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Top 10 Best Hawaii Sailing Trips

Found 100 Sailing Trips activities in Hawaii. Sort by Popularity.
 

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

(4.9 of 1,713 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 $84.99
 
Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast

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

  • Hawaii
  • Superb1,713 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 $84.99
 
 

Deluxe Na Pali Sunset Tour on the Lucky Lady

(4.7 of 1,129 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 $211.99
 
Deluxe Na Pali Sunset Tour on the Lucky Lady

Deluxe Na Pali Sunset Tour on the Lucky Lady

  • Hawaii
  • Superb1,129 reviews4.7

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

    Free Cancellation
    Start From $211.99
 
 

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

(4.9 of 536 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 $54.95
 
OAHU CATAMARAN Sunset Tour on a 40 Foot Catamaran FOOD & BYOB!!!

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

  • Hawaii
  • Superb536 reviews4.9

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

    Free Cancellation
    Start From $54.95
 
 

Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran

(4.7 of 1,304 reviews)

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

Free Cancellation
Start From $84.77
 
Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran

Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran

  • Hawaii
  • Superb1,304 reviews4.7

This is the best way to start your day on Oahu! Come snorkel with us at Turtle Canyon, a green sea t....

    Free Cancellation
    Start From $84.77
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 640 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 $136.19
 
Afternoon Sail & Snorkel to the Captain Cook Monument

Afternoon Sail & Snorkel to the Captain Cook Monument

  • Hawaii
  • Superb640 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 $136.19
 
 

Leila Na Pali Sunset Dinner Sail

(4.7 of 419 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
  • Superb419 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
 
 

Na Pali Coast Kauai Snorkel and Sail

(4.8 of 487 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
  • Superb487 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
 
 

2-Hour Whale Watching from Oahu

(4.5 of 583 reviews)

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

Free Cancellation
Start From $47.00
 
2-Hour Whale Watching from Oahu Likely to Sell Out

2-Hour Whale Watching from Oahu

  • Hawaii
  • Exellent583 reviews4.5

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a ....

    Free Cancellation
    Start From $47.00
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 410 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 $177.73
 
Deluxe Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Deluxe Sail & Snorkel to the Captain Cook Monument

  • Hawaii
  • Superb410 reviews4.9

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

    Free Cancellation
    Start From $177.73
 
 

Waikiki Catamaran Adventure: Snorkel with Sea Turtles

(4.7 of 1,992 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 $108.62
 
Waikiki Catamaran Adventure: Snorkel with Sea Turtles Likely to Sell Out

Waikiki Catamaran Adventure: Snorkel with Sea Turtles

  • Hawaii
  • Superb1,992 reviews4.7

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

    Free Cancellation
    Start From $108.62
 
 

Sunset Boat Cruise: Swim and Cruise Waikiki

(4.7 of 418 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

Free Cancellation
Start From $47.00
 
Sunset Boat Cruise: Swim and Cruise Waikiki Likely to Sell Out

Sunset Boat Cruise: Swim and Cruise Waikiki

  • Hawaii
  • Superb418 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
    Start From $47.00
 
 

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 743 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 Molokini Snorkeling Tour from Maalaea Harbor Likely to Sell Out

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

  • Hawaii
  • Superb743 reviews4.7

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

    Free Cancellation
    Start From $191.78
 
 

Sunset and Manta Ray Snorkel Adventure

(4.9 of 712 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
  • Superb712 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
 
 

Kona-Kohala Coast Sunset Sail by Catamaran

(4.7 of 310 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
  • Superb310 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
 
 

Sunset Sail Experience at Kona from Honokohau

(4.8 of 125 reviews)

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

Free Cancellation
Start From $152.55
 
Sunset Sail Experience at Kona from Honokohau Likely to Sell Out

Sunset Sail Experience at Kona from Honokohau

  • Hawaii
  • Superb125 reviews4.8

Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. ....

    Free Cancellation
    Start From $152.55
 
 

Waikiki Sunset Sail on Hawea Catamaran

(4.8 of 139 reviews)

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

Free Cancellation
Start From $72.96
 
Waikiki Sunset Sail on Hawea Catamaran Likely to Sell Out

Waikiki Sunset Sail on Hawea Catamaran

  • Hawaii
  • Superb139 reviews4.8

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....

    Free Cancellation
    Start From $72.96
 
 

Waikiki Sunset Cocktail Sail with Open Bar

(4.8 of 427 reviews)

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

Free Cancellation
Start From $85.00
 
Waikiki Sunset Cocktail Sail with Open Bar Likely to Sell Out

Waikiki Sunset Cocktail Sail with Open Bar

  • Hawaii
  • Superb427 reviews4.8

This is our most popular sail for the fun-loving crowd! All drinks are included on this lively cruis....

    Free Cancellation
    Start From $85.00
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 410 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 $179.27
 
Deluxe Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Deluxe Sail & Snorkel to the Captain Cook Monument

  • Hawaii
  • Superb410 reviews4.9

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

    Free Cancellation
    Start From $179.27
 
 

Snorkel with Manta Rays Guaranteed

(4.8 of 614 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 $141.57
 
Snorkel with Manta Rays Guaranteed Likely to Sell Out

Snorkel with Manta Rays Guaranteed

  • Hawaii
  • Superb614 reviews4.8

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

    Free Cancellation
    Start From $141.57
 
 

Sunset Sail from Ma'alaea Harbor

(4.6 of 189 reviews)

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

Free Cancellation
Start From $133.05
 
Sunset Sail from Ma'alaea Harbor Likely to Sell Out

Sunset Sail from Ma'alaea Harbor

  • Hawaii
  • Superb189 reviews4.6

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunse....

    Free Cancellation
    Start From $133.05
 
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