Sailing Trips in Hawaii
Top 10 Best Hawaii Sailing Trips
Found 108 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 3Molokini 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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                                            Superb209 reviews4.8
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....
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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                                            Superb233 reviews4.9
As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your....
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
 
                  
                                    12pm Turtle Canyon Snorkel Adventure
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                      Hawaii
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                                            Superb299 reviews4.8
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....
Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harbor
Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your loved ones to experience a beautiful Snorkeling, Sailing Cruise, and Whale Watching (Dec-Apr) on our Small Charming Hawaiian Catamara... More
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                  Likely to Sell Out                  Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harb....
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                      Hawaii
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                                            Superb158 reviews4.7
Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your lov....
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
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                  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....
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
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                  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
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
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                  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
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
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                  Likely to Sell Out                  Polynesian Canoe Morning Sail
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                      Hawaii
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                                            Superb17 reviews5
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....
Private Tour
Waikiki 3pm Tradewind Sail - Open Bar Included
Open Bar: Included with the price of General Admission until 8/31/2025 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 dolphin... More
Private Tour
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                  Likely to Sell Out                  Waikiki 3pm Tradewind Sail - Open Bar Included
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                      Hawaii
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                                            Superb245 reviews4.8
Open Bar: Included with the price of General Admission until 8/31/2025 This is an excellent cruise ....
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
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                  Likely to Sell Out                  Half Day Oahu Combo Adventure: Bike, Sail and Snorkel
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                      Hawaii
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                                            Superb67 reviews4.7
Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour....
Private Tour
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
Experience “Amore” a 42-foot Boston Whaler with unmatched state-of-the-art features make the flagship 420 Outrage a boat like no other. From the expansive bow with innovative seating galore, to the beautifully designed convert... More
Private Tour
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                  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
Experience “Amore” a 42-foot Boston Whaler with unmatched state-of-the-art features make the fla....
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
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                  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
9am 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
 Likely to Sell Out
                  
                  Likely to Sell Out                  9am Turtle Canyon Snorkel Adventure
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                      Hawaii
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                                            Superb266 reviews4.9
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....
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
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                  Likely to Sell Out                  Deluxe Turtle Snorkeling Escapade at Waikiki
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                      Hawaii
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                                            Superb7 reviews4.9
Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....
Private Tour
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
Private Tour
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                  Likely to Sell Out                  Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar
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                      Hawaii
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                                            Good2 reviews3.5
Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cockt....
Private Tour
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
Private Tour
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                  Likely to Sell Out                  Small Group Waikiki Sunset Sailing Tour
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                      Hawaii
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                                            Superb109 reviews4.9
Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it tha....
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
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                  Likely to Sell Out                  Waikiki small group turtle snorkeling & sailing
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                      Hawaii
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                                            Superb78 reviews5
Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples o....
Private Tour
Akialoa Mā’alaea Sunset Sail
Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sunset Sail offers a two-hour journey through the picturesque inter-island channel, showcasing the beauty of Maui, Lāna‘i, and Kah... More
Private Tour
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                  Likely to Sell Out                  Akialoa Mā’alaea Sunset Sail
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                      Hawaii
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                                            Superb78 reviews5
Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sun....
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
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                  Likely to Sell Out                  Friday Night Firework Cruise in Waikiki
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                      Hawaii
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                                            Superb23 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
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
                  
                  Likely to Sell Out                  Private Catamaran Sunset Sail in Waikiki
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                      Hawaii
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                                            Superb8 reviews5
Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foo....
Private Tour
