Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 705 Sailing Trips activities in North America. Sort by Popularity. - Page 94-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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Superb296 reviews4.9
Enjoy some time on the water with this 4-Hour Half Day Sailing Charter located in Fort Lauderdale. Y....
Sunset and Manta Ray Snorkel Adventure
Our most popular tour! Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of a lifetime - snorkeling with the majestic manta rays! Upon arriving, receive an in... More

Sunset and Manta Ray Snorkel Adventure
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North America
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Superb788 reviews4.9
Our most popular tour! Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail....
Key West Sailing & Snorkeling: A Reef Adventure
Join us for a snorkel adventure to the only living coral reef in North America. We have several fantastic reefs to choose from on both the north and south sides of Key West, each offering a unique experience. It’s about an hour ... More

Key West Sailing & Snorkeling: A Reef Adventure
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North America
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Superb144 reviews4.7
Join us for a snorkel adventure to the only living coral reef in North America. We have several fant....
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

Waikiki Sunset Boat Cruise
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North America
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Superb31 reviews5
No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed ....
1.5-Hour San Francisco Bay Sailing Tour
For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a semi-private 90-minute cruise of the bay, complete with beer and wine. This double-masted, teak-decked, bronze-fitted beauty hold... More

1.5-Hour San Francisco Bay Sailing Tour
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North America
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Superb384 reviews4.8
For a relaxing afternoon on the water, hop aboard the Privateer, a truly traditional sailboat, for a....
Private 3 Hour Swim, Snorkel & Sail on Daydreams Sailboat
This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area for enjoyment and a luxury salon, galley, cabins and marine head for your use. Get ready for f... More
Private Tour

Private 3 Hour Swim, Snorkel & Sail on Daydreams Sailboat
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North America
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Superb30 reviews5
This is a luxury Sailboat Excursion for up to 12 guests. Our 46 ft Daydreams Sailboat has a great bo....
Private Tour
Wrightsville Beach Sunset Cocktail Sail
Relax aboard our 44' catamaran Bella on this evening sail. Enjoy a Caribbean-inspired cocktail while you cruise our local waterways and watch the sunset. Wind permitting, we'll turn off the engines and enjoy the beauty of sailing!... More
Private Tour

Wrightsville Beach Sunset Cocktail Sail
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North America
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Superb7 reviews5
Relax aboard our 44' catamaran Bella on this evening sail. Enjoy a Caribbean-inspired cocktail while....
Private Tour
Sailing on Historic Schooner Yacht in Salem, MA
Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience the majesty aboard John G. Alden's personal schooner yacht Malabar X. Winner of the 1930 and 1932 Newport to Bermuda race and open... More
Private Tour

Sailing on Historic Schooner Yacht in Salem, MA
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North America
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Superb136 reviews4.9
Set Sail in beautiful Salem, Massachusetts on an incredible and historic schooner yacht. Experience ....
Private Tour
Casco Bay Morning Windjammer Sail
Sail with us for a two-hour morning Windjammer Sail on Casco Bay in Portland, Maine. This is the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds. (NOTE: This is NOT a ... More
Private Tour

Casco Bay Morning Windjammer Sail
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North America
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Superb12 reviews4.9
Sail with us for a two-hour morning Windjammer Sail on Casco Bay in Portland, Maine. This is the per....
Private Tour
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
Private Tour

JFarwell Adventure Yacht Sailing in the Halifax Harbour
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North America
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Superb133 reviews4.9
Halifax's only wind powered sailing experience! This 45' Oceanis Beneteau handles beautifully on the....
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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Superb35 reviews4.9
Explore the waters around Manhattan on a 1-hour private sightseeing cruise. Select a departure time....
Private Tour
Sunset Cocktail Cruise from Anaeho'omalu Bay
Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohala Coast aboard our legendary sailing catamaran Seasmoke. This cruise includes unlimited soft drinks, tropical juices, beers, wines... More
Private Tour

Sunset Cocktail Cruise from Anaeho'omalu Bay
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North America
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Superb57 reviews4.8
Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohal....
Private Tour
Waikiki small group turtle snorkeling & sailing
Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples or families who are up at the crack of dawn during their Hawaiian vacation due to time zone changes. As we start out our tour from ... More
Private Tour

Waikiki small group turtle snorkeling & sailing
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North America
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Superb76 reviews5
Witness the brilliant colors of a sunrise over Diamond Head crater. Ideal for early birds, couples o....
Private Tour
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
Private Tour

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 Tour
Private Customizable Sailing Tour in Cancun
Enjoy a private sailing tour for just you and your party aboard a private sailboat which offers the opportunity to visit wonderful places that can only be known by the sea. From a relaxing private sailing tour in the bay of Can... More
Private Tour

Private Customizable Sailing Tour in Cancun
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North America
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Superb119 reviews4.7
Enjoy a private sailing tour for just you and your party aboard a private sailboat which offers th....
Private Tour

Shallow Water Snorkeling and Dolphin Watching in Key West
All while avoiding the crowded big boats, spend part of your Florida vacation day out on the tropical waters of Key West on Catamaran Echo - making vacation memories since 1991. Enjoy a premium shallow snorkeling and dolphin-watc... More
Free Cancellation
Private Tour
(Saving 10% )

Shallow Water Snorkeling and Dolphin Watching in Key West
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North America
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Superb455 reviews4.6
All while avoiding the crowded big boats, spend part of your Florida vacation day out on the tropica....
Free Cancellation
Private Tour
(Saving 10% )
Brunch Cruise with Buffet in Washington
Come sailing on Seattle’s Tall Ship, a historic 19th-century style gaff-rigged schooner. We offer three public sailing tours daily from Seattle’s downtown waterfront. Our beautiful sailing ship, the Bay Lady, evokes the romanc... More
Private Tour

Brunch Cruise with Buffet in Washington
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North America
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Exellent8 reviews4.1
Come sailing on Seattle’s Tall Ship, a historic 19th-century style gaff-rigged schooner. We offer ....
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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Exellent293 reviews4.4
Discover Isla Mujeres in our luxury 45-foot catamaran over the beautiful Caribbean Sea, enjoying a d....
Private Tour
Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms
Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. This spacious 50-foot catamaran offers a perfect setting to watch the sky transform into a palette of golden hues as the sun dips be... More
Private Tour

Charleston Iconic Sunset Sail - Lux Catamaran w/Bar & Bathrooms
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North America
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Superb22 reviews4.8
Set sail aboard the Palmetto Breeze for a spectacular sunset experience on Charleston’s harbor. Th....
Private Tour
Private Sailing Charter with Captain, BYOB
Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6 guests for a 2.5-hour charter embracing Charleston's scenic Harbor. The golden hour of sunset is our prime booking time, offering... More
Private Tour

Private Sailing Charter with Captain, BYOB
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North America
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Superb59 reviews5
Embark on an exclusive sailing adventure on board "Esprit de Joy," tailor-made for groups of up to 6....
Private Tour