Sailing Trips in Hawaii
Top 10 Best Hawaii Sailing Trips
Found 110 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 3Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming
Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that s... More
Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming
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Hawaii
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Superb196 reviews4.9
Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....
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
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Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast
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Hawaii
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Superb239 reviews4.9
As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your....
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Whale Watching Sail in Honolulu with Open Bar
Observe the majestic humpback whales during their migration from December to March on this 1.5-hour sail in Honolulu. Experience the beauty of Oahu's coastline while searching for dolphins and sea turtles in their natural habitat.... More
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Whale Watching Sail in Honolulu with Open Bar
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Hawaii
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Superb13 reviews5
Observe the majestic humpback whales during their migration from December to March on this 1.5-hour ....
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Lāna'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. Departing daily from 9:30 am - 2:30 pm. We'll check the conditions for t... More
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Lāna'i Coast Snorkel and Sail
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Hawaii
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Superb24 reviews5
Nobody knows the waters of Maui better than our crew. Let us host you on our Gold Coast catamaran as....
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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
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2-Hour Oahu Sunset Catamaran Sail
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Hawaii
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Superb125 reviews4.8
Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran fr....
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Molokini Snorkel and Performance Sail: Mā’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
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Molokini Snorkel and Performance Sail: Mā’alaea Harbor
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Hawaii
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Superb215 reviews4.8
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....
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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
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Midday Whale Watch: Mā’alaea Harbor
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Hawaii
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Superb103 reviews4.9
Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....
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Kona Tradewind Catamaran Day Sail
Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing catamaran. Feel the trade winds fill the sails as you glide across the water, taking in panoramic views of volcanic cliffs, sparklin... More
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Kona Tradewind Catamaran Day Sail
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Hawaii
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Superb43 reviews4.8
Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing ca....
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Waikoloa Catamaran Snorkel Sail Including Lunch
Set sail from Anaeho‘omalu Bay on a 3-hour snorkel and cruise adventure along Waikoloa’s beautiful Kohala Coast. Aboard the spacious Spirit of Aloha catamaran, enjoy a smooth, comfortable ride to one of the region’s best sno... More
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Waikoloa Catamaran Snorkel Sail Including Lunch
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Hawaii
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Superb106 reviews4.7
Set sail from Anaeho‘omalu Bay on a 3-hour snorkel and cruise adventure along Waikoloa’s beautif....
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BYOB Friday Night Fireworks Cruise
BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki. You'll enjoy the view of the city lights and be in awe with this unobstructed view of fireworks from the water! With plenty of... More
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Likely to Sell Out BYOB Friday Night Fireworks Cruise
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Hawaii
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Exellent6 reviews4.3
BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki....
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Small Group Waikiki Sunset Sailing Tour
Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come and enjoy the Golden hour with your loved ones to make memories of a lifetime ,why go with overc... More
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Likely to Sell Out Small Group Waikiki Sunset Sailing Tour
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Hawaii
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Superb111 reviews4.9
Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it tha....
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Friday Night Catamaran Fireworks Sail with Open Bar
Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night, you’ll glide along the coastline and experience an exclusive o... More
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Likely to Sell Out Friday Night Catamaran Fireworks Sail with Open Bar
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Hawaii
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Superb55 reviews4.8
Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village di....
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Kealakekua Bay (Captain Cook Monument) 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 gardens u... More
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Likely to Sell Out Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure
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Hawaii
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Superb703 reviews5
Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the h....
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'Alihilani Golden Hour 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
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Likely to Sell Out 'Alihilani Golden Hour Sail
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Hawaii
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Superb85 reviews4.9
We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sa....
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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
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Likely to Sell Out Hawaiian Canoe Sailing Experience in Maui
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Hawaii
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Superb60 reviews4.7
Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour include....
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Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village
Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the island like never before as you set sail from the only pier in W... More
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Likely to Sell Out Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village
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Hawaii
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Superb23 reviews4.6
Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-bui....
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3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. Yo... More
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Likely to Sell Out 3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People
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Hawaii
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Superb1 review5
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....
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Private Tour
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Sunset Cocktail Cruise on our Sailing Catamaran
Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohala Coast aboard our legendary sailing catamaran Seasmoke. This cruise includes unlimited soft drinks, tropical juices, beers, wines... More
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Likely to Sell Out Sunset Cocktail Cruise on our Sailing Catamaran
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Hawaii
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Superb62 reviews4.8
Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohal....
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Private Tour
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Sunset sail Aboard Manakai Catamaran
Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Woody Brown—a true piece of Hawaiian sailing history. With a smaller guest capacity and open-deck layout, it offers an intimate, lai... More
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Likely to Sell Out Sunset sail Aboard Manakai Catamaran
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Hawaii
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Superb15 reviews5
Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Wood....
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Waikiki Fireworks Cocktail Cruise
Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a beautiful fireworks cruise that will give you a night to remember. ... More
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Private Tour
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Likely to Sell Out Waikiki Fireworks Cocktail Cruise
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Hawaii
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Exellent7 reviews4.4
Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a b....
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Private Tour
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