Sailing Trips in Hawaii
Top 10 Best Hawaii Sailing Trips
Found 103 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 4Polynesian 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

Polynesian Canoe Morning Sail
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Hawaii
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Superb16 reviews5
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....
Pau Hana Sunset Cocktail Cruise
Enjoy the warm tropical breezes and unparalleled views of the Big Island aboard a well-appointed catamaran. This cruise includes unlimited soft drinks, tropical juices, beers, wines, cocktails and a variety of appetizers.. Great f... More

Pau Hana Sunset Cocktail Cruise
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Hawaii
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Superb48 reviews4.8
Enjoy the warm tropical breezes and unparalleled views of the Big Island aboard a well-appointed cat....
Honolulu BYOB Fireworks Boat Cruise
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

Honolulu BYOB Fireworks Boat Cruise
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Hawaii
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Exellent25 reviews4.5
Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insig....
1.5-Hour Koa Kai Adventure Whale Watch
Experience an up-close encounter with our winter residents, the Humpback Whale! These beautiful creatures return to Maui every year to birth their young. During this trip, you will get a chance to hear the whale’s unique songs a... More

1.5-Hour Koa Kai Adventure Whale Watch
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Hawaii
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Superb2 reviews5
Experience an up-close encounter with our winter residents, the Humpback Whale! These beautiful crea....
4-Hour Koa Kai Molokini Adventure Snorkel
Join us on this 3-hour snorkel adventure at Maui's most iconic snorkeling location, Molokini Crater. You will be treated to exceptional service and premium equipment. Koa Kai is a multi-purpose raft that creates a unique close-u... More

4-Hour Koa Kai Molokini Adventure Snorkel
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Hawaii
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Superb10 reviews5
Join us on this 3-hour snorkel adventure at Maui's most iconic snorkeling location, Molokini Crater.....
Private Catamaran Sunset Sail in Waikiki
Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large ... More
Private Tour

Private Catamaran Sunset Sail in Waikiki
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Hawaii
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Superb6 reviews5
Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foo....
Private Tour
Deluxe Turtle Snorkeling Escapade at Waikiki
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
Private Tour

Deluxe Turtle Snorkeling Escapade at Waikiki
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Hawaii
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Superb4 reviews4.8
Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....
Private Tour
Coral Gardens Snorkel & Whale Watch
Sail through Maui’s renowned Au‘Au Channel, a world-class whale-watching destination famous for its calm waters and breathtaking scenery. During whale season, this prime playground offers unmatched opportunities to spot majest... More
Private Tour

Coral Gardens Snorkel & Whale Watch
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Hawaii
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Superb39 reviews4.8
Sail through Maui’s renowned Au‘Au Channel, a world-class whale-watching destination famous for ....
Private Tour
Sunset Sail Experience by Catamaran in Waikiki
Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled catamaran. Take in the views of Honolulu skyline from offshore Waikiki and feel the warmth of the setting Hawaiian sun and tropical ... More
Private Tour

Sunset Sail Experience by Catamaran in Waikiki
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Hawaii
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Superb4 reviews5
Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled ca....
Private Tour
Waikiki Friday Firework Catamaran Tour
The Blue Ocean Waikiki luxury catamaran is the perfect place for guests to enjoy following a breathtaking fireworks just outside the Hilton Hawaiian Village. Every Friday at 6:45pm, you have the opportunity to watch a spectacular ... More
Private Tour

Waikiki Friday Firework Catamaran Tour
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Hawaii
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Superb27 reviews4.7
The Blue Ocean Waikiki luxury catamaran is the perfect place for guests to enjoy following a breatht....
Private Tour
Half Day Oahu Combo Adventure: Bike, Sail and Snorkel
Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour from rainforest to reef combines views high above Honolulu to snorkeling off a catamaran off Waikiki. Explore lush rainforest and... More
Private Tour

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel
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Hawaii
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Superb67 reviews4.7
Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour....
Private Tour
Private Catamaran Charter in Waikiki (7-12 Guests)
(IMPORTANT: Make sure you have over 6 guests selected to see availability for this activity. If you have 1-6 guests, you can book under our other listing labeled for 1-6 guests.) This 48-foot catamaran has a sleek low-profile des... More
Private Tour

Private Catamaran Charter in Waikiki (7-12 Guests)
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Hawaii
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Superb67 reviews4.7
(IMPORTANT: Make sure you have over 6 guests selected to see availability for this activity. If you ....
Private Tour
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
Experience “Amore” a 42-foot Boston Whaler with unmatched state-of-the-art features make the flagship 420 Outrage a boat like no other. From the expansive bow with innovative seating galore, to the beautifully designed convert... More
Private Tour

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
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Hawaii
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Superb7 reviews4.9
Experience “Amore” a 42-foot Boston Whaler with unmatched state-of-the-art features make the fla....
Private Tour
Friday Night Catamaran Fireworks Sail with Open Bar
Who doesn't love fireworks, especially with all inclusive drinks? The famous weekly Hilton Hawaiian Village fireworks display seen from the water feels like you’re right under the action! There's no better way to kick off the we... More
Private Tour

Friday Night Catamaran Fireworks Sail with Open Bar
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Hawaii
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Superb53 reviews4.9
Who doesn't love fireworks, especially with all inclusive drinks? The famous weekly Hilton Hawaiian ....
Private Tour
Waikiki Panorama Sail: Search for Hawaiian Sea Turtles
Snap beautiful photos of Waikiki on this 90-minute sail, where you'll cruise past famous Waikiki Beach and out towards Diamond Head crater. The cruise departs from Kewalo Basin by Ala Moana Beach Park, and includes snacks, non-alc... More
Private Tour

Waikiki Panorama Sail: Search for Hawaiian Sea Turtles
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Hawaii
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Superb32 reviews4.7
Snap beautiful photos of Waikiki on this 90-minute sail, where you'll cruise past famous Waikiki Bea....
Private Tour
Oahu, Waikiki Sunset Catamaran Boat Tour
Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from December-March, of course, the annual humpback whales!... More
Private Tour

Oahu, Waikiki Sunset Catamaran Boat Tour
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Hawaii
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Superb14 reviews4.9
Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē....
Private Tour
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
Private Tour

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....
Private Tour
South Shore Open Sail from Kewalo Harbor Including Drinks
Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! We are a 49-passenger beautiful yellow and red retired Waikiki Beach catamaran now operating from Kewalo... More
Private Tour

South Shore Open Sail from Kewalo Harbor Including Drinks
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Hawaii
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Superb14 reviews5
Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconi....
Private Tour
Waikiki Private Sunset Sail Romantic and Private
Adventure Awaits aboard our Fabulous 48' private yacht. Bring along your family and friends for a spectacular Hawaiian sunset on your private yacht. Get a chance to see whales, dolphins and sea turtles. Immerse yourself in a bucke... More
Private Tour

Waikiki Private Sunset Sail Romantic and Private
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Hawaii
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Superb14 reviews5
Adventure Awaits aboard our Fabulous 48' private yacht. Bring along your family and friends for a sp....
Private Tour
#1 eFoil 2 hr group + 2 hr wing foil or windsurf or kayak lesson
You will receive special Ocean Safety training prior to your adventure. Our two way radio helmets help us to give precise specific info as needed so you learn faster and safer. We will share with you the best locations to launch f... More
Private Tour

#1 eFoil 2 hr group + 2 hr wing foil or windsurf or kayak lesson
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Hawaii
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Superb4 reviews5
You will receive special Ocean Safety training prior to your adventure. Our two way radio helmets he....
Private Tour