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Top 10 Best Hawaii Sailing Trips

Found 117 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 3
 

Waikiki small group turtle snorkeling & sailing

(5 of 83 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
Start From $99.00
 
Waikiki small group turtle snorkeling & sailing Likely to Sell Out

Waikiki small group turtle snorkeling & sailing

  • Hawaii
  • Superb83 reviews5

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

    Free Cancellation
    Start From $99.00
 
 

Kona Tradewind Catamaran Day Sail

(4.8 of 42 reviews)

Set sail aboard the spacious Honi Olani catamaran for a scenic 90-minute adventure along the stunning Kona coastline. This relaxing daytime cruise is perfect for spotting Hawaii’s incredible marine wildlife—keep your eyes peel... More

Free Cancellation
Start From $119.00
 
Kona Tradewind Catamaran Day Sail Likely to Sell Out

Kona Tradewind Catamaran Day Sail

  • Hawaii
  • Superb42 reviews4.8

Set sail aboard the spacious Honi Olani catamaran for a scenic 90-minute adventure along the stunnin....

    Free Cancellation
    Start From $119.00
 
 

12pm Turtle Canyon Snorkel Adventure

(4.8 of 300 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

Special Offer
Free Cancellation
Start From $72.05
(Saving 15% ) $84.77
 
-15% 12pm Turtle Canyon Snorkel Adventure Likely to Sell Out

12pm Turtle Canyon Snorkel Adventure

  • Hawaii
  • Superb300 reviews4.8

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

    Special Offer
    Free Cancellation
    Start From $72.05
    (Saving 15% ) $84.77
 
 

Private Catamaran Sunset Sail in Waikiki

(5 of 8 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 $900.00
 
Private Catamaran Sunset Sail in Waikiki Likely to Sell Out

Private Catamaran Sunset Sail in Waikiki

  • Hawaii
  • Superb8 reviews5

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

    Free Cancellation
    Private Tour
    Start From $900.00
 
 

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

(4.8 of 210 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: Mā’alaea Harbor Likely to Sell Out

Molokini Snorkel and Performance Sail: Mā’alaea Harbor

  • Hawaii
  • Superb210 reviews4.8

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
 
 

Sunset Cruise & Whale Watching from Oahu

(4.6 of 64 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 $61.19
 
Sunset Cruise & Whale Watching from Oahu Likely to Sell Out

Sunset Cruise & Whale Watching from Oahu

  • Hawaii
  • Superb64 reviews4.6

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

    Free Cancellation
    Private Tour
    Start From $61.19
 
 

Sunset sail Aboard Manakai Catamaran

(5 of 11 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
Private Tour
Start From $49.82
 
Sunset sail Aboard Manakai Catamaran Likely to Sell Out

Sunset sail Aboard Manakai Catamaran

  • Hawaii
  • Superb11 reviews5

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

    Free Cancellation
    Private Tour
    Start From $49.82
 
 

Lāna'i Coast Snorkel and Sail

(5 of 2 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

Free Cancellation
Private Tour
Start From $216.22
 
Lāna'i Coast Snorkel and Sail Likely to Sell Out

Lāna'i Coast Snorkel and Sail

  • Hawaii
  • Superb2 reviews5

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

    Free Cancellation
    Private Tour
    Start From $216.22
 
 

Sunset Cruise with the Whales from Anaeho'omalu Bay

(4.8 of 46 reviews)

Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the biggest guests of all -- the Humpback Whales -- and you have perfect way to begin your evening in paradise! Cruise along the Kohala... More

Free Cancellation
Private Tour
Start From $165.00
 
Sunset Cruise with the Whales from Anaeho'omalu Bay Likely to Sell Out

Sunset Cruise with the Whales from Anaeho'omalu Bay

  • Hawaii
  • Superb46 reviews4.8

Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the b....

    Free Cancellation
    Private Tour
    Start From $165.00
 
 

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
Private Tour
Start From $100.22
 
Midday Whale Watch: Mā’alaea Harbor Likely to Sell Out

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
    Private Tour
    Start From $100.22
 
 

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

(5 of 685 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

Free Cancellation
Private Tour
Start From $189.00
 
Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure Likely to Sell Out

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

  • Hawaii
  • Superb685 reviews5

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

    Free Cancellation
    Private Tour
    Start From $189.00
 
 

Waikiki 3pm Tradewind Sail - Open Bar Included

(4.8 of 245 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
Private Tour
Start From $53.36
 
Waikiki 3pm Tradewind Sail - Open Bar Included Likely to Sell Out

Waikiki 3pm Tradewind Sail - Open Bar Included

  • Hawaii
  • Superb245 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $53.36
 
 

Waikiki Fireworks Cocktail Cruise

(4.3 of 6 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 $76.58
(Saving 10% ) $85.09
 
-10% Waikiki Fireworks Cocktail Cruise Likely to Sell Out

Waikiki Fireworks Cocktail Cruise

  • Hawaii
  • Exellent6 reviews4.3

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $76.58
    (Saving 10% ) $85.09
 
 

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

(4.7 of 17 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 $80.00
 
Waikiki Sunset Cruise Catamaran Boat Tour on Oahu Likely to Sell Out

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

  • Hawaii
  • Superb17 reviews4.7

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

    Free Cancellation
    Private Tour
    Start From $80.00
 
 

Whale Watching Sail in Honolulu with Open Bar

(5 of 2 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
Private Tour
Start From $49.00
 
Whale Watching Sail in Honolulu with Open Bar Likely to Sell Out

Whale Watching Sail in Honolulu with Open Bar

  • Hawaii
  • Superb2 reviews5

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

    Free Cancellation
    Private Tour
    Start From $49.00
 
 

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

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
    Private Tour
    Start From $69.99
 
 

Leila Na Pali Sunset Dinner Sail

(4.7 of 517 reviews)

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjoy appetizers, craft beer, wine, and Koloa Rum Mai-Tais aboard our sleek and spacious sailing catamaran, Leila. Your captain will s... More

Free Cancellation
Private Tour
Start From $263.82
 
Leila Na Pali Sunset Dinner Sail Likely to Sell Out

Leila Na Pali Sunset Dinner Sail

  • Hawaii
  • Superb517 reviews4.7

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjo....

    Free Cancellation
    Private Tour
    Start From $263.82
 
 

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 811 reviews)

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in the warmth of paradise. From the experienced snorkeler to those... More

Free Cancellation
Private Tour
Start From $202.59
 
Four Winds Molokini Snorkeling Tour from Maalaea Harbor Likely to Sell Out

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

  • Hawaii
  • Superb811 reviews4.7

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....

    Free Cancellation
    Private Tour
    Start From $202.59
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 712 reviews)

A three hour tour you won't want to miss! 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 a... More

Free Cancellation
Private Tour
Start From $136.19
 
Afternoon Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Afternoon Sail & Snorkel to the Captain Cook Monument

  • Hawaii
  • Superb712 reviews4.9

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathta....

    Free Cancellation
    Private Tour
    Start From $136.19
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 245 reviews)

A three hour tour you won't want to miss! 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 adve... More

Free Cancellation
Private Tour
Start From $136.19
 
Afternoon Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Afternoon Sail & Snorkel to the Captain Cook Monument

  • Hawaii
  • Superb245 reviews4.9

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtakin....

    Free Cancellation
    Private Tour
    Start From $136.19
 
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