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Top 10 Best Hawaii Sailing Trips

Found 104 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 4
 

Friday Night Firework Cruise in Waikiki

(4.8 of 21 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
Start From $69.99
 
Friday Night Firework Cruise in Waikiki

Friday Night Firework Cruise in Waikiki

  • Hawaii
  • Superb21 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
    Start From $69.99
 
 

Snorkel Sail Adventure off Ka'anapali Beach, Maui

(4.9 of 9 reviews)

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, an endangered Hawaiian Green Sea turtle called a ‘Honu’. A hot buff... More

Free Cancellation
Start From $172.85
 
Snorkel Sail Adventure off Ka'anapali Beach, Maui

Snorkel Sail Adventure off Ka'anapali Beach, Maui

  • Hawaii
  • Superb9 reviews4.9

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You w....

    Free Cancellation
    Start From $172.85
 
 

2hr Luxury Private Sailing Catamaran for 7-12 People

(4.9 of 9 reviews)

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

Free Cancellation
Private Tour
Start From $1,495.00
 
2hr Luxury Private Sailing Catamaran for 7-12 People

2hr Luxury Private Sailing Catamaran for 7-12 People

  • Hawaii
  • Superb9 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $1,495.00
 
 

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
Private Tour
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
    Private Tour
    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
Private Tour
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
    Private Tour
    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
Private Tour
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
    Private Tour
    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
Private Tour
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
    Private Tour
    Start From $79.00
 
 

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
 
 

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
 
 

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
Private Tour
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
    Private Tour
    Start From $169.00
 
 

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
 
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