Sailing Trips in Hawaii
Top 10 Best Hawaii Sailing Trips
Found 108 Sailing Trips activities in Hawaii. Sort by Popularity.Deluxe Na Pali Sunset Tour on the Lucky Lady
Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredible scenery topped off with a spectacular sunset. Look for dolphins, whales, and other marine critters as you sip a drink, snap som... More
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                                    Deluxe Na Pali Sunset Tour on the Lucky Lady
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                      Hawaii
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                                            Superb1,440 reviews4.7
Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredib....
Free Cancellation
(Saving 10% )
Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast
All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Waikiki Sunset Cruise, an unmatched experience complete with premium drinks, indescribable views, and music. As we sail alongside Oa... More
 
                  
                                    Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast
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                      Hawaii
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                                            Superb2,123 reviews4.9
All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Wa....
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed
2025 VIATOR TOP 20 BEST EXCURSIONS award in the UNITED STATES including the TOP RATED SNORKEL EXCURSION in the US!! Best value in Waikiki! See turtles GUARANTEED or receive a FULL REFUND! Brand new PREMIUM snorkel equipment inclu... More
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                                    Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed
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                      Hawaii
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                                            Superb1,214 reviews4.9
2025 VIATOR TOP 20 BEST EXCURSIONS award in the UNITED STATES including the TOP RATED SNORKEL EXCURS....
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Waikiki Turtle Snorkeling Boat Tour and Adventure
**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!** Join us for a **2-hour snorkeling adventure** at **Turtle Canyon**, one of Oahu’s top snorkeling spots! Cruise along the stunning **Waikiki coastlin... More
 
                  
                                    Waikiki Turtle Snorkeling Boat Tour and Adventure
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                      Hawaii
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                                            Superb1,197 reviews4.7
**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!** Join us for a **2-ho....
Day's End Cocktail Sunset Sail
Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. This isn’t a dinner cruise, it’s happy hour reimagined (a true ‘pau hana’ at sea) with handcrafted drin... More
 
                  
                                    Day's End Cocktail Sunset Sail
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                      Hawaii
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                                            Superb56 reviews4.7
Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most sce....
Waikoloa Signature Catamaran Sunset Sail
Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamaran. Catch the moment the sun slips below the horizon. You may even see the green flash. Board from Anaehoomalu Bay (A-Bay) to sail... More
 
                  
                                    Waikoloa Signature Catamaran Sunset Sail
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                      Hawaii
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                                            Superb382 reviews4.7
Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamar....
Kona Catamaran Sunset Sail
Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. Catch the moment the sun slips below the horizon...you may even see the green flash. Enjoy the blue Pacific Ocean and maybe catch ... More
 
                  
                                    Kona Catamaran Sunset Sail
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                      Hawaii
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                                            Superb184 reviews4.8
Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. ....
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB
2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for a beautiful Hawaiian sunset!! We have been sailing the Pacific waters off of the Island of Oahu since 1985... More
 
                  
                                    Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB
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                      Hawaii
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                                            Superb773 reviews4.9
2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE ....
Turtles & Tacos Luxury Catamaran Snorkel
Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island flavor. Cruise aboard our spacious 65’ catamaran and snorkel alongside Hawaiian green sea turtles and colorful tropical fish at ... More
 
                  
                                    Turtles & Tacos Luxury Catamaran Snorkel
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                      Hawaii
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                                            Superb82 reviews4.8
Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island ....
Sunset Boat Cruise: Swim and Cruise Waikiki
There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way to experience a Hawaiian sunset than from the ocean, with the iconic Waikiki coastline as your backdrop. As the sun begins to se... More
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                                    Sunset Boat Cruise: Swim and Cruise Waikiki
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                      Hawaii
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                                            Superb515 reviews4.7
There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way....
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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
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                  Likely to Sell Out                  Leila Na Pali Sunset Dinner Sail
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                      Hawaii
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                                            Superb510 reviews4.7
Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjo....
Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed
Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and threats to the Hawaiian Sea Turtles "Honu" (Learning pr... More
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                  Likely to Sell Out                  Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed
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                      Hawaii
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                                            Superb2,106 reviews4.7
Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea ....
Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran
This is the best way to start your day on Oahu! Complimentary cold brew coffee from Honolulu’s local favorite ARVO Café, served with a selection of Anahola Granola bars—Original, Chocolate Chip, Tropical, and Mango & Ginger. ... More
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                  Likely to Sell Out                  Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran
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                      Hawaii
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                                            Superb1,586 reviews4.8
This is the best way to start your day on Oahu! Complimentary cold brew coffee from Honolulu’s loc....
Na Pali Coast Kauai Snorkel and Sail
Families and groups-- say YES to an action-packed, five-hour ocean adventure aboard our gorgeous and comfortable 50’ Kauai-built sailing catamaran, Leila. Let’s explore the cliffs, valleys, sea caves and wildlife of the Napali... More
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                  Likely to Sell Out                  Na Pali Coast Kauai Snorkel and Sail
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                      Hawaii
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                                            Superb530 reviews4.8
Families and groups-- say YES to an action-packed, five-hour ocean adventure aboard our gorgeous and....
Waikiki Sunset Cocktail Sail with Open Bar
This is our most popular sail for the fun-loving crowd! All drinks are included on this lively cruise! Strangers become fast friends on this one regardless if your cruising solo or with a crew! We provide juice, soda, bottled wate... More
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                  Likely to Sell Out                  Waikiki Sunset Cocktail Sail with Open Bar
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                      Hawaii
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                                            Superb527 reviews4.8
This is our most popular sail for the fun-loving crowd! All drinks are included on this lively cruis....
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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                                            Superb35 reviews4.9
While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You w....
'Alihilani Sunset Sail
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
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                  Likely to Sell Out                  'Alihilani Sunset Sail
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                      Hawaii
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                                            Superb83 reviews4.9
We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sa....
 Likely to Sell Out
                      
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                  Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon
-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel equipment -Fun, friendly, lifeguard certified crew -BYOB (Bring your own Beverage. No glass bottles)... More
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 Likely to Sell Out
                  
                  Likely to Sell Out                  Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon
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                      Hawaii
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                                            Superb278 reviews4.8
-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel....
Free Cancellation
(Saving 16% )
Deluxe Sail & Snorkel to the Captain Cook Monument
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 adventure will begin in the turquoise waters a... More
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                  Likely to Sell Out                  Deluxe Sail & Snorkel to the Captain Cook Monument
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                      Hawaii
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                                            Superb519 reviews4.9
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient la....
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step aboard, you're greeted by the friendly crew who welcome you with warm aloha spirit. The c... More
 Likely to Sell Out
                  
                  Likely to Sell Out                  Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
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                      Hawaii
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                                            Superb39 reviews4.8
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....
