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Top 10 Best Hawaii Sailing Trips

Found 104 Sailing Trips activities in Hawaii. Sort by Popularity.
 

Waikiki 2 Hour Sunset Sailing Catamaran Swim and Sail Adventure

(4.7 of 614 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 $56.00
 
Waikiki 2 Hour Sunset Sailing Catamaran Swim and Sail Adventure

Waikiki 2 Hour Sunset Sailing Catamaran Swim and Sail Adventure

  • Hawaii
  • Superb614 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 $56.00
 
 
-10% Kona Signature Catamaran Sunset Sail

Kona Signature Catamaran Sunset Sail

(4.8 of 320 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 $98.10
(Saving 10% ) $109.00
 
-10% Kona Signature Catamaran Sunset Sail

Kona Signature Catamaran Sunset Sail

  • Hawaii
  • Superb320 reviews4.8

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

    Special Offer
    Free Cancellation
    Start From $98.10
    (Saving 10% ) $109.00
 
 
-inf% Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup

Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup

(4.9 of 360 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 $99.00
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-inf% Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup

Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup

  • Hawaii
  • Superb360 reviews4.9

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

    Special Offer
    Free Cancellation
    Start From $99.00
    (Saving inf% ) $0.00
 
 
-inf% Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

(4.9 of 1,768 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 $59.99
(Saving inf% ) $0.00
 
-inf% Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

  • Hawaii
  • Superb1,768 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 $59.99
    (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

(4.6 of 73 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
(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

  • Hawaii
  • Superb73 reviews4.6

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

Waikiki: 2-hour Turtle Canyon Snorkeling Adventure

(4.7 of 1,509 reviews)

Join us for a 2-hour snorkeling adventure at Turtle Canyon, one of Oahu’s top snorkeling spots! Cruise along the stunning Waikiki coastline aboard our either 55-ft open-style catamaran or 50-ft double-decker power catamaran and ... More

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Free Cancellation
Start From $80.71
(Saving inf% ) $0.00
 
-inf% Waikiki: 2-hour Turtle Canyon Snorkeling Adventure

Waikiki: 2-hour Turtle Canyon Snorkeling Adventure

  • Hawaii
  • Superb1,509 reviews4.7

Join us for a 2-hour snorkeling adventure at Turtle Canyon, one of Oahu’s top snorkeling spots! Cr....

    Special Offer
    Free Cancellation
    Start From $80.71
    (Saving inf% ) $0.00
 
 
-inf% Waikiki Sunset Cocktail Sail on the Moana Catamaran

Waikiki Sunset Cocktail Sail on the Moana Catamaran

(4.9 of 2,393 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
(Saving inf% ) $0.00
 
-inf% Waikiki Sunset Cocktail Sail on the Moana Catamaran

Waikiki Sunset Cocktail Sail on the Moana Catamaran

  • Hawaii
  • Superb2,393 reviews4.9

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

    Special Offer
    Free Cancellation
    Start From $89.99
    (Saving inf% ) $0.00
 
 
-inf% Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu

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

(4.7 of 598 reviews)

-Open bar fully included: 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 welcome: Keiki ra... More

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

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

  • Hawaii
  • Superb598 reviews4.7

-Open bar fully included: beer, wine, cocktails, and more -21+ only on Fridays! -Direct beach boardi....

    Special Offer
    Free Cancellation
    Start From $84.77
    (Saving inf% ) $0.00
 
 
-inf% Waikiki Sunset Boat Cruise

Waikiki Sunset Boat Cruise

(4.9 of 229 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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Free Cancellation
Start From $50.00
(Saving inf% ) $0.00
 
-inf% Waikiki Sunset Boat Cruise

Waikiki Sunset Boat Cruise

  • Hawaii
  • Superb229 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
 
 
-inf% Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

(4.8 of 348 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

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Start From $99.00
(Saving inf% ) $0.00
 
-inf% Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

  • Hawaii
  • Superb348 reviews4.8

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

    Special Offer
    Free Cancellation
    Start From $99.00
    (Saving inf% ) $0.00
 
 
-inf% Turtles & Tacos Luxury Catamaran Snorkel

Turtles & Tacos Luxury Catamaran Snorkel

(4.7 of 152 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

Turtles & Tacos Luxury Catamaran Snorkel

  • Hawaii
  • Superb152 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% 'Alihilani Lahaina Sunset Sail

'Alihilani Lahaina Sunset Sail

(4.9 of 190 reviews)

We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sails. Our spacious catamarans make for a luxurious experience, allowing for incredible views of Maui and the inter islands from the... More

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Free Cancellation
Start From $117.30
(Saving inf% ) $0.00
 
-inf% 'Alihilani Lahaina Sunset Sail

'Alihilani Lahaina Sunset Sail

  • Hawaii
  • Superb190 reviews4.9

We pride ourselves on sailing, so enjoy the natural sounds as we turn of our motors and raise our sa....

    Special Offer
    Free Cancellation
    Start From $117.30
    (Saving inf% ) $0.00
 
 
-inf% Kauai: Leila Na Pali Sunset Dinner Sail

Kauai: Leila Na Pali Sunset Dinner Sail

(4.6 of 591 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
(Saving inf% ) $0.00
 
-inf% Kauai: Leila Na Pali Sunset Dinner Sail

Kauai: Leila Na Pali Sunset Dinner Sail

  • Hawaii
  • Superb591 reviews4.6

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
 
 
-inf% Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

(4.7 of 1,607 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
(Saving inf% ) $0.00
 
-inf% Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

  • Hawaii
  • Superb1,607 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% Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar

Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar

(5 of 72 reviews)

Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where our experienced crew selects the day’s best snorkel destination based on weather, tides, and ocean conditions. • Explore Lana... More

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Start From $216.22
(Saving inf% ) $0.00
 
-inf% Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar

Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar

  • Hawaii
  • Superb72 reviews5

Experience the flexibility of a true ocean adventure aboard our premium Gold Coast catamaran, where ....

    Special Offer
    Free Cancellation
    Start From $216.22
    (Saving inf% ) $0.00
 
 
-15% Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed

Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed

(4.7 of 2,133 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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Free Cancellation
Start From $84.15
(Saving 15% ) $99.00
 
-15% Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed

Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed

  • Hawaii
  • Superb2,133 reviews4.7

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

    Special Offer
    Free Cancellation
    Start From $84.15
    (Saving 15% ) $99.00
 
 
-inf% Waikiki Turtle Snorkel and Sail on Hawea Catamaran

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

(4.8 of 1,766 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

Special Offer
Free Cancellation
Start From $89.56
(Saving inf% ) $0.00
 
-inf% Waikiki Turtle Snorkel and Sail on Hawea Catamaran

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

  • Hawaii
  • Superb1,766 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
 
 
-inf% Snorkel Sail Adventure off Ka'anapali Beach in Maui

Snorkel Sail Adventure off Ka'anapali Beach in Maui

(5 of 49 reviews)

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, an endangered Hawaiian Green Sea turtle called a ‘Honu’. A hot buff... More

Special Offer
Free Cancellation
Start From $193.17
(Saving inf% ) $0.00
 
-inf% Snorkel Sail Adventure off Ka'anapali Beach in Maui

Snorkel Sail Adventure off Ka'anapali Beach in Maui

  • Hawaii
  • Superb49 reviews5

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You w....

    Special Offer
    Free Cancellation
    Start From $193.17
    (Saving inf% ) $0.00
 
 
-inf% Akialoa Mā’alaea Sunset Sail

Akialoa Mā’alaea Sunset Sail

(4.9 of 27 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

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Start From $108.11
(Saving inf% ) $0.00
 
-inf% Akialoa Mā’alaea Sunset Sail

Akialoa Mā’alaea Sunset Sail

  • Hawaii
  • Superb27 reviews4.9

Witness the stunning sunsets of Maui from the comfort of a luxury sailing catamaran. The Akialoa Sun....

    Special Offer
    Free Cancellation
    Start From $108.11
    (Saving inf% ) $0.00
 
 
-inf% Honolulu Sunset Sail from Kewalo Harbor Including Drinks

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

(4.8 of 206 reviews)

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic beverages). Sail the south shore from Kaka'ako Waterfront to Waikiki, with beautiful views ... More

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Start From $61.50
(Saving inf% ) $0.00
 
-inf% Honolulu Sunset Sail from Kewalo Harbor Including Drinks

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

  • Hawaii
  • Superb206 reviews4.8

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....

    Special Offer
    Free Cancellation
    Start From $61.50
    (Saving inf% ) $0.00
 
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