Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 712 Sailing Trips activities in North America. Sort by Popularity. - Page 6Schooner Clearwater- Sailing Cruise-Clearwater Beach
Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater will be a memorable visit!!! ;) *Children under age 5-not permitted to sail. *Not Suitable for Guests with mobility issues. *Parti... More
Schooner Clearwater- Sailing Cruise-Clearwater Beach
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North America
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Superb222 reviews4.9
Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater wi....
Private Luxury Yacht Charters, BYOB & Dolphins
We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the historic sites of Charleston from the water on one of our sailboats. We offer hourly, daily, or customized tours according to you... More
Private Tour
Private Luxury Yacht Charters, BYOB & Dolphins
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North America
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Superb394 reviews5
We are a family owned luxury yacht charter business. Come enjoy a BYOB day of sailing and seeing the....
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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Superb61 reviews4.8
Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohal....
Private Tour
9am Turtle Canyon Snorkel Adventure
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim with amazing green sea turtles, beautiful tropical fish, and other incredible marine life? Our snorkel guides help you feel confid... More
Private Tour
9am Turtle Canyon Snorkel Adventure
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North America
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Superb267 reviews4.9
What better way to start your day than to slip into the refreshing waters of Turtle Canyon and swim ....
Private Tour
Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open Bar
*Step into luxury when you board one of our fully-equipped sailboats. *Receive a friendly greeting from our crew who will provide you with unmatched service throughout the excursion. *Take a moment for a photo opportunity with y... More
Private Tour
Likely to Sell Out Luxury Sunset Sailing Cruise in Cancun with Light Dinner and Open....
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North America
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Exellent80 reviews4.5
*Step into luxury when you board one of our fully-equipped sailboats. *Receive a friendly greeting ....
Private Tour
Premium Isla Mujeres Tour by Private Catamaran
We specialize in making this all-day trip unique, a unique and beautiful experience for all our guests. This trip can always be customized as desired, as we offer 2 options to our customers. Our trained team is always there to pro... More
Private Tour
Likely to Sell Out Premium Isla Mujeres Tour by Private Catamaran
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North America
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Superb332 reviews4.9
We specialize in making this all-day trip unique, a unique and beautiful experience for all our gues....
Private Tour
Private 6 Hrs 47 ft. Catamaran Snorkel & Cielo Charter (30p. max)
Sail in style aboard Cozumel’s largest and most spacious catamaran—a 47ft Nautitech—on an unforgettable journey to the famous El Cielo sandbar! Just 5–10 minutes by taxi from any cruise terminal or downtown, enjoy award-wi... More
Private Tour
Likely to Sell Out Private 6 Hrs 47 ft. Catamaran Snorkel & Cielo Charter (30p. max)
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North America
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Superb16 reviews4.8
Sail in style aboard Cozumel’s largest and most spacious catamaran—a 47ft Nautitech—on an unfo....
Private Tour
Polynesian Canoe Day Sail
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and b... More
Private Tour
Likely to Sell Out Polynesian Canoe Day Sail
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North America
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Superb29 reviews4.9
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....
Private Tour
2.5 Hour Private Sunset Sailing Tour in San Diego up to 12 guests
Sea Monkey Adventures is San Diego’s first family-friendly sailing tour company, dedicated to helping families create unforgettable memories. Our vessel is thoughtfully designed to be warm and inviting, featuring handcrafted yel... More
Private Tour
Likely to Sell Out 2.5 Hour Private Sunset Sailing Tour in San Diego up to 12 guests
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North America
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Superb73 reviews5
Sea Monkey Adventures is San Diego’s first family-friendly sailing tour company, dedicated to help....
Private Tour
Private Sailboat + Captain for a Day Experience
RECENTLY AWARDED #7 WORLDWIDE AS BEST SAILING AND DAY CRUISES OPTIONS BY TRIPADVISOR TRAVELER'S CHOICE AWARDS 2022!!! Everyone´s favorite! Enjoy an easy ride around the most relevant landmarks in the lagoon on board of a beautif... More
Private Tour
Likely to Sell Out Private Sailboat + Captain for a Day Experience
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North America
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Superb569 reviews5
RECENTLY AWARDED #7 WORLDWIDE AS BEST SAILING AND DAY CRUISES OPTIONS BY TRIPADVISOR TRAVELER'S CHOI....
Private Tour
Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine
Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where you are welcome to jump in and enjoy an evening snorkel. If you do not feel like getting in the water, no worries, the bar is open! ... More
Private Tour
Likely to Sell Out Key West 2 Reef Snorkel Tour & Sunset Cruise with Beer & Wine
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North America
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Superb146 reviews4.7
Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where yo....
Private Tour
2hr. INTERACTIVE Sailing Experience on San Francisco Bay
This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a private yacht with a USCG licensed captain and crew where you'll sail beneath the Golden Gate Bridge, across the San Francisco waterfr... More
Private Tour
Likely to Sell Out 2hr. INTERACTIVE Sailing Experience on San Francisco Bay
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North America
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Superb84 reviews5
This is an Interactive Sailing Experience on San Francisco Bay with a maximum 6 passengers on a priv....
Private Tour
New York Sunset Schooner Cruise on the Hudson River
Experience a New York City sunset from the water on this evening sightseeing sail past many famous waterside landmarks. Step aboard the 80-foot, 2-masted sailboat known as Schooner Adirondack - inspired by the pilot schooners of... More
Private Tour
Likely to Sell Out New York Sunset Schooner Cruise on the Hudson River
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North America
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Superb221 reviews4.9
Experience a New York City sunset from the water on this evening sightseeing sail past many famous w....
Private Tour
Polynesian Canoe Sunset Sail
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) offering a one-of-a-kind native Hawaiian cultural and educational experience. Come sail along the beautiful Waikiki coastline and b... More
Private Tour
Likely to Sell Out Polynesian Canoe Sunset Sail
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North America
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Superb125 reviews4.9
Kamoauli is a locally owned, all-wood, double-hulled, traditional Polynesian canoe (wa’a kaulua) o....
Private Tour
Puerto Vallarta Luxury Sailing with Premium Open bar & lunch
Sail across Banderas Bay in luxury aboard our exclusive Leopard and Beneteau yachts, taking in breathtaking views of Puerto Vallarta’s coastline and the majestic Sierra Madre mountains. This small-group experience offers a perfe... More
Private Tour
Likely to Sell Out Puerto Vallarta Luxury Sailing with Premium Open bar & lunch
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North America
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Superb295 reviews4.8
Sail across Banderas Bay in luxury aboard our exclusive Leopard and Beneteau yachts, taking in breat....
Private Tour
Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses
Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moët cruise, to sip Moët & Chandon champagne and indulge your palate while being washed in the colors of the Key West sunset! Incl... More
Private Tour
Likely to Sell Out Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses
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North America
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Superb935 reviews4.9
Avoid the crowds and Sail on Key West’s beautiful shallow waters on this Adults Only Sunset & Moë....
Private Tour
Likely to Sell Out Laguna Grill - Private Boat with on-board BBQ and Drinks Included
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North America
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Superb130 reviews5
One of a kind in Bacalar! Cruise, swim, eat and drink in Bacalars most complete activity. Enjoy natu....
Private Tour
Sunset Sail Aboard the 47 ft Daydreams Sailboat
Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Grand Lagoon and along the coast of Shell Island. Enjoy a relaxing sail in the Gulf of Mexico and look for dolphins along the way. Wit... More
Private Tour
Likely to Sell Out Sunset Sail Aboard the 47 ft Daydreams Sailboat
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North America
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Superb32 reviews4.9
Your 2 hour sunset charter on our 47-foot sailboat Daydreams will include a scenic trip through Gran....
Private Tour
Portland Tall Ship Cruise on Casco Bay
What better way to see the delights of Portland than from the sea in one of the famous schooner tall ships. Join us for this mid morning cruise that will make your visit to Portland live long in the memory.... More
Private Tour
Likely to Sell Out Portland Tall Ship Cruise on Casco Bay
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North America
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Superb234 reviews4.6
What better way to see the delights of Portland than from the sea in one of the famous schooner tall....
Private Tour
Likely to Sell Out
Hear the whales! World class whale watching!
Your whale watching tour in Cabo San Lucas will become magical with the help of professional-grade hydrophones. If whales are communicating, you may be lucky to get the rare opportunity to hear the whale songs live! Our RABEN (Me... More
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Likely to Sell Out Hear the whales! World class whale watching!
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North America
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Superb7 reviews4.9
Your whale watching tour in Cabo San Lucas will become magical with the help of professional-grade h....
Free Cancellation
Private Tour
(Saving 10% )