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Top 10 Best Oahu Sailing Trips

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

2-Hour Whale Watching of Waikiki, Oahu: Guaranteed Sightings

(4.6 of 977 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
 
2-Hour Whale Watching of Waikiki, Oahu: Guaranteed Sightings

2-Hour Whale Watching of Waikiki, Oahu: Guaranteed Sightings

  • Oahu
  • Superb977 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 Catamaran Snorkel Tour: See Turtles 100% Guaranteed

(4.9 of 1,365 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 $49.95
 
Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

Oahu Catamaran Snorkel Tour: See Turtles 100% Guaranteed

  • Oahu
  • Superb1,365 reviews4.9

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

    Free Cancellation
    Start From $49.95
 
 
-15% Turtle Canyon Snorkel from Waikiki

Turtle Canyon Snorkel from Waikiki

(4.7 of 1,259 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

Special Offer
Free Cancellation
Start From $68.60
(Saving 15% ) $80.71
 
-15% Turtle Canyon Snorkel from Waikiki

Turtle Canyon Snorkel from Waikiki

  • Oahu
  • Superb1,259 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
 
 

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

(4.9 of 2,195 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
  • Superb2,195 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 Turtle Snorkel and Sail on Hawea Catamaran

(4.8 of 1,641 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
  • Superb1,641 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
 
 

Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

(4.7 of 170 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
  • Superb170 reviews4.7

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

    Free Cancellation
    Start From $79.00
 
 

Waikiki Sunset Whale Watching Cruise: Guaranteed Whale Sightings

(4.4 of 74 reviews)

Experience the breathtaking beauty of nature with our Sunset Whale Watch excursion. Join us for an unforgettable journey as we set sail into the golden hues of the evening sky, where you'll have the chance to witness majestic whal... More

Free Cancellation
Start From $67.97
 
Waikiki Sunset Whale Watching Cruise: Guaranteed Whale Sightings

Waikiki Sunset Whale Watching Cruise: Guaranteed Whale Sightings

  • Oahu
  • Exellent74 reviews4.4

Experience the breathtaking beauty of nature with our Sunset Whale Watch excursion. Join us for an u....

    Free Cancellation
    Start From $67.97
 
 

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

(4.9 of 825 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 $44.99
 
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB

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

  • Oahu
  • Superb825 reviews4.9

2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE ....

    Free Cancellation
    Start From $44.99
 
 

Waikiki Sunset Cocktail Sail with Open Bar

(4.8 of 547 reviews)

Experience Waikiki’s favorite sunset sail, perfect for social adventurers and party seekers. This lively evening cruise invites solo travelers and groups alike to unwind with unlimited drinks—including Maui Brewing beers, wine... More

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

Waikiki Sunset Cocktail Sail with Open Bar

  • Oahu
  • Superb547 reviews4.8

Experience Waikiki’s favorite sunset sail, perfect for social adventurers and party seekers. This ....

    Free Cancellation
    Start From $84.77
 
 

Sunset Boat Cruise: Swim and Cruise Waikiki

(4.7 of 533 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 $58.64
 
Sunset Boat Cruise: Swim and Cruise Waikiki

Sunset Boat Cruise: Swim and Cruise Waikiki

  • Oahu
  • Superb533 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 $58.64
 
 

Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

(4.7 of 2,109 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 $149.95
 
Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

Waikiki Catamaran Snorkel Sail with Lunch: Turtles Guaranteed

  • Oahu
  • Superb2,109 reviews4.7

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

    Free Cancellation
    Start From $149.95
 
 

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

(4.7 of 936 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

Free Cancellation
Start From $84.99
 
Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

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

  • Oahu
  • Superb936 reviews4.7

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

    Free Cancellation
    Start From $84.99
 
 

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

(4.9 of 166 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
  • Superb166 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
 
 

Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming

(4.9 of 188 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
  • Superb188 reviews4.9

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

    Free Cancellation
    Start From $79.00
 
 

2-Hour Oahu Sunset Catamaran Sail

(4.8 of 121 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 $130.00
 
2-Hour Oahu Sunset Catamaran Sail

2-Hour Oahu Sunset Catamaran Sail

  • Oahu
  • Superb121 reviews4.8

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

    Free Cancellation
    Start From $130.00
 
 

Waikiki small group turtle snorkeling & sailing

(5 of 86 reviews)

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples or families who are up at the crack of dawn during their Hawaiian vacation due to time zone changes. As we start out our tour from ... More

Free Cancellation
Start From $99.00
 
Waikiki small group turtle snorkeling & sailing Likely to Sell Out

Waikiki small group turtle snorkeling & sailing

  • Oahu
  • Superb86 reviews5

Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples o....

    Free Cancellation
    Start From $99.00
 
 

Waikiki Fireworks Cocktail Cruise

(4.3 of 6 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

Free Cancellation
Start From $85.09
 
Waikiki Fireworks Cocktail Cruise Likely to Sell Out

Waikiki Fireworks Cocktail Cruise

  • Oahu
  • Exellent6 reviews4.3

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

    Free Cancellation
    Start From $85.09
 
 

Small Group Waikiki Sunset Sailing Tour

(4.9 of 110 reviews)

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it than on our boat, The Universe. Come and enjoy the Golden hour with your loved ones to make memories of a lifetime ,why go with overc... More

Free Cancellation
Start From $99.00
 
Small Group Waikiki Sunset Sailing Tour Likely to Sell Out

Small Group Waikiki Sunset Sailing Tour

  • Oahu
  • Superb110 reviews4.9

Hawaii is well known for its majestic sunsets, and there is truly no better way to experience it tha....

    Free Cancellation
    Start From $99.00
 
 

Polynesian Canoe Day Sail

(4.9 of 29 reviews)

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and b... More

Free Cancellation
Start From $200.00
 
Polynesian Canoe Day Sail Likely to Sell Out

Polynesian Canoe Day Sail

  • Oahu
  • Superb29 reviews4.9

Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....

    Free Cancellation
    Start From $200.00
 
 

Waikiki Friday Night Fireworks Boat 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

Free Cancellation
Start From $60.00
 
Waikiki Friday Night Fireworks Boat Cruise Likely to Sell Out

Waikiki Friday Night Fireworks Boat Cruise

  • Oahu
  • Exellent31 reviews4.5

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

    Free Cancellation
    Start From $60.00
 
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