Sailing Trips in Hawaii
Top 10 Best Hawaii Sailing Trips
Found 110 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 4Kealakekua 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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Superb695 reviews5
Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the h....
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
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
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Hawaii
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Superb43 reviews4.8
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....
Maui: Kaanapali Beach 5-hour Snorkel w/ BBQ Lunch & Open Bar
5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and an open bar. This is our award-winning snorkel tour that... More
Maui: Kaanapali Beach 5-hour Snorkel w/ BBQ Lunch & Open Bar
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Hawaii
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Superb6 reviews5
5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest ....
Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar
Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience offers breathtaking views of the sunset complemented by deligh... More
Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar
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Hawaii
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Exellent5 reviews4.4
Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cockt....
Waikiki Sunset Boat Cruise
No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as we cruise the Waikiki coastline with views of Diamond head cra... More
Waikiki Sunset Boat Cruise
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Hawaii
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Superb96 reviews4.9
No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed ....
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
Deluxe Turtle Snorkeling Escapade at Waikiki
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Hawaii
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Superb8 reviews4.9
Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....
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
Likely to Sell Out Private Catamaran Sunset Sail in Waikiki
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Hawaii
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Superb9 reviews5
Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foo....
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 a... More
Private Tour
Likely to Sell Out Afternoon Sail & Snorkel to the Captain Cook Monument
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Hawaii
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Superb721 reviews4.9
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathta....
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
Likely to Sell Out Afternoon Sail & Snorkel to the Captain Cook Monument
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Hawaii
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Superb246 reviews4.9
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtakin....
Private Tour
Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun
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
Likely to Sell Out Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun
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Hawaii
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Superb157 reviews4.8
Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....
Private Tour
Likely to Sell Out
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
Free Cancellation
Private Tour
(Saving 30% )
Likely to Sell Out Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast
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Hawaii
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Superb236 reviews4.9
As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your....
Free Cancellation
Private Tour
(Saving 30% )
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
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....
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
Likely to Sell Out Sunset Sail Experience by Catamaran in Waikiki
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Hawaii
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Superb6 reviews4.8
Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled ca....
Private Tour
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
Likely to Sell Out 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
Moana’s Luxury semi-private Sunset Cruise on Nalu
The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May, Guests can look forward to Humpback Whale watching at no additional cost. Dolphins, Sea turtle... More
Private Tour
Likely to Sell Out Moana’s Luxury semi-private Sunset Cruise on Nalu
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Hawaii
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Superb9 reviews4.6
The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizabl....
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
Likely to Sell Out Kona Tradewind Catamaran Day Sail
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Hawaii
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Superb42 reviews4.8
Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing ca....
Private Tour
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
Private Tour
Likely to Sell Out 2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
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Hawaii
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Superb16 reviews4.8
Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experien....
Private Tour
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
Private Tour
Likely to Sell Out Private Catamaran Charter in Waikiki (1-6 Guests)
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Hawaii
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Superb21 reviews5
Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the....
Private Tour
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
Private Tour
Likely to Sell Out 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....
Private Tour
2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 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
Likely to Sell Out 2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People
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Hawaii
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Superb14 reviews4.8
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....
Private Tour