Menu

Top 10 Best Hawaii Sailing Trips

Found 114 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 4
 

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

Free Cancellation
Start From $276.00
 
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....

    Free Cancellation
    Start From $276.00
 
 

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 Likely to Sell Out

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
 
 

Waikiki small group turtle snorkeling & sailing

(5 of 92 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
  • Superb92 reviews5

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

    Free Cancellation
    Start From $99.00
 
 

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
 
 

Waikiki Turtle Snorkeling Adventure(8am)

(4.9 of 9 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
Start From $100.00
 
Waikiki Turtle Snorkeling Adventure(8am) Likely to Sell Out

Waikiki Turtle Snorkeling Adventure(8am)

  • Hawaii
  • Superb9 reviews4.9

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

    Free Cancellation
    Start From $100.00
 
 

2 Hour Swim, Snorkel & Sail (Kewalo Harbor)

(5 of 2 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
 
2 Hour Swim, Snorkel & Sail (Kewalo Harbor) Likely to Sell Out

2 Hour Swim, Snorkel & Sail (Kewalo Harbor)

  • Hawaii
  • Superb2 reviews5

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

    Free Cancellation
    Start From $70.00
 
 

Sunset sail Aboard Manakai Catamaran

(5 of 16 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 Likely to Sell Out

Sunset sail Aboard Manakai Catamaran

  • Hawaii
  • Superb16 reviews5

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

    Free Cancellation
    Start From $49.82
 
 

Small Group Waikiki Sunset Sailing Tour

(4.9 of 114 reviews)

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come and enjoy the Golden hour with your loved ones to make memories of a lifetime ,why go with overc... More

Free Cancellation
Start From $99.00
 
Small Group Waikiki Sunset Sailing Tour Likely to Sell Out

Small Group Waikiki Sunset Sailing Tour

  • Hawaii
  • Superb114 reviews4.9

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it tha....

    Free Cancellation
    Start From $99.00
 
 

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 Likely to Sell Out

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
 
 

Waikiki Fireworks Cocktail Cruise

(4.5 of 8 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
Start From $76.58
(Saving 10% ) $85.09
 
-10% Waikiki Fireworks Cocktail Cruise Likely to Sell Out

Waikiki Fireworks Cocktail Cruise

  • Hawaii
  • Exellent8 reviews4.5

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

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

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
Start From $200.00
(Saving inf% ) $0.00
 
-inf% Polynesian Canoe Morning Sail Likely to Sell Out

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
    Start From $200.00
    (Saving inf% ) $0.00
 
 

Private Catamaran Charter in Waikiki (1-6 Guests)

(5 of 23 reviews)

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large lounging nets on the front of the boat, as well as 2 small nets on the back of the boat. Not only does Hawa... More

Special Offer
Free Cancellation
Private Tour
Start From $900.00
(Saving inf% ) $0.00
 
-inf% Private Catamaran Charter in Waikiki (1-6 Guests) Likely to Sell Out

Private Catamaran Charter in Waikiki (1-6 Guests)

  • Hawaii
  • Superb23 reviews5

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $900.00
    (Saving inf% ) $0.00
 
 

Akialoa Mā’alaea Sunset Sail

(4.7 of 13 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

Special Offer
Free Cancellation
Private Tour
Start From $108.11
(Saving inf% ) $0.00
 
-inf% Akialoa Mā’alaea Sunset Sail Likely to Sell Out

Akialoa Mā’alaea Sunset Sail

  • Hawaii
  • Superb13 reviews4.7

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $108.11
    (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
 
 

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
 
 

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
 
 

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 Likely to Sell Out

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
 
 

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
 
 

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

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

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

Honolulu Sailing and Snorkeling Activity

(4.7 of 15 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
  • Superb15 reviews4.7

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
 
2 3 4 5 6
Booking.com
Booking.com
Booking.com