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Top 10 Best Oahu Sailing Trips

Found 70 Sailing Trips activities in Oahu. Sort by Popularity.
 

Waikiki, Oahu 2-Hour Whale Watching: Guaranteed Sightings

(4.6 of 1,333 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

Free Cancellation
Start From $53.31
 
Waikiki, Oahu 2-Hour Whale Watching: Guaranteed Sightings

Waikiki, Oahu 2-Hour Whale Watching: Guaranteed Sightings

  • Oahu
  • Superb1,333 reviews4.6

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

    Free Cancellation
    Start From $53.31
 
 

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

(4.9 of 2,281 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
 
Oahu's Waikiki Coast: Moana’s Sunset Cocktail Sail

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

  • Oahu
  • Superb2,281 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
 
 

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

(4.9 of 1,591 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

Free Cancellation
Start From $49.95
 
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

  • Oahu
  • Superb1,591 reviews4.9

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

    Free Cancellation
    Start From $49.95
 
 
-15% Waikiki: 2 hours - Turtle Canyon Snorkeling Adventure

Waikiki: 2 hours - Turtle Canyon Snorkeling Adventure

(4.7 of 1,402 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 hours - Turtle Canyon Snorkeling Adventure

Waikiki: 2 hours - Turtle Canyon Snorkeling Adventure

  • Oahu
  • Superb1,402 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
 
 
-inf% Waikiki Turtle Snorkel and Sail on Hawea Catamaran

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

(4.8 of 1,686 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

  • Oahu
  • Superb1,686 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
 
 
-15% Waikiki 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure

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

(4.7 of 554 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

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

  • Oahu
  • Superb554 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
 
 
-inf% Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

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

(4.9 of 906 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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Free Cancellation
Start From $49.99
(Saving inf% ) $0.00
 
-inf% Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

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

  • Oahu
  • Superb906 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
 
 
-inf% Waikiki Sunset Boat Cruise

Waikiki Sunset Boat Cruise

(4.9 of 128 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

  • Oahu
  • Superb128 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% Waikiki: Sunset Cruise from Beach & Cocktail Open Bar | Oahu

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

(4.8 of 574 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 -Sail toward Diamond Head on the famous Waikiki trade winds -Perfec... 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

  • Oahu
  • Superb574 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
 
 
-inf% Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

(4.7 of 2,117 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 $149.95
(Saving inf% ) $0.00
 
-inf% Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

  • Oahu
  • Superb2,117 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
 
 
-inf% Honolulu Sunset Sail from Kewalo Harbor Including Drinks

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

(4.9 of 182 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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Free Cancellation
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

  • Oahu
  • Superb182 reviews4.9

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
 
 
-inf% Waikiki Turtle Snorkeling Tour 6 Activities + Sailing Cruise

Waikiki Turtle Snorkeling Tour 6 Activities + Sailing Cruise

(4.8 of 167 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

Special Offer
Free Cancellation
Start From $90.00
(Saving inf% ) $0.00
 
-inf% Waikiki Turtle Snorkeling Tour 6 Activities + Sailing Cruise

Waikiki Turtle Snorkeling Tour 6 Activities + Sailing Cruise

  • Oahu
  • Superb167 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
 
 
-inf% Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

(4.8 of 310 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 $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

  • Oahu
  • Superb310 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% Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

(4.7 of 957 reviews)

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for your snorkel adventure, you’re choosing the tour with the most professionalis... More

Special Offer
Free Cancellation
Start From $84.99
(Saving inf% ) $0.00
 
-inf% Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventu....

  • Oahu
  • Superb957 reviews4.7

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On....

    Special Offer
    Free Cancellation
    Start From $84.99
    (Saving inf% ) $0.00
 
 
-inf% 2-Hour Oahu Sunset Catamaran Sail

2-Hour Oahu Sunset Catamaran Sail

(4.8 of 128 reviews)

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. Sip a cocktail and enjoy warm wind in your hair as you scan for dolphins and listen for ... More

Special Offer
Free Cancellation
Start From $130.00
(Saving inf% ) $0.00
 
-inf% 2-Hour Oahu Sunset Catamaran Sail

2-Hour Oahu Sunset Catamaran Sail

  • Oahu
  • Superb128 reviews4.8

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran fr....

    Special Offer
    Free Cancellation
    Start From $130.00
    (Saving inf% ) $0.00
 
 
-inf% Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

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

(4.8 of 297 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

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

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

  • Oahu
  • Superb297 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
 
 
-inf% Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming

Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming

(4.9 of 204 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 $79.00
(Saving inf% ) $0.00
 
-inf% Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming

Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming

  • Oahu
  • Superb204 reviews4.9

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

    Special Offer
    Free Cancellation
    Start From $79.00
    (Saving inf% ) $0.00
 
 
-inf% Waikiki Sunset Cruise from Oahu

Waikiki Sunset Cruise from Oahu

(4.8 of 54 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

Waikiki Sunset Cruise from Oahu

  • Oahu
  • Superb54 reviews4.8

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
 
 
-inf% Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

(4.6 of 250 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

Special Offer
Free Cancellation
Start From $79.00
(Saving inf% ) $0.00
 
-inf% Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

  • Oahu
  • Superb250 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
 
 
-inf% Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

(4.9 of 251 reviews)

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your very own piece of paradise. Just far away enough from the bustling travelers and crowded beaches, the crystal-clear water will br... More

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Start From $49.99
(Saving inf% ) $0.00
 
-inf% Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

  • Oahu
  • Superb251 reviews4.9

As you swim off of the coast of the world famous Waikiki beach, you’ll realize you’ve found your....

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