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Top 10 Best Hawaii Sailing Trips

Found 117 Sailing Trips activities in Hawaii. Sort by Popularity.
 

Deluxe Na Pali Sunset Tour on the Lucky Lady

(4.7 of 1,466 reviews)

Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredible scenery topped off with a spectacular sunset. Look for dolphins, whales, and other marine critters as you sip a drink, snap som... More

Free Cancellation
Start From $222.86
 
Deluxe Na Pali Sunset Tour on the Lucky Lady

Deluxe Na Pali Sunset Tour on the Lucky Lady

  • Hawaii
  • Superb1,466 reviews4.7

Tour the Na Pali coast aboard a Luxury Catamaran, Lucky Lady for an afternoon that features incredib....

    Free Cancellation
    Start From $222.86
 
 

Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast

(4.9 of 2,167 reviews)

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Waikiki Sunset Cruise, an unmatched experience complete with premium drinks, indescribable views, and music. As we sail alongside Oa... More

Free Cancellation
Start From $89.99
 
Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast

Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast

  • Hawaii
  • Superb2,167 reviews4.9

All aboard! There is no better place to be during Oahu’s magnificent golden sunsets than on our Wa....

    Free Cancellation
    Start From $89.99
 
 

Oahu Catamaran Snorkel Tour with Guaranteed Turtles

(4.9 of 1,307 reviews)

Experience one Viator's 2025 Top 20 Best Excursions in the country. This Oahu catamaran snorkel tour offers unbeatable value and family-friendly fun from Waikiki. Swim alongside Hawaiian green sea turtles and vibrant tropical fis... More

Free Cancellation
Start From $49.95
 
Oahu Catamaran Snorkel Tour with Guaranteed Turtles

Oahu Catamaran Snorkel Tour with Guaranteed Turtles

  • Hawaii
  • Superb1,307 reviews4.9

Experience one Viator's 2025 Top 20 Best Excursions in the country. This Oahu catamaran snorkel tour....

    Free Cancellation
    Start From $49.95
 
 

Turtles & Tacos Luxury Catamaran Snorkel

(4.8 of 89 reviews)

Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island flavor. Cruise aboard our spacious 65’ catamaran and snorkel alongside Hawaiian green sea turtles and colorful tropical fish at ... More

Free Cancellation
Start From $199.00
 
Turtles & Tacos Luxury Catamaran Snorkel

Turtles & Tacos Luxury Catamaran Snorkel

  • Hawaii
  • Superb89 reviews4.8

Laid-back, fresh, and full of fun, this mid-morning snorkel sail is all about good vibes and island ....

    Free Cancellation
    Start From $199.00
 
 

Waikoloa Signature Catamaran Sunset Sail

(4.7 of 388 reviews)

Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamaran. Catch the moment the sun slips below the horizon. You may even see the green flash. Board from Anaehoomalu Bay (A-Bay) to sail... More

Free Cancellation
Start From $149.00
 
Waikoloa Signature Catamaran Sunset Sail

Waikoloa Signature Catamaran Sunset Sail

  • Hawaii
  • Superb388 reviews4.7

Explore the Waikoloa and Kohala-Kona coastline aboard The Spirit of Aloha, a 54-foot sailing catamar....

    Free Cancellation
    Start From $149.00
 
 

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

(4.8 of 1,612 reviews)

Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This popular Oahu tour blends marine exploration and island relaxation in one extraordinary outing. Swim among sea turtles and tropical fi... More

Free Cancellation
Start From $89.56
 
Waikiki Turtle Snorkel and Sail on Hawea Catamaran

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

  • Hawaii
  • Superb1,612 reviews4.8

Experience the best of Waikiki on a Turtle Snorkel & Sail combo aboard the Hawea Catamaran. This pop....

    Free Cancellation
    Start From $89.56
 
 

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

(4.9 of 813 reviews)

2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for a beautiful Hawaiian sunset!! We have been sailing the Pacific waters off of the Island of Oahu since 1985... More

Free Cancellation
Start From $54.99
 
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

  • Hawaii
  • Superb813 reviews4.9

2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE ....

    Free Cancellation
    Start From $54.99
 
 

Waikiki Sunset Cocktail Sail with Open Bar

(4.8 of 540 reviews)

Experience Waikiki’s favorite sunset sail, perfect for social adventurers and party seekers. This lively evening cruise invites solo travelers and groups alike to unwind with unlimited drinks—including Maui Brewing beers, wine... More

Free Cancellation
Start From $84.77
 
Waikiki Sunset Cocktail Sail with Open Bar

Waikiki Sunset Cocktail Sail with Open Bar

  • Hawaii
  • Superb540 reviews4.8

Experience Waikiki’s favorite sunset sail, perfect for social adventurers and party seekers. This ....

    Free Cancellation
    Start From $84.77
 
 

Turtle Canyon Snorkel * Turtles guaranteed!!!

(4.7 of 1,211 reviews)

**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!****Gauranteed**** Join us for a **2-hour snorkeling adventure** at **Turtle Canyon**, one of Oahu’s top snorkeling spots! Cruise along the stunning **W... More

Free Cancellation
Start From $80.71
 
Turtle Canyon Snorkel * Turtles guaranteed!!!

Turtle Canyon Snorkel * Turtles guaranteed!!!

  • Hawaii
  • Superb1,211 reviews4.7

**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!****Gauranteed**** Join ....

    Free Cancellation
    Start From $80.71
 
 

Kauai’s Na Pali Coast Snorkel and Sail Tour

(4.8 of 535 reviews)

Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour catamaran journey combines spectacular sightseeing, exciting snorkeling, and all-inclusive comfort, making it the top choice for fami... More

Free Cancellation
Start From $292.48
 
Kauai’s Na Pali Coast Snorkel and Sail Tour Likely to Sell Out

Kauai’s Na Pali Coast Snorkel and Sail Tour

  • Hawaii
  • Superb535 reviews4.8

Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour cat....

    Free Cancellation
    Start From $292.48
 
 

Sunset Boat Cruise: Swim and Cruise Waikiki

(4.7 of 526 reviews)

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way to experience a Hawaiian sunset than from the ocean, with the iconic Waikiki coastline as your backdrop. As the sun begins to se... More

Free Cancellation
Start From $50.71
 
Sunset Boat Cruise: Swim and Cruise Waikiki Likely to Sell Out

Sunset Boat Cruise: Swim and Cruise Waikiki

  • Hawaii
  • Superb526 reviews4.7

There’s no better place to take a dip than the crystal-clear waters of Waikiki—and no better way....

    Free Cancellation
    Start From $50.71
 
 

Kona Catamaran Sunset Sail

(4.8 of 193 reviews)

Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. Catch the moment the sun slips below the horizon...you may even see the green flash. Enjoy the blue Pacific Ocean and maybe catch ... More

Free Cancellation
Start From $149.00
 
Kona Catamaran Sunset Sail Likely to Sell Out

Kona Catamaran Sunset Sail

  • Hawaii
  • Superb193 reviews4.8

Explore the beautiful Kona coastline from while aboard the Honi Olani, a 53-foot sailing catamaran. ....

    Free Cancellation
    Start From $149.00
 
 

Luxury Catamaran Whale Watch

(5 of 45 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 $159.00
 
Luxury Catamaran Whale Watch Likely to Sell Out

Luxury Catamaran Whale Watch

  • Hawaii
  • Superb45 reviews5

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

    Free Cancellation
    Start From $159.00
 
 

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

(4.8 of 285 reviews)

-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel equipment -Fun, friendly, lifeguard certified crew -BYOB (Bring your own Beverage. No glass bottles)... More

Free Cancellation
Start From $99.00
 
Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon Likely to Sell Out

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

  • Hawaii
  • Superb285 reviews4.8

-Guaranteed Hawaiian sea turtles at Turtle Canyon -Ample shade and seating on board -Premium snorkel....

    Free Cancellation
    Start From $99.00
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 522 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 a... More

Free Cancellation
Start From $177.73
 
Deluxe Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Deluxe Sail & Snorkel to the Captain Cook Monument

  • Hawaii
  • Superb522 reviews4.9

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

    Free Cancellation
    Start From $177.73
 
 

Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

(4.7 of 2,108 reviews)

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea Turtles firsthand! Guests will learn about the life cycle, behaviors, and threats to the Hawaiian Sea Turtles "Honu" (Learning pr... More

Free Cancellation
Start From $149.95
 
Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed Likely to Sell Out

Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

  • Hawaii
  • Superb2,108 reviews4.7

Welcome aboard Hawaii Nautical, you're invited to observe, learn, and experience Hawaiian Green Sea ....

    Free Cancellation
    Start From $149.95
 
 

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

(4.8 of 42 reviews)

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step aboard, you're greeted by the friendly crew who welcome you with warm aloha spirit. The c... More

Free Cancellation
Start From $289.00
 
Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only) Likely to Sell Out

Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)

  • Hawaii
  • Superb42 reviews4.8

Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....

    Free Cancellation
    Start From $289.00
 
 

Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

(4.7 of 147 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

Free Cancellation
Start From $79.00
 
Best Waikiki Whale Watching in Honolulu: Whales Guaranteed Likely to Sell Out

Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

  • Hawaii
  • Superb147 reviews4.7

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

    Free Cancellation
    Start From $79.00
 
 

Day's End Cocktail Sunset Sail

(4.8 of 62 reviews)

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. This isn’t a dinner cruise, it’s happy hour reimagined (a true ‘pau hana’ at sea) with handcrafted drin... More

Free Cancellation
Start From $159.00
 
Day's End Cocktail Sunset Sail Likely to Sell Out

Day's End Cocktail Sunset Sail

  • Hawaii
  • Superb62 reviews4.8

Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most sce....

    Free Cancellation
    Start From $159.00
 
 

2-Hour Whale Watching Waikiki Oahu Guaranteed sightings!

(4.6 of 919 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 $50.71
 
2-Hour Whale Watching Waikiki Oahu Guaranteed sightings! Likely to Sell Out

2-Hour Whale Watching Waikiki Oahu Guaranteed sightings!

  • Hawaii
  • Superb919 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 $50.71
 
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