Sailing Trips in Hawaii
Top 10 Best Hawaii Sailing Trips
Found 107 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 52hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People
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
Private Tour
2hr Luxury Private Sailing Catamaran in Waikiki for 1-6 People
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Hawaii
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Superb14 reviews4.8
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....
Private Tour
Private Oahu Sunset Charter with Tasting and Drinks
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
Private Tour
Private Oahu Sunset Charter with Tasting and Drinks
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Hawaii
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Superb55 reviews5
This Experience is for up to 6 guests. Get the ultimate all-inclusive experience on a 46-foot world....
Private Tour
2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)
(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
Private Tour
2 Hour Private Catamaran Charter in Waikiki (7-12 Guests)
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Hawaii
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Superb2 reviews5
(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it....
Private Tour
BYOB Friday Night Fireworks Cruise
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
Private Tour
BYOB Friday Night Fireworks Cruise
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Hawaii
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Exellent6 reviews4.3
BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki....
Private Tour
Lahaina Maui Whale Watch Motors Off Sailing in Humpback Sanctuary
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
Private Tour
Lahaina Maui Whale Watch Motors Off Sailing in Humpback Sanctuary
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Hawaii
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Superb38 reviews4.9
Experience Maui’s magnificent humpback whales on a 2-hour whale watch aboard a sailing catamaran i....
Private Tour
Sunset sail Aboard Manakai Catamaran
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
Private Tour
Sunset sail Aboard Manakai Catamaran
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Hawaii
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Superb25 reviews5
Step aboard Mana Kai, a handcrafted catamaran built by William Brown, son of legendary waterman Wood....
Private Tour
Sunset Sail Experience by Catamaran in Waikiki
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
Private Tour
Sunset Sail Experience by Catamaran in Waikiki
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Hawaii
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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....
Private Tour
Maui Turtle Snorkel & Sail with Lunch & Open Bar out of Maalaea
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
Private Tour
Maui Turtle Snorkel & Sail with Lunch & Open Bar out of Maalaea
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Hawaii
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Superb42 reviews4.8
This sailing experience blends adventure and tranquility against a backdrop of Maui’s pristine lan....
Private Tour
#1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson
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
Private Tour
#1 eFoil 1.25 hr or 2 hr wing foil or windsurf or kayak lesson
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Hawaii
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Superb4 reviews5
You will receive special Ocean Safety training prior to your adventure. Our two way radio helmets he....
Private Tour
Afternoon Ali'i Adventure
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
Private Tour
Afternoon Ali'i Adventure
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Hawaii
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Superb6 reviews5
Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowd....
Private Tour
Maui: Catamaran Sunset Whale Watch with Cocktails
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
Private Tour
Maui: Catamaran Sunset Whale Watch with Cocktails
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Hawaii
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Superb2 reviews5
Experience the best of whale season at sunset! Watch humpbacks breach and play from the deck of a 65....
Private Tour
2hr Luxury Private Sailing Catamaran for 7-12 People
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
Private Tour
2hr Luxury Private Sailing Catamaran for 7-12 People
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Hawaii
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Superb4 reviews5
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....
Private Tour
Waikiki Sunset Cruise and Iconic Views with Swimming
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
Private Tour
Waikiki Sunset Cruise and Iconic Views with Swimming
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Hawaii
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Superb4 reviews5
Set sail on a spacious catamaran for a memorable sunset cruise that begins with a refreshing swim in....
Private Tour
Honolulu Sailing and Snorkeling Activity
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Hawaii
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Superb4 reviews5
You’re guaranteed to see an array of endemic reef fish, colorful corals, and other unique marine c....
Private Tour
Moana’s Luxury semi-private Sunset Cruise on Nalu
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
Private Tour
Moana’s Luxury semi-private Sunset Cruise on Nalu
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Hawaii
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Superb22 reviews4.8
The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizabl....
Private Tour
Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu
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
Private Tour
Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu
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Hawaii
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Superb36 reviews4.8
Enjoy the Hawaiian Ocean, your way! The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, ....
Private Tour
Lahaina Maui Afternoon Whale Watch Sail in Humpback Sanctuary
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
Private Tour
Lahaina Maui Afternoon Whale Watch Sail in Humpback Sanctuary
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Hawaii
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Superb1 review5
Maui is the place to see humpback whales. Each year these magnificent creatures migrate south from A....
Private Tour
Waikiki private Day Tour and Sunset sail for couples
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
Private Tour
Waikiki private Day Tour and Sunset sail for couples
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Hawaii
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Superb17 reviews5
Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This privat....
Private Tour
Sound of the Ocean Whale Watch Sail
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
Private Tour
Sound of the Ocean Whale Watch Sail
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Hawaii
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Superb1 review5
Step aboard a boat and experience whale watching like never before. On this special cruise, see hump....
Private Tour
Kona Coast Luxury Private Yacht Charter
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
Private Tour
Kona Coast Luxury Private Yacht Charter
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Hawaii
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Superb1 review5
Indulge in a personalized sailing experience aboard the luxurious 51-ft Lagoon catamaran, No Wiki. T....
Private Tour