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Top 10 Best Hawaii Sailing Trips

Found 104 Sailing Trips activities in Hawaii. Sort by Popularity.
 

Deluxe Na Pali Sunset Tour on the Lucky Lady

(4.7 of 992 reviews)

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

Free Cancellation
Start From $206.55
 
Deluxe Na Pali Sunset Tour on the Lucky Lady

Deluxe Na Pali Sunset Tour on the Lucky Lady

  • Hawaii
  • Superb992 reviews4.7

Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredib....

    Free Cancellation
    Start From $206.55
 
 

Moana’s Sunset Cocktail Sail along Oahu's Waikiki Coast

(4.9 of 1,263 reviews)

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

Free Cancellation
Start From $69.99
 
Moana’s Sunset Cocktail Sail along Oahu's Waikiki Coast

Moana’s Sunset Cocktail Sail along Oahu's Waikiki Coast

  • Hawaii
  • Superb1,263 reviews4.9

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Wa....

    Free Cancellation
    Start From $69.99
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 326 reviews)

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

Free Cancellation
Start From $177.72
 
Deluxe Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Deluxe Sail & Snorkel to the Captain Cook Monument

  • Hawaii
  • Superb326 reviews4.9

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient la....

    Free Cancellation
    Start From $177.72
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 588 reviews)

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

Free Cancellation
Start From $134.64
 
Afternoon Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Afternoon Sail & Snorkel to the Captain Cook Monument

  • Hawaii
  • Superb588 reviews4.9

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathta....

    Free Cancellation
    Start From $134.64
 
 

Hawaiian Sea Turtle Snorkel Sail from Waikiki with Lunch Included

(4.7 of 1,931 reviews)

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

Free Cancellation
Start From $125.43
 
Hawaiian Sea Turtle Snorkel Sail from Waikiki with Lunch Included Likely to Sell Out

Hawaiian Sea Turtle Snorkel Sail from Waikiki with Lunch Included

  • Hawaii
  • Superb1,931 reviews4.7

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea ....

    Free Cancellation
    Start From $125.43
 
 

OAHU CATAMARANS Sunset Tour on a 40 Foot Catamaran FOOD & BYOB!!!

(4.9 of 414 reviews)

Join us for a beautiful Hawaiian sunset!! We have been sailing the Pacific waters off of the Island of Oahu since 1985 and are proud to boast a perfect safety record. Passengers are limited to 50% of Coast Guard rated capacity for... More

Free Cancellation
Start From $49.99
 
OAHU CATAMARANS Sunset Tour on a 40 Foot Catamaran FOOD & BYOB!!! Likely to Sell Out

OAHU CATAMARANS Sunset Tour on a 40 Foot Catamaran FOOD & BYOB!!!

  • Hawaii
  • Superb414 reviews4.9

Join us for a beautiful Hawaiian sunset!! We have been sailing the Pacific waters off of the Island ....

    Free Cancellation
    Start From $49.99
 
 

Four Winds II Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 697 reviews)

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

Free Cancellation
Start From $191.78
 
Four Winds II Molokini Snorkeling Tour from Maalaea Harbor Likely to Sell Out

Four Winds II Molokini Snorkeling Tour from Maalaea Harbor

  • Hawaii
  • Superb697 reviews4.7

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....

    Free Cancellation
    Start From $191.78
 
 

Moana’s Guided Turtle Snorkel & Sailing Adventure at Waikiki

(4.7 of 783 reviews)

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

Free Cancellation
Start From $69.99
 
Moana’s Guided Turtle Snorkel & Sailing Adventure at Waikiki Likely to Sell Out

Moana’s Guided Turtle Snorkel & Sailing Adventure at Waikiki

  • Hawaii
  • Superb783 reviews4.7

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On....

    Free Cancellation
    Start From $69.99
 
 

Sunset Boat Cruise (Swim & Cruise)

(4.7 of 359 reviews)

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

Special Offer
Free Cancellation
Start From $42.30
(Saving 10% ) $47.00
 
-10% Sunset Boat Cruise (Swim & Cruise) Likely to Sell Out

Sunset Boat Cruise (Swim & Cruise)

  • Hawaii
  • Superb359 reviews4.7

There is no better place to swim than Waikiki and no better way to watch the sunset than from the Wa....

    Special Offer
    Free Cancellation
    Start From $42.30
    (Saving 10% ) $47.00
 
 

[Blue Ocean Snorkeling] Waikiki Turtle Canyon Snorkeling 6 in 1

(4.8 of 64 reviews)

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

Free Cancellation
Start From $98.00
 
[Blue Ocean Snorkeling] Waikiki Turtle Canyon Snorkeling 6 in 1 Likely to Sell Out

[Blue Ocean Snorkeling] Waikiki Turtle Canyon Snorkeling 6 in 1

  • Hawaii
  • Superb64 reviews4.8

Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....

    Free Cancellation
    Start From $98.00
 
 

Na Pali Coast Kauai Snorkel and Sail

(4.8 of 447 reviews)

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

Free Cancellation
Start From $275.28
 
Na Pali Coast Kauai Snorkel and Sail Likely to Sell Out

Na Pali Coast Kauai Snorkel and Sail

  • Hawaii
  • Superb447 reviews4.8

Families and groups-- say YES to an action-packed, five-hour ocean adventure aboard our gorgeous and....

    Free Cancellation
    Start From $275.28
 
 

Kaneohe Sandbar Snorkeling Tour, 2nd Tour

(4.9 of 362 reviews)

Highlight #1 Family friendly package! Fun and memorable time for all. / Paddle boards / Zayak for children / Water toys / Snorkeling gears / Life jacket / Soft drinks / Snacks & fruits Highlight #2 Bring your own food & drinks ... More

Free Cancellation
Start From $159.00
 
Kaneohe Sandbar Snorkeling Tour, 2nd Tour Likely to Sell Out

Kaneohe Sandbar Snorkeling Tour, 2nd Tour

  • Hawaii
  • Superb362 reviews4.9

Highlight #1 Family friendly package! Fun and memorable time for all. / Paddle boards / Zayak for c....

    Free Cancellation
    Start From $159.00
 
 

Snorkel with Manta Rays Guaranteed

(4.8 of 556 reviews)

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village. Travel Channel says “its one of the top ten things to do in your life time”, and Sea Paradise has been offering its guests th... More

Free Cancellation
Start From $140.03
 
Snorkel with Manta Rays Guaranteed Likely to Sell Out

Snorkel with Manta Rays Guaranteed

  • Hawaii
  • Superb556 reviews4.8

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village.....

    Free Cancellation
    Start From $140.03
 
 

Kona-Kohala Coast Sunset Sail by Catamaran

(4.7 of 282 reviews)

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

Free Cancellation
Start From $152.55
 
Kona-Kohala Coast Sunset Sail by Catamaran Likely to Sell Out

Kona-Kohala Coast Sunset Sail by Catamaran

  • Hawaii
  • Superb282 reviews4.7

Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamar....

    Free Cancellation
    Start From $152.55
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 385 reviews)

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

Free Cancellation
Start From $177.72
 
Deluxe Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Deluxe Sail & Snorkel to the Captain Cook Monument

  • Hawaii
  • Superb385 reviews4.9

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient ....

    Free Cancellation
    Start From $177.72
 
 

Honolulu Sunset Sail Kewalo Harbor

(4.9 of 12 reviews)

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic beverages). Sail the south shore from Kaka'ako Waterfront to Waikiki, with beautiful views o... More

Free Cancellation
Start From $60.00
 
Honolulu Sunset Sail Kewalo Harbor Likely to Sell Out

Honolulu Sunset Sail Kewalo Harbor

  • Hawaii
  • Superb12 reviews4.9

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....

    Free Cancellation
    Start From $60.00
 
 

Leila Na Pali Sunset Dinner Sail

(4.7 of 373 reviews)

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

Free Cancellation
Start From $240.86
 
Leila Na Pali Sunset Dinner Sail Likely to Sell Out

Leila Na Pali Sunset Dinner Sail

  • Hawaii
  • Superb373 reviews4.7

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjo....

    Free Cancellation
    Start From $240.86
 
 

Sunset and Manta Ray Snorkel Adventure

(4.9 of 661 reviews)

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of a lifetime - snorkeling with the majestic manta rays!  Upon arriving, receive an in... More

Free Cancellation
Start From $141.26
 
Sunset and Manta Ray Snorkel Adventure Likely to Sell Out

Sunset and Manta Ray Snorkel Adventure

  • Hawaii
  • Superb661 reviews4.9

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail....

    Free Cancellation
    Start From $141.26
 
 

Turtle Town 3-Hour Snorkel and Sail Adventure from Maalaea Harbor

(4.6 of 85 reviews)

Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Maui's snorkeling and boat trips are often overpriced and target tourists who don't know any better. Treat yourself and your loved ones on a beautiful Charmi... More

Free Cancellation
Start From $139.00
 
Turtle Town 3-Hour Snorkel and Sail Adventure from Maalaea Harbor Likely to Sell Out

Turtle Town 3-Hour Snorkel and Sail Adventure from Maalaea Harbor

  • Hawaii
  • Superb85 reviews4.6

Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Maui's snorkeling and boat ....

    Free Cancellation
    Start From $139.00
 
 

Kealakekua Snorkel and Sail Adventure

(5 of 555 reviews)

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 garde... More

Free Cancellation
Start From $173.57
 
Kealakekua Snorkel and Sail Adventure Likely to Sell Out

Kealakekua Snorkel and Sail Adventure

  • Hawaii
  • Superb555 reviews5

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast.  Scan the....

    Free Cancellation
    Start From $173.57
 
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