Sailing Trips in Hawaii
Top 10 Best Hawaii Sailing Trips
Found 110 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 42 Hour 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
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Likely to Sell Out 2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)
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Hawaii
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Superb10 reviews5
(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it....
Private Tour
Morning Whale Watch: Lahaina 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 Morning Whale Watch: Lahaina Harbor
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Hawaii
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Superb26 reviews4.9
Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....
Private Tour
Waikiki Sunset Cruise and Iconic Views with Swimming
Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in the crystal-clear waters off Waikīkī Beach. Glide along the iconic Gold Coast as the sun sets, painting the sky with vibrant co... More
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Likely to Sell Out Waikiki Sunset Cruise and Iconic Views with Swimming
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Hawaii
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Superb1 review5
Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in....
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
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Likely to Sell Out Waikiki small group turtle snorkeling & sailing
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Hawaii
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Superb90 reviews5
Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples o....
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
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Likely to Sell Out Snorkel Sail Adventure off Ka'anapali Beach, Maui
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Hawaii
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Superb36 reviews4.9
While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You w....
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
Likely to Sell Out Polynesian Canoe Morning Sail
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Hawaii
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Superb18 reviews5
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....
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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Superb24 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 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
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Likely to Sell Out Waikiki 3pm Tradewind Sail - Open Bar Included
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Hawaii
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Superb247 reviews4.8
Open Bar: Included with the price of General Admission until 8/31/2025 This is an excellent cruise ....
Private Tour
Paragon Lahaina Performance Sail
Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui performance sail from Lahaina Harbor. Enjoy the afternoon hours at sea in the glassy, miraculous ‘au’au Channel is like floating inside an infi... More
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Likely to Sell Out Paragon Lahaina Performance Sail
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Hawaii
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Superb4 reviews5
Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui performance sail f....
Private Tour
Sunset Cruise with the Whales on our Sailing Catamaran
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
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Likely to Sell Out Sunset Cruise with the Whales on our Sailing Catamaran
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Hawaii
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Superb50 reviews4.8
Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the 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
Likely to Sell Out 12pm Turtle Canyon Snorkel Adventure
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Hawaii
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Superb307 reviews4.8
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....
Private Tour
South Shore Open Sail from Kewalo Harbor Including Drinks
Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! Our sails always have complimentary drinks (alcoholic beverages available for adults 21+ with valid ID o... More
Private Tour
Likely to Sell Out South Shore Open Sail from Kewalo Harbor Including Drinks
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Hawaii
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Superb22 reviews4.8
Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconi....
Private Tour
Midmorning Whale Watch from Lahaina 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 Midmorning Whale Watch from Lahaina Harbor
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Hawaii
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Good3 reviews3.3
Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....
Private Tour
Polynesian Canoe Sunset Sail
Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and bec... More
Private Tour
Likely to Sell Out Polynesian Canoe Sunset Sail
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Hawaii
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Superb126 reviews4.9
Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (wa’a kaulua) off....
Private Tour
Waikiki Friday Night Fireworks Cruise + Fireworks Festival 3/15
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
Likely to Sell Out Waikiki Friday Night Fireworks Cruise + Fireworks Festival 3/15
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Hawaii
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Exellent31 reviews4.5
Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insig....
Private Tour
Sunset Sail from Ma'alaea Harbor in Maui
Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing catamaran, Ocean Spirit. It’s the perfect way to expe... More
Private Tour
Likely to Sell Out Sunset Sail from Ma'alaea Harbor in Maui
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Hawaii
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Superb215 reviews4.6
Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunse....
Private Tour
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests
Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experience Maui’s golden hour from the water. Departing from Ma‘alaea, this intimate evening cruise offers stunning views of the coast... More
Private Tour
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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Superb17 reviews4.8
Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experien....
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
Likely to Sell Out Private Catamaran Charter in Waikiki (1-6 Guests)
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Hawaii
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Superb22 reviews5
Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the....
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
Likely to Sell Out Deluxe Turtle Snorkeling Escapade at Waikiki
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Hawaii
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Superb8 reviews4.9
Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....
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 Private Catamaran Sunset Sail in Waikiki
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Hawaii
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Superb10 reviews5
Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foo....
Private Tour