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Top 10 Best Hawaii Sailing Trips

Found 104 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 3
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 254 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
Start From $135.64
 
Afternoon Sail & Snorkel to the Captain Cook Monument

Afternoon Sail & Snorkel to the Captain Cook Monument

  • Hawaii
  • Superb254 reviews4.9

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

    Free Cancellation
    Start From $135.64
 
 
-10% Kona Tradewind Catamaran Day Sail

Kona Tradewind Catamaran Day Sail

(4.8 of 50 reviews)

Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing catamaran. Feel the trade winds fill the sails as you glide across the water, taking in panoramic views of volcanic cliffs, sparklin... More

Special Offer
Free Cancellation
Start From $80.10
(Saving 10% ) $89.00
 
-10% Kona Tradewind Catamaran Day Sail

Kona Tradewind Catamaran Day Sail

  • Hawaii
  • Superb50 reviews4.8

Experience the beauty of the Kona Coast from a new perspective aboard the Spirit of Aloha sailing ca....

    Special Offer
    Free Cancellation
    Start From $80.10
    (Saving 10% ) $89.00
 
 
-inf% Midday Whale Watch: Mā’alaea Harbor

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
Start From $100.22
(Saving inf% ) $0.00
 
-inf% Midday Whale Watch: Mā’alaea Harbor

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
    Start From $100.22
    (Saving inf% ) $0.00
 
 
-inf% Molokini Crater Snorkel, Sailing Adventure with Breakfast & Lunch

Molokini Crater Snorkel, Sailing Adventure with Breakfast & Lunch

(4.8 of 222 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

Special Offer
Free Cancellation
Start From $200.00
(Saving inf% ) $0.00
 
-inf% Molokini Crater Snorkel, Sailing Adventure with Breakfast & Lunch

Molokini Crater Snorkel, Sailing Adventure with Breakfast & Lunch

  • Hawaii
  • Superb222 reviews4.8

Sail Maui is proud to offer a destination snorkel sail to Molokini, one of Maui’s most incredib....

    Special Offer
    Free Cancellation
    Start From $200.00
    (Saving inf% ) $0.00
 
 
-inf% Deluxe Sail & Snorkel to the Captain Cook Monument

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 480 reviews)

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 adventure will begin in the turquoise waters... More

Special Offer
Free Cancellation
Start From $178.72
(Saving inf% ) $0.00
 
-inf% Deluxe Sail & Snorkel to the Captain Cook Monument

Deluxe Sail & Snorkel to the Captain Cook Monument

  • Hawaii
  • Superb480 reviews4.9

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient ....

    Special Offer
    Free Cancellation
    Start From $178.72
    (Saving inf% ) $0.00
 
 
-inf% Luxury Catamaran Whale Watch

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

Special Offer
Free Cancellation
Start From $119.00
(Saving inf% ) $0.00
 
-inf% Luxury Catamaran Whale Watch

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....

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

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

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

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

Waikiki Friday Night Fireworks Cruise

(4.6 of 32 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

Special Offer
Free Cancellation
Private Tour
Start From $60.00
(Saving inf% ) $0.00
 
-inf% Waikiki Friday Night Fireworks Cruise Likely to Sell Out

Waikiki Friday Night Fireworks Cruise

  • Hawaii
  • Superb32 reviews4.6

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insig....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $60.00
    (Saving inf% ) $0.00
 
 

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

Special Offer
Free Cancellation
Private Tour
Start From $90.01
(Saving inf% ) $0.00
 
-inf% 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....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $90.01
    (Saving inf% ) $0.00
 
 

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

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
  • Superb25 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
 
 

Waikoloa Catamaran Snorkel Sail Including Lunch

(4.6 of 110 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

Special Offer
Free Cancellation
Private Tour
Start From $170.10
(Saving 10% ) $189.00
 
-10% Waikoloa Catamaran Snorkel Sail Including Lunch Likely to Sell Out

Waikoloa Catamaran Snorkel Sail Including Lunch

  • Hawaii
  • Superb110 reviews4.6

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $170.10
    (Saving 10% ) $189.00
 
 

2-Hour Oahu Sunset Catamaran Sail

(4.8 of 135 reviews)

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. Sip a cocktail and enjoy warm wind in your hair as you scan for dolphins and listen for ... More

Special Offer
Free Cancellation
Private Tour
Start From $130.00
(Saving inf% ) $0.00
 
-inf% 2-Hour Oahu Sunset Catamaran Sail Likely to Sell Out

2-Hour Oahu Sunset Catamaran Sail

  • Hawaii
  • Superb135 reviews4.8

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran fr....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $130.00
    (Saving inf% ) $0.00
 
 

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

(4.7 of 970 reviews)

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for your snorkel adventure, you’re choosing the tour with the most professionalis... More

Special Offer
Free Cancellation
Private Tour
Start From $84.99
(Saving inf% ) $0.00
 
-inf% Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure Likely to Sell Out

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventu....

  • Hawaii
  • Superb970 reviews4.7

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $84.99
    (Saving inf% ) $0.00
 
 

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

Special Offer
Free Cancellation
Private Tour
Start From $53.31
(Saving inf% ) $0.00
 
-inf% Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu Likely to Sell Out

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 ....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $53.31
    (Saving inf% ) $0.00
 
 

Sunset and Manta Ray Snorkel Adventure

(4.9 of 870 reviews)

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of a lifetime - snorkeling with the majestic manta rays!  Upon arriving, receive an in... More

Special Offer
Free Cancellation
Private Tour
Start From $154.51
(Saving inf% ) $0.00
 
-inf% Sunset and Manta Ray Snorkel Adventure Likely to Sell Out

Sunset and Manta Ray Snorkel Adventure

  • Hawaii
  • Superb870 reviews4.9

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $154.51
    (Saving inf% ) $0.00
 
 

North Shore Catamaran Charters

(5 of 1 review)

Perfect for families, couples, and ocean lovers seeking an unforgettable Hawaiian experience. Witness the majestic whales and stunning sunsets on the North Shore of Oahu. Explore the crystal-clear waters aboard your Summer snorkel... More

Special Offer
Free Cancellation
Private Tour
Start From $142.00
(Saving inf% ) $0.00
 
-inf% North Shore Catamaran Charters Likely to Sell Out

North Shore Catamaran Charters

  • Hawaii
  • Superb1 review5

Perfect for families, couples, and ocean lovers seeking an unforgettable Hawaiian experience. Witnes....

    Special Offer
    Free Cancellation
    Private Tour
    Start From $142.00
    (Saving inf% ) $0.00
 
 

Polynesian Canoe Sunset Sail

(4.9 of 128 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 $250.00
(Saving inf% ) $0.00
 
-inf% Polynesian Canoe Sunset Sail Likely to Sell Out

Polynesian Canoe Sunset Sail

  • Hawaii
  • Superb128 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 $250.00
    (Saving inf% ) $0.00
 
 

Maui Sunset Sail

(4.6 of 221 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
  • Superb221 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
 
 

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

(5 of 718 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

Special Offer
Free Cancellation
Private Tour
Start From $189.00
(Saving inf% ) $0.00
 
-inf% Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure Likely to Sell Out

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

  • Hawaii
  • Superb718 reviews5

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $189.00
    (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
 
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