Menu

Top 10 Best Hawaii Sailing Trips

Found 104 Sailing Trips activities in Hawaii. Sort by Popularity.
 
-5% 2-Hour Whale Watching from Oahu

2-Hour Whale Watching from Oahu

(4.6 of 898 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

Special Offer
Free Cancellation
Start From $48.17
(Saving 5% ) $50.71
 
-5% 2-Hour Whale Watching from Oahu

2-Hour Whale Watching from Oahu

  • Hawaii
  • Superb898 reviews4.6

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

    Special Offer
    Free Cancellation
    Start From $48.17
    (Saving 5% ) $50.71
 
 

Deluxe Na Pali Sunset Tour on the Lucky Lady

(4.7 of 1,276 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 $219.42
 
Deluxe Na Pali Sunset Tour on the Lucky Lady

Deluxe Na Pali Sunset Tour on the Lucky Lady

  • Hawaii
  • Superb1,276 reviews4.7

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

    Free Cancellation
    Start From $219.42
 
 

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

(4.9 of 1,891 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
  • Superb1,891 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
 
 

Waikiki Catamaran Adventure: Snorkel with Sea Turtles

(4.7 of 2,052 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

Waikiki Catamaran Adventure: Snorkel with Sea Turtles

  • Hawaii
  • Superb2,052 reviews4.7

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

    Free Cancellation
    Start From $108.62
 
 

Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran

(4.8 of 1,427 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
  • Superb1,427 reviews4.8

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
 
 

Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harbor

(4.7 of 136 reviews)

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

Free Cancellation
Start From $139.00
 
Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harbor Likely to Sell Out

Discover the Magic of Coral Garden’s Turtle Town - Maalaea Harb....

  • Hawaii
  • Superb136 reviews4.7

Avoid the over-crowded 50-100 passenger boats. We take 30-40 passengers. Treat yourself and your lov....

    Free Cancellation
    Start From $139.00
 
 

Leila Na Pali Sunset Dinner Sail

(4.7 of 458 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
  • Superb458 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
 
 

Oahu Sunset Tour on a 40 Foot Catamaran: Food and BYOB

(4.9 of 611 reviews)

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

Free Cancellation
Start From $54.95
 
Oahu Sunset Tour on a 40 Foot Catamaran: Food and BYOB Likely to Sell Out

Oahu Sunset Tour on a 40 Foot Catamaran: Food and BYOB

  • Hawaii
  • Superb611 reviews4.9

AFTER 36 DAYS THE KAHALA KAI IS BACK IN THE WATER AFTER A FULL AND COMPLETE REFURBURSHMENT! PLEASE C....

    Free Cancellation
    Start From $54.95
 
 

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 779 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 $202.59
 
Four Winds Molokini Snorkeling Tour from Maalaea Harbor Likely to Sell Out

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

  • Hawaii
  • Superb779 reviews4.7

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

    Free Cancellation
    Start From $202.59
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 457 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
  • Superb457 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 Sunset Cocktail Sail with Open Bar

(4.7 of 469 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
  • Superb469 reviews4.7

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
 
 

Turtles & Tacos Luxury Catamaran Snorkel

(5 of 12 reviews)

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

Free Cancellation
Start From $169.00
 
Turtles & Tacos Luxury Catamaran Snorkel Likely to Sell Out

Turtles & Tacos Luxury Catamaran Snorkel

  • Hawaii
  • Superb12 reviews5

As you step aboard the spacious catamaran, you're immediately greeted by the friendly crew, who are ....

    Free Cancellation
    Start From $169.00
 
 

Kona-Kohala Coast Sunset Sail by Catamaran

(4.7 of 338 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
  • Superb338 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
 
 

Na Pali Coast Kauai Snorkel and Sail

(4.8 of 508 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
  • Superb508 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
 
 

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

(4.8 of 140 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 $120.69
 
Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun Likely to Sell Out

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

  • Hawaii
  • Superb140 reviews4.8

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

    Free Cancellation
    Start From $120.69
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 669 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 Likely to Sell Out

Afternoon Sail & Snorkel to the Captain Cook Monument

  • Hawaii
  • Superb669 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
 
 

Sunset Boat Cruise: Swim and Cruise Waikiki

(4.7 of 444 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 and Cruise Waikiki Likely to Sell Out

Sunset Boat Cruise: Swim and Cruise Waikiki

  • Hawaii
  • Superb444 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
 
 

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

(4.7 of 901 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 $84.99
 
Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure Likely to Sell Out

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventu....

  • Hawaii
  • Superb901 reviews4.7

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

    Free Cancellation
    Start From $84.99
 
 

Day's End Cocktail Sunset Sail

(4.7 of 19 reviews)

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

Free Cancellation
Start From $149.00
 
Day's End Cocktail Sunset Sail Likely to Sell Out

Day's End Cocktail Sunset Sail

  • Hawaii
  • Superb19 reviews4.7

Bring the whole family along for this upscale evening of outstanding food and beverages. We set the ....

    Free Cancellation
    Start From $149.00
 
 

Sunset Sail Experience at Kona from Honokohau

(4.8 of 144 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
  • Superb144 reviews4.8

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

    Free Cancellation
    Start From $152.55
 
1 2 3 4 5
Booking.com
Booking.com
Booking.com