Sailing Trips in Hawaii
Top 10 Best Hawaii Sailing Trips
Found 114 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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Superb204 reviews4.9
Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....
Waikiki Sunset Cruise Catamaran Boat Tour on Oahu
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
Waikiki Sunset Cruise Catamaran Boat Tour on Oahu
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Hawaii
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Superb17 reviews4.7
Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē....
Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise
Our sunset turtle snorkeling tour delivers a unique all-in-one Waikiki ocean experience, combining adventure, relaxation, and unforgettable views in one trip. We reach Turtle Canyon quickly, giving you more time in the water to s... More
Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise
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Hawaii
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Superb17 reviews4.7
Our sunset turtle snorkeling tour delivers a unique all-in-one Waikiki ocean experience, combining a....
Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon
-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel equipment -Fun, friendly, lifeguard certified crew -BYOB (Bring your own Beverage. No glass bottles)... More
Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon
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Hawaii
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Superb316 reviews4.8
-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel....
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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Superb859 reviews4.9
Our most popular tour! Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail....
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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Superb254 reviews4.9
As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your....
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
Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure
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Hawaii
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Superb710 reviews5
Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the h....
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experience Maui’s golden hour from the water. Departing from Ma‘alaea, this intimate evening cruise offers stunning views of the coast... More
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
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Hawaii
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Superb18 reviews4.8
Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experien....
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
Molokini Snorkel and Performance Sail: Mā’alaea Harbor
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Hawaii
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Superb217 reviews4.8
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....
Luxury 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 50' luxury yacht. Immerse yourself in a gorgeous Hawaiian sunset the only way, from... More
Private Tour
Luxury Diamond Head Sunset Sail
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Hawaii
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Superb3 reviews5
Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sa....
Private Tour
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
Private Tour
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....
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! Our sails always have complimentary drinks (alcoholic beverages available for adults 21+ with valid ID o... More
Private Tour
South Shore Open Sail from Kewalo Harbor Including Drinks
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Hawaii
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Superb24 reviews4.8
Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconi....
Private Tour
Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar
Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where our experienced crew selects the day’s best snorkel destination based on weather, tides, and ocean conditions. • Explore Lana... More
Private Tour
Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar
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Hawaii
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Superb36 reviews5
Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where ....
Private Tour
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
Private Tour
Afternoon Sail & Snorkel to the Captain Cook Monument
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Hawaii
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Superb250 reviews4.9
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtakin....
Private Tour
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
Private Tour
Kona Tradewind Catamaran Day Sail
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Hawaii
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Superb44 reviews4.8
Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing ca....
Private Tour
Waikiki: Afternoon Sail with Open Bar | Oahu - Best Value
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
Private Tour
Waikiki: Afternoon Sail with Open Bar | Oahu - Best Value
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Hawaii
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Superb251 reviews4.8
This is an excellent cruise for families and sailors wanting to relax and enjoy a beautiful afternoo....
Private Tour
Friday Night Firework Cruise in Waikiki
After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fireworks explode over the city’s skyline, truly making this the ultimate party experience. Enjoy the Premium drinks of your choice ... More
Private Tour
Friday Night Firework Cruise in Waikiki
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Hawaii
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Superb30 reviews4.7
After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fire....
Private Tour
Oahu: 3 Hours - Kane‘ohe Sandbar Splash and Snorkeling Adventure
Discover an unforgettable side of O‘ahu most visitors never experience! Our Kāneʻohe Sandbar Splash & Snorkeling Adventure takes you beyond Waikiki to the serene waters of Kāneʻohe Bay, framed by the dramatic Ko‘olau mount... More
Private Tour
Likely to Sell Out Oahu: 3 Hours - Kane‘ohe Sandbar Splash and Snorkeling Adventur....
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Hawaii
Discover an unforgettable side of O‘ahu most visitors never experience! Our Kāneʻohe Sandbar Spl....
Private Tour
Coral Gardens Coastal Snorkel & Sail
This sailing experience blends adventure and tranquility against a backdrop of Maui’s pristine landscapes. Arrive at Coral Gardens, a sheltered snorkeling haven with calm, crystal-clear waters teeming with vibrant coral reefs a... More
Private Tour
Likely to Sell Out Coral Gardens Coastal Snorkel & Sail
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Hawaii
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Superb39 reviews4.8
This sailing experience blends adventure and tranquility against a backdrop of Maui’s pristine lan....
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
Likely to Sell Out Half Day Oahu Combo Adventure: Bike, Sail and Snorkel
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Hawaii
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Superb68 reviews4.7
Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour....
Private Tour