Sailing Trips in Hawaii
Top 10 Best Hawaii Sailing Trips
Found 100 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 312pm 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

12pm Turtle Canyon Snorkel Adventure
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Hawaii
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Superb278 reviews4.8
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....
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

Friday Night Firework Cruise in Waikiki
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Hawaii
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Superb22 reviews4.7
After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fire....
Molokini Snorkel and Performance Sail from Ma'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 from Ma'alaea Harbor
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Hawaii
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Superb198 reviews4.9
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....
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

Afternoon Sail & Snorkel to the Captain Cook Monument
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Hawaii
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Superb229 reviews4.9
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtakin....
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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Superb93 reviews4.9
Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it tha....
Kealakekua 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 Snorkel and Sail Adventure
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Hawaii
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Superb639 reviews5
Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the h....
Luxury Catamaran Whale Watch
Come join us to observe the playful habits of Maui's most consistent return visitor - the humpback whale. The waters off West Maui have long been the favored vacation spot of these massive marine mammals. The Alii Class Yachts pro... More

Luxury Catamaran Whale Watch
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Hawaii
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Superb40 reviews5
Come join us to observe the playful habits of Maui's most consistent return visitor - the humpback w....
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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Superb19 reviews5
No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed ....
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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Superb7 reviews5
Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foo....
Private Tour

Polynesian Canoe Day 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
Free Cancellation
Private Tour
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Polynesian Canoe Day Sail
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Hawaii
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Superb26 reviews4.8
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....
Free Cancellation
Private Tour
(Saving 10% )
Private Catamaran Charter in Waikiki (7-12 Guests)
(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6 guests, you can book under our other listing labeled for 1-6 guests.) This 48-foot ca... More
Private Tour

Private Catamaran Charter in Waikiki (7-12 Guests)
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Hawaii
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Superb26 reviews4.8
(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it....
Private Tour
Private Charter Snorkel Sail Adventure off Kaanapali Beach
PRIVATE CHARTER - 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 ‘H... More
Private Tour

Private Charter Snorkel Sail Adventure off Kaanapali Beach
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Hawaii
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Superb26 reviews4.8
PRIVATE CHARTER - While snorkeling along West Maui’s coastline, experience warm waters abundant wi....
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

Moana’s Luxury semi-private Sunset Cruise on Nalu
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Hawaii
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Exellent7 reviews4.4
The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizabl....
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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Superb69 reviews5
Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples o....
Private Tour
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
Private Tour

Oahu 3pm Tradewind Sail from Honolulu
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Hawaii
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Superb233 reviews4.8
This is an excellent cruise for families and sailors wanting to relax and enjoy a beautiful afternoo....
Private Tour

Waikiki Fireworks Cocktail Cruise
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Hawaii
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Very Good3 reviews4
Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a 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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Superb103 reviews4.9
Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran f....
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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Superb12 reviews4.6
Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki....
Private Tour
BYOB Friday Night Fireworks Cruise
BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki. You'll enjoy the view of the city lights and be in awe with this unobstructed view of fireworks from the water! With plenty of... More
Private Tour

BYOB Friday Night Fireworks Cruise
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Hawaii
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Exellent5 reviews4.2
BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki....
Private Tour
Afternoon Catamaran Sail with Local Culture, Cocktails and Snacks
As you step aboard the spacious catamaran, you're immediately greeted by the friendly crew, who are eager to guide you on an unforgettable journey. The vessel is equipped with all the amenities you need for a comfortable and enjoy... More
Private Tour

Afternoon Catamaran Sail with Local Culture, Cocktails and Snacks
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Hawaii
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Exellent5 reviews4.2
As you step aboard the spacious catamaran, you're immediately greeted by the friendly crew, who are ....
Private Tour