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Top 10 Best Hawaii Sailing Trips

Found 107 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 5
 

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

  • Hawaii
  • 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
 
 

Private Oahu Sunset Charter with Tasting and Drinks

(5 of 55 reviews)

This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world renown yacht for a maximum of 6 people while enjoying the West Oahu Sunset on this 2.5-hour experience. There’s more than enoug... More

Free Cancellation
Private Tour
Start From $1,413.61
 
Private Oahu Sunset Charter with Tasting and Drinks

Private Oahu Sunset Charter with Tasting and Drinks

  • Hawaii
  • Superb55 reviews5

This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world....

    Free Cancellation
    Private Tour
    Start From $1,413.61
 
 

2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)

(5 of 2 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
 
2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)

2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)

  • Hawaii
  • Superb2 reviews5

(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
 
 

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

BYOB Friday Night Fireworks Cruise

  • Hawaii
  • 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
 
 

Lahaina Maui Whale Watch Motors Off Sailing in Humpback Sanctuary

(4.9 of 38 reviews)

Experience Maui’s magnificent humpback whales on a 2-hour whale watch aboard a sailing catamaran in the ʻAuʻau Channel, home to one of Hawaii’s greatest concentrations of humpbacks. Morning conditions often bring smooth sea... More

Free Cancellation
Private Tour
Start From $110.28
 
Lahaina Maui Whale Watch Motors Off Sailing in Humpback Sanctuary

Lahaina Maui Whale Watch Motors Off Sailing in Humpback Sanctuary

  • Hawaii
  • Superb38 reviews4.9

Experience Maui’s magnificent humpback whales on a 2-hour whale watch aboard a sailing catamaran i....

    Free Cancellation
    Private Tour
    Start From $110.28
 
 

Sunset sail Aboard Manakai Catamaran

(5 of 25 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

Sunset sail Aboard Manakai Catamaran

  • Hawaii
  • Superb25 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

Sunset Sail Experience by Catamaran in Waikiki

  • Hawaii
  • 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
 
 

Maui Turtle Snorkel & Sail with Lunch & Open Bar out of Maalaea

(4.8 of 42 reviews)

This sailing experience blends adventure and tranquility against a backdrop of Maui’s pristine landscapes. Arrive at Coral Gardens, a sheltered snorkeling haven with calm, crystal-clear waters teeming with vibrant coral reefs a... More

Free Cancellation
Private Tour
Start From $126.82
 
Maui Turtle Snorkel & Sail with Lunch & Open Bar out of Maalaea

Maui Turtle Snorkel & Sail with Lunch & Open Bar out of Maalaea

  • Hawaii
  • Superb42 reviews4.8

This sailing experience blends adventure and tranquility against a backdrop of Maui’s pristine lan....

    Free Cancellation
    Private Tour
    Start From $126.82
 
 

#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
 
 

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

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
 
 

Maui: Catamaran Sunset Whale Watch with Cocktails

(5 of 2 reviews)

Experience the best of whale season at sunset! Watch humpbacks breach and play from the deck of a 65' luxury catamaran as the sun sets with an ice-cold cocktail in hand. Guaranteed humpback whale sightings on every charter. Expe... More

Free Cancellation
Private Tour
Start From $189.00
 
Maui: Catamaran Sunset Whale Watch with Cocktails

Maui: Catamaran Sunset Whale Watch with Cocktails

  • Hawaii
  • Superb2 reviews5

Experience the best of whale season at sunset! Watch humpbacks breach and play from the deck of a 65....

    Free Cancellation
    Private Tour
    Start From $189.00
 
 

2hr Luxury Private Sailing Catamaran for 7-12 People

(5 of 4 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

2hr Luxury Private Sailing Catamaran for 7-12 People

  • Hawaii
  • Superb4 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 $1,495.00
 
 

Waikiki Sunset Cruise and Iconic Views with Swimming

(5 of 4 reviews)

Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in the crystal-clear waters off Waikīkī Beach. Glide along the iconic Gold Coast as the sun sets, painting the sky with vibrant co... More

Free Cancellation
Private Tour
Start From $65.00
 
Waikiki Sunset Cruise and Iconic Views with Swimming

Waikiki Sunset Cruise and Iconic Views with Swimming

  • Hawaii
  • Superb4 reviews5

Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in....

    Free Cancellation
    Private Tour
    Start From $65.00
 
 

Honolulu Sailing and Snorkeling Activity

(5 of 4 reviews)

You’re guaranteed to see an array of endemic reef fish, colorful corals, and other unique marine creatures that call the Hawaiian islands home.... More

Free Cancellation
Private Tour
Start From $105.00
 
Honolulu Sailing and Snorkeling Activity

Honolulu Sailing and Snorkeling Activity

  • Hawaii
  • Superb4 reviews5

You’re guaranteed to see an array of endemic reef fish, colorful corals, and other unique marine c....

    Free Cancellation
    Private Tour
    Start From $105.00
 
 

Moana’s Luxury semi-private Sunset Cruise on Nalu

(4.8 of 22 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

Moana’s Luxury semi-private Sunset Cruise on Nalu

  • Hawaii
  • Superb22 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $149.99
 
 

Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu

(4.8 of 36 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

Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu

  • Hawaii
  • Superb36 reviews4.8

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

    Free Cancellation
    Private Tour
    Start From $249.99
 
 

Lahaina Maui Afternoon Whale Watch Sail in Humpback Sanctuary

(5 of 1 review)

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 $110.28
 
Lahaina Maui Afternoon Whale Watch Sail in Humpback Sanctuary

Lahaina Maui Afternoon Whale Watch Sail in Humpback Sanctuary

  • Hawaii
  • Superb1 review5

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

    Free Cancellation
    Private Tour
    Start From $110.28
 
 

Waikiki private Day Tour and Sunset sail for couples

(5 of 17 reviews)

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This private tour was specifically created for Newlywed couples on their honeymoon, celebrating an Anniversary, or just in love, celebrating ... More

Free Cancellation
Private Tour
Start From $300.00
 
Waikiki private Day Tour and Sunset sail for couples

Waikiki private Day Tour and Sunset sail for couples

  • Hawaii
  • Superb17 reviews5

Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This privat....

    Free Cancellation
    Private Tour
    Start From $300.00
 
 

Sound of the Ocean Whale Watch Sail

(5 of 1 review)

Step aboard a boat and experience whale watching like never before. On this special cruise, see humpback whales in their natural habitat and hear them too. With a partnership with the award-winning immersive experience “Sounds ... More

Free Cancellation
Private Tour
Start From $163.68
 
Sound of the Ocean Whale Watch Sail

Sound of the Ocean Whale Watch Sail

  • Hawaii
  • Superb1 review5

Step aboard a boat and experience whale watching like never before. On this special cruise, see hump....

    Free Cancellation
    Private Tour
    Start From $163.68
 
 

Kona Coast Luxury Private Yacht Charter

(5 of 1 review)

Indulge in a personalized sailing experience aboard the luxurious 51-ft Lagoon catamaran, No Wiki. This private charter offers an unforgettable journey along the stunning Kona Coast, where you can snorkel vibrant reefs or simply r... More

Free Cancellation
Private Tour
Start From $1,195.00
 
Kona Coast Luxury Private Yacht Charter

Kona Coast Luxury Private Yacht Charter

  • Hawaii
  • Superb1 review5

Indulge in a personalized sailing experience aboard the luxurious 51-ft Lagoon catamaran, No Wiki. T....

    Free Cancellation
    Private Tour
    Start From $1,195.00
 
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