Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 714 Sailing Trips activities in North America. Sort by Popularity. - Page 18Vancouver Sailing Experience on a 50 Foot Sailboat
I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over 45 years. I have raced competitively for 20 of those, have extensive sailing and local knowledge, 12 years experience volunteering... More
Vancouver Sailing Experience on a 50 Foot Sailboat
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North America
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Superb114 reviews5
I have been living aboard full time for the past 12 years, sailing the Vancouver waterways for over ....
Private Yacht Charter in Cabo for Up to 8 People
Experience Cabo San Lucas exclusively aboard a private yacht for up to 8 people. Enjoy a personalized experience sailing in front of the iconic Arch, with a stop for snorkeling in crystal clear waters. Ideal for groups seeking pri... More
Private Tour
Private Yacht Charter in Cabo for Up to 8 People
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North America
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Superb4 reviews5
Experience Cabo San Lucas exclusively aboard a private yacht for up to 8 people. Enjoy a personalize....
Private Tour
Private Sailboat tour in Cabo San Lucas with Papillon Yachts
Enjoy a sailing cruise with our open bar and freshly made snacks, our friendly crew will take care of you to make this an unforgettable experience. Our all-inclusive and all-private tour will make sure you have everything you need... More
Private Tour
Private Sailboat tour in Cabo San Lucas with Papillon Yachts
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North America
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Superb206 reviews5
Enjoy a sailing cruise with our open bar and freshly made snacks, our friendly crew will take care o....
Private Tour
Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise
Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chill out in comfy seats, with beautiful views of the bay and National Seashore. Or explore the Condor: walk around, do the Titanic po... More
Private Tour
Condor Sailing Fun, Relaxing Public Dolphin & Sightseeing Cruise
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North America
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Superb87 reviews5
Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chil....
Private Tour
Suncoast Sailing's Day Sailing Experience!
Step aboard Suncoast Horizon, a real schooner and experience what sailing is actually supposed to feel like. No roaring engines. No canned tour script. Just wind in the sails, salt in the air, and the kind of quiet glide across t... More
Private Tour
Suncoast Sailing's Day Sailing Experience!
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North America
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Superb117 reviews4.9
Step aboard Suncoast Horizon, a real schooner and experience what sailing is actually supposed to fe....
Private Tour
New York City Sunset Sail to the Statue of Liberty
Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of Brooklyn and Jersey City from Schooner America. This classic sailboat is 105-feet in length and has about 3600 square feet of sail ... More
Private Tour
New York City Sunset Sail to the Statue of Liberty
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North America
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Superb78 reviews4.8
Experience a sunset from New York Harbor and enjoy sweeping views of Manhattan's skyline, parts of B....
Private Tour
Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club
Embark on a full-day adventure to Isla Mujeres, Cancun's most popular island getaway. Snorkel among vibrant tropical fish, then relax on Playa Norte, one of Mexico's finest beaches. Departing from the pier, begin with a 30-minut... More
Private Tour
Isla Mujeres Day Tour with Catamaran, Snorkeling & Beach Club
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North America
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Exellent172 reviews4.5
Embark on a full-day adventure to Isla Mujeres, Cancun's most popular island getaway. Snorkel among ....
Private Tour
Whale Watching with Lunch and transportation included
Experience the "Whale-tastic Adventure" in Cabo San Lucas during the winter season, where you'll have front-row seats to witness the playful and majestic antics of whales in their natural habitat. Setting sail from the Marina, you... More
Private Tour
Whale Watching with Lunch and transportation included
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North America
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Exellent20 reviews4.4
Experience the "Whale-tastic Adventure" in Cabo San Lucas during the winter season, where you'll hav....
Private Tour
Sunday Mimosa Brunch Charleston Harbor Sail - Food Included
Kick back and soak up the ultimate Sunday vibes on our Sunday Funday Mimosa Bar Sail. Step aboard our a spacious and stylish 50-foot catamaran, and set sail for a relaxing and refreshing 2-hour cruise through Charleston’s histor... More
Private Tour
Sunday Mimosa Brunch Charleston Harbor Sail - Food Included
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North America
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Superb12 reviews5
Kick back and soak up the ultimate Sunday vibes on our Sunday Funday Mimosa Bar Sail. Step aboard ou....
Private Tour
Fort Lauderdale Sailing Charter
Embark on an unforgettable journey starting in Fort Lauderdale on the iconic New River, often called the “Venice of America.” This scenic waterway offers a beautiful blend of natural mangroves, luxurious waterfront homes, and ... More
Private Tour
Fort Lauderdale Sailing Charter
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North America
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Superb404 reviews5
Embark on an unforgettable journey starting in Fort Lauderdale on the iconic New River, often called....
Private Tour
Private Sailing Charter in Savannah GA
Set sail on a private trimaran charter in Savannah, where every moment is tailored just for you. Whether it's a family outing, an intimate wedding, or a vibrant bachelorette party, enjoy the spacious and stable design of our boat,... More
Private Tour
Private Sailing Charter in Savannah GA
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North America
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Superb7 reviews5
Set sail on a private trimaran charter in Savannah, where every moment is tailored just for you. Whe....
Private Tour
El Cielito beach by Private Boat
Awarded Private Snorkel Tour! Have fun aboard your Private boat and experience Cozumel water treasures in this incredible snorkeling adventure. This 4 hours family-friendly Private tour will take you out to the most renowned ree... More
Private Tour
El Cielito beach by Private Boat
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North America
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Superb142 reviews4.8
Awarded Private Snorkel Tour! Have fun aboard your Private boat and experience Cozumel water treasu....
Private Tour
Sunset Sail in Miami: Complimentary Champagne Toast
Sunset Cruise, Cast away the day with the perfect way to end the day. This evening cruise calls for sun dresses, sandals and chilled wine. Take advantage of one of Florida's finest highlights upon our comfortable 80 ft catamaran a... More
Private Tour
Sunset Sail in Miami: Complimentary Champagne Toast
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North America
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Superb241 reviews4.8
Sunset Cruise, Cast away the day with the perfect way to end the day. This evening cruise calls for ....
Private Tour
Riviera Maya Half-Day Sailing Experience with Lunch and Open Bar
This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can see different colors of blue so that makes the experience better. The snorkeling is amazing, as you will see much colorful fish, st... More
Private Tour
Riviera Maya Half-Day Sailing Experience with Lunch and Open Bar
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North America
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Exellent80 reviews4.4
This is a luxury sailing catamaran and it's just 30 minutes away from Tulum. When you sail you can s....
Private Tour
Shallow Water Snorkeling and Dolphin Watching in Key West
Avoid the crowded big boats. Trips on this Sailing Catamaran are 1/2 full maximum! Book with a 2 week cancelation policy from vender, and there’s weather refunds of course. Premium drinks & snacks included! Enjoy a premium sha... More
Private Tour
Shallow Water Snorkeling and Dolphin Watching in Key West
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North America
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Superb476 reviews4.6
Avoid the crowded big boats. Trips on this Sailing Catamaran are 1/2 full maximum! Book with a 2 wee....
Private Tour
Full-Day Private Sailing & Los Arcos Snorkeling, Puerto Vallarta
Enjoy a private tour on an exclusive sailboat with a fully customizable experience through Puerto Vallarta´s Bay. You will be able to Sail, Snorkel, Swim and even Paddelboard in Los Arcos National Park, capturing beautiful views ... More
Private Tour
Full-Day Private Sailing & Los Arcos Snorkeling, Puerto Vallarta
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North America
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Superb114 reviews4.9
Enjoy a private tour on an exclusive sailboat with a fully customizable experience through Puerto Va....
Private Tour
Chicago's Fireworks Show aboard Tall Ship Windy!
Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in town! Grab a cool drink from our full bar, relax, and enjoy a lei... More
Private Tour
Chicago's Fireworks Show aboard Tall Ship Windy!
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North America
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Superb26 reviews4.7
Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Na....
Private Tour
Seattle’s Original Sailing Cruise (Est. 1984) – 70ft Boat - BYOB
This is a boat ride like nothing else in Seattle! Our 70ft custom built sailboats were created to race around the world, and now are perfectly at home on Puget Sound. Sit back and relax as our trained crew hoist the sails and turn... More
Private Tour
Likely to Sell Out Seattle’s Original Sailing Cruise (Est. 1984) – 70ft Boat - B....
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North America
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Superb217 reviews4.9
This is a boat ride like nothing else in Seattle! Our 70ft custom built sailboats were created to ra....
Private Tour
2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks
With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepared to offer you a memorable day on the sea. 2.5 hour tour length is perfect for seeing all the beautiful sights. Catamarans reall... More
Private Tour
Likely to Sell Out 2.5-Hour Small-Group Catamaran Sailing Adventure with Drinks
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North America
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Superb114 reviews5
With over 38 years of experience sharing our love of sailing with San Diego visitors, we are prepare....
Private Tour
Newport Sunset Sail on Classic Sailboat
Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a relaxing sail around Narragansett Bay on a classic sailboat and see all of Newport's iconic sights from the water including histor... More
Private Tour
Likely to Sell Out Newport Sunset Sail on Classic Sailboat
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North America
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Superb60 reviews4.7
Sunset sailing is one of the best evening activities to do during your stay in Newport, RI. Enjoy a ....
Private Tour