Sailing Trips in Hawaii
Top 10 Best Hawaii Sailing Trips
Found 104 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 2Na Pali Coast Kauai Snorkel and Sail
Families and groups-- say YES to an action-packed, five-hour ocean adventure aboard our gorgeous and comfortable 50’ Kauai-built sailing catamaran, Leila. Let’s explore the cliffs, valleys, sea caves and wildlife of the Napali... More

Na Pali Coast Kauai Snorkel and Sail
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Hawaii
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Superb504 reviews4.8
Families and groups-- say YES to an action-packed, five-hour ocean adventure aboard our gorgeous and....
Kealakekua Snorkel and Sail Adventure
Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the horizon for dolphins and whales (seasonal) from our shaded cabin or sunny splash nets. Snorkel calm waters and lush coral garde... More

Kealakekua Snorkel and Sail Adventure
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Hawaii
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Superb615 reviews5
Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the....
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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Hawaii
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Superb32 reviews5
Come join us to observe the playful habits of Maui's most consistent return visitor - the humpback w....
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 o... More

Honolulu Sunset Sail from Kewalo Harbor Including Drinks
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Hawaii
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Superb100 reviews4.9
Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....
Sunset and Manta Ray Snorkel Adventure
Our most popular tour! Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of a lifetime - snorkeling with the majestic manta rays! Upon arriving, receive an in... More

Sunset and Manta Ray Snorkel Adventure
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Hawaii
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Superb744 reviews4.9
Our most popular tour! Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail....
Snorkel with Manta Rays Guaranteed
Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village. Travel Channel says “its one of the top ten things to do in your life time”, and Sea Paradise has been offering its guests th... More

Snorkel with Manta Rays Guaranteed
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Hawaii
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Superb658 reviews4.8
Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village.....
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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Hawaii
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Superb50 reviews4.7
Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the L....
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast
As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far away enough from the bustling travelers and crowded beaches, the crystal-clear water will br... More

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast
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Hawaii
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Superb132 reviews4.9
As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your....
9am Turtle Canyon Snorkel Adventure
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life? Our snorkel guides help you feel confid... More

9am Turtle Canyon Snorkel Adventure
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Hawaii
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Superb239 reviews4.9
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....
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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Hawaii
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Superb13 reviews4.6
Bring the whole family along for this upscale evening of outstanding food and beverages. We set the ....
Sail and Turtle Snorkeling Tour in Waikiki
Experience the Best boat tour in Waikiki with our Turtle Canyon Snorkeling Tour Get ready for an epic 2-hour boat adventure that combines the thrill of sailing past Diamond Head with the magic of snorkeling with turtles in their ... More

Sail and Turtle Snorkeling Tour in Waikiki
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Hawaii
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Superb227 reviews4.9
Experience the Best boat tour in Waikiki with our Turtle Canyon Snorkeling Tour Get ready for an ep....
Afternoon Sail & Snorkel to the Captain Cook Monument
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adve... More

Afternoon Sail & Snorkel to the Captain Cook Monument
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Hawaii
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Superb215 reviews4.9
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtakin....
Sunset Sail Experience at Kona from Honokohau
Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. Catch the moment the sun slips below the horizon...you may even see the green flash. Enjoy the blue Pacific Ocean and maybe catch ... More

Sunset Sail Experience at Kona from Honokohau
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Hawaii
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Superb143 reviews4.8
Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. ....
Oahu 3pm Whale Watching from Honolulu
This is an excellent cruise for families and sailors wanting to relax and enjoy a beautiful afternoon in the sun. We'll be keeping a sharp eye out for dolphins, whales and other sea life while getting as close as possible so you c... More

Oahu 3pm Whale Watching from Honolulu
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Hawaii
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Superb225 reviews4.8
This is an excellent cruise for families and sailors wanting to relax and enjoy a beautiful afternoo....
Private 5Hrs Island Tour with 2Hrs Sail and Snorkel with Turtles
This 8 hour private tour includes a 5 hour custom tour of the island, and a 2.5 hour sail on a sailboat including swimming or snorkeling with turtles. You can pick and choose the stops on the island tour and go at your own pace. ... More
Private Tour

Private 5Hrs Island Tour with 2Hrs Sail and Snorkel with Turtles
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Hawaii
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Superb3 reviews5
This 8 hour private tour includes a 5 hour custom tour of the island, and a 2.5 hour sail on a sailb....
Private Tour
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
Private Tour

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
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Hawaii
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Superb19 reviews4.8
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....
Private Tour
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
Private Tour

Molokini Snorkel and Performance Sail from Ma'alaea Harbor
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Hawaii
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Superb195 reviews4.9
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....
Private Tour
2-Hour Oahu Sunset Catamaran Sail
Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. Sip a cocktail and enjoy warm wind in your hair as you scan for dolphins and listen for... More
Private Tour

2-Hour Oahu Sunset Catamaran Sail
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Hawaii
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Superb99 reviews4.9
Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran f....
Private Tour
Polynesian Canoe Sunset Sail
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and b... More
Private Tour

Polynesian Canoe Sunset Sail
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Hawaii
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Superb118 reviews4.9
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....
Private Tour
Pau Hana Sunset Cruise with the Whales
Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the biggest guests of all -- the Humpback Whales -- and you have perfect way to begin your evening in paradise! Cruise along the Kohala... More
Private Tour

Pau Hana Sunset Cruise with the Whales
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Hawaii
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Superb45 reviews4.8
Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the b....
Private Tour