Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 672 Sailing Trips activities in North America. Sort by Popularity. - Page 33Private Sunset Sail for 3-6 People
Experience a private group charter with up to six passengers while sailing along the San Diego Bay. If you’re looking for a night of family fun, or to celebrate with your friends look no further. Leave your worries behind as yo... More
Private Tour

Private Sunset Sail for 3-6 People
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North America
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Superb12 reviews4.7
Experience a private group charter with up to six passengers while sailing along the San Diego Bay.....
Private Tour
Key West Haunted Night Sail on Schooner America 2.0
Join us aboard Schooner America 2.0 for a night sail with haunting nautical tales come to life under the Key West night sky. During this night boat ride, we'll cruise through the waters of Key West while listening to mysterious t... More
Private Tour

Key West Haunted Night Sail on Schooner America 2.0
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North America
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Superb12 reviews4.7
Join us aboard Schooner America 2.0 for a night sail with haunting nautical tales come to life under....
Private Tour
San Diego Private Morning Sail up to 12 guests
This private morning sail is a great way to start the day. Mornings are best to go see San Diego's wildlife because there is little wind and few waves, allowing us to easily cross over to Point Loma. The bay will most likely have ... More
Private Tour

San Diego Private Morning Sail up to 12 guests
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North America
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Superb30 reviews5
This private morning sail is a great way to start the day. Mornings are best to go see San Diego's w....
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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North America
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Superb30 reviews5
PRIVATE CHARTER - While snorkeling along West Maui’s coastline, experience warm waters abundant wi....
Private Tour
Private Long Island Sound Sailing Experience
Sail the Long Island Sound with Captain Steve. Sit back and relax as we tour Manhasset Bay, nestled between Great Neck's Kings Point and Port Washington's Sands Point. Oogle at the multi million dollar Mansions lining the coast un... More
Private Tour

Private Long Island Sound Sailing Experience
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North America
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Superb30 reviews5
Sail the Long Island Sound with Captain Steve. Sit back and relax as we tour Manhasset Bay, nestled ....
Private Tour
Private Sailing for up to 10 people 4 hrs
Sail through the bay of Puerto Vallarta celebrating your birthday, a special date for you or just to have fun with your friends in private. It is a charming classic-style sailboat, where you can enjoy the pleasure of sailing thro... More
Private Tour

Private Sailing for up to 10 people 4 hrs
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North America
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Superb30 reviews5
Sail through the bay of Puerto Vallarta celebrating your birthday, a special date for you or just to....
Private Tour
Luxury Yacht 58 ft for up to 20 people 4 hrs
Azimut yachts are designed to pamper the most demanding tastes. Feel the pleasure of sailing aboard this luxury yacht along the coast of Bahía de Banderas. You will enjoy every moment and every place in this tropical paradise. L... More
Private Tour

Luxury Yacht 58 ft for up to 20 people 4 hrs
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North America
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Superb30 reviews5
Azimut yachts are designed to pamper the most demanding tastes. Feel the pleasure of sailing aboard ....
Private Tour
3-Night Private Charter in Lake Clark National Park
An exciting private adventure exploring Lake Clark in the luxury of our 50ft sailing catamaran, the only live aboard yacht on Lake Clark. Enjoy meals prepared by your onboard chef. Relax in our beanbags and hammocks while enjoyin... More
Private Tour

3-Night Private Charter in Lake Clark National Park
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North America
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Superb2 reviews5
An exciting private adventure exploring Lake Clark in the luxury of our 50ft sailing catamaran, the ....
Private Tour
Monday Ladies Night Sail- Charleston's Luxury Catamaran w/Bar
Mermaid Monday Ladies’ Night Sail: Fun, Friends & Fabulous Harbor Views Calling all ladies! Mermaid Monday is Charleston’s hottest ladies' night, and you’re invited to join the fun. With $10 off regular tickets and irresisti... More
Private Tour

Monday Ladies Night Sail- Charleston's Luxury Catamaran w/Bar
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North America
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Superb2 reviews5
Mermaid Monday Ladies’ Night Sail: Fun, Friends & Fabulous Harbor Views Calling all ladies! Mermai....
Private Tour
Private tour at Sea of Cortés: Sunset tour or Snorkel
We kick off our day with the best available transportation service for our clients, featuring brand-new, fully-equipped vehicles for your comfort. Upon arriving at Puerto Los Cabos Marina, our sailboat will be waiting to begin the... More
Private Tour

Private tour at Sea of Cortés: Sunset tour or Snorkel
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North America
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Superb2 reviews5
We kick off our day with the best available transportation service for our clients, featuring brand-....
Private Tour
Dock Side Adventure Kayak, Paddle Boarding, Sunfish sailboats
Enjoy the day hanging out on our 30 ft Double Deck Slide Boat. Have full access to all of our water toys. Relax and listen to music in the shade. Barbecue lunch or dinner and watch the sunset. Swim off the Slide Boat or relax on o... More
Private Tour

Dock Side Adventure Kayak, Paddle Boarding, Sunfish sailboats
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North America
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Superb2 reviews5
Enjoy the day hanging out on our 30 ft Double Deck Slide Boat. Have full access to all of our water ....
Private Tour
Scientific and Cultural Tour in Bacalar with an Expert
Embark on an exclusive journey to the enchanting Bacalar Lagoon with our private tour, guided by a local expert and dedicated naturalist committed to the preservation and study of this unique ecosystem. Our guide, fluent in Englis... More
Private Tour

Scientific and Cultural Tour in Bacalar with an Expert
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North America
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Superb1 review5
Embark on an exclusive journey to the enchanting Bacalar Lagoon with our private tour, guided by a l....
Private Tour
Platinum Private Catamaran Sailing Tour
If you like to take the opportunity to meet the amazing whales and are visiting Los Cabos during the dates of December 15th thru April 15th, you can enjoy this amazing adventure for 2 hours departing at 09:00 am in the morning. If... More
Private Tour

Platinum Private Catamaran Sailing Tour
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North America
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Superb3 reviews5
If you like to take the opportunity to meet the amazing whales and are visiting Los Cabos during the....
Private Tour
Adult Only - Cabo San Lucas Romantic Sunset Cruise
Finding the right for you Sunset Cruise experience can be sometimes overwhelming and more in a destination as diverse as Los Cabos. This experience offers the perfect blend of relaxation, not crowded, Adult only, laid-back fun, de... More
Private Tour

Adult Only - Cabo San Lucas Romantic Sunset Cruise
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North America
Finding the right for you Sunset Cruise experience can be sometimes overwhelming and more in a desti....
Private Tour
Private Sunset Sail for Two
Experience intimacy while sailing along the San Diego Bay. Leave your worries behind as you cruise along the vibrant waterfront and marvel at the cityscape. Create a memory of a lifetime while sailing past Downtown, Point Loma, an... More
Private Tour

Private Sunset Sail for Two
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North America
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Superb5 reviews5
Experience intimacy while sailing along the San Diego Bay. Leave your worries behind as you cruise a....
Private Tour
Nights of Lights Sailboat Tour St Augustine Sailing
What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experience aboard a luxury sailing yacht. While many tours offer a simple ride, St Augustine Sailing provides an intimate, serene setting ... More
Private Tour

Nights of Lights Sailboat Tour St Augustine Sailing
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North America
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Superb3 reviews5
What sets St Augustine Sailing apart from other Nights of Lights boat tours is the elevated experien....
Private Tour
Private 3 hour Bird Watching Tour in Monterey Bay
Enjoy a 3 hour cruise to search for and see local seabirds of the Monterey Bay. A vessel under sail is much quieter and therefore up close encounters with seabirds are common. This tour is great for birders who are looking for an ... More
Private Tour

Private 3 hour Bird Watching Tour in Monterey Bay
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North America
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Superb1 review5
Enjoy a 3 hour cruise to search for and see local seabirds of the Monterey Bay. A vessel under sail ....
Private Tour
Magic Night Boat Dinner with Show & Speedboat Experience at Cancun (1 day tour)
Discover the magic of the Caribbean Sea with two of the most popular tours in Cancun. If you are looking for an exciting activity, experience an intrepid adventure in our guided speed boat and snorkeling tour. Our speed boats ar... More
Private Tour

Magic Night Boat Dinner with Show & Speedboat Experience at Cancu....
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North America
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Superb1 review5
Discover the magic of the Caribbean Sea with two of the most popular tours in Cancun. If you are l....
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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North America
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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
Public Schooner Sail in Greenport
You haven't truly visited the North Fork if you haven't been on the water! A sailing trip is hands down the best ways to see the East End of Long Island, and sailing aboard our unique schooner makes the experience extra special. U... More
Private Tour

Public Schooner Sail in Greenport
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North America
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Superb12 reviews5
You haven't truly visited the North Fork if you haven't been on the water! A sailing trip is hands d....
Private Tour