Sailing Trips in Hawaii
Top 10 Best Hawaii Sailing Trips
Found 104 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 3Pau 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....
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

Small Group Waikiki Sunset Sailing Tour
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Hawaii
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Superb89 reviews4.9
Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it tha....
Kona Coastline Escape: Sail with Dolphins & Turtles on Honi Olani
Set sail on the Honi Olani, a 53-foot sailing catamaran, and explore the stunning Kona coastline. This 1.5-hour journey from Honokohau Harbor offers a chance to bask in the sun and enjoy the ocean breeze while taking in the breath... More

Kona Coastline Escape: Sail with Dolphins & Turtles on Honi Olani
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Hawaii
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Superb35 reviews4.8
Set sail on the Honi Olani, a 53-foot sailing catamaran, and explore the stunning Kona coastline. Th....
Oahu 3pm Tradewind Sail from Honolulu
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

Oahu 3pm Tradewind Sail from Honolulu
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Hawaii
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Superb226 reviews4.8
This is an excellent cruise for families and sailors wanting to relax and enjoy a beautiful afternoo....
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

Private Catamaran Charter in Waikiki (1-6 Guests)
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Hawaii
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Superb16 reviews5
Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the....
Private Tour
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
Snorkel Sail Adventure off Ka'anapali Beach, Maui
While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, an endangered Hawaiian Green Sea turtle called a ‘Honu’. A hot buff... More
Private Tour

Snorkel Sail Adventure off Ka'anapali Beach, Maui
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Hawaii
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Superb9 reviews4.9
While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You w....
Private Tour
Pau Hana Sunset Cruise with the Whales
Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the biggest guests of all -- the Humpback Whales -- and you have perfect way to begin your evening in paradise! Cruise along the Kohala... More
Private Tour

Pau Hana Sunset Cruise with the Whales
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Hawaii
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Superb46 reviews4.8
Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the b....
Private Tour
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
Private Tour

2-Hour Oahu Sunset Catamaran Sail
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Hawaii
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Superb102 reviews4.9
Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran f....
Private Tour

Waikiki Fireworks Cocktail Cruise
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Hawaii
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Exellent4 reviews4.3
Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a b....
Private Tour
12pm Turtle Canyon Snorkel Adventure
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life? Our snorkel guides help you feel confid... More
Private Tour

12pm Turtle Canyon Snorkel Adventure
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Hawaii
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Superb270 reviews4.8
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....
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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Superb5 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
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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Superb21 reviews4.8
After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fire....
Private Tour
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
Private Tour

Waikiki small group turtle snorkeling & sailing
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Hawaii
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Superb60 reviews5
Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples o....
Private Tour
Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu
Enjoy the Hawaiian Ocean, your way! 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... More
Private Tour

Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu
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Hawaii
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Superb26 reviews4.9
Enjoy the Hawaiian Ocean, your way! The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, ....
Private Tour
Waikiki Boat Party Cruise with live DJ
Get ready for the ultimate Day Club experience on the water! Departing from Kewalo Basin Harbor, this exclusive 4-hour catamaran party cruise features an open bar with Vodka, Rum, Whiskey, Gin, Tequila, Champagne, Beer, plus Juice... More
Private Tour

Waikiki Boat Party Cruise with live DJ
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Hawaii
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Superb26 reviews4.9
Get ready for the ultimate Day Club experience on the water! Departing from Kewalo Basin Harbor, thi....
Private Tour
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch
Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise lets you see whales (December through March), fish, even green s... More
Private Tour

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch
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Hawaii
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Exellent11 reviews4.5
Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki....
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
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

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
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
Private Tour

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 Tour