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Top 10 Best Oahu Sailing Trips

Found 63 Sailing Trips activities in Oahu. Sort by Popularity.
 

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

(4.9 of 433 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 $90.00
 
Waikiki Turtle Snorkeling & 6-in-1 Adventure with Free Pickup

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

  • Oahu
  • Superb433 reviews4.9

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

    Free Cancellation
    Start From $90.00
 
 

Waikiki Sunset Cocktail Sail on the Moana Catamaran

(4.9 of 2,418 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

Waikiki Sunset Cocktail Sail on the Moana Catamaran

  • Oahu
  • Superb2,418 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 2 Hour Sunset Sailing Catamaran Swim and Sail Adventure

(4.7 of 621 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

  • Oahu
  • Superb621 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 1,516 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 the 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

  • Oahu
  • Superb1,516 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
 
 

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

(4.8 of 1,778 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

  • Oahu
  • Superb1,778 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 Snorkel Tour: See Turtles 100% Guaranteed

(4.9 of 1,787 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 $49.99
 
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

  • Oahu
  • Superb1,787 reviews4.9

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

    Free Cancellation
    Start From $49.99
 
 

Waikiki Sunset Boat Cruise

(4.9 of 246 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

Waikiki Sunset Boat Cruise

  • Oahu
  • Superb246 reviews4.9

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

    Free Cancellation
    Start From $50.00
 
 

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

(4.8 of 621 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

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

  • Oahu
  • Superb621 reviews4.8

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

    Free Cancellation
    Start From $84.77
 
 

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

(4.8 of 214 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

Free Cancellation
Start From $61.50
 
Honolulu Sunset Sail from Kewalo Harbor Including Drinks

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

  • Oahu
  • Superb214 reviews4.8

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

    Free Cancellation
    Start From $61.50
 
 

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

(4.9 of 1,003 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

  • Oahu
  • Superb1,003 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 Catamaran Snorkel with Lunch Option: Turtles Guaranteed

(4.7 of 2,135 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

Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed

  • Oahu
  • Superb2,135 reviews4.7

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

    Free Cancellation
    Start From $99.00
 
 
-10% Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

(4.8 of 361 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 $89.10
(Saving 10% ) $99.00
 
-10% Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

  • Oahu
  • Superb361 reviews4.8

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

    Special Offer
    Free Cancellation
    Start From $89.10
    (Saving 10% ) $99.00
 
 
-inf% Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise

Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise

(5 of 47 reviews)

Our Sunset Turtle Snorkeling Tour offers a unique all-in-one Waikiki ocean experience, combining adventure, relaxation, and a beautiful Hawaiian sunset in one unforgettable trip. Start your adventure at Turtle Canyon, where you c... More

Special Offer
Free Cancellation
Start From $119.00
(Saving inf% ) $0.00
 
-inf% Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise

Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise

  • Oahu
  • Superb47 reviews5

Our Sunset Turtle Snorkeling Tour offers a unique all-in-one Waikiki ocean experience, combining adv....

    Special Offer
    Free Cancellation
    Start From $119.00
    (Saving inf% ) $0.00
 
 

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

(4.8 of 64 reviews)

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village display from the best seat on Oahu—the water. Every Friday night, you’ll glide along the coastline and experience an exclusive o... More

Special Offer
Free Cancellation
Start From $90.01
(Saving inf% ) $0.00
 
-inf% Waikiki: Fireworks Cruise from Beach & Cocktail Open Bar | Oahu Likely to Sell Out

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

  • Oahu
  • Superb64 reviews4.8

Set sail with Waikiki’s top-rated fireworks cruise and enjoy the famous Hilton Hawaiian Village di....

    Special Offer
    Free Cancellation
    Start From $90.01
    (Saving inf% ) $0.00
 
 

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

(4.8 of 321 reviews)

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll g... More

Special Offer
Free Cancellation
Start From $72.96
(Saving inf% ) $0.00
 
-inf% Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea Likely to Sell Out

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

  • Oahu
  • Superb321 reviews4.8

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....

    Special Offer
    Free Cancellation
    Start From $72.96
    (Saving inf% ) $0.00
 
 

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

(4.5 of 61 reviews)

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the island like never before as you set sail from the only pier in W... More

Special Offer
Free Cancellation
Start From $119.95
(Saving inf% ) $0.00
 
-inf% Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village Likely to Sell Out

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

  • Oahu
  • Exellent61 reviews4.5

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-bui....

    Special Offer
    Free Cancellation
    Start From $119.95
    (Saving inf% ) $0.00
 
 

Waikiki Sunset Cruise from Oahu

(4.7 of 75 reviews)

Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks and a submerged glass-bottom viewing room, you’ll have an ideal vantage point to observe marine life such as dolphins, whales, sea... More

Special Offer
Free Cancellation
Start From $45.00
(Saving inf% ) $0.00
 
-inf% Waikiki Sunset Cruise from Oahu Likely to Sell Out

Waikiki Sunset Cruise from Oahu

  • Oahu
  • Superb75 reviews4.7

Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks an....

    Special Offer
    Free Cancellation
    Start From $45.00
    (Saving inf% ) $0.00
 
 

Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

(4.9 of 215 reviews)

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that s... More

Special Offer
Free Cancellation
Start From $71.10
(Saving 10% ) $79.00
 
-10% Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming Likely to Sell Out

Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming

  • Oahu
  • Superb215 reviews4.9

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....

    Special Offer
    Free Cancellation
    Start From $71.10
    (Saving 10% ) $79.00
 
 

Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu

(4.6 of 1,335 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

Special Offer
Free Cancellation
Start From $53.31
(Saving inf% ) $0.00
 
-inf% Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu Likely to Sell Out

Waikiki 2 Hour Whale Watching with Guaranteed Sightings on Oahu

  • Oahu
  • Superb1,335 reviews4.6

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

    Special Offer
    Free Cancellation
    Start From $53.31
    (Saving inf% ) $0.00
 
 

Waikiki Fireworks Cocktail Cruise

(4.6 of 9 reviews)

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a beautiful fireworks cruise that will give you a night to remember.... More

Special Offer
Free Cancellation
Start From $76.58
(Saving 10% ) $85.09
 
-10% Waikiki Fireworks Cocktail Cruise Likely to Sell Out

Waikiki Fireworks Cocktail Cruise

  • Oahu
  • Superb9 reviews4.6

Majestic provides a intimate ambiance and exceptional service. We provide a romantic setting on a b....

    Special Offer
    Free Cancellation
    Start From $76.58
    (Saving 10% ) $85.09
 
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