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady
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Hawaii
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Superb1,594 reviews4.7
Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredib....
'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
Likely to Sell Out 'Alihilani Lahaina Sunset Sail
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Hawaii
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Superb150 reviews4.9
We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sa....
Maui: Kaanapali Beach 5-hour Snorkel w/ BBQ Lunch & Open Bar
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
Likely to Sell Out Maui: Kaanapali Beach 5-hour Snorkel w/ BBQ Lunch & Open Bar
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Hawaii
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Superb24 reviews4.8
5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest ....
Likely to Sell Out
Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon
-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel equipment -Fun, friendly, lifeguard certified crew -BYOB (Bring your own Beverage. No glass bottles)... More
Free Cancellation
(Saving 20% )
Likely to Sell Out Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon
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Hawaii
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Superb321 reviews4.8
-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel....
Free Cancellation
(Saving 20% )
Likely to Sell Out
Honolulu Sunset Sail from Kewalo Harbor Including Drinks
Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic beverages). Sail the south shore from Kaka'ako Waterfront to Waikiki, with beautiful views ... More
Free Cancellation
(Saving inf% )
Likely to Sell Out Honolulu Sunset Sail from Kewalo Harbor Including Drinks
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Hawaii
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Superb198 reviews4.8
Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....
Free Cancellation
(Saving inf% )