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Top 10 Best Hawaii Sailing Trips

Found 104 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 5
 

#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

  • Hawaii
  • 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
 
 

Hilton Hawaiian Village Sunset Cocktail Cruise

(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
 
Hilton Hawaiian Village Sunset Cocktail Cruise

Hilton Hawaiian Village Sunset Cocktail Cruise

  • Hawaii

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
 
 

3 Hour Luxury Private Sailing Catamaran for 7-12 People

(1 of 1 review)

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

  • Hawaii

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
 
 

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

  • Hawaii
  • 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
 
 

Explore Turtle Canyons Waikiki Snorkel and Sail Adventure

(4.5 of 4 reviews)

Enjoy your best day in Hawaii and discover a new Adventure! This sailing with snorkeling experience is amazing for you to relax and have fun. ... More

Free Cancellation
Private Tour
Start From $1,199.00
 
Explore Turtle Canyons Waikiki Snorkel and Sail Adventure Likely to Sell Out

Explore Turtle Canyons Waikiki Snorkel and Sail Adventure

  • Hawaii
  • Exellent4 reviews4.5

Enjoy your best day in Hawaii and discover a new Adventure! This sailing with snorkeling experience ....

    Free Cancellation
    Private Tour
    Start From $1,199.00
 
 

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

  • Hawaii
  • 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

  • Hawaii

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

    Free Cancellation
    Private Tour
    Start From $699.00
 
 

Hawaiian Sail and Snorkel in Kailua-Kona, Hawaii

(4.9 of 10 reviews)

Welcome to the only place in Hawaii where the spirit of ancient Hawaiian seafaring meets modern expectations on the pristine waters of the Kona coast. Immerse yourself in a unique and unforgettable experience as we invite you to j... More

Free Cancellation
Private Tour
Start From $125.00
 
Hawaiian Sail and Snorkel in Kailua-Kona, Hawaii Likely to Sell Out

Hawaiian Sail and Snorkel in Kailua-Kona, Hawaii

  • Hawaii
  • Superb10 reviews4.9

Welcome to the only place in Hawaii where the spirit of ancient Hawaiian seafaring meets modern expe....

    Free Cancellation
    Private Tour
    Start From $125.00
 
 

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

  • Hawaii
  • 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
 
 

Morning Pali Coast Snorkel and Performance Sail

(4.8 of 4 reviews)

The Pali Coast Snorkel & Performance Sail tour cruises the Pali coastline, particularly Coral Gardens which boasts a unique blend of coral and sea life tucked into the cliffs near the West Maui Mountains. Enjoy the best conditions... More

Free Cancellation
Private Tour
Start From $129.73
 
Morning Pali Coast Snorkel and Performance Sail Likely to Sell Out

Morning Pali Coast Snorkel and Performance Sail

  • Hawaii
  • Superb4 reviews4.8

The Pali Coast Snorkel & Performance Sail tour cruises the Pali coastline, particularly Coral Garden....

    Free Cancellation
    Private Tour
    Start From $129.73
 
 

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

  • Hawaii
  • 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
 
 

Afternoon Sail With the Whales from Ma'alaea Harbor

(5 of 2 reviews)

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, the ‘Au ‘au channel off the coast of Maui boasts the greatest number. ... More

Free Cancellation
Private Tour
Start From $91.89
 
Afternoon Sail With the Whales from Ma'alaea Harbor Likely to Sell Out

Afternoon Sail With the Whales from Ma'alaea Harbor

  • Hawaii
  • Superb2 reviews5

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....

    Free Cancellation
    Private Tour
    Start From $91.89
 
 

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

  • Hawaii
  • 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 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)

  • Hawaii
  • 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
 
 

2 Hours Small Group Fireworks Night in Waikiki

(5 of 2 reviews)

Enjoy a relaxing sail to Diamond head and Experience an unforgettable evening with Friday fireworks in small intimate group . See this vibrant display from a whole new perspective as the colorful lights reflect off the sea. Kick b... More

Free Cancellation
Private Tour
Start From $549.00
 
2 Hours Small Group Fireworks Night in Waikiki Likely to Sell Out

2 Hours Small Group Fireworks Night in Waikiki

  • Hawaii
  • Superb2 reviews5

Enjoy a relaxing sail to Diamond head and Experience an unforgettable evening with Friday fireworks ....

    Free Cancellation
    Private Tour
    Start From $549.00
 
 

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

  • Hawaii
  • 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
 
 

Afternoon Ali'i Adventure

(5 of 4 reviews)

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowded tours, we limit our trips to a maximum of 22 guests, allowing for a semi-private experience aboard our spacious 50' catamaran. ... More

Free Cancellation
Private Tour
Start From $276.00
 
Afternoon Ali'i Adventure Likely to Sell Out

Afternoon Ali'i Adventure

  • Hawaii
  • Superb4 reviews5

Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowd....

    Free Cancellation
    Private Tour
    Start From $276.00
 
 

Early Sail with the Whales from Ma'alaea Harbor

(3.3 of 3 reviews)

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from Alaska, and although you can see them throughout Hawaii, the ‘Au ‘au channel off the coast of Maui boasts the greatest number. ... More

Free Cancellation
Private Tour
Start From $91.89
 
Early Sail with the Whales from Ma'alaea Harbor Likely to Sell Out

Early Sail with the Whales from Ma'alaea Harbor

  • Hawaii
  • Good3 reviews3.3

Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....

    Free Cancellation
    Private Tour
    Start From $91.89
 
 

Private Cruise Swim with Dolphin

(3.3 of 3 reviews)

Exclusive private cruise for up to 20 guests on a 40 passenger catamaran boat ideal for parties and anniversaries. An Impressive Swimming Experience with Wild Dolphins at the West Coast of Oahu. Learning about the ecosystem of wil... More

Free Cancellation
Private Tour
Start From $3,769.63
 
Private Cruise Swim with Dolphin Likely to Sell Out

Private Cruise Swim with Dolphin

  • Hawaii
  • Good3 reviews3.3

Exclusive private cruise for up to 20 guests on a 40 passenger catamaran boat ideal for parties and ....

    Free Cancellation
    Private Tour
    Start From $3,769.63
 
 

Private Charter Snorkel Sail Adventure off Kaanapali Beach

(3.3 of 3 reviews)

PRIVATE CHARTER - While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You will see a variety of tropical fish, and if you’re lucky, an endangered Hawaiian Green Sea turtle called a ‘H... More

Free Cancellation
Private Tour
Start From $6,301.24
 
Private Charter Snorkel Sail Adventure off Kaanapali Beach Likely to Sell Out

Private Charter Snorkel Sail Adventure off Kaanapali Beach

  • Hawaii
  • Good3 reviews3.3

PRIVATE CHARTER - While snorkeling along West Maui’s coastline, experience warm waters abundant wi....

    Free Cancellation
    Private Tour
    Start From $6,301.24
 
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