Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 727 Sailing Trips activities in North America. Sort by Popularity. - Page 28Sunset Sailing Tour of San Diego Bay up to 6 Guests
A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautiful San Diego. Pacifica Sailing Charters offers several different types of sunset sailing charters and boat tours. Our sunset sailin... More

Sunset Sailing Tour of San Diego Bay up to 6 Guests
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North America
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Superb1 review5
A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautifu....
Luxury Diamond Head Sunset Sail
Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sail features a two hour cruise aboard a private 50' luxury yacht. Immerse yourself in a gorgeous Hawaiian sunset the only way, from... More
Private Tour

Luxury Diamond Head Sunset Sail
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North America
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Superb3 reviews5
Hawaii’s Best Sunset Cruise is the experience you don’t want to miss. Our Diamond Head Sunset Sa....
Private Tour
Luxury Private Sunset Experience in San Jose
Enjoy an amazing experience offering a luxury, unique, complete and breathtaking private sunset tour. The Luxury Private Sailing boat have capacity from 1 to 16 people, the rate offered here is for 8 people, if like to add more pl... More
Private Tour

Luxury Private Sunset Experience in San Jose
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North America
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Superb3 reviews5
Enjoy an amazing experience offering a luxury, unique, complete and breathtaking private sunset tour....
Private Tour
4 Hour Private Sail for up to 6 people
This private excursion allows a party of six passengers to cruise the San Diego Bay and Coast on a customizable charter. Create your own adventure on a vintage sailing yacht for 4 hours with an experienced captain.... More
Private Tour

4 Hour Private Sail for up to 6 people
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North America
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Superb12 reviews4.8
This private excursion allows a party of six passengers to cruise the San Diego Bay and Coast on a c....
Private Tour
Cabo's Premier Catamaran Snorkeling: Explore the Waters!
Embark aboard our CaboMar catamaran for an unforgettable snorkeling adventure. First, we’ll cruise by some of Cabo's most iconic spots: Playa del Amor, El Arco, and the Sea Lion Reserve. At each location, we’ll stop for about ... More
Private Tour

Cabo's Premier Catamaran Snorkeling: Explore the Waters!
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North America
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Superb12 reviews4.8
Embark aboard our CaboMar catamaran for an unforgettable snorkeling adventure. First, we’ll cruise....
Private Tour
Catamaran Cruise in Riviera Maya with Snorkeling and Lunch
Enjoy the cool ocean breeze and the sparkling turquoise sea as you cruise along the Mexican Caribbean on our spacious catamaran. With music, drinks, and a lively host to keep the good vibes going, this isn’t just a tour — itâ€... More
Free Cancellation
Private Tour
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Catamaran Cruise in Riviera Maya with Snorkeling and Lunch
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North America
Enjoy the cool ocean breeze and the sparkling turquoise sea as you cruise along the Mexican Caribbea....
Free Cancellation
Private Tour
(Saving 29% )
South Beach Miami BACHELORETTE Boat Day!
Enjoy a yacht-day bachelorette trip where everything is already set to go right from the biggest and best marina in SOUTH BEACH... We've found the boats, brought on the food and drinks, and made sure that everything that a good y... More
Private Tour

South Beach Miami BACHELORETTE Boat Day!
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North America
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Superb1 review5
Enjoy a yacht-day bachelorette trip where everything is already set to go right from the biggest and....
Private Tour
Snorkel in the beautiful reef of Puerto Morelos with transport
The most amazing and exciting tour in the Mexican Caribbean is here. Visit the national park of reefs in Puerto Morelos. Sail through the turquoise clear water of the Caribbean Sea and arrive to the Mesoamerican reef. Our captain... More
Private Tour

Snorkel in the beautiful reef of Puerto Morelos with transport
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North America
The most amazing and exciting tour in the Mexican Caribbean is here. Visit the national park of reef....
Private Tour
2 Hours Private Guided Sailing Adventure in Pensacola Beach
This 2 hour sailing excursion may take place in Pensacola Bay, passing by areas of Sabine Island, Deer Point, Fair Point and Deadman's Island. We may also sail east under the Bob Sikes (Pensacola Beach) Bridge, exploring areas of ... More
Private Tour

2 Hours Private Guided Sailing Adventure in Pensacola Beach
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North America
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Superb4 reviews5
This 2 hour sailing excursion may take place in Pensacola Bay, passing by areas of Sabine Island, De....
Private Tour
Private Catamaran Sunset Cruise with Dolphin watching
One of the best ways to relax on your vacation is to view a sunset aboard Destin sailing Adventures. Sit back and relax while Captain Kip takes you to the best spots to view the sunset, and see a dolphin.... More
Private Tour

Private Catamaran Sunset Cruise with Dolphin watching
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North America
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Superb4 reviews5
One of the best ways to relax on your vacation is to view a sunset aboard Destin sailing Adventures.....
Private Tour
Private Yacht Charter in Cabo San Lucas – Cruise to The Arch
Enjoy a private yachting experience in Cabo San Lucas without committing to a full-day tour. Perfect for couples, families, or small groups, this 2-hour cruise offers front-row views of El Arco, Lover’s Beach, and local sea lion... More
Private Tour

Private Yacht Charter in Cabo San Lucas – Cruise to The Arch
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North America
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Superb4 reviews5
Enjoy a private yachting experience in Cabo San Lucas without committing to a full-day tour. Perfect....
Private Tour
Private Paddle Tour at Sunrise
With this amazing experience through the Bacalar Lagoon you will live unbeatable moments for 3.5 hours, we have all the necessary equipment for this activity to be complete. We are an ecologically responsible company that promotes... More
Private Tour

Private Paddle Tour at Sunrise
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North America
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Superb211 reviews5
With this amazing experience through the Bacalar Lagoon you will live unbeatable moments for 3.5 hou....
Private Tour
Private Transparent Boat Tour in the Sea of Cozumel
Incredible experience in a 100% transparent boat, we are also the only tour currently that offers snorkeling, sunken ships, there is more probability of finding marine life on this tour since we are on the second largest reef in t... More
Private Tour

Private Transparent Boat Tour in the Sea of Cozumel
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North America
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Superb211 reviews5
Incredible experience in a 100% transparent boat, we are also the only tour currently that offers sn....
Private Tour
Private Sail on the Cape Fear River Aboard a Classic Yacht
Our private charters offer insider access to the Cape Fear River under the guidance of a local captain who has sailed these waters - and the wide Atlantic beyond - professionally for more than a decade. Our steward's comparable ex... More
Private Tour

Private Sail on the Cape Fear River Aboard a Classic Yacht
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North America
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Superb211 reviews5
Our private charters offer insider access to the Cape Fear River under the guidance of a local capta....
Private Tour
6-Hour Sailing Charter from Fort Lauderdale
Enjoy some time on the water with this 6-Hour Full Day Sailing Charter located in Fort Lauderdale. Your sail is entirely customizable, and travelers have the option to use their time docked or sailing out to sea. Once on the water... More
Private Tour

6-Hour Sailing Charter from Fort Lauderdale
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North America
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Superb3 reviews5
Enjoy some time on the water with this 6-Hour Full Day Sailing Charter located in Fort Lauderdale. Y....
Private Tour
Marina Del Rey Luxury Yacht Experience
Discover the perfect blend of relaxation, fun, and local insight on the water with our exclusive Marina del Rey yacht experience, hosted by our friendly and knowledgeable captains. Whether you’re seeking a laid-back day cruising... More
Private Tour

Marina Del Rey Luxury Yacht Experience
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North America
Discover the perfect blend of relaxation, fun, and local insight on the water with our exclusive Mar....
Private Tour
Private Sunset Sailing
A private and exclusive Sunset Sailing Adventure discovering a Sunset that will never repeat. Premium Open Bar and a Cheese and Cold Cuts table as snacks. Go in style and go Private. Since Covid-19 additional measures and precauti... More
Private Tour

Private Sunset Sailing
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North America
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Superb1 review5
A private and exclusive Sunset Sailing Adventure discovering a Sunset that will never repeat. Premiu....
Private Tour
Whale Shark Snorkel Tour in Cancun (Snack Lunch included)
Experience this must-do activity in the Caribbean Sea and swim with this impressive animal. The whale shark adventure is the most enigmatic activity in Mexico. It is a very docile animal that is just as impressive as any other a... More
Private Tour

Whale Shark Snorkel Tour in Cancun (Snack Lunch included)
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North America
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Superb1 review5
Experience this must-do activity in the Caribbean Sea and swim with this impressive animal. The whal....
Private Tour
Discover Hobie-Cat Sailing and Fish your own Lunch
Becoming able to sail a sailboat only with the wind is a skill that will give you the sense of Freedom that only the ocean can give. You'll realize that you will be able to get to some of the most beautiful places on the planet wi... More
Private Tour

Discover Hobie-Cat Sailing and Fish your own Lunch
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North America
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Superb6 reviews5
Becoming able to sail a sailboat only with the wind is a skill that will give you the sense of Freed....
Private Tour
Key West Stargazing Cruise aboard Schooner America 2.0
Join us aboard Schooner America 2.0 in Key West for a fun night time experience. During this stargazing cruise, guests can enjoy unobstructed views of the sweeping night sky and a fun adventure in Key West at night. Please note th... More
Private Tour

Key West Stargazing Cruise aboard Schooner America 2.0
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North America
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Superb1 review5
Join us aboard Schooner America 2.0 in Key West for a fun night time experience. During this stargaz....
Private Tour