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Top 10 Best Hawaii Sailing Trips

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

Sunset sail Aboard Manakai Catamaran

(5 of 13 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

Free Cancellation
Start From $49.82
 
Sunset sail Aboard Manakai Catamaran

Sunset sail Aboard Manakai Catamaran

  • Hawaii
  • Superb13 reviews5

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

    Free Cancellation
    Start From $49.82
 
 

Whale Watching Sail in Honolulu with Open Bar

(5 of 8 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

Free Cancellation
Start From $49.00
 
Whale Watching Sail in Honolulu with Open Bar

Whale Watching Sail in Honolulu with Open Bar

  • Hawaii
  • Superb8 reviews5

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

    Free Cancellation
    Start From $49.00
 
 

12pm Turtle Canyon Snorkel Adventure

(4.8 of 304 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
Start From $84.77
 
12pm Turtle Canyon Snorkel Adventure

12pm Turtle Canyon Snorkel Adventure

  • Hawaii
  • Superb304 reviews4.8

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

    Free Cancellation
    Start From $84.77
 
 

Snorkel Sail Adventure off Ka'anapali Beach, Maui

(4.9 of 36 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 $192.17
 
Snorkel Sail Adventure off Ka'anapali Beach, Maui

Snorkel Sail Adventure off Ka'anapali Beach, Maui

  • Hawaii
  • Superb36 reviews4.9

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

    Free Cancellation
    Start From $192.17
 
 

Waikiki Friday Night Fireworks Cruise + Fireworks Festival 3/15

(4.5 of 31 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 $60.00
 
Waikiki Friday Night Fireworks Cruise + Fireworks Festival 3/15

Waikiki Friday Night Fireworks Cruise + Fireworks Festival 3/15

  • Hawaii
  • Exellent31 reviews4.5

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

    Free Cancellation
    Start From $60.00
 
 

Friday Night Catamaran Fireworks Sail with Open Bar

(4.8 of 56 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

Free Cancellation
Start From $90.01
 
Friday Night Catamaran Fireworks Sail with Open Bar

Friday Night Catamaran Fireworks Sail with Open Bar

  • Hawaii
  • Superb56 reviews4.8

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

    Free Cancellation
    Start From $90.01
 
 

Waikiki 3pm Tradewind Sail - Open Bar Included

(4.8 of 246 reviews)

Open Bar: Included with the price of General Admission until 8/31/2025 This is an excellent cruise for families and sailors wanting to relax and enjoy a beautiful afternoon in the sun. We'll be keeping a sharp eye out for dolphin... More

Free Cancellation
Start From $53.36
 
Waikiki 3pm Tradewind Sail - Open Bar Included

Waikiki 3pm Tradewind Sail - Open Bar Included

  • Hawaii
  • Superb246 reviews4.8

Open Bar: Included with the price of General Admission until 8/31/2025 This is an excellent cruise ....

    Free Cancellation
    Start From $53.36
 
 

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

(4.7 of 68 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
Start From $196.63
 
Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

  • Hawaii
  • Superb68 reviews4.7

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

    Free Cancellation
    Start From $196.63
 
 

Akialoa Mā’alaea Sunset Sail

(4.3 of 6 reviews)

Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sunset Sail offers a two-hour journey through the picturesque inter-island channel, showcasing the beauty of Maui, Lāna‘i, and Kah... More

Free Cancellation
Start From $108.11
 
Akialoa Mā’alaea Sunset Sail

Akialoa Mā’alaea Sunset Sail

  • Hawaii
  • Exellent6 reviews4.3

Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sun....

    Free Cancellation
    Start From $108.11
 
 

Friday Night Firework Cruise in Waikiki

(4.7 of 23 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
  • Superb23 reviews4.7

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
 
 

Daily Swim, Snorkel & Sail (Kewalo Harbor)

(4.7 of 23 reviews)

A beautiful swim and boat ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and whales (seasonal). Our snorkel, swim and sail is the perfect combination of warm sun, refreshing salty water, and b... More

Free Cancellation
Start From $70.00
 
Daily Swim, Snorkel & Sail (Kewalo Harbor)

Daily Swim, Snorkel & Sail (Kewalo Harbor)

  • Hawaii
  • Superb23 reviews4.7

A beautiful swim and boat ride along the south shore of Oahu, potentially viewing sea turtles, dolph....

    Free Cancellation
    Start From $70.00
 
 

Midday Whale Watch: Mā’alaea Harbor

(4.9 of 100 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
Start From $100.22
 
Midday Whale Watch: Mā’alaea Harbor

Midday Whale Watch: Mā’alaea Harbor

  • Hawaii
  • Superb100 reviews4.9

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

    Free Cancellation
    Start From $100.22
 
 

Waikoloa Catamaran Snorkel Sail Including Lunch

(4.6 of 105 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

Free Cancellation
Start From $189.95
 
Waikoloa Catamaran Snorkel Sail Including Lunch

Waikoloa Catamaran Snorkel Sail Including Lunch

  • Hawaii
  • Superb105 reviews4.6

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

    Free Cancellation
    Start From $189.95
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 533 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

Deluxe Sail & Snorkel to the Captain Cook Monument

  • Hawaii
  • Superb533 reviews4.9

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient la....

    Free Cancellation
    Start From $177.73
 
 

Half-Day Deluxe Molokini Snorkel Excursion in Maui

(4.9 of 103 reviews)

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical fish and coral reefs. Your adventure continues with a second snorkel... More

Free Cancellation
Start From $309.00
 
Half-Day Deluxe Molokini Snorkel Excursion in Maui

Half-Day Deluxe Molokini Snorkel Excursion in Maui

  • Hawaii
  • Superb103 reviews4.9

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-re....

    Free Cancellation
    Start From $309.00
 
 

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

Free Cancellation
Start From $165.00
 
Sunset Cocktail Cruise on our Sailing Catamaran

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....

    Free Cancellation
    Start From $165.00
 
 

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

(4.7 of 31 reviews)

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise lets you see whales (December through March), fish, even green s... More

Free Cancellation
Start From $156.79
 
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

  • Hawaii
  • Superb31 reviews4.7

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki....

    Free Cancellation
    Start From $156.79
 
 

Honolulu Sailing and Snorkeling Activity

(4.7 of 31 reviews)

You’re guaranteed to see an array of endemic reef fish, colorful corals, and other unique marine creatures that call the Hawaiian islands home. ... More

Free Cancellation
Start From $105.00
 
Honolulu Sailing and Snorkeling Activity Likely to Sell Out

Honolulu Sailing and Snorkeling Activity

  • Hawaii
  • Superb31 reviews4.7

You’re guaranteed to see an array of endemic reef fish, colorful corals, and other unique marine c....

    Free Cancellation
    Start From $105.00
 
 

Polynesian Canoe Sunset Sail

(4.9 of 126 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 $250.00
 
Polynesian Canoe Sunset Sail Likely to Sell Out

Polynesian Canoe Sunset Sail

  • Hawaii
  • Superb126 reviews4.9

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

    Free Cancellation
    Start From $250.00
 
 

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

(4.8 of 297 reviews)

-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel equipment -Fun, friendly, lifeguard certified crew -BYOB (Bring your own Beverage. No glass bottles)... More

Special Offer
Free Cancellation
Start From $89.10
(Saving 10% ) $99.00
 
-10% Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon Likely to Sell Out

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

  • Hawaii
  • Superb297 reviews4.8

-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel....

    Special Offer
    Free Cancellation
    Start From $89.10
    (Saving 10% ) $99.00
 
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