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Top 10 Best Hawaii Sailing Trips

Found 109 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 3
 

Waikoloa Catamaran Snorkel Sail Including Lunch

(4.6 of 109 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 $189.00
 
Waikoloa Catamaran Snorkel Sail Including Lunch

Waikoloa Catamaran Snorkel Sail Including Lunch

  • Hawaii
  • Superb109 reviews4.6

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

    Free Cancellation
    Start From $189.00
 
 

Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise

(5 of 10 reviews)

Our sunset turtle snorkeling tour delivers a unique all-in-one Waikiki ocean experience, combining adventure, relaxation, and unforgettable views in one trip. We reach Turtle Canyon quickly, giving you more time in the water to s... More

Free Cancellation
Start From $120.00
 
Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise

Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise

  • Hawaii
  • Superb10 reviews5

Our sunset turtle snorkeling tour delivers a unique all-in-one Waikiki ocean experience, combining a....

    Free Cancellation
    Start From $120.00
 
 

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

(4.5 of 34 reviews)

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the island like never before as you set sail from the only pier in W... More

Free Cancellation
Start From $119.95
 
Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

  • Hawaii
  • Exellent34 reviews4.5

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-bui....

    Free Cancellation
    Start From $119.95
 
 

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

(4.9 of 256 reviews)

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far away enough from the bustling travelers and crowded beaches, the crystal-clear water will br... More

Free Cancellation
Start From $49.99
 
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

  • Hawaii
  • Superb256 reviews4.9

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your....

    Free Cancellation
    Start From $49.99
 
 

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

(4.5 of 43 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 $109.95
 
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

  • Hawaii
  • Exellent43 reviews4.5

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

    Free Cancellation
    Start From $109.95
 
 

Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

(4.8 of 59 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
 
Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu Likely to Sell Out

Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu

  • Hawaii
  • Superb59 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
 
 

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
 
 

Waikiki Friday Night Fireworks Cruise

(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 Likely to Sell Out

Waikiki Friday Night Fireworks Cruise

  • 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
 
 

2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)

(5 of 2 reviews)

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6 guests, you can book under our other listing labeled for 1-6 guests.) This 48-foot ca... More

Free Cancellation
Private Tour
Start From $1,200.00
 
2 Hour Private Catamaran Charter in Waikiki (7-12 Guests) Likely to Sell Out

2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)

  • Hawaii
  • Superb2 reviews5

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it....

    Free Cancellation
    Private Tour
    Start From $1,200.00
 
 

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

(5 of 714 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
  • Superb714 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
 
 

Private Catamaran Charter in Waikiki (1-6 Guests)

(5 of 25 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

Free Cancellation
Private Tour
Start From $900.00
 
Private Catamaran Charter in Waikiki (1-6 Guests) Likely to Sell Out

Private Catamaran Charter in Waikiki (1-6 Guests)

  • Hawaii
  • Superb25 reviews5

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

    Free Cancellation
    Private Tour
    Start From $900.00
 
 

Half-Day Deluxe Molokini Snorkel Excursion in Maui

(4.9 of 127 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
Private Tour
Start From $289.00
 
Half-Day Deluxe Molokini Snorkel Excursion in Maui Likely to Sell Out

Half-Day Deluxe Molokini Snorkel Excursion in Maui

  • Hawaii
  • Superb127 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $289.00
 
 

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

Free Cancellation
Private Tour
Start From $108.11
 
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....

    Free Cancellation
    Private Tour
    Start From $108.11
 
 

Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value

(4.8 of 255 reviews)

-Open bar fully included in $50 ticket: beer, wine, cocktails, and more -AMAZING value catamaran sail in Waikiki -Direct beach boarding — no harbor shuttle, no bus, no wasted time -Sail toward Diamond Head on the famous Waikiki ... More

Special Offer
Free Cancellation
Private Tour
Start From $40.02
(Saving 25% ) $53.36
 
-25% Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value Likely to Sell Out

Waikiki: Afternoon Sail from Beach & Open Bar | Oahu - Best Value

  • Hawaii
  • Superb255 reviews4.8

-Open bar fully included in $50 ticket: beer, wine, cocktails, and more -AMAZING value catamaran sai....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $40.02
    (Saving 25% ) $53.36
 
 

Friday Night Firework Cruise in Waikiki

(4.8 of 33 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

Special Offer
Free Cancellation
Private Tour
Start From $69.99
(Saving inf% ) $0.00
 
-inf% Friday Night Firework Cruise in Waikiki Likely to Sell Out

Friday Night Firework Cruise in Waikiki

  • Hawaii
  • Superb33 reviews4.8

After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fire....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $69.99
    (Saving inf% ) $0.00
 
 

Waikiki small group turtle snorkeling & sailing

(5 of 99 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

Special Offer
Free Cancellation
Private Tour
Start From $99.00
(Saving inf% ) $0.00
 
-inf% Waikiki small group turtle snorkeling & sailing Likely to Sell Out

Waikiki small group turtle snorkeling & sailing

  • Hawaii
  • Superb99 reviews5

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $99.00
    (Saving inf% ) $0.00
 
 

Hawaiian Canoe Sailing Experience in Maui

(4.6 of 63 reviews)

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning Hawaiian history and culture. Cold water and snorkel gear are... More

Special Offer
Free Cancellation
Private Tour
Start From $179.00
(Saving inf% ) $0.00
 
-inf% Hawaiian Canoe Sailing Experience in Maui Likely to Sell Out

Hawaiian Canoe Sailing Experience in Maui

  • Hawaii
  • Superb63 reviews4.6

Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour include....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $179.00
    (Saving inf% ) $0.00
 
 

Private Catamaran Sunset Sail in Waikiki

(5 of 11 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

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

Private Catamaran Sunset Sail in Waikiki

  • Hawaii
  • Superb11 reviews5

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

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

Honolua Snorkel Sail from Lahaina

(4.9 of 61 reviews)

Sail to the storied waters of Honolua Bay, long valued in Hawaiian culture and now protected as a Marine Life Conservation District. Along the way, watch for wild dolphins, then snorkel among Hawaiian green sea turtles in this vib... More

Special Offer
Free Cancellation
Private Tour
Start From $180.92
(Saving inf% ) $0.00
 
-inf% Honolua Snorkel Sail from Lahaina Likely to Sell Out

Honolua Snorkel Sail from Lahaina

  • Hawaii
  • Superb61 reviews4.9

Sail to the storied waters of Honolua Bay, long valued in Hawaiian culture and now protected as a Ma....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $180.92
    (Saving inf% ) $0.00
 
 

Small Group Waikiki Sunset Sailing Tour

(4.9 of 115 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

Special Offer
Free Cancellation
Private Tour
Start From $99.00
(Saving inf% ) $0.00
 
-inf% Small Group Waikiki Sunset Sailing Tour Likely to Sell Out

Small Group Waikiki Sunset Sailing Tour

  • Hawaii
  • Superb115 reviews4.9

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $99.00
    (Saving inf% ) $0.00
 
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