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Top 10 Best Hawaii Sailing Trips

Found 110 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 3
 

Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming

(4.9 of 196 reviews)

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that s... More

Free Cancellation
Start From $79.00
 
Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming

Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming

  • Hawaii
  • Superb196 reviews4.9

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....

    Free Cancellation
    Start From $79.00
 
 
-30% Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

(4.9 of 239 reviews)

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far away enough from the bustling travelers and crowded beaches, the crystal-clear water will br... More

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Start From $34.99
(Saving 30% ) $49.99
 
-30% Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

  • Hawaii
  • Superb239 reviews4.9

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your....

    Special Offer
    Free Cancellation
    Start From $34.99
    (Saving 30% ) $49.99
 
 
-inf% Whale Watching Sail in Honolulu with Open Bar

Whale Watching Sail in Honolulu with Open Bar

(5 of 13 reviews)

Observe the majestic humpback whales during their migration from December to March on this 1.5-hour sail in Honolulu. Experience the beauty of Oahu's coastline while searching for dolphins and sea turtles in their natural habitat.... More

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Start From $53.36
(Saving inf% ) $0.00
 
-inf% Whale Watching Sail in Honolulu with Open Bar

Whale Watching Sail in Honolulu with Open Bar

  • Hawaii
  • Superb13 reviews5

Observe the majestic humpback whales during their migration from December to March on this 1.5-hour ....

    Special Offer
    Free Cancellation
    Start From $53.36
    (Saving inf% ) $0.00
 
 
-inf% Lāna'i Coast Snorkel and Sail

Lāna'i Coast Snorkel and Sail

(5 of 24 reviews)

Nobody knows the waters of Maui better than our crew. Let us host you on our Gold Coast catamaran as we explore and snorkel the incredible coastline of Maui. Departing daily from 9:30 am - 2:30 pm. We'll check the conditions for t... More

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Start From $216.22
(Saving inf% ) $0.00
 
-inf% Lāna'i Coast Snorkel and Sail

Lāna'i Coast Snorkel and Sail

  • Hawaii
  • Superb24 reviews5

Nobody knows the waters of Maui better than our crew. Let us host you on our Gold Coast catamaran as....

    Special Offer
    Free Cancellation
    Start From $216.22
    (Saving inf% ) $0.00
 
 
-inf% 2-Hour Oahu Sunset Catamaran Sail

2-Hour Oahu Sunset Catamaran Sail

(4.8 of 125 reviews)

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. Sip a cocktail and enjoy warm wind in your hair as you scan for dolphins and listen for ... More

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Start From $130.00
(Saving inf% ) $0.00
 
-inf% 2-Hour Oahu Sunset Catamaran Sail

2-Hour Oahu Sunset Catamaran Sail

  • Hawaii
  • Superb125 reviews4.8

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran fr....

    Special Offer
    Free Cancellation
    Start From $130.00
    (Saving inf% ) $0.00
 
 
-inf% Molokini Snorkel and Performance Sail: Mā’alaea Harbor

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

(4.8 of 215 reviews)

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredible snorkeling destinations. The unique, crescent shaped crater is a natural marine preserve, and is home to over 250 species of t... More

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Start From $200.00
(Saving inf% ) $0.00
 
-inf% Molokini Snorkel and Performance Sail: Mā’alaea Harbor

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

  • Hawaii
  • Superb215 reviews4.8

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....

    Special Offer
    Free Cancellation
    Start From $200.00
    (Saving inf% ) $0.00
 
 
-inf% Midday Whale Watch: Mā’alaea Harbor

Midday Whale Watch: Mā’alaea Harbor

(4.9 of 103 reviews)

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, the ‘Au ‘au channel off the coast of Maui boasts the greatest number. ... More

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Start From $100.22
(Saving inf% ) $0.00
 
-inf% Midday Whale Watch: Mā’alaea Harbor

Midday Whale Watch: Mā’alaea Harbor

  • Hawaii
  • Superb103 reviews4.9

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....

    Special Offer
    Free Cancellation
    Start From $100.22
    (Saving inf% ) $0.00
 
 
-inf% Kona Tradewind Catamaran Day Sail

Kona Tradewind Catamaran Day Sail

(4.8 of 43 reviews)

Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing catamaran. Feel the trade winds fill the sails as you glide across the water, taking in panoramic views of volcanic cliffs, sparklin... More

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Start From $89.00
(Saving inf% ) $0.00
 
-inf% Kona Tradewind Catamaran Day Sail

Kona Tradewind Catamaran Day Sail

  • Hawaii
  • Superb43 reviews4.8

Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing ca....

    Special Offer
    Free Cancellation
    Start From $89.00
    (Saving inf% ) $0.00
 
 
-inf% Waikoloa Catamaran Snorkel Sail Including Lunch

Waikoloa Catamaran Snorkel Sail Including Lunch

(4.7 of 106 reviews)

Set sail from Anaeho‘omalu Bay on a 3-hour snorkel and cruise adventure along Waikoloa’s beautiful Kohala Coast. Aboard the spacious Spirit of Aloha catamaran, enjoy a smooth, comfortable ride to one of the region’s best sno... More

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Free Cancellation
Start From $189.00
(Saving inf% ) $0.00
 
-inf% Waikoloa Catamaran Snorkel Sail Including Lunch

Waikoloa Catamaran Snorkel Sail Including Lunch

  • Hawaii
  • Superb106 reviews4.7

Set sail from Anaeho‘omalu Bay on a 3-hour snorkel and cruise adventure along Waikoloa’s beautif....

    Special Offer
    Free Cancellation
    Start From $189.00
    (Saving inf% ) $0.00
 
 

BYOB Friday Night Fireworks Cruise

(4.3 of 6 reviews)

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki. You'll enjoy the view of the city lights and be in awe with this unobstructed view of fireworks from the water! With plenty of... More

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Start From $138.95
(Saving inf% ) $0.00
 
-inf% BYOB Friday Night Fireworks Cruise Likely to Sell Out

BYOB Friday Night Fireworks Cruise

  • Hawaii
  • Exellent6 reviews4.3

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki....

    Special Offer
    Free Cancellation
    Start From $138.95
    (Saving inf% ) $0.00
 
 

Small Group Waikiki Sunset Sailing Tour

(4.9 of 111 reviews)

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come and enjoy the Golden hour with your loved ones to make memories of a lifetime ,why go with overc... More

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Start From $99.00
(Saving inf% ) $0.00
 
-inf% Small Group Waikiki Sunset Sailing Tour Likely to Sell Out

Small Group Waikiki Sunset Sailing Tour

  • Hawaii
  • Superb111 reviews4.9

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it tha....

    Special Offer
    Free Cancellation
    Start From $99.00
    (Saving inf% ) $0.00
 
 

Friday Night Catamaran Fireworks Sail with Open Bar

(4.8 of 55 reviews)

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night, you’ll glide along the coastline and experience an exclusive o... More

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Free Cancellation
Start From $90.01
(Saving inf% ) $0.00
 
-inf% Friday Night Catamaran Fireworks Sail with Open Bar Likely to Sell Out

Friday Night Catamaran Fireworks Sail with Open Bar

  • Hawaii
  • Superb55 reviews4.8

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village di....

    Special Offer
    Free Cancellation
    Start From $90.01
    (Saving inf% ) $0.00
 
 

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

(5 of 703 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 gardens u... More

Special Offer
Free Cancellation
Start From $189.00
(Saving inf% ) $0.00
 
-inf% Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure Likely to Sell Out

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

  • Hawaii
  • Superb703 reviews5

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

    Special Offer
    Free Cancellation
    Start From $189.00
    (Saving inf% ) $0.00
 
 

'Alihilani Golden Hour Sail

(4.9 of 85 reviews)

We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sails. Our spacious catamarans make for a luxurious experience, allowing for incredible views of Maui and the inter islands from the... More

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Free Cancellation
Start From $107.10
(Saving inf% ) $0.00
 
-inf% 'Alihilani Golden Hour Sail Likely to Sell Out

'Alihilani Golden Hour Sail

  • Hawaii
  • Superb85 reviews4.9

We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sa....

    Special Offer
    Free Cancellation
    Start From $107.10
    (Saving inf% ) $0.00
 
 

Hawaiian Canoe Sailing Experience in Maui

(4.7 of 60 reviews)

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning Hawaiian history and culture. Cold water and snorkel gear are... More

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Free Cancellation
Start From $179.00
(Saving inf% ) $0.00
 
-inf% Hawaiian Canoe Sailing Experience in Maui Likely to Sell Out

Hawaiian Canoe Sailing Experience in Maui

  • Hawaii
  • Superb60 reviews4.7

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour include....

    Special Offer
    Free Cancellation
    Start From $179.00
    (Saving inf% ) $0.00
 
 

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

(4.6 of 23 reviews)

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the island like never before as you set sail from the only pier in W... More

Special Offer
Free Cancellation
Start From $151.00
(Saving inf% ) $0.00
 
-inf% Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village Likely to Sell Out

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

  • Hawaii
  • Superb23 reviews4.6

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-bui....

    Special Offer
    Free Cancellation
    Start From $151.00
    (Saving inf% ) $0.00
 
 

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People

(5 of 1 review)

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. Yo... More

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Free Cancellation
Private Tour
Start From $1,595.00
(Saving inf% ) $0.00
 
-inf% 3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People Likely to Sell Out

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People

  • Hawaii
  • Superb1 review5

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $1,595.00
    (Saving inf% ) $0.00
 
 

Sunset Cocktail Cruise on our Sailing Catamaran

(4.8 of 62 reviews)

Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohala Coast aboard our legendary sailing catamaran Seasmoke. This cruise includes unlimited soft drinks, tropical juices, beers, wines... More

Special Offer
Free Cancellation
Private Tour
Start From $165.00
(Saving inf% ) $0.00
 
-inf% Sunset Cocktail Cruise on our Sailing Catamaran Likely to Sell Out

Sunset Cocktail Cruise on our Sailing Catamaran

  • Hawaii
  • Superb62 reviews4.8

Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohal....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $165.00
    (Saving inf% ) $0.00
 
 

Sunset sail Aboard Manakai Catamaran

(5 of 15 reviews)

Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Woody Brown—a true piece of Hawaiian sailing history. With a smaller guest capacity and open-deck layout, it offers an intimate, lai... More

Special Offer
Free Cancellation
Private Tour
Start From $49.82
(Saving inf% ) $0.00
 
-inf% Sunset sail Aboard Manakai Catamaran Likely to Sell Out

Sunset sail Aboard Manakai Catamaran

  • Hawaii
  • Superb15 reviews5

Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Wood....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $49.82
    (Saving inf% ) $0.00
 
 

Waikiki Fireworks Cocktail Cruise

(4.4 of 7 reviews)

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a beautiful fireworks cruise that will give you a night to remember. ... More

Special Offer
Free Cancellation
Private Tour
Start From $85.09
(Saving inf% ) $0.00
 
-inf% Waikiki Fireworks Cocktail Cruise Likely to Sell Out

Waikiki Fireworks Cocktail Cruise

  • Hawaii
  • Exellent7 reviews4.4

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a b....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $85.09
    (Saving inf% ) $0.00
 
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