Sailing Trips in Hawaii
Top 10 Best Hawaii Sailing Trips
Found 103 Sailing Trips activities in Hawaii. Sort by Popularity.2-Hour Whale Watching from Oahu
Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never forget to see this amazing creature. If you are lucky enough, you might see dolphins, sea ... More

2-Hour Whale Watching from Oahu
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Hawaii
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Superb831 reviews4.6
Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a ....
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

Deluxe Na Pali Sunset Tour on the Lucky Lady
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Hawaii
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Superb1,242 reviews4.7
Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredib....
Waikiki Catamaran Adventure: Snorkel with Sea Turtles
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

Waikiki Catamaran Adventure: Snorkel with Sea Turtles
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Hawaii
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Superb2,040 reviews4.7
Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea ....
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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Superb1,862 reviews4.9
All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Wa....
Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran
This is the best way to start your day on Oahu! Come snorkel with us at Turtle Canyon, a green sea turtle cleaning station. Our crew shows you not only turtles but also hidden creatures such as he’e (octopus) and ka hoku kai (st... More

Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran
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Hawaii
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Superb1,398 reviews4.8
This is the best way to start your day on Oahu! Come snorkel with us at Turtle Canyon, a green sea t....
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

Leila Na Pali Sunset Dinner Sail
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Hawaii
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Superb449 reviews4.7
Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjo....

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
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Sunset Cruise & Whale Watching from Oahu
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Hawaii
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Exellent57 reviews4.5
Experience the breathtaking beauty of nature with our Sunset Whale Watch excursion. Join us for an u....
Free Cancellation
(Saving 10% )
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

Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harb....
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Hawaii
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Superb131 reviews4.6
Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your lov....
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

Four Winds Molokini Snorkeling Tour from Maalaea Harbor
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Hawaii
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Superb771 reviews4.7
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....
Turtles & Tacos Luxury Catamaran Snorkel
As you step aboard the spacious catamaran, you're immediately greeted by the friendly crew, who are eager to guide you on an unforgettable journey. The vessel is equipped with all the amenities you need for a comfortable and enjoy... More

Turtles & Tacos Luxury Catamaran Snorkel
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Hawaii
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Superb11 reviews5
As you step aboard the spacious catamaran, you're immediately greeted by the friendly crew, who are ....
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

Deluxe Sail & Snorkel to the Captain Cook Monument
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Hawaii
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Superb445 reviews4.9
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient la....
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

Afternoon Sail & Snorkel to the Captain Cook Monument
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Hawaii
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Superb663 reviews4.9
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathta....
Oahu Sunset Tour on a 40 Foot Catamaran: Food and BYOB
AFTER 36 DAYS THE KAHALA KAI IS BACK IN THE WATER AFTER A FULL AND COMPLETE REFURBURSHMENT! PLEASE COME SEE OUR COMPLETELY REIMAGINED VESSEL! Join us for a beautiful Hawaiian sunset!! We have been sailing the Pacific waters off o... More

Oahu Sunset Tour on a 40 Foot Catamaran: Food and BYOB
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Hawaii
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Superb598 reviews4.9
AFTER 36 DAYS THE KAHALA KAI IS BACK IN THE WATER AFTER A FULL AND COMPLETE REFURBURSHMENT! PLEASE C....
Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun
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

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun
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Hawaii
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Superb132 reviews4.8
Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....

Sunset Boat Cruise: Swim and Cruise Waikiki
There is no better place to swim than Waikiki and no better way to watch the sunset than from the Waikiki Coastline. Be amazed by the natural beauty as day turns to night and twilight blankets us with an array of amazing colors ... More
Free Cancellation
(Saving 10% )

Sunset Boat Cruise: Swim and Cruise Waikiki
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Hawaii
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Superb437 reviews4.7
There is no better place to swim than Waikiki and no better way to watch the sunset than from the Wa....
Free Cancellation
(Saving 10% )
Kona-Kohala Coast Sunset Sail by Catamaran
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

Kona-Kohala Coast Sunset Sail by Catamaran
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Hawaii
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Superb334 reviews4.7
Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamar....
Sunset Sail from Ma'alaea Harbor
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 ex... More

Sunset Sail from Ma'alaea Harbor
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Hawaii
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Superb203 reviews4.6
Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunse....
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

Waikiki Sunset Cocktail Sail with Open Bar
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Hawaii
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Superb456 reviews4.7
This is our most popular sail for the fun-loving crowd! All drinks are included on this lively cruis....
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... More

Deluxe Sail & Snorkel to the Captain Cook Monument
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Hawaii
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Superb432 reviews4.9
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient ....
Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure
Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for your snorkel adventure, you’re choosing the tour with the most professionalis... More

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventu....
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Hawaii
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Superb885 reviews4.7
Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On....