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Top 10 Best Hawaii Sailing Trips

Found 103 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 4
 

Polynesian Canoe Morning Sail

(5 of 16 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
Start From $200.00
 
Polynesian Canoe Morning Sail

Polynesian Canoe Morning Sail

  • Hawaii
  • Superb16 reviews5

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

    Free Cancellation
    Start From $200.00
 
 

Pau Hana Sunset Cocktail Cruise

(4.8 of 48 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 $165.00
 
Pau Hana Sunset Cocktail Cruise

Pau Hana Sunset Cocktail Cruise

  • Hawaii
  • Superb48 reviews4.8

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

    Free Cancellation
    Start From $165.00
 
 

Honolulu BYOB Fireworks Boat Cruise

(4.5 of 25 reviews)

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring your favorite beverages and join us for Waikiki's weekly fireworks displ... More

Free Cancellation
Start From $75.00
 
Honolulu BYOB Fireworks Boat Cruise

Honolulu BYOB Fireworks Boat Cruise

  • Hawaii
  • Exellent25 reviews4.5

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insig....

    Free Cancellation
    Start From $75.00
 
 

1.5-Hour Koa Kai Adventure Whale Watch

(5 of 2 reviews)

Experience an up-close encounter with our winter residents, the Humpback Whale! These beautiful creatures return to Maui every year to birth their young. During this trip, you will get a chance to hear the whale’s unique songs a... More

Free Cancellation
Start From $79.00
 
1.5-Hour Koa Kai Adventure Whale Watch Likely to Sell Out

1.5-Hour Koa Kai Adventure Whale Watch

  • Hawaii
  • Superb2 reviews5

Experience an up-close encounter with our winter residents, the Humpback Whale! These beautiful crea....

    Free Cancellation
    Start From $79.00
 
 

4-Hour Koa Kai Molokini Adventure Snorkel

(5 of 10 reviews)

Join us on this 3-hour snorkel adventure at Maui's most iconic snorkeling location, Molokini Crater. You will be treated to exceptional service and premium equipment. Koa Kai is a multi-purpose raft that creates a unique close-u... More

Free Cancellation
Start From $169.00
 
4-Hour Koa Kai Molokini Adventure Snorkel Likely to Sell Out

4-Hour Koa Kai Molokini Adventure Snorkel

  • Hawaii
  • Superb10 reviews5

Join us on this 3-hour snorkel adventure at Maui's most iconic snorkeling location, Molokini Crater.....

    Free Cancellation
    Start From $169.00
 
 

Private Catamaran Sunset Sail in Waikiki

(5 of 6 reviews)

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large ... More

Free Cancellation
Private Tour
Start From $300.00
 
Private Catamaran Sunset Sail in Waikiki Likely to Sell Out

Private Catamaran Sunset Sail in Waikiki

  • Hawaii
  • Superb6 reviews5

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foo....

    Free Cancellation
    Private Tour
    Start From $300.00
 
 

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 $110.00
 
Deluxe Turtle Snorkeling Escapade at Waikiki Likely to Sell Out

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 $110.00
 
 

Coral Gardens Snorkel & Whale Watch

(4.8 of 39 reviews)

Sail through Maui’s renowned Au‘Au Channel, a world-class whale-watching destination famous for its calm waters and breathtaking scenery. During whale season, this prime playground offers unmatched opportunities to spot majest... More

Free Cancellation
Private Tour
Start From $129.73
 
Coral Gardens Snorkel & Whale Watch Likely to Sell Out

Coral Gardens Snorkel & Whale Watch

  • Hawaii
  • Superb39 reviews4.8

Sail through Maui’s renowned Au‘Au Channel, a world-class whale-watching destination famous for ....

    Free Cancellation
    Private Tour
    Start From $129.73
 
 

Sunset Sail Experience by Catamaran in Waikiki

(5 of 4 reviews)

Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled catamaran. Take in the views of Honolulu skyline from offshore Waikiki and feel the warmth of the setting Hawaiian sun and tropical ... More

Free Cancellation
Private Tour
Start From $92.31
 
Sunset Sail Experience by Catamaran in Waikiki Likely to Sell Out

Sunset Sail Experience by Catamaran in Waikiki

  • Hawaii
  • Superb4 reviews5

Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled ca....

    Free Cancellation
    Private Tour
    Start From $92.31
 
 

Waikiki Friday Firework Catamaran Tour

(4.7 of 27 reviews)

The Blue Ocean Waikiki luxury catamaran is the perfect place for guests to enjoy following a breathtaking fireworks just outside the Hilton Hawaiian Village. Every Friday at 6:45pm, you have the opportunity to watch a spectacular ... More

Free Cancellation
Private Tour
Start From $69.99
 
Waikiki Friday Firework Catamaran Tour Likely to Sell Out

Waikiki Friday Firework Catamaran Tour

  • Hawaii
  • Superb27 reviews4.7

The Blue Ocean Waikiki luxury catamaran is the perfect place for guests to enjoy following a breatht....

    Free Cancellation
    Private Tour
    Start From $69.99
 
 

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

(4.7 of 67 reviews)

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour from rainforest to reef combines views high above Honolulu to snorkeling off a catamaran off Waikiki. Explore lush rainforest and... More

Free Cancellation
Private Tour
Start From $196.63
 
Half Day Oahu Combo Adventure: Bike, Sail and Snorkel Likely to Sell Out

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

  • Hawaii
  • Superb67 reviews4.7

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour....

    Free Cancellation
    Private Tour
    Start From $196.63
 
 

Private Catamaran Charter in Waikiki (7-12 Guests)

(4.7 of 67 reviews)

(IMPORTANT: Make sure you have over 6 guests selected to see availability for this activity. If you have 1-6 guests, you can book under our other listing labeled for 1-6 guests.) This 48-foot catamaran has a sleek low-profile des... More

Free Cancellation
Private Tour
Start From $1,200.00
 
Private Catamaran Charter in Waikiki (7-12 Guests) Likely to Sell Out

Private Catamaran Charter in Waikiki (7-12 Guests)

  • Hawaii
  • Superb67 reviews4.7

(IMPORTANT: Make sure you have over 6 guests selected to see availability for this activity. If you ....

    Free Cancellation
    Private Tour
    Start From $1,200.00
 
 

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

(4.9 of 7 reviews)

Experience “Amore” a 42-foot Boston Whaler with unmatched state-of-the-art features make the flagship 420 Outrage a boat like no other. From the expansive bow with innovative seating galore, to the beautifully designed convert... More

Free Cancellation
Private Tour
Start From $284.09
 
2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests Likely to Sell Out

2-Hour Maalaea Luxury Powerboat Sunset Cruise for up to 6 Guests

  • Hawaii
  • Superb7 reviews4.9

Experience “Amore” a 42-foot Boston Whaler with unmatched state-of-the-art features make the fla....

    Free Cancellation
    Private Tour
    Start From $284.09
 
 

Friday Night Catamaran Fireworks Sail with Open Bar

(4.9 of 53 reviews)

Who doesn't love fireworks, especially with all inclusive drinks? The famous weekly Hilton Hawaiian Village fireworks display seen from the water feels like you’re right under the action! There's no better way to kick off the we... More

Free Cancellation
Private Tour
Start From $92.57
 
Friday Night Catamaran Fireworks Sail with Open Bar Likely to Sell Out

Friday Night Catamaran Fireworks Sail with Open Bar

  • Hawaii
  • Superb53 reviews4.9

Who doesn't love fireworks, especially with all inclusive drinks? The famous weekly Hilton Hawaiian ....

    Free Cancellation
    Private Tour
    Start From $92.57
 
 

Waikiki Panorama Sail: Search for Hawaiian Sea Turtles

(4.7 of 32 reviews)

Snap beautiful photos of Waikiki on this 90-minute sail, where you'll cruise past famous Waikiki Beach and out towards Diamond Head crater. The cruise departs from Kewalo Basin by Ala Moana Beach Park, and includes snacks, non-alc... More

Free Cancellation
Private Tour
Start From $82.96
 
Waikiki Panorama Sail: Search for Hawaiian Sea Turtles Likely to Sell Out

Waikiki Panorama Sail: Search for Hawaiian Sea Turtles

  • Hawaii
  • Superb32 reviews4.7

Snap beautiful photos of Waikiki on this 90-minute sail, where you'll cruise past famous Waikiki Bea....

    Free Cancellation
    Private Tour
    Start From $82.96
 
 

Oahu, Waikiki Sunset Catamaran Boat Tour

(4.9 of 14 reviews)

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from December-March, of course, the annual humpback whales!... More

Free Cancellation
Private Tour
Start From $83.40
 
Oahu, Waikiki Sunset Catamaran Boat Tour Likely to Sell Out

Oahu, Waikiki Sunset Catamaran Boat Tour

  • Hawaii
  • Superb14 reviews4.9

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē....

    Free Cancellation
    Private Tour
    Start From $83.40
 
 

Diamond Head Sunset Sail

(4.7 of 15 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 luxury yacht. Immerse yourself in a gorgeous Hawaiian sunset the only way, from the... More

Free Cancellation
Private Tour
Start From $695.00
 
Diamond Head Sunset Sail Likely to Sell Out

Diamond Head Sunset Sail

  • Hawaii
  • Superb15 reviews4.7

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 $695.00
 
 

South Shore Open Sail from Kewalo Harbor Including Drinks

(5 of 14 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 $47.50
 
South Shore Open Sail from Kewalo Harbor Including Drinks Likely to Sell Out

South Shore Open Sail from Kewalo Harbor Including Drinks

  • Hawaii
  • Superb14 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 $47.50
 
 

Waikiki Private Sunset Sail Romantic and Private

(5 of 14 reviews)

Adventure Awaits aboard our Fabulous 48' private yacht. Bring along your family and friends for a spectacular Hawaiian sunset on your private yacht. Get a chance to see whales, dolphins and sea turtles. Immerse yourself in a bucke... More

Free Cancellation
Private Tour
Start From $799.00
 
Waikiki Private Sunset Sail Romantic and Private Likely to Sell Out

Waikiki Private Sunset Sail Romantic and Private

  • Hawaii
  • Superb14 reviews5

Adventure Awaits aboard our Fabulous 48' private yacht. Bring along your family and friends for a sp....

    Free Cancellation
    Private Tour
    Start From $799.00
 
 

#1 eFoil 2 hr group + 2 hr wing foil or windsurf or kayak lesson

(5 of 4 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 $299.00
 
#1 eFoil 2 hr group + 2 hr wing foil or windsurf or kayak lesson Likely to Sell Out

#1 eFoil 2 hr group + 2 hr wing foil or windsurf or kayak lesson

  • Hawaii
  • Superb4 reviews5

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

    Free Cancellation
    Private Tour
    Start From $299.00
 
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