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Top 10 Best Hawaii Sailing Trips

Found 110 Sailing Trips activities in Hawaii. Sort by Popularity.
 
-11% Waikiki, Oahu 2-Hour Whale Watching: Guaranteed Sightings

Waikiki, Oahu 2-Hour Whale Watching: Guaranteed Sightings

(4.6 of 1,228 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

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(Saving 11% ) $50.71
 
-11% Waikiki, Oahu 2-Hour Whale Watching: Guaranteed Sightings

Waikiki, Oahu 2-Hour Whale Watching: Guaranteed Sightings

  • Hawaii
  • Superb1,228 reviews4.6

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

    Special Offer
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    Start From $45.31
    (Saving 11% ) $50.71
 
 
-inf% Waikiki: 2 hours - Turtle Canyon Snorkeling Adventure

Waikiki: 2 hours - Turtle Canyon Snorkeling Adventure

(4.7 of 1,368 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

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-inf% Waikiki: 2 hours - Turtle Canyon Snorkeling Adventure

Waikiki: 2 hours - Turtle Canyon Snorkeling Adventure

  • Hawaii
  • Superb1,368 reviews4.7

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

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    Start From $80.71
    (Saving inf% ) $0.00
 
 
-inf% Kauai: Deluxe Na Pali Coast Sunset Cruise aboard Lucky Lady

Kauai: Deluxe Na Pali Coast Sunset Cruise aboard Lucky Lady

(4.7 of 1,540 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

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Start From $222.86
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-inf% Kauai: Deluxe Na Pali Coast Sunset Cruise aboard Lucky Lady

Kauai: Deluxe Na Pali Coast Sunset Cruise aboard Lucky Lady

  • Hawaii
  • Superb1,540 reviews4.7

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

    Special Offer
    Free Cancellation
    Start From $222.86
    (Saving inf% ) $0.00
 
 
-inf% Kona Signature Catamaran Sunset Sail

Kona Signature Catamaran Sunset Sail

(4.8 of 238 reviews)

End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloha. Enjoy panoramic views of the ocean and coastline as the sky transforms with vibrant hues of orange, pink and gold. Relax on d... More

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Start From $109.00
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-inf% Kona Signature Catamaran Sunset Sail

Kona Signature Catamaran Sunset Sail

  • Hawaii
  • Superb238 reviews4.8

End your day in paradise with a sunset sail along the beautiful Kona Coast aboard the Spirit of Aloh....

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    Free Cancellation
    Start From $109.00
    (Saving inf% ) $0.00
 
 
-inf% Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

(4.9 of 1,494 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

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Start From $49.95
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-inf% Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

  • Hawaii
  • Superb1,494 reviews4.9

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

    Special Offer
    Free Cancellation
    Start From $49.95
    (Saving inf% ) $0.00
 
 
-inf% Oahu's Waikiki Coast: Moana’s Sunset Cocktail Sail

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

(4.9 of 2,235 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

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Start From $89.99
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-inf% Oahu's Waikiki Coast: Moana’s Sunset Cocktail Sail

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

  • Hawaii
  • Superb2,235 reviews4.9

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

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    Free Cancellation
    Start From $89.99
    (Saving inf% ) $0.00
 
 
-inf% Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar

Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar

(4.5 of 15 reviews)

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cocktail Sail. Departing from Ka’anapali Beach, this 2-hour experience offers breathtaking views of the sunset complemented by deligh... More

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-inf% Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar

Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar

  • Hawaii
  • Exellent15 reviews4.5

Set sail on a luxurious journey along West Maui's stunning coastline with the Holo Holo Sunset Cockt....

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    Start From $141.98
    (Saving inf% ) $0.00
 
 
-inf% Turtles & Tacos Luxury Catamaran Snorkel

Turtles & Tacos Luxury Catamaran Snorkel

(4.7 of 110 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

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Start From $199.00
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-inf% Turtles & Tacos Luxury Catamaran Snorkel

Turtles & Tacos Luxury Catamaran Snorkel

  • Hawaii
  • Superb110 reviews4.7

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

    Special Offer
    Free Cancellation
    Start From $199.00
    (Saving inf% ) $0.00
 
 
-inf% Waikiki Turtle Snorkel and Sail on Hawea Catamaran

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

(4.8 of 1,668 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

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Start From $89.56
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-inf% Waikiki Turtle Snorkel and Sail on Hawea Catamaran

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

  • Hawaii
  • Superb1,668 reviews4.8

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

    Special Offer
    Free Cancellation
    Start From $89.56
    (Saving inf% ) $0.00
 
 
-12% Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure

Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure

(4.7 of 542 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

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Start From $44.80
(Saving 12% ) $50.71
 
-12% Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure

Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure

  • Hawaii
  • Superb542 reviews4.7

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

    Special Offer
    Free Cancellation
    Start From $44.80
    (Saving 12% ) $50.71
 
 

Maui: Kaanapali Beach 5-hour Snorkel w/ BBQ Lunch & Open Bar

(4.7 of 12 reviews)

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and an open bar. This is our award-winning snorkel tour that... More

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Start From $203.16
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-inf% Maui: Kaanapali Beach 5-hour Snorkel w/ BBQ Lunch & Open Bar Likely to Sell Out

Maui: Kaanapali Beach 5-hour Snorkel w/ BBQ Lunch & Open Bar

  • Hawaii
  • Superb12 reviews4.7

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest ....

    Special Offer
    Free Cancellation
    Start From $203.16
    (Saving inf% ) $0.00
 
 

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 824 reviews)

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in the warmth of paradise. From the experienced snorkeler to those... More

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Start From $202.59
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-inf% Four Winds Molokini Snorkeling Tour from Maalaea Harbor Likely to Sell Out

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

  • Hawaii
  • Superb824 reviews4.7

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....

    Special Offer
    Free Cancellation
    Start From $202.59
    (Saving inf% ) $0.00
 
 

Kauai’s Na Pali Coast Snorkel and Sail Tour

(4.8 of 551 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

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Start From $292.48
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-inf% Kauai’s Na Pali Coast Snorkel and Sail Tour Likely to Sell Out

Kauai’s Na Pali Coast Snorkel and Sail Tour

  • Hawaii
  • Superb551 reviews4.8

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

    Special Offer
    Free Cancellation
    Start From $292.48
    (Saving inf% ) $0.00
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 542 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

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-inf% Deluxe Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Deluxe Sail & Snorkel to the Captain Cook Monument

  • Hawaii
  • Superb542 reviews4.9

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

    Special Offer
    Free Cancellation
    Start From $177.73
    (Saving inf% ) $0.00
 
 

Day's End Cocktail Sunset Sail

(4.7 of 75 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

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Start From $159.00
(Saving inf% ) $0.00
 
-inf% Day's End Cocktail Sunset Sail Likely to Sell Out

Day's End Cocktail Sunset Sail

  • Hawaii
  • Superb75 reviews4.7

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

    Special Offer
    Free Cancellation
    Start From $159.00
    (Saving inf% ) $0.00
 
 

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

(4.9 of 865 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

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Start From $49.99
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-inf% Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB Likely to Sell Out

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

  • Hawaii
  • Superb865 reviews4.9

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

    Special Offer
    Free Cancellation
    Start From $49.99
    (Saving inf% ) $0.00
 
 

Kauai: Leila Na Pali Sunset Dinner Sail

(4.7 of 535 reviews)

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjoy appetizers, craft beer, wine, and Koloa Rum Mai-Tais aboard our sleek and spacious sailing catamaran, Leila. Your captain will s... More

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Start From $263.82
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-inf% Kauai: Leila Na Pali Sunset Dinner Sail Likely to Sell Out

Kauai: Leila Na Pali Sunset Dinner Sail

  • Hawaii
  • Superb535 reviews4.7

Let us wine & dine you as we sail off into the sunset along Kauai’s spectacular Napali Coast. Enjo....

    Special Offer
    Free Cancellation
    Start From $263.82
    (Saving inf% ) $0.00
 
 

Waikiki Sunset Cocktail Sail with Open Bar

(4.8 of 560 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

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Free Cancellation
Start From $84.77
(Saving inf% ) $0.00
 
-inf% Waikiki Sunset Cocktail Sail with Open Bar Likely to Sell Out

Waikiki Sunset Cocktail Sail with Open Bar

  • Hawaii
  • Superb560 reviews4.8

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

    Special Offer
    Free Cancellation
    Start From $84.77
    (Saving inf% ) $0.00
 
 

Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

(4.6 of 236 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

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Start From $79.00
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-inf% Best Waikiki Whale Watching in Honolulu: Whales Guaranteed Likely to Sell Out

Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

  • Hawaii
  • Superb236 reviews4.6

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

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

Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

(4.7 of 2,114 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

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Start From $134.95
(Saving 10% ) $149.95
 
-10% Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed Likely to Sell Out

Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

  • Hawaii
  • Superb2,114 reviews4.7

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

    Special Offer
    Free Cancellation
    Start From $134.95
    (Saving 10% ) $149.95
 
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