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Top 10 Best Hawaii Sailing Trips

Found 104 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 3
 

Pau Hana Sunset Cocktail Cruise

(4.8 of 48 reviews)

Enjoy the warm tropical breezes and unparalleled views of the Big Island aboard a well-appointed catamaran. This cruise includes unlimited soft drinks, tropical juices, beers, wines, cocktails and a variety of appetizers.. Great f... More

Free Cancellation
Start From $165.00
 
Pau Hana Sunset Cocktail Cruise

Pau Hana Sunset Cocktail Cruise

  • Hawaii
  • Superb48 reviews4.8

Enjoy the warm tropical breezes and unparalleled views of the Big Island aboard a well-appointed cat....

    Free Cancellation
    Start From $165.00
 
 

Small Group Waikiki Sunset Sailing Tour

(4.9 of 89 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

  • Hawaii
  • Superb89 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
 
 

Kona Coastline Escape: Sail with Dolphins & Turtles on Honi Olani

(4.8 of 35 reviews)

Set sail on the Honi Olani, a 53-foot sailing catamaran, and explore the stunning Kona coastline. This 1.5-hour journey from Honokohau Harbor offers a chance to bask in the sun and enjoy the ocean breeze while taking in the breath... More

Free Cancellation
Start From $117.76
 
Kona Coastline Escape: Sail with Dolphins & Turtles on Honi Olani Likely to Sell Out

Kona Coastline Escape: Sail with Dolphins & Turtles on Honi Olani

  • Hawaii
  • Superb35 reviews4.8

Set sail on the Honi Olani, a 53-foot sailing catamaran, and explore the stunning Kona coastline. Th....

    Free Cancellation
    Start From $117.76
 
 

Oahu 3pm Tradewind Sail from Honolulu

(4.8 of 226 reviews)

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 dolphins, whales and other sea life while getting as close as possible so you c... More

Free Cancellation
Start From $59.10
 
Oahu 3pm Tradewind Sail from Honolulu Likely to Sell Out

Oahu 3pm Tradewind Sail from Honolulu

  • Hawaii
  • Superb226 reviews4.8

This is an excellent cruise for families and sailors wanting to relax and enjoy a beautiful afternoo....

    Free Cancellation
    Start From $59.10
 
 

Private Catamaran Charter in Waikiki (1-6 Guests)

(5 of 16 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)

  • Hawaii
  • Superb16 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
 
 

Private Catamaran Sunset Sail in Waikiki

(5 of 6 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

  • Hawaii
  • Superb6 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
 
 

Snorkel Sail Adventure off Ka'anapali Beach, Maui

(4.9 of 9 reviews)

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 ‘Honu’. A hot buff... More

Free Cancellation
Private Tour
Start From $172.85
 
Snorkel Sail Adventure off Ka'anapali Beach, Maui Likely to Sell Out

Snorkel Sail Adventure off Ka'anapali Beach, Maui

  • Hawaii
  • Superb9 reviews4.9

While snorkeling along West Maui’s coastline, experience warm waters abundant with sea life. You w....

    Free Cancellation
    Private Tour
    Start From $172.85
 
 

Pau Hana Sunset Cruise with the Whales

(4.8 of 46 reviews)

Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the biggest guests of all -- the Humpback Whales -- and you have perfect way to begin your evening in paradise! Cruise along the Kohala... More

Free Cancellation
Private Tour
Start From $165.00
 
Pau Hana Sunset Cruise with the Whales Likely to Sell Out

Pau Hana Sunset Cruise with the Whales

  • Hawaii
  • Superb46 reviews4.8

Combine unparalleled views of the Hawaiian coastline from a stable and spacious catamaran with the b....

    Free Cancellation
    Private Tour
    Start From $165.00
 
 

2-Hour Oahu Sunset Catamaran Sail

(4.9 of 102 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
Private Tour
Start From $125.00
 
2-Hour Oahu Sunset Catamaran Sail Likely to Sell Out

2-Hour Oahu Sunset Catamaran Sail

  • Hawaii
  • Superb102 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $125.00
 
 

Waikiki Fireworks Cocktail Cruise

(4.3 of 4 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

  • Hawaii
  • Exellent4 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
 
 

12pm Turtle Canyon Snorkel Adventure

(4.8 of 270 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
Private Tour
Start From $96.30
 
12pm Turtle Canyon Snorkel Adventure Likely to Sell Out

12pm Turtle Canyon Snorkel Adventure

  • Hawaii
  • Superb270 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $96.30
 
 

Sunset Sail Experience by Catamaran in Waikiki

(5 of 5 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

  • Hawaii
  • Superb5 reviews5

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
 
 

Friday Night Firework Cruise in Waikiki

(4.8 of 21 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

  • Hawaii
  • Superb21 reviews4.8

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
 
 

Waikiki small group turtle snorkeling & sailing

(5 of 60 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

  • Hawaii
  • Superb60 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
 
 

Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu

(4.9 of 26 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 $120.99
 
Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu Likely to Sell Out

Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu

  • Hawaii
  • Superb26 reviews4.9

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

    Free Cancellation
    Private Tour
    Start From $120.99
 
 

Waikiki Boat Party Cruise with live DJ

(4.9 of 26 reviews)

Get ready for the ultimate Day Club experience on the water! Departing from Kewalo Basin Harbor, this exclusive 4-hour catamaran party cruise features an open bar with Vodka, Rum, Whiskey, Gin, Tequila, Champagne, Beer, plus Juice... More

Free Cancellation
Private Tour
Start From $149.00
 
Waikiki Boat Party Cruise with live DJ Likely to Sell Out

Waikiki Boat Party Cruise with live DJ

  • Hawaii
  • Superb26 reviews4.9

Get ready for the ultimate Day Club experience on the water! Departing from Kewalo Basin Harbor, thi....

    Free Cancellation
    Private Tour
    Start From $149.00
 
 

Hilton Hawaiian Village Turtle Snorkel with Optional Lunch

(4.5 of 11 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

  • Hawaii
  • Exellent11 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
 
 

Deluxe Turtle Snorkeling Escapade at Waikiki

(4.8 of 4 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 $110.00
 
Deluxe Turtle Snorkeling Escapade at Waikiki Likely to Sell Out

Deluxe Turtle Snorkeling Escapade at Waikiki

  • Hawaii
  • Superb4 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $110.00
 
 

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 Likely to Sell Out

Private 5Hrs Island Tour with 2Hrs Sail and Snorkel with Turtles

  • Hawaii
  • 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
 
 

4-Hour Koa Kai Molokini Adventure Snorkel

(5 of 10 reviews)

Join us on this 3-hour snorkel adventure at Maui's most iconic snorkeling location, Molokini Crater. You will be treated to exceptional service and premium equipment. Koa Kai is a multi-purpose raft that creates a unique close-u... More

Free Cancellation
Private Tour
Start From $169.00
 
4-Hour Koa Kai Molokini Adventure Snorkel Likely to Sell Out

4-Hour Koa Kai Molokini Adventure Snorkel

  • Hawaii
  • Superb10 reviews5

Join us on this 3-hour snorkel adventure at Maui's most iconic snorkeling location, Molokini Crater.....

    Free Cancellation
    Private Tour
    Start From $169.00
 
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