Sailing Trips in Hawaii
Top 10 Best Hawaii Sailing Trips
Found 99 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 5Private 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
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Private Catamaran Charter in Waikiki (7-12 Guests)
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Hawaii
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Superb15 reviews5
(IMPORTANT: Make sure you have *over* 6 guests selected to see availability for this activity, or it....
Private Tour

Explore Turtle Canyons Waikiki Snorkel and Sail Adventure
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Hawaii
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Exellent4 reviews4.5
Enjoy your best day in Hawaii and discover a new Adventure! This sailing with snorkeling experience ....
Private Tour
Friday Night Waikiki Fireworks Sail
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
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Friday Night Waikiki Fireworks Sail
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Hawaii
Sunset, Sailing and Fireworks! Highlights of Hawaii! Top Rated Sailing adventure in Waikiki. Enjoy a....
Private Tour
Private Whale Watching Sailing Adventure
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
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Private Whale Watching Sailing Adventure
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Hawaii
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Good2 reviews3.5
From the comfort of your private luxury yacht, enjoy an amazing experience with Hawaii’s humpback ....
Private Tour
Coral Gardens Coastal Snorkel & Sail
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
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Coral Gardens Coastal Snorkel & Sail
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Hawaii
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Superb39 reviews4.8
This sailing experience blends adventure and tranquility against a backdrop of Maui’s pristine lan....
Private Tour
Luxury Diamond Head Sunset Sail
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
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Luxury Diamond Head Sunset Sail
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Hawaii
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Superb3 reviews5
Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sa....
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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
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2hr Luxury Private Sailing Catamaran for 7-12 People
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Hawaii
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Superb1 review5
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....
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Private South Shore Sail Charter
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
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Private South Shore Sail Charter
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Hawaii
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Superb2 reviews5
Manu Kai's south shore sails offer stunning views of Waikiki, Ala Moana, and Kaka'ako! Sit back and ....
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
Free Cancellation
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Moana’s VIP Waikiki Turtle Snorkeling Experience on Nalu
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Hawaii
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Superb29 reviews4.9
Enjoy the Hawaiian Ocean, your way! The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, ....
Free Cancellation
Private Tour
(Saving 8% )
Private Charter Snorkel Sail Adventure off Kaanapali Beach
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
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Private Charter Snorkel Sail Adventure off Kaanapali Beach
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Hawaii
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Superb29 reviews4.9
PRIVATE CHARTER - While snorkeling along West Maui’s coastline, experience warm waters abundant wi....
Private Tour
Private Swim and Sail Charter (Kewalo Harbor)
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
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Private Swim and Sail Charter (Kewalo Harbor)
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Hawaii
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Superb29 reviews4.9
A beautiful ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and....
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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Exellent8 reviews4.5
The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizabl....
Private Tour
2 Hours Small Group Fireworks Night in Waikiki
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
Private Tour

2 Hours Small Group Fireworks Night in Waikiki
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Hawaii
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Exellent8 reviews4.5
Enjoy a relaxing sail to Diamond head and Experience an unforgettable evening with Friday fireworks ....
Private Tour
Private Morning Ceremony Sailing Charter
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
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Private Morning Ceremony Sailing Charter
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Hawaii
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Exellent8 reviews4.5
This is a 90-minute sailing trip to attend to ceremonies, ash scatterings, organization charters, an....
Private Tour
Kanoa Yacht Charter: 2-Hour Sail off Waikiki
Start your luxurious voyage at Kewalo Basin Harbor, located at 1025 Ala Moana Blvd - Pier E, Slip 223. With prime parking on-site, your journey begins the moment you arrive. For those without wheels, don't fret! The dock is a quic... More
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Kanoa Yacht Charter: 2-Hour Sail off Waikiki
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Hawaii
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Exellent8 reviews4.5
Start your luxurious voyage at Kewalo Basin Harbor, located at 1025 Ala Moana Blvd - Pier E, Slip 22....
Private Tour
Private Cruise Swim with Dolphin
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
Private Tour

Private Cruise Swim with Dolphin
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Hawaii
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Exellent8 reviews4.5
Exclusive private cruise for up to 20 guests on a 40 passenger catamaran boat ideal for parties and ....
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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Superb15 reviews5
Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This privat....
Private Tour
Private Luxury Sailboat Charters of Honolulu
Oahu’s private luxury sailboat charter, Sailing Beauty, is operated by a mother and son team. While aboard this fully renovated 41' vessel, view the most treasured maritime life and landscapes of Oahu on a Day Sail and create gr... More
Private Tour

Private Luxury Sailboat Charters of Honolulu
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Hawaii
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Superb15 reviews5
Oahu’s private luxury sailboat charter, Sailing Beauty, is operated by a mother and son team. Whil....
Private Tour
Lana'i Coast Snorkel and Sail
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
Private Tour

Lana'i Coast Snorkel and Sail
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Hawaii
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Superb15 reviews5
Nobody knows the waters of Maui better than our crew. Let us host you on our Gold Coast catamaran as....
Private Tour