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Top 10 Best Hawaii Sailing Trips

Found 114 Sailing Trips activities in Hawaii. Sort by Popularity.
 

Kona Signature Catamaran Sunset Sail

(4.8 of 261 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
 
Kona Signature Catamaran Sunset Sail

Kona Signature Catamaran Sunset Sail

  • Hawaii
  • Superb261 reviews4.8

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

    Free Cancellation
    Start From $109.00
 
 
-15% Waikiki: 2-hour Turtle Canyon Snorkeling Adventure

Waikiki: 2-hour Turtle Canyon Snorkeling Adventure

(4.7 of 1,422 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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Start From $68.60
(Saving 15% ) $80.71
 
-15% Waikiki: 2-hour Turtle Canyon Snorkeling Adventure

Waikiki: 2-hour Turtle Canyon Snorkeling Adventure

  • Hawaii
  • Superb1,422 reviews4.7

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

    Special Offer
    Free Cancellation
    Start From $68.60
    (Saving 15% ) $80.71
 
 

Kauai: Leila Na Pali Sunset Dinner Sail

(4.7 of 553 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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-inf% Kauai: Leila Na Pali Sunset Dinner Sail Likely to Sell Out

Kauai: Leila Na Pali Sunset Dinner Sail

  • Hawaii
  • Superb553 reviews4.7

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

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

Waikiki Sunset Cocktail Sail on the Moana Catamaran

(4.9 of 2,305 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% Waikiki Sunset Cocktail Sail on the Moana Catamaran Likely to Sell Out

Waikiki Sunset Cocktail Sail on the Moana Catamaran

  • Hawaii
  • Superb2,305 reviews4.9

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

    Special Offer
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    Start From $89.99
    (Saving inf% ) $0.00
 
 

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

(4.7 of 564 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 $47.60
(Saving 15% ) $56.00
 
-15% Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure Likely to Sell Out

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

  • Hawaii
  • Superb564 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 $47.60
    (Saving 15% ) $56.00
 
 

Turtles & Tacos Luxury Catamaran Snorkel

(4.8 of 126 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
(Saving inf% ) $0.00
 
-inf% Turtles & Tacos Luxury Catamaran Snorkel Likely to Sell Out

Turtles & Tacos Luxury Catamaran Snorkel

  • Hawaii
  • Superb126 reviews4.8

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
 
 

Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

(4.7 of 1,577 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 Sunset Cruise aboard Lucky Lady Likely to Sell Out

Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

  • Hawaii
  • Superb1,577 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
 
 

Waikiki Sunset Boat Cruise

(4.9 of 137 reviews)

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as we cruise the Waikiki coastline with views of Diamond head cra... More

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Start From $50.00
(Saving inf% ) $0.00
 
-inf% Waikiki Sunset Boat Cruise Likely to Sell Out

Waikiki Sunset Boat Cruise

  • Hawaii
  • Superb137 reviews4.9

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed ....

    Special Offer
    Free Cancellation
    Start From $50.00
    (Saving inf% ) $0.00
 
 

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

(4.4 of 35 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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Start From $141.98
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-inf% Maui: Ka'anapali Luxury Sunset Cocktail Sail with Open Bar Likely to Sell Out

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

  • Hawaii
  • Exellent35 reviews4.4

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

    Special Offer
    Free Cancellation
    Start From $141.98
    (Saving inf% ) $0.00
 
 

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

(4.9 of 1,622 reviews)

The water is clean, clear, and safe following the recent storms! 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. ... More

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Start From $59.99
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-inf% Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed Likely to Sell Out

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

  • Hawaii
  • Superb1,622 reviews4.9

The water is clean, clear, and safe following the recent storms! Experience one Viator's 2025 Top 2....

    Special Offer
    Free Cancellation
    Start From $59.99
    (Saving inf% ) $0.00
 
 

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

(4.8 of 1,692 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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Free Cancellation
Start From $89.56
(Saving inf% ) $0.00
 
-inf% Waikiki Turtle Snorkel and Sail on Hawea Catamaran Likely to Sell Out

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

  • Hawaii
  • Superb1,692 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
 
 

Kauai’s Na Pali Coast Snorkel and Sail Tour

(4.8 of 564 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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Free Cancellation
Start From $292.48
(Saving inf% ) $0.00
 
-inf% Kauai’s Na Pali Coast Snorkel and Sail Tour Likely to Sell Out

Kauai’s Na Pali Coast Snorkel and Sail Tour

  • Hawaii
  • Superb564 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
 
 

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

(4.9 of 923 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 $54.99
(Saving inf% ) $0.00
 
-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
  • Superb923 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 $54.99
    (Saving inf% ) $0.00
 
 

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

(4.8 of 20 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
(Saving inf% ) $0.00
 
-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
  • Superb20 reviews4.8

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
 
 

Waikiki Turtle Snorkeling Tour with Free Pickup

(4.8 of 175 reviews)

Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamaran. This all-in-one 6-in-1 ocean tour includes snorkeling, kayaking, stand-up paddleboarding (SUP), sea scooters, and more—offeri... More

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Start From $90.00
(Saving inf% ) $0.00
 
-inf% Waikiki Turtle Snorkeling Tour with Free Pickup Likely to Sell Out

Waikiki Turtle Snorkeling Tour with Free Pickup

  • Hawaii
  • Superb175 reviews4.8

Experience a special turtle snorkeling adventure in Waikiki aboard a smooth and comfortable catamara....

    Special Offer
    Free Cancellation
    Start From $90.00
    (Saving inf% ) $0.00
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 555 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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Start From $177.73
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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
  • Superb555 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
 
 

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

(4.8 of 575 reviews)

-Open bar fully included in $80 ticket: beer, wine, cocktails, and more -21+ only on Fridays! -Direct beach boarding — no harbor shuttle, no bus, no wasted time -Spacious 45-foot catamaran with near 360 degree view -Families wel... More

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Start From $84.77
(Saving inf% ) $0.00
 
-inf% Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu Likely to Sell Out

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

  • Hawaii
  • Superb575 reviews4.8

-Open bar fully included in $80 ticket: beer, wine, cocktails, and more -21+ only on Fridays! -Direc....

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

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 831 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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Free Cancellation
Start From $202.59
(Saving inf% ) $0.00
 
-inf% Four Winds Molokini Snorkeling Tour from Maalaea Harbor Likely to Sell Out

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

  • Hawaii
  • Superb831 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
 
 

Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed

(4.7 of 2,118 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 $149.95
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-inf% Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed Likely to Sell Out

Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed

  • Hawaii
  • Superb2,118 reviews4.7

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

    Special Offer
    Free Cancellation
    Start From $149.95
    (Saving inf% ) $0.00
 
 

Day's End Cocktail Sunset Sail

(4.7 of 83 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
  • Superb83 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
 
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