Sailing Trips in Hawaii
Top 10 Best Hawaii Sailing Trips
Found 104 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 3BYOB Waikiki Sunset Swim and Diamond Head Sailing
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

BYOB Waikiki Sunset Swim and Diamond Head Sailing
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Hawaii
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Superb143 reviews5
Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....
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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Superb195 reviews4.9
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....
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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Superb13 reviews5
Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the....
Private Tour
Polynesian Canoe Sunset 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
Private Tour

Polynesian Canoe Sunset Sail
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Hawaii
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Superb118 reviews4.9
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....
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
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
Midday Sail with the Whales Ma'alaea
Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, the ‘Au ‘au channel off the coast of Maui boasts the greatest number. ... More
Private Tour

Midday Sail with the Whales Ma'alaea
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Hawaii
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Superb100 reviews4.9
Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....
Private Tour
Waikiki Sail and Snorkel Adventure Best of Hawaii 2023
Immerse yourself in a vibrant underwater wonderland as you snorkel through coral reefs teeming with an array of tropical fish. The clear waters of Turtle Canyons reveal a kaleidoscope of colors, from dazzling schools of fish to vi... More
Private Tour

Waikiki Sail and Snorkel Adventure Best of Hawaii 2023
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Hawaii
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Very Good4 reviews4
Immerse yourself in a vibrant underwater wonderland as you snorkel through coral reefs teeming with ....
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
Private Tour

Polynesian Canoe Day Sail
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Hawaii
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Superb25 reviews4.8
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....
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
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
Private Tour

Waikiki Sunset Boat Cruise
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Hawaii
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Superb10 reviews5
No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed ....
Private Tour
Polynesian 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
Private Tour

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....
Private Tour
Half-Day Deluxe Molokini Snorkel Excursion in Maui
Since 1978, we have been proudly sailing the seas of Maui, whisking guests away on exhilarating snorkeling trips, romantic sunset cruises, and everything in between. We’re honored to play a part in introducing our visitors to th... More
Private Tour

Half-Day Deluxe Molokini Snorkel Excursion in Maui
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Hawaii
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Superb72 reviews4.9
Since 1978, we have been proudly sailing the seas of Maui, whisking guests away on exhilarating snor....
Private Tour
2hr Luxury Private Sailing Catamaran for 7-12 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

2hr Luxury Private Sailing Catamaran for 7-12 People
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Hawaii
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Superb72 reviews4.9
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....
Private Tour
Morning Sail With the Whales Ma'alaea
Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, the ‘Au ‘au channel off the coast of Maui boasts the greatest number. ... More
Private Tour

Morning Sail With the Whales Ma'alaea
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Hawaii
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Superb10 reviews5
Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....
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
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
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
Private Tour

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....
Private Tour
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
Private Tour

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....
Private Tour
'Alihilani Sunset Sail from Ma'alaea Harbor
We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sails. Our spacious catamarans make for a luxurious experience, allowing for incredible views of Maui and the inter islands while wa... More
Private Tour

'Alihilani Sunset Sail from Ma'alaea Harbor
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Hawaii
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Superb74 reviews5
We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sa....
Private Tour