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Top 10 Best Oahu Sailing Trips

Found 64 Sailing Trips activities in Oahu. Sort by Popularity. - Page 3
 

2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People

(4.8 of 14 reviews)

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. Yo... More

Free Cancellation
Private Tour
Start From $1,150.00
 
2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People

2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People

  • Oahu
  • Superb14 reviews4.8

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....

    Free Cancellation
    Private Tour
    Start From $1,150.00
 
 
-10% Polynesian Canoe Morning Sail

Polynesian Canoe Morning Sail

(5 of 16 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

Special Offer
Free Cancellation
Private Tour
Start From $180.00
(Saving 10% ) $200.00
 
-10% Polynesian Canoe Morning Sail

Polynesian Canoe Morning Sail

  • Oahu
  • Superb16 reviews5

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

    Special Offer
    Free Cancellation
    Private Tour
    Start From $180.00
    (Saving 10% ) $200.00
 
 

Waikiki Panorama Sail: Search for Hawaiian Sea Turtles

(4.7 of 32 reviews)

Snap beautiful photos of Waikiki on this 90-minute sail, where you'll cruise past famous Waikiki Beach and out towards Diamond Head crater. The cruise departs from Kewalo Basin by Ala Moana Beach Park, and includes snacks, non-alc... More

Free Cancellation
Private Tour
Start From $82.96
 
Waikiki Panorama Sail: Search for Hawaiian Sea Turtles

Waikiki Panorama Sail: Search for Hawaiian Sea Turtles

  • Oahu
  • Superb32 reviews4.7

Snap beautiful photos of Waikiki on this 90-minute sail, where you'll cruise past famous Waikiki Bea....

    Free Cancellation
    Private Tour
    Start From $82.96
 
 

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 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
 
 

Waikiki Private Sunset Sail Romantic and Private

(5 of 3 reviews)

Adventure Awaits aboard our Fabulous 48' private yacht. Bring along your family and friends for a spectacular Hawaiian sunset on your private yacht. Get a chance to see whales, dolphins and sea turtles. Immerse yourself in a bucke... More

Free Cancellation
Private Tour
Start From $799.00
 
Waikiki Private Sunset Sail Romantic and Private

Waikiki Private Sunset Sail Romantic and Private

  • Oahu
  • Superb3 reviews5

Adventure Awaits aboard our Fabulous 48' private yacht. Bring along your family and friends for a sp....

    Free Cancellation
    Private Tour
    Start From $799.00
 
 

#1 eFoil 2 hr group + 2 hr wing foil or windsurf or kayak lesson

(5 of 4 reviews)

You will receive special Ocean Safety training prior to your adventure. Our two way radio helmets help us to give precise specific info as needed so you learn faster and safer. We will share with you the best locations to launch f... More

Free Cancellation
Private Tour
Start From $299.00
 
#1 eFoil 2 hr group + 2 hr wing foil or windsurf or kayak lesson

#1 eFoil 2 hr group + 2 hr wing foil or windsurf or kayak lesson

  • Oahu
  • Superb4 reviews5

You will receive special Ocean Safety training prior to your adventure. Our two way radio helmets he....

    Free Cancellation
    Private Tour
    Start From $299.00
 
 

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

(1 of 1 review)

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

Free Cancellation
Private Tour
Start From $151.00
 
Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

  • Oahu

Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-bui....

    Free Cancellation
    Private Tour
    Start From $151.00
 
 

Luxury Diamond Head Sunset Sail

(5 of 3 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 50' luxury yacht. Immerse yourself in a gorgeous Hawaiian sunset the only way, from... More

Free Cancellation
Private Tour
Start From $1,398.00
 
Luxury Diamond Head Sunset Sail

Luxury Diamond Head Sunset Sail

  • Oahu
  • Superb3 reviews5

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 $1,398.00
 
 

3 Hour Luxury Private Sailing Catamaran for 7-12 People

(5 of 3 reviews)

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. Yo... More

Free Cancellation
Private Tour
Start From $1,995.00
 
3 Hour Luxury Private Sailing Catamaran for 7-12 People

3 Hour Luxury Private Sailing Catamaran for 7-12 People

  • Oahu
  • Superb3 reviews5

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....

    Free Cancellation
    Private Tour
    Start From $1,995.00
 
 

BYOB Friday Night Fireworks Cruise

(4.2 of 5 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
  • Exellent5 reviews4.2

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 Waikiki Fireworks Sail

(3 of 1 review)

Sunset, Sailing and Fireworks! Highlights of Hawaii! Top Rated Sailing adventure in Waikiki. Enjoy a spectacular Hawaiian sunset and the Friday Night Fireworks onboard a luxury private yacht.... More

Free Cancellation
Private Tour
Start From $699.00
 
Friday Night Waikiki Fireworks Sail Likely to Sell Out

Friday Night Waikiki Fireworks Sail

  • Oahu

Sunset, Sailing and Fireworks! Highlights of Hawaii! Top Rated Sailing adventure in Waikiki. Enjoy a....

    Free Cancellation
    Private Tour
    Start From $699.00
 
 

Private Whale Watching Sailing Adventure

(3.5 of 2 reviews)

From the comfort of your private luxury yacht, enjoy an amazing experience with Hawaii’s humpback whales. Departing near Waikiki, enjoy a leisurely sail against the majestic backdrop of Diamond Head as you scan the water for maj... More

Free Cancellation
Private Tour
Start From $695.00
 
Private Whale Watching Sailing Adventure Likely to Sell Out

Private Whale Watching Sailing Adventure

  • Oahu
  • Good2 reviews3.5

From the comfort of your private luxury yacht, enjoy an amazing experience with Hawaii’s humpback ....

    Free Cancellation
    Private Tour
    Start From $695.00
 
 

2hr Luxury Private Sailing Catamaran for 7-12 People

(3.5 of 2 reviews)

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. Yo... More

Free Cancellation
Private Tour
Start From $1,495.00
 
2hr Luxury Private Sailing Catamaran for 7-12 People Likely to Sell Out

2hr Luxury Private Sailing Catamaran for 7-12 People

  • Oahu
  • Good2 reviews3.5

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....

    Free Cancellation
    Private Tour
    Start From $1,495.00
 
 

Moana’s Luxury semi-private Sunset Cruise on Nalu

(4.3 of 6 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 $121.99
 
Moana’s Luxury semi-private Sunset Cruise on Nalu Likely to Sell Out

Moana’s Luxury semi-private Sunset Cruise on Nalu

  • Oahu
  • Exellent6 reviews4.3

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

    Free Cancellation
    Private Tour
    Start From $121.99
 
 

Private South Shore Sail Charter

(5 of 2 reviews)

Manu Kai's south shore sails offer stunning views of Waikiki, Ala Moana, and Kaka'ako! Sit back and enjoy complimentary drinks while getting the ocean breeze, some Hawaiian sunshine, and even a splash or two! Experience the south ... More

Free Cancellation
Private Tour
Start From $1,000.00
 
Private South Shore Sail Charter Likely to Sell Out

Private South Shore Sail Charter

  • Oahu
  • Superb2 reviews5

Manu Kai's south shore sails offer stunning views of Waikiki, Ala Moana, and Kaka'ako! Sit back and ....

    Free Cancellation
    Private Tour
    Start From $1,000.00
 
 

Private Swim and Sail Charter (Kewalo Harbor)

(5 of 2 reviews)

A beautiful ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and whales (seasonal). This experience is customization in its duration and activity *Viewing marine life is not guaranteed but we do... More

Free Cancellation
Private Tour
Start From $1,800.00
 
Private Swim and Sail Charter (Kewalo Harbor) Likely to Sell Out

Private Swim and Sail Charter (Kewalo Harbor)

  • Oahu
  • Superb2 reviews5

A beautiful ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and....

    Free Cancellation
    Private Tour
    Start From $1,800.00
 
 

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People

(5 of 2 reviews)

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allow more flexibility with the day’s schedule and activities. Book a sail, swim, and snorkel time that works with your schedule. Yo... More

Free Cancellation
Private Tour
Start From $1,595.00
 
3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People Likely to Sell Out

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People

  • Oahu
  • Superb2 reviews5

Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....

    Free Cancellation
    Private Tour
    Start From $1,595.00
 
 

Private Morning Ceremony Sailing Charter

(5 of 2 reviews)

This is a 90-minute sailing trip to attend to ceremonies, ash scatterings, organization charters, and more. We offer this experience at a discounted rate to accommodate groups wanting to do private charters in the morning to celeb... More

Free Cancellation
Private Tour
Start From $1,000.00
 
Private Morning Ceremony Sailing Charter Likely to Sell Out

Private Morning Ceremony Sailing Charter

  • Oahu
  • Superb2 reviews5

This is a 90-minute sailing trip to attend to ceremonies, ash scatterings, organization charters, an....

    Free Cancellation
    Private Tour
    Start From $1,000.00
 
 

Kanoa Yacht Charter: 2-Hour Sail off Waikiki

(5 of 2 reviews)

Start your luxurious voyage at Kewalo Basin Harbor, located at 1025 Ala Moana Blvd - Pier E, Slip 223. With prime parking on-site, your journey begins the moment you arrive. For those without wheels, don't fret! The dock is a quic... More

Free Cancellation
Private Tour
Start From $2,000.00
 
Kanoa Yacht Charter: 2-Hour Sail off Waikiki Likely to Sell Out

Kanoa Yacht Charter: 2-Hour Sail off Waikiki

  • Oahu
  • Superb2 reviews5

Start your luxurious voyage at Kewalo Basin Harbor, located at 1025 Ala Moana Blvd - Pier E, Slip 22....

    Free Cancellation
    Private Tour
    Start From $2,000.00
 
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