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Top 10 Best Oahu Sailing Trips

Found 68 Sailing Trips activities in Oahu. Sort by Popularity. - Page 2
 

12pm Turtle Canyon Snorkel Adventure

(4.8 of 299 reviews)

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life? Our snorkel guides help you feel confid... More

Free Cancellation
Start From $84.77
 
12pm Turtle Canyon Snorkel Adventure

12pm Turtle Canyon Snorkel Adventure

  • Oahu
  • Superb299 reviews4.8

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....

    Free Cancellation
    Start From $84.77
 
 

Polynesian Canoe Morning Sail

(5 of 17 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 Morning Sail

Polynesian Canoe Morning Sail

  • Oahu
  • Superb17 reviews5

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

    Free Cancellation
    Start From $200.00
 
 

Waikiki 3pm Tradewind Sail - Open Bar Included

(4.8 of 245 reviews)

Open Bar: Included with the price of General Admission until 8/31/2025 This is an excellent cruise for families and sailors wanting to relax and enjoy a beautiful afternoon in the sun. We'll be keeping a sharp eye out for dolphin... More

Free Cancellation
Start From $53.36
 
Waikiki 3pm Tradewind Sail - Open Bar Included

Waikiki 3pm Tradewind Sail - Open Bar Included

  • Oahu
  • Superb245 reviews4.8

Open Bar: Included with the price of General Admission until 8/31/2025 This is an excellent cruise ....

    Free Cancellation
    Start From $53.36
 
 

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

(4.7 of 67 reviews)

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour from rainforest to reef combines views high above Honolulu to snorkeling off a catamaran off Waikiki. Explore lush rainforest and... More

Free Cancellation
Start From $196.63
 
Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

Half Day Oahu Combo Adventure: Bike, Sail and Snorkel

  • Oahu
  • Superb67 reviews4.7

Join our Honolulu bike tour on the Bike, Sail & Snorkel adventure. This exhilarating Oahu combo tour....

    Free Cancellation
    Start From $196.63
 
 

9am Turtle Canyon Snorkel Adventure

(4.9 of 266 reviews)

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life? Our snorkel guides help you feel confid... More

Free Cancellation
Start From $84.77
 
9am Turtle Canyon Snorkel Adventure

9am Turtle Canyon Snorkel Adventure

  • Oahu
  • Superb266 reviews4.9

What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....

    Free Cancellation
    Start From $84.77
 
 

Polynesian Canoe Sunset Sail

(4.9 of 124 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 $250.00
 
Polynesian Canoe Sunset Sail

Polynesian Canoe Sunset Sail

  • Oahu
  • Superb124 reviews4.9

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

    Free Cancellation
    Start From $250.00
 
 

Diamond Head Sunset Sail

(4.7 of 15 reviews)

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sail features a two hour cruise aboard a private luxury yacht. Immerse yourself in a gorgeous Hawaiian sunset the only way, from the... More

Free Cancellation
Private Tour
Start From $695.00
 
Diamond Head Sunset Sail

Diamond Head Sunset Sail

  • Oahu
  • Superb15 reviews4.7

Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sa....

    Free Cancellation
    Private Tour
    Start From $695.00
 
 

Private Catamaran Charter in Waikiki (1-6 Guests)

(5 of 21 reviews)

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large lounging nets on the front of the boat, as well as 2 small nets on the back of the boat. Not only does Hawa... More

Free Cancellation
Private Tour
Start From $900.00
 
Private Catamaran Charter in Waikiki (1-6 Guests) Likely to Sell Out

Private Catamaran Charter in Waikiki (1-6 Guests)

  • Oahu
  • Superb21 reviews5

Our 48-foot catamaran has a sleek low-profile design which makes it optimal for stability out on the....

    Free Cancellation
    Private Tour
    Start From $900.00
 
 

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
Private Tour
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
    Private Tour
    Start From $85.09
 
 

Small Group Waikiki Sunset Sailing Tour

(4.9 of 109 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
Private Tour
Start From $99.00
 
Small Group Waikiki Sunset Sailing Tour Likely to Sell Out

Small Group Waikiki Sunset Sailing Tour

  • Oahu
  • Superb109 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Waikiki small group turtle snorkeling & sailing

(5 of 78 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
Private Tour
Start From $99.00
 
Waikiki small group turtle snorkeling & sailing Likely to Sell Out

Waikiki small group turtle snorkeling & sailing

  • Oahu
  • Superb78 reviews5

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

    Free Cancellation
    Private Tour
    Start From $99.00
 
 

Deluxe Turtle Snorkeling Escapade at Waikiki

(4.9 of 7 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
Private Tour
Start From $121.00
 
Deluxe Turtle Snorkeling Escapade at Waikiki Likely to Sell Out

Deluxe Turtle Snorkeling Escapade at Waikiki

  • Oahu
  • Superb7 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $121.00
 
 

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

(4.5 of 22 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

Free Cancellation
Private Tour
Start From $156.79
 
Hilton Hawaiian Village Turtle Snorkel with Optional Lunch Likely to Sell Out

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

  • Oahu
  • Exellent22 reviews4.5

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

    Free Cancellation
    Private Tour
    Start From $156.79
 
 

BYOB Friday Night Fireworks Cruise

(4.3 of 6 reviews)

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki. You'll enjoy the view of the city lights and be in awe with this unobstructed view of fireworks from the water! With plenty of... More

Free Cancellation
Private Tour
Start From $138.95
 
BYOB Friday Night Fireworks Cruise Likely to Sell Out

BYOB Friday Night Fireworks Cruise

  • Oahu
  • Exellent6 reviews4.3

BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki....

    Free Cancellation
    Private Tour
    Start From $138.95
 
 

Friday Night Firework Cruise in Waikiki

(4.7 of 23 reviews)

After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fireworks explode over the city’s skyline, truly making this the ultimate party experience. Enjoy the Premium drinks of your choice ... More

Free Cancellation
Private Tour
Start From $69.99
 
Friday Night Firework Cruise in Waikiki Likely to Sell Out

Friday Night Firework Cruise in Waikiki

  • Oahu
  • Superb23 reviews4.7

After the sun goes down, the fun goes up! On Friday nights, you’ll be front and center as the fire....

    Free Cancellation
    Private Tour
    Start From $69.99
 
 

Moana’s Luxury semi-private Sunset Cruise on Nalu

(4.6 of 9 reviews)

The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizable experience. From November to May, Guests can look forward to Humpback Whale watching at no additional cost. Dolphins, Sea turtle... More

Free Cancellation
Private Tour
Start From $149.99
 
Moana’s Luxury semi-private Sunset Cruise on Nalu Likely to Sell Out

Moana’s Luxury semi-private Sunset Cruise on Nalu

  • Oahu
  • Superb9 reviews4.6

The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizabl....

    Free Cancellation
    Private Tour
    Start From $149.99
 
 

Private Catamaran Sunset Sail in Waikiki

(5 of 8 reviews)

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foot catamaran, Hawaiian Style, has a sleek low-profile design which makes it optimal for stability out on the ocean. It has 2 large ... More

Free Cancellation
Private Tour
Start From $900.00
 
Private Catamaran Sunset Sail in Waikiki Likely to Sell Out

Private Catamaran Sunset Sail in Waikiki

  • Oahu
  • Superb8 reviews5

Established in 2017. As a private charter company, we always cater to your preferences. Our 48-foo....

    Free Cancellation
    Private Tour
    Start From $900.00
 
 

South Shore Open Sail from Kewalo Harbor Including Drinks

(5 of 19 reviews)

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconic catamarans in Honolulu! We are a 49-passenger beautiful yellow and red retired Waikiki Beach catamaran now operating from Kewalo... More

Free Cancellation
Private Tour
Start From $47.50
 
South Shore Open Sail from Kewalo Harbor Including Drinks Likely to Sell Out

South Shore Open Sail from Kewalo Harbor Including Drinks

  • Oahu
  • Superb19 reviews5

Join us for a 90-minute daytime sailing experience from Kewalo Basin Harbor on one of the most iconi....

    Free Cancellation
    Private Tour
    Start From $47.50
 
 

Sunset sail Aboard Manakai Catamaran

(5 of 7 reviews)

Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Woody Brown—a true piece of Hawaiian sailing history. With a smaller guest capacity and open-deck layout, it offers an intimate, lai... More

Free Cancellation
Private Tour
Start From $49.82
 
Sunset sail Aboard Manakai Catamaran Likely to Sell Out

Sunset sail Aboard Manakai Catamaran

  • Oahu
  • Superb7 reviews5

Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Wood....

    Free Cancellation
    Private Tour
    Start From $49.82
 
 

Sunset Sail Experience by Catamaran in Waikiki

(4.8 of 6 reviews)

Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled catamaran. Take in the views of Honolulu skyline from offshore Waikiki and feel the warmth of the setting Hawaiian sun and tropical ... More

Free Cancellation
Private Tour
Start From $92.31
 
Sunset Sail Experience by Catamaran in Waikiki Likely to Sell Out

Sunset Sail Experience by Catamaran in Waikiki

  • Oahu
  • Superb6 reviews4.8

Enjoy the end of your day on a relaxing 2-hour Waikiki Sunset Sail aboard a 38.6 foot twin-hulled ca....

    Free Cancellation
    Private Tour
    Start From $92.31
 
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