Sailing Trips in Hawaii
Top 10 Best Hawaii Sailing Trips
Found 104 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 53 Hour 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

3 Hour 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
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
Private Tour

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....
Private Tour
1.5-Hour Koa Kai Adventure Whale Watch
Experience an up-close encounter with our winter residents, the Humpback Whale! These beautiful creatures return to Maui every year to birth their young. During this trip, you will get a chance to hear the whale’s unique songs a... More
Private Tour

1.5-Hour Koa Kai Adventure Whale Watch
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Hawaii
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Superb2 reviews5
Experience an up-close encounter with our winter residents, the Humpback Whale! These beautiful crea....
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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Exellent5 reviews4.2
BYOB Fireworks Cruise! Relax and enjoy the views as you cruise along the beautiful coast of Waikiki....
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
Private Tour

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
Hawaiian Sail and Snorkel in Kailua-Kona, Hawaii
Welcome to the only place in Hawaii where the spirit of ancient Hawaiian seafaring meets modern expectations on the pristine waters of the Kona coast. Immerse yourself in a unique and unforgettable experience as we invite you to j... More
Private Tour

Hawaiian Sail and Snorkel in Kailua-Kona, Hawaii
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Hawaii
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Superb10 reviews4.9
Welcome to the only place in Hawaii where the spirit of ancient Hawaiian seafaring meets modern expe....
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
Private Tour

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
Waikiki Sunset Boat Cruise
No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as we cruise the Waikiki coastline with views of Diamond head cra... More
Private Tour

Waikiki Sunset Boat Cruise
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Hawaii
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Superb10 reviews5
No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed ....
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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Superb10 reviews5
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....
Private Tour
Morning Pali Coast Snorkel and Performance Sail
The Pali Coast Snorkel & Performance Sail tour cruises the Pali coastline, particularly Coral Gardens which boasts a unique blend of coral and sea life tucked into the cliffs near the West Maui Mountains. Enjoy the best conditions... More
Private Tour

Morning Pali Coast Snorkel and Performance Sail
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Hawaii
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Superb4 reviews4.8
The Pali Coast Snorkel & Performance Sail tour cruises the Pali coastline, particularly Coral Garden....
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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Exellent6 reviews4.3
The “MOANA” (moh-AH-nah), the Hawaiian word meaning Ocean, will be showcased in this customizabl....
Private Tour
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
Private Tour

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
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
Private Tour

Private Swim and Sail Charter (Kewalo Harbor)
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Hawaii
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Superb2 reviews5
A beautiful ride along the south shore of Oahu, potentially viewing sea turtles, dolphins, fish, and....
Private Tour
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

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
3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 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

3hr Luxury Private Sailing Catamaran in Waikiki for 1 to 6 People
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Hawaii
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Superb2 reviews5
Create a cruise where you can explore and get away from the crowds of Waikiki. Private charters allo....
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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Superb12 reviews5
Why go with an overcrowded catamaran, when you can enjoy the privacy with your love one .This privat....
Private Tour
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
Private Tour

Private Charter Snorkel Sail Adventure off Kaanapali Beach
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Hawaii
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Superb12 reviews5
PRIVATE CHARTER - While snorkeling along West Maui’s coastline, experience warm waters abundant wi....
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
Private Tour

Private Morning Ceremony Sailing Charter
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Hawaii
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Superb12 reviews5
This is a 90-minute sailing trip to attend to ceremonies, ash scatterings, organization charters, an....
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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Superb12 reviews5
Enjoy a relaxing sail to Diamond head and Experience an unforgettable evening with Friday fireworks ....
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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Superb4 reviews5
Experience the ultimate in luxury and exclusivity with our Afternoon Ali’i Adventure. Unlike crowd....
Private Tour