Sailing Trips in Hawaii
Top 10 Best Hawaii Sailing Trips
Found 114 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 4Afternoon Ali'i Adventure
Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests, allowing for a semi-private experience aboard our spacious 50' catamaran. ... More
Likely to Sell Out Afternoon Ali'i Adventure
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Hawaii
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Superb6 reviews5
Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowd....
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
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....
Waikiki small group turtle snorkeling & sailing
Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples or families who are up at the crack of dawn during their Hawaiian vacation due to time zone changes. As we start out our tour from ... More
Likely to Sell Out Waikiki small group turtle snorkeling & sailing
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Hawaii
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Superb92 reviews5
Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples o....
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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Superb89 reviews4.9
From December through April, the waters off Maui come alive with the sights and sounds of the majest....
Waikiki Turtle Snorkeling Adventure(8am)
Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamaran. Our Turtle Snorkeling Package offers a unique opportunity to snorkel with friendly turtles in the heart of Waikiki's picturesq... More
Likely to Sell Out Waikiki Turtle Snorkeling Adventure(8am)
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Hawaii
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Superb9 reviews4.9
Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....
2 Hour Swim, Snorkel & Sail (Kewalo Harbor)
A beautiful swim and boat ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and whales (seasonal). Our snorkel, swim and sail is the perfect combination of warm sun, refreshing salty water, and b... More
Likely to Sell Out 2 Hour Swim, Snorkel & Sail (Kewalo Harbor)
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Hawaii
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Superb2 reviews5
A beautiful swim and boat ride along the south shore of Oahu, potentially viewing sea turtles, dolph....
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
Likely to Sell Out Sunset sail Aboard Manakai Catamaran
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Hawaii
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Superb16 reviews5
Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Wood....
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
Likely to Sell Out Small Group Waikiki Sunset Sailing Tour
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Hawaii
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Superb114 reviews4.9
Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it tha....
Waikiki Friday Night Fireworks Cruise + Fireworks Festival 3/15
Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring your favorite beverages and join us for Waikiki's weekly fireworks displ... More
Likely to Sell Out Waikiki Friday Night Fireworks Cruise + Fireworks Festival 3/15
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Hawaii
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Exellent31 reviews4.5
Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insig....
Likely to Sell Out
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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Likely to Sell Out Waikiki Fireworks Cocktail Cruise
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Hawaii
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Exellent8 reviews4.5
Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a b....
Free Cancellation
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Likely to Sell Out
Polynesian Canoe Morning 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
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Likely to Sell Out Polynesian Canoe Morning Sail
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Hawaii
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Superb18 reviews5
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....
Free Cancellation
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Likely to Sell Out
Private Catamaran Charter in Waikiki (1-6 Guests)
Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large lounging nets on the front of the boat, as well as 2 small nets on the back of the boat. Not only does Hawa... More
Free Cancellation
Private Tour
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Likely to Sell Out Private Catamaran Charter in Waikiki (1-6 Guests)
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Hawaii
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Superb23 reviews5
Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the....
Free Cancellation
Private Tour
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Likely to Sell Out
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
Free Cancellation
Private Tour
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Likely to Sell Out Akialoa Mā’alaea Sunset Sail
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Hawaii
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Superb13 reviews4.7
Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sun....
Free Cancellation
Private Tour
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Likely to Sell Out
Waikiki Sunset Cruise and Iconic Views with Swimming
Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in the crystal-clear waters off Waikīkī Beach. Glide along the iconic Gold Coast as the sun sets, painting the sky with vibrant co... More
Free Cancellation
Private Tour
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Likely to Sell Out Waikiki Sunset Cruise and Iconic Views with Swimming
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Hawaii
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Superb2 reviews5
Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in....
Free Cancellation
Private Tour
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Likely to Sell Out
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
Free Cancellation
Private Tour
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Likely to Sell Out Best Waikiki Whale Watching in Honolulu: Whales Guaranteed
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Hawaii
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Superb250 reviews4.6
Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well a....
Free Cancellation
Private Tour
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Likely to Sell Out
Waikiki Beach Whale Watching: Catamaran Sail & 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
Free Cancellation
Private Tour
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Likely to Sell Out Waikiki Beach Whale Watching: Catamaran Sail & 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 ....
Free Cancellation
Private Tour
(Saving inf% )
Likely to Sell Out
Private 5Hr Island Tour with 2.5Hr 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
Free Cancellation
Private Tour
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Likely to Sell Out Private 5Hr Island Tour with 2.5Hr 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....
Free Cancellation
Private Tour
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Likely to Sell Out
Afternoon Sail With the Whales from Lahaina 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
Free Cancellation
Private Tour
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Likely to Sell Out Afternoon Sail With the Whales from Lahaina Harbor
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Hawaii
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Superb1 review5
Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....
Free Cancellation
Private Tour
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Likely to Sell Out
Diamond Head Sunset Sail
Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sail features a two hour cruise aboard a private luxury yacht. Immerse yourself in a gorgeous Hawaiian sunset the only way, from the... More
Free Cancellation
Private Tour
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Likely to Sell Out Diamond Head Sunset Sail
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Hawaii
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Superb15 reviews4.7
Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sa....
Free Cancellation
Private Tour
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Likely to Sell Out
Honolulu Sailing and Snorkeling Activity
You’re guaranteed to see an array of endemic reef fish, colorful corals, and other unique marine creatures that call the Hawaiian islands home.... More
Free Cancellation
Private Tour
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Likely to Sell Out Honolulu Sailing and Snorkeling Activity
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Hawaii
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Superb15 reviews4.7
You’re guaranteed to see an array of endemic reef fish, colorful corals, and other unique marine c....
Free Cancellation
Private Tour
(Saving inf% )