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Top 10 Best Hawaii Sailing Trips

Found 109 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 5
 

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

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
 
 
-10% Polynesian Canoe Morning Sail

Polynesian Canoe Morning Sail

(5 of 18 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

Special Offer
Free Cancellation
Private Tour
Start From $180.00
(Saving 10% ) $200.00
 
-10% Polynesian Canoe Morning Sail

Polynesian Canoe Morning Sail

  • Hawaii
  • Superb18 reviews5

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $180.00
    (Saving 10% ) $200.00
 
 
-inf% Private 5Hr Island Tour with 2.5Hr Sail and Snorkel with Turtles

Private 5Hr Island Tour with 2.5Hr Sail and Snorkel with Turtles

(5 of 3 reviews)

This 8 hour private tour includes a 5 hour custom tour of the island, and a 2.5 hour sail on a sailboat including swimming or snorkeling with turtles. You can pick and choose the stops on the island tour and go at your own pace. ... More

Special Offer
Free Cancellation
Private Tour
Start From $1,200.00
(Saving inf% ) $0.00
 
-inf% Private 5Hr Island Tour with 2.5Hr Sail and Snorkel with Turtles

Private 5Hr Island Tour with 2.5Hr Sail and Snorkel with Turtles

  • Hawaii
  • Superb3 reviews5

This 8 hour private tour includes a 5 hour custom tour of the island, and a 2.5 hour sail on a sailb....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $1,200.00
    (Saving inf% ) $0.00
 
 

Sunset sail Aboard Manakai Catamaran

(5 of 21 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

Special Offer
Free Cancellation
Private Tour
Start From $49.82
(Saving inf% ) $0.00
 
-inf% Sunset sail Aboard Manakai Catamaran Likely to Sell Out

Sunset sail Aboard Manakai Catamaran

  • Hawaii
  • Superb21 reviews5

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $49.82
    (Saving inf% ) $0.00
 
 

Morning Whale Watch: Lahaina Harbor

(4.9 of 29 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

Special Offer
Free Cancellation
Private Tour
Start From $100.22
(Saving inf% ) $0.00
 
-inf% Morning Whale Watch: Lahaina Harbor Likely to Sell Out

Morning Whale Watch: Lahaina Harbor

  • Hawaii
  • Superb29 reviews4.9

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $100.22
    (Saving inf% ) $0.00
 
 

Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

(5 of 13 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

Special Offer
Free Cancellation
Private Tour
Start From $53.36
(Saving inf% ) $0.00
 
-inf% Waikiki Beach Whale Watching: Catamaran Sail & Open Bar Likely to Sell Out

Waikiki Beach Whale Watching: Catamaran Sail & Open Bar

  • Hawaii
  • Superb13 reviews5

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $53.36
    (Saving inf% ) $0.00
 
 

Waikiki Heritage and Diamond Head Wildlife Sail

(4.7 of 32 reviews)

Set sail along the iconic Waikiki coastline for a laid-back 1.5-hour afternoon on the water. This experience emphasizes relaxation, scenic views of Oʻahu’s south shore, and casual wildlife watching—keep an eye out for dolphin... More

Special Offer
Free Cancellation
Private Tour
Start From $119.00
(Saving inf% ) $0.00
 
-inf% Waikiki Heritage and Diamond Head Wildlife Sail Likely to Sell Out

Waikiki Heritage and Diamond Head Wildlife Sail

  • Hawaii
  • Superb32 reviews4.7

Set sail along the iconic Waikiki coastline for a laid-back 1.5-hour afternoon on the water. This ex....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $119.00
    (Saving inf% ) $0.00
 
 

Midday Whale Watch: Mā’alaea Harbor

(4.9 of 104 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

Special Offer
Free Cancellation
Private Tour
Start From $100.22
(Saving inf% ) $0.00
 
-inf% Midday Whale Watch: Mā’alaea Harbor Likely to Sell Out

Midday Whale Watch: Mā’alaea Harbor

  • Hawaii
  • Superb104 reviews4.9

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $100.22
    (Saving inf% ) $0.00
 
 

#1 eFoil 1.25 hr or 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

Special Offer
Free Cancellation
Private Tour
Start From $450.00
(Saving inf% ) $0.00
 
-inf% #1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson Likely to Sell Out

#1 eFoil 1.25 hr or 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....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $450.00
    (Saving inf% ) $0.00
 
 

Waikiki Private Sunset Sail Romantic and Private

(5 of 4 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

Special Offer
Free Cancellation
Private Tour
Start From $799.00
(Saving inf% ) $0.00
 
-inf% Waikiki Private Sunset Sail Romantic and Private Likely to Sell Out

Waikiki Private Sunset Sail Romantic and Private

  • Hawaii
  • Superb4 reviews5

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $799.00
    (Saving inf% ) $0.00
 
 

Waikiki Sail and Snorkel Adventure Best of Hawaii 2023

(4 of 4 reviews)

Immerse yourself in a vibrant underwater wonderland as you snorkel through coral reefs teeming with an array of tropical fish. The clear waters of Turtle Canyons reveal a kaleidoscope of colors, from dazzling schools of fish to vi... More

Special Offer
Free Cancellation
Private Tour
Start From $695.00
(Saving inf% ) $0.00
 
-inf% Waikiki Sail and Snorkel Adventure Best of Hawaii 2023 Likely to Sell Out

Waikiki Sail and Snorkel Adventure Best of Hawaii 2023

  • Hawaii
  • Very Good4 reviews4

Immerse yourself in a vibrant underwater wonderland as you snorkel through coral reefs teeming with ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $695.00
    (Saving inf% ) $0.00
 
 

3 Hour Luxury Private Sailing Catamaran for 7-12 People

(4 of 4 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

Special Offer
Free Cancellation
Private Tour
Start From $1,995.00
(Saving inf% ) $0.00
 
-inf% 3 Hour Luxury Private Sailing Catamaran for 7-12 People Likely to Sell Out

3 Hour Luxury Private Sailing Catamaran for 7-12 People

  • Hawaii
  • Very Good4 reviews4

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $1,995.00
    (Saving inf% ) $0.00
 
 

Private Whale Watching Sailing Adventure

(3.5 of 2 reviews)

From the comfort of your private luxury yacht, enjoy an amazing experience with Hawaii’s humpback whales. Departing near Waikiki, enjoy a leisurely sail against the majestic backdrop of Diamond Head as you scan the water for maj... More

Special Offer
Free Cancellation
Private Tour
Start From $695.00
(Saving inf% ) $0.00
 
-inf% Private Whale Watching Sailing Adventure Likely to Sell Out

Private Whale Watching Sailing Adventure

  • Hawaii
  • Good2 reviews3.5

From the comfort of your private luxury yacht, enjoy an amazing experience with Hawaii’s humpback ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $695.00
    (Saving inf% ) $0.00
 
 

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

Special Offer
Free Cancellation
Private Tour
Start From $1,398.00
(Saving inf% ) $0.00
 
-inf% Luxury Diamond Head Sunset Sail Likely to Sell Out

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....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $1,398.00
    (Saving inf% ) $0.00
 
 

Explore Turtle Canyons Waikiki Snorkel and Sail Adventure

(4.5 of 4 reviews)

Enjoy your best day in Hawaii and discover a new Adventure! This sailing with snorkeling experience is amazing for you to relax and have fun.... More

Special Offer
Free Cancellation
Private Tour
Start From $1,199.00
(Saving inf% ) $0.00
 
-inf% Explore Turtle Canyons Waikiki Snorkel and Sail Adventure Likely to Sell Out

Explore Turtle Canyons Waikiki Snorkel and Sail Adventure

  • Hawaii
  • Exellent4 reviews4.5

Enjoy your best day in Hawaii and discover a new Adventure! This sailing with snorkeling experience ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $1,199.00
    (Saving inf% ) $0.00
 
 

Waikiki Sunset Cruise and Iconic Views with Swimming

(5 of 2 reviews)

Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in the crystal-clear waters off Waikīkī Beach. Glide along the iconic Gold Coast as the sun sets, painting the sky with vibrant co... More

Special Offer
Free Cancellation
Private Tour
Start From $65.00
(Saving inf% ) $0.00
 
-inf% Waikiki Sunset Cruise and Iconic Views with Swimming Likely to Sell Out

Waikiki Sunset Cruise and Iconic Views with Swimming

  • Hawaii
  • Superb2 reviews5

Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $65.00
    (Saving inf% ) $0.00
 
 

2hr Luxury Private Sailing Catamaran for 7-12 People

(5 of 3 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

Special Offer
Free Cancellation
Private Tour
Start From $1,495.00
(Saving inf% ) $0.00
 
-inf% 2hr Luxury Private Sailing Catamaran for 7-12 People Likely to Sell Out

2hr Luxury Private Sailing Catamaran for 7-12 People

  • Hawaii
  • Superb3 reviews5

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $1,495.00
    (Saving inf% ) $0.00
 
 

Honolulu Sailing and Snorkeling Activity

(5 of 3 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

Special Offer
Free Cancellation
Private Tour
Start From $105.00
(Saving inf% ) $0.00
 
-inf% Honolulu Sailing and Snorkeling Activity Likely to Sell Out

Honolulu Sailing and Snorkeling Activity

  • Hawaii
  • Superb3 reviews5

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $105.00
    (Saving inf% ) $0.00
 
 

Private South Shore Sail Charter

(5 of 2 reviews)

Manu Kai's south shore sails offer stunning views of Waikiki, Ala Moana, and Kaka'ako! Sit back and enjoy complimentary drinks while getting the ocean breeze, some Hawaiian sunshine, and even a splash or two! Experience the south ... More

Special Offer
Free Cancellation
Private Tour
Start From $1,000.00
(Saving inf% ) $0.00
 
-inf% Private South Shore Sail Charter Likely to Sell Out

Private South Shore Sail Charter

  • Hawaii
  • Superb2 reviews5

Manu Kai's south shore sails offer stunning views of Waikiki, Ala Moana, and Kaka'ako! Sit back and ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $1,000.00
    (Saving inf% ) $0.00
 
 

Moana’s Luxury semi-private Sunset Cruise on Nalu

(4.8 of 18 reviews)

The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May, Guests can look forward to Humpback Whale watching at no additional cost. Dolphins, Sea turtle... More

Special Offer
Free Cancellation
Private Tour
Start From $149.99
(Saving inf% ) $0.00
 
-inf% Moana’s Luxury semi-private Sunset Cruise on Nalu Likely to Sell Out

Moana’s Luxury semi-private Sunset Cruise on Nalu

  • Hawaii
  • Superb18 reviews4.8

The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizabl....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $149.99
    (Saving inf% ) $0.00
 
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