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Top 10 Best Hawaii Sailing Trips

Found 109 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 4
 

Waikiki: 2-Hour Whale Watching with Guaranteed Sightings on Oahu

(4.6 of 1,335 reviews)

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a lifetime experience that you will never forget to see this amazing creature. If you are lucky enough, you might see dolphins, sea ... More

Free Cancellation
Start From $53.31
 
Waikiki: 2-Hour Whale Watching with Guaranteed Sightings on Oahu

Waikiki: 2-Hour Whale Watching with Guaranteed Sightings on Oahu

  • Hawaii
  • Superb1,335 reviews4.6

Humpback whales visit Hawaii each year and give birth in our warm tropical waters, it's a once in a ....

    Free Cancellation
    Start From $53.31
 
 

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

(4.7 of 19 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
Start From $70.00
 
Waikiki Sunset Cruise Catamaran Boat Tour on Oahu Likely to Sell Out

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

  • Hawaii
  • Superb19 reviews4.7

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (LÄ“â€....

    Free Cancellation
    Start From $70.00
 
 

Experience Maalaea Harbor Sailing Snorkeling Adventure

(4.7 of 19 reviews)

Spend a leisurely afternoon sailing aboard the widest and most stable and luxurious catamaran in Maui, where your adventure takes you to the stunning waters of Molokini or a secret turtle sanctuary. Enjoy hand-shaken Mai Tais and ... More

Free Cancellation
Start From $149.00
 
Experience Maalaea Harbor Sailing Snorkeling Adventure Likely to Sell Out

Experience Maalaea Harbor Sailing Snorkeling Adventure

  • Hawaii
  • Superb19 reviews4.7

Spend a leisurely afternoon sailing aboard the widest and most stable and luxurious catamaran in Mau....

    Free Cancellation
    Start From $149.00
 
 

Luxury Catamaran Whale Watch

(4.9 of 89 reviews)

From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way to witness the wonder than from the deck of our 65’ catamaran. This two-hour ex... More

Free Cancellation
Start From $119.00
 
Luxury Catamaran Whale Watch Likely to Sell Out

Luxury Catamaran Whale Watch

  • Hawaii
  • Superb89 reviews4.9

From December through April, the waters off Maui come alive with the sights and sounds of the majest....

    Free Cancellation
    Start From $119.00
 
 

Sunset Sail Experience by Catamaran in Waikiki

(4.8 of 6 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
Start From $92.31
 
Sunset Sail Experience by Catamaran in Waikiki Likely to Sell Out

Sunset Sail Experience by Catamaran in Waikiki

  • Hawaii
  • Superb6 reviews4.8

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

    Free Cancellation
    Start From $92.31
 
 

Polynesian Canoe Day Sail

(4.9 of 29 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
Start From $180.00
(Saving 10% ) $200.00
 
-10% Polynesian Canoe Day Sail Likely to Sell Out

Polynesian Canoe Day Sail

  • Hawaii
  • Superb29 reviews4.9

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

    Special Offer
    Free Cancellation
    Start From $180.00
    (Saving 10% ) $200.00
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 250 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

Special Offer
Free Cancellation
Start From $136.19
(Saving inf% ) $0.00
 
-inf% Afternoon Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Afternoon Sail & Snorkel to the Captain Cook Monument

  • Hawaii
  • Superb250 reviews4.9

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

    Special Offer
    Free Cancellation
    Start From $136.19
    (Saving inf% ) $0.00
 
 

2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People

(4.8 of 14 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 $1,150.00
(Saving inf% ) $0.00
 
-inf% 2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People Likely to Sell Out

2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People

  • Hawaii
  • Superb14 reviews4.8

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 $1,150.00
    (Saving inf% ) $0.00
 
 

Coral Gardens Afternoon Turtle Snorkel Sail w/ Lunch & Open Bar

(4.8 of 39 reviews)

This sailing experience blends adventure and tranquility against a backdrop of Maui’s pristine landscapes. Arrive at Coral Gardens, a sheltered snorkeling haven with calm, crystal-clear waters teeming with vibrant coral reefs a... More

Special Offer
Free Cancellation
Private Tour
Start From $116.28
(Saving 5% ) $122.40
 
-5% Coral Gardens Afternoon Turtle Snorkel Sail w/ Lunch & Open Bar Likely to Sell Out

Coral Gardens Afternoon Turtle Snorkel Sail w/ Lunch & Open Bar

  • Hawaii
  • Superb39 reviews4.8

This sailing experience blends adventure and tranquility against a backdrop of Maui’s pristine lan....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $116.28
    (Saving 5% ) $122.40
 
 

Waikiki Turtle Snorkeling Adventure(8am)

(4.9 of 40 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

Special Offer
Free Cancellation
Private Tour
Start From $100.00
(Saving inf% ) $0.00
 
-inf% Waikiki Turtle Snorkeling Adventure(8am) Likely to Sell Out

Waikiki Turtle Snorkeling Adventure(8am)

  • Hawaii
  • Superb40 reviews4.9

Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $100.00
    (Saving inf% ) $0.00
 
 

BYOB Friday Night Fireworks Cruise

(4.3 of 6 reviews)

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki. You'll enjoy the view of the city lights and be in awe with this unobstructed view of fireworks from the water! With plenty of... More

Special Offer
Free Cancellation
Private Tour
Start From $138.95
(Saving inf% ) $0.00
 
-inf% BYOB Friday Night Fireworks Cruise Likely to Sell Out

BYOB Friday Night Fireworks Cruise

  • Hawaii
  • Exellent6 reviews4.3

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $138.95
    (Saving inf% ) $0.00
 
 

South Shore Open Sail from Kewalo Harbor Including Drinks

(4.7 of 27 reviews)

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! Our sails always have complimentary drinks (alcoholic beverages available for adults 21+ with valid ID o... More

Special Offer
Free Cancellation
Private Tour
Start From $47.50
(Saving inf% ) $0.00
 
-inf% South Shore Open Sail from Kewalo Harbor Including Drinks Likely to Sell Out

South Shore Open Sail from Kewalo Harbor Including Drinks

  • Hawaii
  • Superb27 reviews4.7

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconi....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $47.50
    (Saving inf% ) $0.00
 
 

Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

(4.6 of 250 reviews)

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well as ample seating and shade on board. Knowledgeable staff with plenty of interesting whale information Convenient location walking... More

Special Offer
Free Cancellation
Private Tour
Start From $79.00
(Saving inf% ) $0.00
 
-inf% Best Waikiki Whale Watching in Honolulu: Whales Guaranteed Likely to Sell Out

Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

  • Hawaii
  • Superb250 reviews4.6

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well a....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $79.00
    (Saving inf% ) $0.00
 
 

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

Special Offer
Free Cancellation
Private Tour
Start From $196.63
(Saving inf% ) $0.00
 
-inf% Half Day Oahu Combo Adventure: Bike, Sail and Snorkel Likely to Sell Out

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....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $196.63
    (Saving inf% ) $0.00
 
 

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People

(5 of 1 review)

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 $1,595.00
(Saving inf% ) $0.00
 
-inf% 3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People Likely to Sell Out

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People

  • Hawaii
  • Superb1 review5

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 $1,595.00
    (Saving inf% ) $0.00
 
 

Polynesian Canoe Sunset Sail

(4.9 of 127 reviews)

Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and bec... More

Special Offer
Free Cancellation
Private Tour
Start From $225.00
(Saving 10% ) $250.00
 
-10% Polynesian Canoe Sunset Sail Likely to Sell Out

Polynesian Canoe Sunset Sail

  • Hawaii
  • Superb127 reviews4.9

Kamoauli is a locally owned, all-wood, double-hulled, traditional sailing vessel (wa’a kaulua) off....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $225.00
    (Saving 10% ) $250.00
 
 

Afternoon Ali'i Adventure

(5 of 6 reviews)

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests, allowing for a semi-private experience aboard our spacious 50' catamaran. ... More

Special Offer
Free Cancellation
Private Tour
Start From $276.00
(Saving inf% ) $0.00
 
-inf% Afternoon Ali'i Adventure Likely to Sell Out

Afternoon Ali'i Adventure

  • Hawaii
  • Superb6 reviews5

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowd....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $276.00
    (Saving inf% ) $0.00
 
 

Afternoon Sail With the Whales from Lahaina Harbor

(5 of 1 review)

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% Afternoon Sail With the Whales from Lahaina Harbor Likely to Sell Out

Afternoon Sail With the Whales from Lahaina Harbor

  • Hawaii
  • Superb1 review5

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
 
 

Maui Sunset Sail

(4.6 of 220 reviews)

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing catamaran, Ocean Spirit. It’s the perfect way to expe... More

Special Offer
Free Cancellation
Private Tour
Start From $137.82
(Saving inf% ) $0.00
 
-inf% Maui Sunset Sail Likely to Sell Out

Maui Sunset Sail

  • Hawaii
  • Superb220 reviews4.6

Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunse....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $137.82
    (Saving inf% ) $0.00
 
 

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

(4.8 of 18 reviews)

Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experience Maui’s golden hour from the water. Departing from Ma‘alaea, this intimate evening cruise offers stunning views of the coast... More

Special Offer
Free Cancellation
Private Tour
Start From $279.00
(Saving inf% ) $0.00
 
-inf% 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
  • Superb18 reviews4.8

Step aboard Amore, a 42-foot Boston Whaler 420 Outrage designed for luxury and comfort, and experien....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $279.00
    (Saving inf% ) $0.00
 
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