Sailing Trips in Hawaii
Top 10 Best Hawaii Sailing Trips
Found 117 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 3Waikiki 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
Likely to Sell Out Waikiki small group turtle snorkeling & sailing
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Hawaii
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Superb83 reviews5
Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples o....
Kona Tradewind Catamaran Day Sail
Set sail aboard the spacious Honi Olani catamaran for a scenic 90-minute adventure along the stunning Kona coastline. This relaxing daytime cruise is perfect for spotting Hawaii’s incredible marine wildlife—keep your eyes peel... More
Likely to Sell Out Kona Tradewind Catamaran Day Sail
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Hawaii
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Superb42 reviews4.8
Set sail aboard the spacious Honi Olani catamaran for a scenic 90-minute adventure along the stunnin....
Likely to Sell Out
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
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Likely to Sell Out 12pm Turtle Canyon Snorkel Adventure
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Hawaii
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Superb300 reviews4.8
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....
Free Cancellation
(Saving 15% )
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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Superb8 reviews5
Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foo....
Private Tour
Molokini 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
Private Tour
Likely to Sell Out Molokini Snorkel and Performance Sail: Mā’alaea Harbor
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Hawaii
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Superb210 reviews4.8
Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....
Private Tour
Sunset Cruise & Whale Watching from Oahu
Experience the breathtaking beauty of nature with our Sunset Whale Watch excursion. Join us for an unforgettable journey as we set sail into the golden hues of the evening sky, where you'll have the chance to witness majestic whal... More
Private Tour
Likely to Sell Out Sunset Cruise & Whale Watching from Oahu
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Hawaii
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Superb64 reviews4.6
Experience the breathtaking beauty of nature with our Sunset Whale Watch excursion. Join us for an u....
Private Tour
Sunset sail Aboard Manakai Catamaran
Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Woody Brown—a true piece of Hawaiian sailing history. With a smaller guest capacity and open-deck layout, it offers an intimate, lai... More
Private Tour
Likely to Sell Out Sunset sail Aboard Manakai Catamaran
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Hawaii
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Superb11 reviews5
Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Wood....
Private Tour
Lāna'i Coast Snorkel and Sail
Nobody knows the waters of Maui better than our crew. Let us host you on our Gold Coast catamaran as we explore and snorkel the incredible coastline of Maui. Departing daily from 9:30 am - 2:30 pm. We'll check the conditions for t... More
Private Tour
Likely to Sell Out Lāna'i Coast Snorkel and Sail
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Hawaii
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Superb2 reviews5
Nobody knows the waters of Maui better than our crew. Let us host you on our Gold Coast catamaran as....
Private Tour
Sunset Cruise with the Whales from Anaeho'omalu Bay
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
Likely to Sell Out Sunset Cruise with the Whales from Anaeho'omalu Bay
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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
Midday Whale Watch: Mā’alaea Harbor
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
Likely to Sell Out Midday Whale Watch: Mā’alaea Harbor
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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
Kealakekua 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
Private Tour
Likely to Sell Out Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure
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Hawaii
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Superb685 reviews5
Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the h....
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
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
Likely to Sell Out
Waikiki Fireworks Cocktail Cruise
Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a beautiful fireworks cruise that will give you a night to remember. ... More
Free Cancellation
Private Tour
(Saving 10% )
Likely to Sell Out Waikiki Fireworks Cocktail Cruise
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Hawaii
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Exellent6 reviews4.3
Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a b....
Free Cancellation
Private Tour
(Saving 10% )
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
Whale Watching Sail in Honolulu with Open Bar
Observe the majestic humpback whales during their migration from December to March on this 1.5-hour sail in Honolulu. Experience the beauty of Oahu's coastline while searching for dolphins and sea turtles in their natural habitat.... More
Private Tour
Likely to Sell Out Whale Watching Sail in Honolulu with Open Bar
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Hawaii
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Superb2 reviews5
Observe the majestic humpback whales during their migration from December to March on this 1.5-hour ....
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
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
Leila Na Pali Sunset Dinner Sail
Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjoy appetizers, craft beer, wine, and Koloa Rum Mai-Tais aboard our sleek and spacious sailing catamaran, Leila. Your captain will s... More
Private Tour
Likely to Sell Out Leila Na Pali Sunset Dinner Sail
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Hawaii
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Superb517 reviews4.7
Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjo....
Private Tour
Four Winds Molokini Snorkeling Tour from Maalaea Harbor
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in the warmth of paradise. From the experienced snorkeler to those... More
Private Tour
Likely to Sell Out Four Winds Molokini Snorkeling Tour from Maalaea Harbor
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Hawaii
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Superb811 reviews4.7
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....
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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Superb712 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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Superb245 reviews4.9
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtakin....
Private Tour