Sailing Trips in Hawaii
Top 10 Best Hawaii Sailing Trips
Found 97 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

Deluxe Na Pali Sunset Tour on the Lucky Lady
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Hawaii
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Superb1,300 reviews4.7
Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredib....
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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Superb1,917 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! 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

Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran
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Hawaii
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Superb1,439 reviews4.8
This is the best way to start your day on Oahu! Complimentary cold brew coffee from Honolulu’s loc....
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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Superb917 reviews4.6
Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a ....
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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Superb2,062 reviews4.7
Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea ....
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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Superb139 reviews4.7
Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your lov....
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed
AFTER 36 DAYS THE KAHALA KAI IS BACK IN THE WATER AFTER A FULL AND COMPLETE REFURBURSHMENT! PLEASE COME SEE OUR COMPLETELY REIMAGINED VESSEL! Best value in Waikiki! See turtles GUARANTEED or receive a FULL REFUND! Brand new PREMI... More

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed
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Hawaii
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Superb829 reviews4.9
AFTER 36 DAYS THE KAHALA KAI IS BACK IN THE WATER AFTER A FULL AND COMPLETE REFURBURSHMENT! PLEASE C....
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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Superb462 reviews4.7
Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjo....
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

Na Pali Coast Kauai Snorkel and Sail
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Hawaii
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Superb509 reviews4.8
Families and groups-- say YES to an action-packed, five-hour ocean adventure aboard our gorgeous and....
Oahu Catamaran Waikiki Sunset on 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 Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB
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Hawaii
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Superb620 reviews4.9
AFTER 36 DAYS THE KAHALA KAI IS BACK IN THE WATER AFTER A FULL AND COMPLETE REFURBURSHMENT! PLEASE C....
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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Superb671 reviews4.9
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathta....
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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Superb474 reviews4.8
This is our most popular sail for the fun-loving crowd! All drinks are included on this lively cruis....
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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Superb20 reviews4.8
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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Superb461 reviews4.9
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient la....

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll g... More
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Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
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Hawaii
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Superb206 reviews4.9
Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....
Free Cancellation
(Saving 15% )
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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Superb341 reviews4.7
Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamar....
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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Superb783 reviews4.7
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....
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

Sunset Boat Cruise: Swim and Cruise Waikiki
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Hawaii
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Superb446 reviews4.7
There is no better place to swim than Waikiki and no better way to watch the sunset than from the Wa....
Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor
Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the Lahaina harbor wildfires, moored outside of the harbor breakwall. Now operating from Ma'alaea Harbor, we invite you to join our cap... More

Sunset Sail on a Small Charming Hawaiian Catamaran Maalaea Harbor
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Hawaii
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Superb54 reviews4.7
Experience the resilience and spirit of Maui aboard the Winona, a vessel that bravely survived the L....
Day's End Cocktail Sunset Sail
Bring the whole family along for this upscale evening of outstanding food and beverages. We set the sails and chase the sun as it sets into the distant horizon of the azure water of the South Pacific. This casual dining experience... More

Day's End Cocktail Sunset Sail
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Hawaii
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Superb21 reviews4.7
Bring the whole family along for this upscale evening of outstanding food and beverages. We set the ....