Sailing Trips in Hawaii
Top 10 Best Hawaii Sailing Trips
Found 110 Sailing Trips activities in Hawaii. Sort by Popularity.2-Hour Whale Watching of Waikiki, Oahu: Guaranteed Sightings
Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never forget to see this amazing creature. If you are lucky enough, you might see dolphins, sea ... More
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2-Hour Whale Watching of Waikiki, Oahu: Guaranteed Sightings
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Hawaii
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Superb1,035 reviews4.6
Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a ....
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Deluxe Na Pali Sunset Tour on the 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
Deluxe Na Pali Sunset Tour on the Lucky Lady
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Hawaii
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Superb1,506 reviews4.7
Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredib....
Turtle Canyon Snorkel from Waikiki
**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!****Gauranteed**** Join us for a **2-hour snorkeling adventure** at **Turtle Canyon**, one of Oahu’s top snorkeling spots! Cruise along the stunning **W... More
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Turtle Canyon Snorkel from Waikiki
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Hawaii
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Superb1,282 reviews4.7
**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!****Gauranteed**** Join ....
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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
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed
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Hawaii
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Superb1,406 reviews4.9
Experience one Viator's 2025 Top 20 Best Excursions in the country. This Oahu catamaran snorkel tour....
Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast
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
Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast
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Hawaii
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Superb2,202 reviews4.9
All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Wa....
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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Superb212 reviews4.8
End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloh....
Best Waikiki Whale Watching in Honolulu: Whales Guaranteed
Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well as ample seating and shade on board. Knowledgeable staff with plenty of interesting whale information Convenient location walking... More
Best Waikiki Whale Watching in Honolulu: Whales Guaranteed
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Hawaii
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Superb187 reviews4.7
Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well a....
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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Superb521 reviews4.7
Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjo....
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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Superb103 reviews4.7
Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island ....
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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Superb1,649 reviews4.8
Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This pop....
Kauai’s Na Pali Coast Snorkel and Sail Tour
Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour catamaran journey combines spectacular sightseeing, exciting snorkeling, and all-inclusive comfort, making it the top choice for fami... More
Likely to Sell Out Kauai’s Na Pali Coast Snorkel and Sail Tour
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Hawaii
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Superb541 reviews4.8
Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour cat....
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
Likely to Sell Out Four Winds Molokini Snorkeling Tour from Maalaea Harbor
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Hawaii
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Superb820 reviews4.7
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....
Waikoloa Signature Catamaran Sunset Sail
End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. Departing from Anaeho‘omalu Bay, the Spirit of Aloha catamaran offers a smooth, comfortable ride with panoramic views of Mauna Kea... More
Likely to Sell Out Waikoloa Signature Catamaran Sunset Sail
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Hawaii
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Superb395 reviews4.7
End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. De....
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
Likely to Sell Out Day's End Cocktail Sunset Sail
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Hawaii
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Superb70 reviews4.7
Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most sce....
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB
2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for a beautiful Hawaiian sunset!! We have been sailing the Pacific waters off of the Island of Oahu since 1985... More
Likely to Sell Out Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB
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Hawaii
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Superb832 reviews4.9
2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE ....
Waikiki Catamaran Snorkel Sail with Lunch: 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 Sail with Lunch: Turtles Guaranteed
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Hawaii
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Superb2,109 reviews4.7
Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea ....
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
Likely to Sell Out Luxury Catamaran Whale Watch
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Hawaii
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Superb63 reviews4.9
From December through April, the waters off Maui come alive with the sights and sounds of the majest....
Waikiki Sunset Cocktail Sail with Open Bar
Experience Waikiki’s favorite sunset sail, perfect for social adventurers and party seekers. This lively evening cruise invites solo travelers and groups alike to unwind with unlimited drinks—including Maui Brewing beers, wine... More
Likely to Sell Out Waikiki Sunset Cocktail Sail with Open Bar
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Hawaii
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Superb551 reviews4.8
Experience Waikiki’s favorite sunset sail, perfect for social adventurers and party seekers. This ....
Sunset Boat Cruise: Swim and Cruise Waikiki
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
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Likely to Sell Out Sunset Boat Cruise: Swim and Cruise Waikiki
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Hawaii
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Superb533 reviews4.7
There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way....
Free Cancellation
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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
Likely to Sell Out Honolulu Sunset Sail from Kewalo Harbor Including Drinks
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Hawaii
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Superb166 reviews4.9
Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....