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Top 10 Best Hawaii Sailing Trips

Found 109 Sailing Trips activities in Hawaii. Sort by Popularity.
 

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

(4.7 of 587 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 & Sail Adventure

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

  • Hawaii
  • Superb587 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
 
 

Waikiki: 2-hour Turtle Canyon Snorkeling Adventure

(4.7 of 1,473 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

Free Cancellation
Start From $80.71
 
Waikiki: 2-hour Turtle Canyon Snorkeling Adventure

Waikiki: 2-hour Turtle Canyon Snorkeling Adventure

  • Hawaii
  • Superb1,473 reviews4.7

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

    Free Cancellation
    Start From $80.71
 
 

Kona Signature Catamaran Sunset Sail

(4.8 of 291 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

Free Cancellation
Start From $109.00
 
Kona Signature Catamaran Sunset Sail

Kona Signature Catamaran Sunset Sail

  • Hawaii
  • Superb291 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
 
 

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

(4.5 of 57 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

Free Cancellation
Start From $141.98
 
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
  • Exellent57 reviews4.5

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

    Free Cancellation
    Start From $141.98
 
 

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

(4.9 of 1,700 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 $59.99
 
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed Likely to Sell Out

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

  • Hawaii
  • Superb1,700 reviews4.9

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

    Free Cancellation
    Start From $59.99
 
 

Turtles & Tacos Luxury Catamaran Snorkel

(4.7 of 140 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 Likely to Sell Out

Turtles & Tacos Luxury Catamaran Snorkel

  • Hawaii
  • Superb140 reviews4.7

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
 
 

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

(5 of 55 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

Free Cancellation
Start From $216.22
 
Luxury Maui to Lanai Snorkel Sail w/ Breakfast, Lunch & Open Bar Likely to Sell Out

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

  • Hawaii
  • Superb55 reviews5

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

    Free Cancellation
    Start From $216.22
 
 

Snorkel Sail Adventure off Ka'anapali Beach, Maui

(5 of 41 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

Free Cancellation
Start From $192.17
 
Snorkel Sail Adventure off Ka'anapali Beach, Maui Likely to Sell Out

Snorkel Sail Adventure off Ka'anapali Beach, Maui

  • Hawaii
  • Superb41 reviews5

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

    Free Cancellation
    Start From $192.17
 
 

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

(4.8 of 1,740 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 Likely to Sell Out

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

  • Hawaii
  • Superb1,740 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
 
 

Waikiki Sunset Boat Cruise

(4.9 of 190 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

Free Cancellation
Start From $50.00
 
Waikiki Sunset Boat Cruise Likely to Sell Out

Waikiki Sunset Boat Cruise

  • Hawaii
  • Superb190 reviews4.9

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

    Free Cancellation
    Start From $50.00
 
 

Waikiki Sunset Cocktail Sail on the Moana Catamaran

(4.9 of 2,356 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
 
Waikiki Sunset Cocktail Sail on the Moana Catamaran Likely to Sell Out

Waikiki Sunset Cocktail Sail on the Moana Catamaran

  • Hawaii
  • Superb2,356 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
 
 

Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed

(4.7 of 2,123 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 $99.00
 
Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed Likely to Sell Out

Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed

  • Hawaii
  • Superb2,123 reviews4.7

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

    Free Cancellation
    Start From $99.00
 
 

Kauai: Leila Na Pali Sunset Dinner Sail

(4.6 of 578 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

Free Cancellation
Start From $263.82
 
Kauai: Leila Na Pali Sunset Dinner Sail Likely to Sell Out

Kauai: Leila Na Pali Sunset Dinner Sail

  • Hawaii
  • Superb578 reviews4.6

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

    Free Cancellation
    Start From $263.82
 
 

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

(4.7 of 584 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

Free Cancellation
Start From $84.77
 
Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu Likely to Sell Out

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

  • Hawaii
  • Superb584 reviews4.7

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

    Free Cancellation
    Start From $84.77
 
 

Waikiki Turtle Snorkeling Tour with Free Pickup

(4.8 of 228 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

Free Cancellation
Start From $95.00
 
Waikiki Turtle Snorkeling Tour with Free Pickup Likely to Sell Out

Waikiki Turtle Snorkeling Tour with Free Pickup

  • Hawaii
  • Superb228 reviews4.8

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

    Free Cancellation
    Start From $95.00
 
 

Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

(4.7 of 1,594 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
 
Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady Likely to Sell Out

Kauai: Deluxe Na Pali Sunset Cruise aboard Lucky Lady

  • Hawaii
  • Superb1,594 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
 
 

'Alihilani Lahaina Sunset Sail

(4.9 of 150 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

Free Cancellation
Start From $117.30
 
'Alihilani Lahaina Sunset Sail Likely to Sell Out

'Alihilani Lahaina Sunset Sail

  • Hawaii
  • Superb150 reviews4.9

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

    Free Cancellation
    Start From $117.30
 
 

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

(4.8 of 24 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

Free Cancellation
Start From $203.16
 
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
  • Superb24 reviews4.8

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

    Free Cancellation
    Start From $203.16
 
 

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

(4.8 of 321 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

Special Offer
Free Cancellation
Start From $79.20
(Saving 20% ) $99.00
 
-20% Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon Likely to Sell Out

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

  • Hawaii
  • Superb321 reviews4.8

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

    Special Offer
    Free Cancellation
    Start From $79.20
    (Saving 20% ) $99.00
 
 

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

(4.8 of 198 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

Special Offer
Free Cancellation
Start From $61.50
(Saving inf% ) $0.00
 
-inf% Honolulu Sunset Sail from Kewalo Harbor Including Drinks Likely to Sell Out

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

  • Hawaii
  • Superb198 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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