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Top 10 Best Oahu Sailing Trips

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

Waikiki: 2-hour Turtle Canyon Snorkeling Adventure

(4.7 of 1,455 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 Likely to Sell Out

Waikiki: 2-hour Turtle Canyon Snorkeling Adventure

  • Oahu
  • Superb1,455 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 2-Hour Sunset Sailing Catamaran – Swim & Sail Adventure

(4.7 of 577 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

Special Offer
Free Cancellation
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

  • Oahu
  • Superb577 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
 
 

Waikiki Sunset Cocktail Sail on the Moana Catamaran

(4.9 of 2,343 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

Special Offer
Free Cancellation
Start From $89.99
(Saving inf% ) $0.00
 
-inf% Waikiki Sunset Cocktail Sail on the Moana Catamaran Likely to Sell Out

Waikiki Sunset Cocktail Sail on the Moana Catamaran

  • Oahu
  • Superb2,343 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
 
 

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

(4.8 of 1,720 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 Likely to Sell Out

Waikiki Turtle Snorkel and Sail on Hawea Catamaran

  • Oahu
  • Superb1,720 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
 
 

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

(4.9 of 1,664 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

Special Offer
Free Cancellation
Start From $59.99
(Saving inf% ) $0.00
 
-inf% Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed Likely to Sell Out

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

  • Oahu
  • Superb1,664 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
 
 

Waikiki Turtle Snorkeling Tour with Free Pickup

(4.8 of 212 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 $95.00
(Saving inf% ) $0.00
 
-inf% Waikiki Turtle Snorkeling Tour with Free Pickup Likely to Sell Out

Waikiki Turtle Snorkeling Tour with Free Pickup

  • Oahu
  • Superb212 reviews4.8

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

    Special Offer
    Free Cancellation
    Start From $95.00
    (Saving inf% ) $0.00
 
 

Waikiki Sunset Boat Cruise

(4.9 of 175 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

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

Waikiki Sunset Boat Cruise

  • Oahu
  • Superb175 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
 
 

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

(4.9 of 947 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

Special Offer
Free Cancellation
Start From $59.98
(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

  • Oahu
  • Superb947 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 $59.98
    (Saving inf% ) $0.00
 
 

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

(4.8 of 192 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

  • Oahu
  • Superb192 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
 
 

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

(4.8 of 579 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

Special Offer
Free Cancellation
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

  • Oahu
  • Superb579 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
 
 

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

Special Offer
Free Cancellation
Start From $99.00
(Saving inf% ) $0.00
 
-inf% Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed Likely to Sell Out

Waikiki Catamaran Snorkel with Lunch Option: Turtles Guaranteed

  • Oahu
  • 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 $99.00
    (Saving inf% ) $0.00
 
 

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

(4.6 of 28 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
  • Superb28 reviews4.6

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
 
 

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

(4.8 of 303 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
  • Superb303 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
 
 

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

(4.7 of 964 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 Likely to Sell Out

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

  • Oahu
  • Superb964 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
 
 

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

(4.8 of 317 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 Likely to Sell Out

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

  • Oahu
  • Superb317 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
 
 

Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise

(5 of 10 reviews)

Our sunset turtle snorkeling tour delivers a unique all-in-one Waikiki ocean experience, combining adventure, relaxation, and unforgettable views in one trip. We reach Turtle Canyon quickly, giving you more time in the water to s... More

Special Offer
Free Cancellation
Start From $120.00
(Saving inf% ) $0.00
 
-inf% Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise Likely to Sell Out

Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise

  • Oahu
  • Superb10 reviews5

Our sunset turtle snorkeling tour delivers a unique all-in-one Waikiki ocean experience, combining a....

    Special Offer
    Free Cancellation
    Start From $120.00
    (Saving inf% ) $0.00
 
 

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

(4.9 of 256 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

Special Offer
Free Cancellation
Start From $49.99
(Saving inf% ) $0.00
 
-inf% Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast Likely to Sell Out

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

  • Oahu
  • Superb256 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
 
 

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

(4.5 of 41 reviews)

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise lets you see whales (December through March), fish, even green s... More

Special Offer
Free Cancellation
Start From $109.95
(Saving inf% ) $0.00
 
-inf% Hilton Hawaiian Village Turtle Snorkel with Optional Lunch Likely to Sell Out

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

  • Oahu
  • Exellent41 reviews4.5

Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki....

    Special Offer
    Free Cancellation
    Start From $109.95
    (Saving inf% ) $0.00
 
 

Waikiki Friday Night Fireworks Cruise

(4.5 of 31 reviews)

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insights on local culture, marine life, and island tips. Bring your favorite beverages and join us for Waikiki's weekly fireworks displ... More

Special Offer
Free Cancellation
Start From $60.00
(Saving inf% ) $0.00
 
-inf% Waikiki Friday Night Fireworks Cruise Likely to Sell Out

Waikiki Friday Night Fireworks Cruise

  • Oahu
  • Exellent31 reviews4.5

Experience authentic aloha vibes with us. Our knowledgeable guides and crew are ready to share insig....

    Special Offer
    Free Cancellation
    Start From $60.00
    (Saving inf% ) $0.00
 
 

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 $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
  • Superb204 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
 
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