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Top 10 Best Hawaii Sailing Trips

Found 100 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 3
 

Pau Hana Sunset Cocktail Cruise

(4.9 of 47 reviews)

Enjoy the warm tropical breezes and unparalleled views of the Big Island aboard a well-appointed catamaran. This cruise includes unlimited soft drinks, tropical juices, beers, wines, cocktails and a variety of appetizers.. Great f... More

Free Cancellation
Start From $160.00
 
Pau Hana Sunset Cocktail Cruise

Pau Hana Sunset Cocktail Cruise

  • Hawaii
  • Superb47 reviews4.9

Enjoy the warm tropical breezes and unparalleled views of the Big Island aboard a well-appointed cat....

    Free Cancellation
    Start From $160.00
 
 

2-Hour Oahu Sunset Catamaran Sail

(4.8 of 77 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

Free Cancellation
Start From $121.00
 
2-Hour Oahu Sunset Catamaran Sail

2-Hour Oahu Sunset Catamaran Sail

  • Hawaii
  • Superb77 reviews4.8

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

    Free Cancellation
    Start From $121.00
 
 

Luxury Diamond Head Sunset Sail

(5 of 3 reviews)

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sail features a two hour cruise aboard a private 50' luxury yacht. Immerse yourself in a gorgeous Hawaiian sunset the only way, from... More

Free Cancellation
Private Tour
Start From $1,398.00
 
Luxury Diamond Head Sunset Sail

Luxury Diamond Head Sunset Sail

  • Hawaii
  • Superb3 reviews5

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sa....

    Free Cancellation
    Private Tour
    Start From $1,398.00
 
 

Molokini Snorkel and Performance Sail from Ma'alaea Harbor

(4.9 of 156 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

Free Cancellation
Private Tour
Start From $200.00
 
Molokini Snorkel and Performance Sail from Ma'alaea Harbor

Molokini Snorkel and Performance Sail from Ma'alaea Harbor

  • Hawaii
  • Superb156 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $200.00
 
 

Small Group Waikiki Sunset Sailing Tour

(4.9 of 65 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

Free Cancellation
Private Tour
Start From $99.00
 
Small Group Waikiki Sunset Sailing Tour

Small Group Waikiki Sunset Sailing Tour

  • Hawaii
  • Superb65 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

12pm Turtle Canyon Snorkel Adventure

(4.7 of 242 reviews)

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life? Our snorkel guides help you feel confid... More

Free Cancellation
Private Tour
Start From $96.30
 
12pm Turtle Canyon Snorkel Adventure

12pm Turtle Canyon Snorkel Adventure

  • Hawaii
  • Superb242 reviews4.7

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....

    Free Cancellation
    Private Tour
    Start From $96.30
 
 

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

(4.8 of 122 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
Private Tour
Start From $99.00
 
Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

  • Hawaii
  • Superb122 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

'Alihilani Sunset Sail from Ma'alaea Harbor

(5 of 66 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 while wa... More

Free Cancellation
Private Tour
Start From $112.90
 
'Alihilani Sunset Sail from Ma'alaea Harbor

'Alihilani Sunset Sail from Ma'alaea Harbor

  • Hawaii
  • Superb66 reviews5

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

    Free Cancellation
    Private Tour
    Start From $112.90
 
 

Deluxe Turtle Snorkeling Escapade at Waikiki

(4.8 of 4 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
Private Tour
Start From $99.00
 
Deluxe Turtle Snorkeling Escapade at Waikiki

Deluxe Turtle Snorkeling Escapade at Waikiki

  • Hawaii
  • Superb4 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

#1 eFoil, wing foil, windsurf or kiteboard lesson in Kailua, Oahu

(5 of 3 reviews)

You will receive special Ocean Safety training prior to your adventure. Our two way radio helmets help us to give precise specific info as needed so you learn faster and safer. We will share with you the best locations to launch f... More

Free Cancellation
Private Tour
Start From $175.00
 
#1 eFoil, wing foil, windsurf or kiteboard lesson in Kailua, Oahu

#1 eFoil, wing foil, windsurf or kiteboard lesson in Kailua, Oahu

  • Hawaii
  • Superb3 reviews5

You will receive special Ocean Safety training prior to your adventure. Our two way radio helmets he....

    Free Cancellation
    Private Tour
    Start From $175.00
 
 

Sunset Cruise & Whale Watching from Oahu

(3.4 of 10 reviews)

Experience the breathtaking beauty of nature with our Sunset Whale Watch excursion. Join us for an unforgettable journey as we set sail into the golden hues of the evening sky, where you'll have the chance to witness majestic whal... More

Free Cancellation
Private Tour
Start From $57.00
 
Sunset Cruise & Whale Watching from Oahu Likely to Sell Out

Sunset Cruise & Whale Watching from Oahu

  • Hawaii
  • Good10 reviews3.4

Experience the breathtaking beauty of nature with our Sunset Whale Watch excursion. Join us for an u....

    Free Cancellation
    Private Tour
    Start From $57.00
 
 

Hilton Hawaiian Village Sunset Cocktail Cruise

(3.4 of 10 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

Free Cancellation
Private Tour
Start From $151.00
 
Hilton Hawaiian Village Sunset Cocktail Cruise Likely to Sell Out

Hilton Hawaiian Village Sunset Cocktail Cruise

  • Hawaii
  • Good10 reviews3.4

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

    Free Cancellation
    Private Tour
    Start From $151.00
 
 

Friday Night Firework Cruise in Waikiki

(4.8 of 19 reviews)

After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fireworks explode over the city’s skyline, truly making this the ultimate party experience. Enjoy the Premium drinks of your choice ... More

Free Cancellation
Private Tour
Start From $69.99
 
Friday Night Firework Cruise in Waikiki Likely to Sell Out

Friday Night Firework Cruise in Waikiki

  • Hawaii
  • Superb19 reviews4.8

After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fire....

    Free Cancellation
    Private Tour
    Start From $69.99
 
 

Polynesian Canoe Sunset Sail

(4.9 of 117 reviews)

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and b... More

Free Cancellation
Private Tour
Start From $220.00
 
Polynesian Canoe Sunset Sail Likely to Sell Out

Polynesian Canoe Sunset Sail

  • Hawaii
  • Superb117 reviews4.9

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....

    Free Cancellation
    Private Tour
    Start From $220.00
 
 

Day's End Cocktail Sunset Sail

(4.5 of 10 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
Private Tour
Start From $169.00
 
Day's End Cocktail Sunset Sail Likely to Sell Out

Day's End Cocktail Sunset Sail

  • Hawaii
  • Exellent10 reviews4.5

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

    Free Cancellation
    Private Tour
    Start From $169.00
 
 

Waikiki Fireworks Cruise

(5 of 4 reviews)

Our boat is designed for a maximum of 12 people, ensuring an intimate and private experience for all our guests. Our small group size allows for more personalized and attentive service from our crew, ensuring that you have a memor... More

Free Cancellation
Private Tour
Start From $55.00
 
Waikiki Fireworks Cruise Likely to Sell Out

Waikiki Fireworks Cruise

  • Hawaii
  • Superb4 reviews5

Our boat is designed for a maximum of 12 people, ensuring an intimate and private experience for all....

    Free Cancellation
    Private Tour
    Start From $55.00
 
 

Waikiki small group turtle snorkeling & sailing

(5 of 51 reviews)

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples or families who are up at the crack of dawn during their Hawaiian vacation due to time zone changes. As we start out our tour from ... More

Free Cancellation
Private Tour
Start From $99.00
 
Waikiki small group turtle snorkeling & sailing Likely to Sell Out

Waikiki small group turtle snorkeling & sailing

  • Hawaii
  • Superb51 reviews5

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples o....

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

South Shore Open Sail from Kewalo Harbor Including Drinks

(5 of 8 reviews)

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! We are a 49-passenger beautiful yellow and red retired Waikiki Beach catamaran now operating from Kewalo... More

Free Cancellation
Private Tour
Start From $45.00
 
South Shore Open Sail from Kewalo Harbor Including Drinks Likely to Sell Out

South Shore Open Sail from Kewalo Harbor Including Drinks

  • Hawaii
  • Superb8 reviews5

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconi....

    Free Cancellation
    Private Tour
    Start From $45.00
 
 

Luxury Catamaran Whale Watch

(5 of 11 reviews)

Come join us to observe the playful habits of Maui's most consistent return visitor - the humpback whale. The waters off West Maui have long been the favored vacation spot of these massive marine mammals. The Alii Nui provides max... More

Free Cancellation
Private Tour
Start From $159.00
 
Luxury Catamaran Whale Watch Likely to Sell Out

Luxury Catamaran Whale Watch

  • Hawaii
  • Superb11 reviews5

Come join us to observe the playful habits of Maui's most consistent return visitor - the humpback w....

    Free Cancellation
    Private Tour
    Start From $159.00
 
 

Midday Sail with the Whales Ma'alaea

(4.9 of 99 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

Free Cancellation
Private Tour
Start From $91.89
 
Midday Sail with the Whales Ma'alaea Likely to Sell Out

Midday Sail with the Whales Ma'alaea

  • Hawaii
  • Superb99 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $91.89
 
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