Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 693 Sailing Trips activities in North America. Sort by Popularity. - Page 9Sunset Sail Cruise in Key West
Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's most photographed ship! The Schooner Jolly II Rover is the only squared rigged, topsail scho... More

Sunset Sail Cruise in Key West
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North America
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Superb228 reviews4.9
Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We ....

One Hour Cruise Around Marina del Rey
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North America
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Exellent6 reviews4.3
Explore Los Angeles' best-kept secret on a classic boat tour of Marina del Rey. See the city, admire....
Kealakekua Snorkel and Sail Adventure
Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the horizon for dolphins and whales (seasonal) from our shaded cabin or sunny splash nets. Snorkel calm waters and lush coral gardens u... More

Kealakekua Snorkel and Sail Adventure
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North America
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Superb639 reviews5
Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the h....
4-Hour Fort Lauderdale Sailing Charter
Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Your sail is entirely customizable, and travelers have the option(PRIVATE CRUISES) to use their time docked or sailing out to sea. ... More

4-Hour Fort Lauderdale Sailing Charter
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North America
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Superb290 reviews4.9
Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Y....
JFarwell Adventure Yacht Sailing in the Halifax Harbour
Halifax's only wind powered sailing experience! This 45' Oceanis Beneteau handles beautifully on the water, and offers a great introduction to sailing. Guests are encouraged to be as hands on with the sailing process as they would... More

JFarwell Adventure Yacht Sailing in the Halifax Harbour
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North America
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Superb124 reviews4.9
Halifax's only wind powered sailing experience! This 45' Oceanis Beneteau handles beautifully on the....
Sail & Splash Excursion in Ft. Lauderdale
Come sail and play in Fort Lauderdale’s “Aquatic Playground” on this unforgettable excursion aboard our state of the art catamaran, the Spirit of Lauderdale. Enjoy one of the best cruise Ft Lauderdale has to offer . Sit back... More

Sail & Splash Excursion in Ft. Lauderdale
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North America
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Superb267 reviews4.8
Come sail and play in Fort Lauderdale’s “Aquatic Playground” on this unforgettable excursion a....
Private Morning Sail, Dolphin and History Tour on Mystique
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charter company in Charleston's history. For over 12 years, our sailing yachts are the highest quality and operated by two professional ... More
Private Tour

Private Morning Sail, Dolphin and History Tour on Mystique
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North America
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Superb75 reviews5
Welcome to Mystique, the beautiful 43ft sailing yacht operated by the longest running private charte....
Private Tour
Rosé Golden Hour Sunset Sail
Set sail into the sunset aboard Rosé, our 36-foot luxury sailing catamaran. This 2-hour sunset cruise offers panoramic views of the Hilton Head coastline with complimentary light bites and drinks on board. Whether you're going wi... More
Private Tour

Rosé Golden Hour Sunset Sail
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North America
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Superb2 reviews5
Set sail into the sunset aboard Rosé, our 36-foot luxury sailing catamaran. This 2-hour sunset crui....
Private Tour
Newport Sightseeing Day Sailing Experience on Schooner Adirondack
See Newport, Rhode Island from the water on an exciting sunset sail around Newport Harbor on Schooner Adirondack. You'll pass by many iconic sights, bridges, lighthouses and more during this 1.5-hour experience!... More
Private Tour

Newport Sightseeing Day Sailing Experience on Schooner Adirondack
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North America
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Superb27 reviews4.9
See Newport, Rhode Island from the water on an exciting sunset sail around Newport Harbor on Schoone....
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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Superb27 reviews4.9
PRIVATE CHARTER - While snorkeling along West Maui’s coastline, experience warm waters abundant wi....
Private Tour
Hawaiian Canoe Sailing Experience in Maui
Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour includes snorkeling with sea turtles, seasonal whale watching, and learning Hawaiian history and culture. Cold water and snorkel gear are... More
Private Tour

Hawaiian Canoe Sailing Experience in Maui
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North America
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Superb58 reviews4.8
Sail, Snorkel, and Paddle the beautiful Wailea coast in a Hawaiian Outrigger Canoe. The tour include....
Private Tour
Halifax Sunset Cruise Ft. a Live Musician
Experience golden hour, that magical time of night when the sun makes its way below the horizon, on the Halifax Sunset Cruise aboard our signature ship, the Tall Ship Silva. Purchase wine, beer, cocktails, and other beverages from... More
Private Tour

Halifax Sunset Cruise Ft. a Live Musician
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North America
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Superb2 reviews5
Experience golden hour, that magical time of night when the sun makes its way below the horizon, on ....
Private Tour
Sunset Cruise on the Scenic & Calming Chesapeake Bay
Watching the sunset over the twin beaches on the Western Shores of the Chesapeake Bay! A great way to close out a summer day with beautiful photos of the sunset. You must call 24 hours before your cruise time to see if the minimum... More
Private Tour

Sunset Cruise on the Scenic & Calming Chesapeake Bay
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North America
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Superb11 reviews4.7
Watching the sunset over the twin beaches on the Western Shores of the Chesapeake Bay! A great way t....
Private Tour
Suncoast Sailing's Sunset Sailing Experience!
Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Treasure Island, Florida! You’ll set sail about an hour before sunset to give you plenty of time to catch the full range of hues p... More
Private Tour

Suncoast Sailing's Sunset Sailing Experience!
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North America
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Superb222 reviews4.9
Set sail aboard the iconic schooner Suncoast Horizon as we set sail in the picturesque waters of Tre....
Private Tour
Sunset Sail from Ma'alaea Harbor
Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunset over the Pacific Ocean.This relaxing cruise is aboard our luxury sailing catamaran, Ocean Spirit. It’s the perfect way to ex... More
Private Tour

Sunset Sail from Ma'alaea Harbor
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North America
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Superb208 reviews4.6
Enjoy tantalizing pupus (appetizers) and island-style music against the backdrop of a stunning sunse....
Private Tour
Full-Day Luxurious Catamaran Adventure - Cancún to Isla Mujeres
Discover Isla Mujeres in our luxury 45-foot catamaran over the beautiful Caribbean Sea, enjoying a delicious drink and the entertainment from the crew. Unique and quality service is our priority. We are sure that you will love all... More
Private Tour

Full-Day Luxurious Catamaran Adventure - Cancún to Isla Mujeres
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North America
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Exellent289 reviews4.4
Discover Isla Mujeres in our luxury 45-foot catamaran over the beautiful Caribbean Sea, enjoying a d....
Private Tour
Private Luxury Daytime Boat Tour in New York City - 1 Hour
Explore the waters around Manhattan on a 1-hour private sightseeing cruise. Select a departure time, then climb aboard a luxurious, 28-foot powerboat cruiser and enjoy a relaxing and comfortable journey around lower Manhattan. En... More
Private Tour

Private Luxury Daytime Boat Tour in New York City - 1 Hour
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North America
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Superb34 reviews4.9
Explore the waters around Manhattan on a 1-hour private sightseeing cruise. Select a departure time....
Private Tour
Kona Coastline Escape: Sail with Dolphins & Turtles on Honi Olani
Set sail on the Honi Olani, a 53-foot sailing catamaran, and explore the stunning Kona coastline. This 1.5-hour journey from Honokohau Harbor offers a chance to bask in the sun and enjoy the ocean breeze while taking in the breath... More
Private Tour

Kona Coastline Escape: Sail with Dolphins & Turtles on Honi Olani
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North America
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Superb36 reviews4.8
Set sail on the Honi Olani, a 53-foot sailing catamaran, and explore the stunning Kona coastline. Th....
Private Tour
Snorkel & Millionaire Row - Private Miami Boat Tour w/ Drinks
Get ready for the ultimate party experience on our 22ft boat in Miami Beach, perfect for groups of friends, bachelorette parties, and anyone looking to celebrate in style. Cruise the sparkling waters of Miami while enjoying your ... More
Private Tour

Snorkel & Millionaire Row - Private Miami Boat Tour w/ Drinks
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North America
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Superb266 reviews4.8
Get ready for the ultimate party experience on our 22ft boat in Miami Beach, perfect for groups of f....
Private Tour
6 hours on a Private Yacht in Puerto Vallarta - Snorkeling & Beaches
Sail on a private trip aboard our 50-foot private yacht, ideal for up to 18 passengers. We are sure that with us you will know the best part of our beautiful bay of Puerto Vallarta. Do not miss the opportunity we offer you to make... More
Private Tour

6 hours on a Private Yacht in Puerto Vallarta - Snorkeling & Beac....
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North America
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Superb12 reviews5
Sail on a private trip aboard our 50-foot private yacht, ideal for up to 18 passengers. We are sure ....
Private Tour