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Top 10 Best Oahu Sailing Trips

Found 68 Sailing Trips activities in Oahu. Sort by Popularity.
 

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

(4.9 of 2,128 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
 
Moana’s Sunset Cocktail Sail Along Oahu's Waikiki Coast

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

  • Oahu
  • Superb2,128 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
 
 
-10% Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

(4.9 of 1,227 reviews)

2025 VIATOR TOP 20 BEST EXCURSIONS award in the UNITED STATES including the TOP RATED SNORKEL EXCURSION in the US!! Best value in Waikiki! See turtles GUARANTEED or receive a FULL REFUND! Brand new PREMIUM snorkel equipment inclu... More

Special Offer
Free Cancellation
Start From $40.45
(Saving 10% ) $44.95
 
-10% Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

  • Oahu
  • Superb1,227 reviews4.9

2025 VIATOR TOP 20 BEST EXCURSIONS award in the UNITED STATES including the TOP RATED SNORKEL EXCURS....

    Special Offer
    Free Cancellation
    Start From $40.45
    (Saving 10% ) $44.95
 
 

Waikiki Turtle Snorkeling Boat Tour and Adventure

(4.7 of 1,200 reviews)

**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!** Join us for a **2-hour snorkeling adventure** at **Turtle Canyon**, one of Oahu’s top snorkeling spots! Cruise along the stunning **Waikiki coastlin... More

Free Cancellation
Start From $80.71
 
Waikiki Turtle Snorkeling Boat Tour and Adventure

Waikiki Turtle Snorkeling Boat Tour and Adventure

  • Oahu
  • Superb1,200 reviews4.7

**Turtle Canyon Snorkel Adventure – Swim with Hawaiian Green Sea Turtles!** Join us for a **2-ho....

    Free Cancellation
    Start From $80.71
 
 
-10% 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 780 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 $49.49
(Saving 10% ) $54.99
 
-10% Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

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

  • Oahu
  • Superb780 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 $49.49
    (Saving 10% ) $54.99
 
 
-8% Sunset Boat Cruise: Swim and Cruise Waikiki

Sunset Boat Cruise: Swim and Cruise Waikiki

(4.7 of 517 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 $43.10
(Saving 8% ) $47.00
 
-8% Sunset Boat Cruise: Swim and Cruise Waikiki

Sunset Boat Cruise: Swim and Cruise Waikiki

  • Oahu
  • Superb517 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 $43.10
    (Saving 8% ) $47.00
 
 

Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran

(4.8 of 1,588 reviews)

This is the best way to start your day on Oahu! Complimentary cold brew coffee from Honolulu’s local favorite ARVO Café, served with a selection of Anahola Granola bars—Original, Chocolate Chip, Tropical, and Mango & Ginger. ... More

Free Cancellation
Start From $89.56
 
Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran

Waikiki Turtle Snorkel & Sail combo on Hawea Catamaran

  • Oahu
  • Superb1,588 reviews4.8

This is the best way to start your day on Oahu! Complimentary cold brew coffee from Honolulu’s loc....

    Free Cancellation
    Start From $89.56
 
 

Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

(4.7 of 2,106 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 $109.00
 
Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

  • Oahu
  • Superb2,106 reviews4.7

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

    Free Cancellation
    Start From $109.00
 
 
-16% Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

(4.8 of 279 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 $83.16
(Saving 16% ) $99.00
 
-16% Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

Best Waikiki Snorkel Tour: Guaranteed Turtles at Turtle Canyon

  • Oahu
  • Superb279 reviews4.8

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

    Special Offer
    Free Cancellation
    Start From $83.16
    (Saving 16% ) $99.00
 
 

Waikiki Sunset Cocktail Sail with Open Bar

(4.8 of 528 reviews)

This is our most popular sail for the fun-loving crowd! All drinks are included on this lively cruise! Strangers become fast friends on this one regardless if your cruising solo or with a crew! We provide juice, soda, bottled wate... More

Free Cancellation
Start From $84.77
 
Waikiki Sunset Cocktail Sail with Open Bar

Waikiki Sunset Cocktail Sail with Open Bar

  • Oahu
  • Superb528 reviews4.8

This is our most popular sail for the fun-loving crowd! All drinks are included on this lively cruis....

    Free Cancellation
    Start From $84.77
 
 

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

(4.8 of 259 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

Free Cancellation
Start From $72.96
 
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
  • Superb259 reviews4.8

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

    Free Cancellation
    Start From $72.96
 
 

Waikiki Sunset Boat Cruise

(5 of 65 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
  • Superb65 reviews5

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

    Free Cancellation
    Start From $50.00
 
 

2-Hour Oahu Sunset Catamaran Sail

(4.9 of 114 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

Free Cancellation
Start From $125.00
 
2-Hour Oahu Sunset Catamaran Sail

2-Hour Oahu Sunset Catamaran Sail

  • Oahu
  • Superb114 reviews4.9

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

    Free Cancellation
    Start From $125.00
 
 

Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming

(5 of 178 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

Free Cancellation
Start From $79.00
 
Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming

Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming

  • Oahu
  • Superb178 reviews5

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

    Free Cancellation
    Start From $79.00
 
 

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

(4.9 of 150 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 o... More

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

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

  • Oahu
  • Superb150 reviews4.9

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
 
 

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

(4.8 of 154 reviews)

Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamaran. Our Turtle Snorkeling Package offers a unique opportunity to snorkel with friendly turtles in the heart of Waikiki's picturesq... More

Free Cancellation
Start From $120.69
 
Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

  • Oahu
  • Superb154 reviews4.8

Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....

    Free Cancellation
    Start From $120.69
 
 

Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

(4.7 of 147 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

Free Cancellation
Start From $79.00
 
Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

  • Oahu
  • Superb147 reviews4.7

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well a....

    Free Cancellation
    Start From $79.00
 
 
-6% Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

(4.7 of 928 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 $84.49
(Saving 6% ) $89.99
 
-6% Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

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

  • Oahu
  • Superb928 reviews4.7

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

    Special Offer
    Free Cancellation
    Start From $84.49
    (Saving 6% ) $89.99
 
 

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

(4.7 of 17 reviews)

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē‘ahi), crystal blue waters, a gorgeous sunset, and from December-March, of course, the annual humpback whales!... More

Free Cancellation
Start From $80.00
 
Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

Waikiki Sunset Cruise Catamaran Boat Tour on Oahu

  • Oahu
  • Superb17 reviews4.7

Our tour offers a plethora of beautiful views such as Waikiki bay itself, Diamond head crater (Lē....

    Free Cancellation
    Start From $80.00
 
 

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

(4.9 of 233 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

Free Cancellation
Start From $49.99
 
Moana’s Swim’n’Sail Cocktail Cruise Along the Waikiki Coast

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

  • Oahu
  • Superb233 reviews4.9

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

    Free Cancellation
    Start From $49.99
 
 

Private 5Hrs Island Tour with 2Hrs Sail and Snorkel with Turtles

(5 of 3 reviews)

This 8 hour private tour includes a 5 hour custom tour of the island, and a 2.5 hour sail on a sailboat including swimming or snorkeling with turtles. You can pick and choose the stops on the island tour and go at your own pace. ... More

Free Cancellation
Private Tour
Start From $1,100.00
 
Private 5Hrs Island Tour with 2Hrs Sail and Snorkel with Turtles

Private 5Hrs Island Tour with 2Hrs Sail and Snorkel with Turtles

  • Oahu
  • Superb3 reviews5

This 8 hour private tour includes a 5 hour custom tour of the island, and a 2.5 hour sail on a sailb....

    Free Cancellation
    Private Tour
    Start From $1,100.00
 
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