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Top 10 Best Hawaii Sailing Trips

Found 108 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 5
 

#1 eFoil 1.25 hr or 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 $450.00
 
#1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson

#1 eFoil 1.25 hr or 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 $450.00
 
 

Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village

(4.1 of 11 reviews)

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

  • Hawaii
  • Exellent11 reviews4.1

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
 
 

Private Catamaran Charter in Waikiki (7-12 Guests)

(4.1 of 11 reviews)

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it will show NO AVAILABILITY. If you have 1-6 guests, you can book under our other listing labeled for 1-6 guests.) This 48-foot ca... More

Free Cancellation
Private Tour
Start From $1,200.00
 
Private Catamaran Charter in Waikiki (7-12 Guests) Likely to Sell Out

Private Catamaran Charter in Waikiki (7-12 Guests)

  • Hawaii
  • Exellent11 reviews4.1

(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it....

    Free Cancellation
    Private Tour
    Start From $1,200.00
 
 

Afternoon Ali'i Adventure

(5 of 6 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
  • Superb6 reviews5

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

    Free Cancellation
    Private Tour
    Start From $276.00
 
 

3 Hour Luxury Private Sailing Catamaran for 7-12 People

(5 of 6 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 Likely to Sell Out

3 Hour Luxury Private Sailing Catamaran for 7-12 People

  • Hawaii
  • Superb6 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
 
 

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
 
 

Midday Whale Watch: Mā’alaea Harbor

(4.9 of 100 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 $86.49
 
Midday Whale Watch: Mā’alaea Harbor Likely to Sell Out

Midday Whale Watch: Mā’alaea Harbor

  • Hawaii
  • Superb100 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $86.49
 
 

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
 
 

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
 
 

Maui: Kaanapali Beach 5-hour Snorkel w/ BBQ Lunch & Open Bar

(5 of 1 review)

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and an open bar. This is our award-winning snorkel tour that... More

Free Cancellation
Private Tour
Start From $192.05
 
Maui: Kaanapali Beach 5-hour Snorkel w/ BBQ Lunch & Open Bar Likely to Sell Out

Maui: Kaanapali Beach 5-hour Snorkel w/ BBQ Lunch & Open Bar

  • Hawaii
  • Superb1 review5

5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest ....

    Free Cancellation
    Private Tour
    Start From $192.05
 
 

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 Likely to Sell Out

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
 
 

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

(5 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 $1,595.00
 
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
  • Superb1 review5

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
 
 

2hr Luxury Private Sailing Catamaran for 7-12 People

(5 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 $1,495.00
 
2hr Luxury Private Sailing Catamaran for 7-12 People Likely to Sell Out

2hr Luxury Private Sailing Catamaran for 7-12 People

  • Hawaii
  • Superb1 review5

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
 
 

Whale Watching Sail in Honolulu with Open Bar

(5 of 1 review)

Observe the majestic humpback whales during their migration from December to March on this 1.5-hour sail in Honolulu. Experience the beauty of Oahu's coastline while searching for dolphins and sea turtles in their natural habitat.... More

Free Cancellation
Private Tour
Start From $53.36
 
Whale Watching Sail in Honolulu with Open Bar Likely to Sell Out

Whale Watching Sail in Honolulu with Open Bar

  • Hawaii
  • Superb1 review5

Observe the majestic humpback whales during their migration from December to March on this 1.5-hour ....

    Free Cancellation
    Private Tour
    Start From $53.36
 
 

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
 
 

Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu

(4.9 of 29 reviews)

Enjoy the Hawaiian Ocean, your way! 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... More

Free Cancellation
Private Tour
Start From $249.99
 
Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu Likely to Sell Out

Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu

  • Hawaii
  • Superb29 reviews4.9

Enjoy the Hawaiian Ocean, your way! The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, ....

    Free Cancellation
    Private Tour
    Start From $249.99
 
 

Private Charter Snorkel Sail Adventure off Kaanapali Beach

(4.9 of 29 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
  • Superb29 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $6,301.24
 
 

Private Swim and Sail Charter (Kewalo Harbor)

(4.9 of 29 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
  • Superb29 reviews4.9

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
 
 

Afternoon Catamaran Sail with Local Culture, Cocktails and Snacks

(5 of 1 review)

Set sail on a midday escape where cocktails meet culture aboard Maui’s most luxurious sailing catamaran. Explore the island through authentic storytelling, coastal beauty, and handcrafted island specialties, both sippable and sa... More

Free Cancellation
Private Tour
Start From $159.00
 
Afternoon Catamaran Sail with Local Culture, Cocktails and Snacks Likely to Sell Out

Afternoon Catamaran Sail with Local Culture, Cocktails and Snacks

  • Hawaii
  • Superb1 review5

Set sail on a midday escape where cocktails meet culture aboard Maui’s most luxurious sailing cata....

    Free Cancellation
    Private Tour
    Start From $159.00
 
 

Lāna'i Coast Snorkel and Sail

(5 of 1 review)

Nobody knows the waters of Maui better than our crew. Let us host you on our Gold Coast catamaran as we explore and snorkel the incredible coastline of Maui. We'll check the conditions for the day and take off across the channel o... More

Free Cancellation
Private Tour
Start From $216.22
 
Lāna'i Coast Snorkel and Sail Likely to Sell Out

Lāna'i Coast Snorkel and Sail

  • Hawaii
  • Superb1 review5

Nobody knows the waters of Maui better than our crew. Let us host you on our Gold Coast catamaran as....

    Free Cancellation
    Private Tour
    Start From $216.22
 
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