Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 766 Sailing Trips activities in North America. Sort by Popularity. - Page 36Bachelorette Sailing Party on San Diego Bay up to 6 Guests
Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 6 guests. Enjoy breathtaking views of downtown, the naval base, aircraft carriers, destroyers, and submarines, not to mention an incredible abundance of sea l... More
Bachelorette Sailing Party on San Diego Bay up to 6 Guests
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North America
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Superb19 reviews5
Nothing beats a Catamaran Bachelorette Party on San Diego bay for up to 6 guests. Enjoy breathtaking....
Private Sunset Sail in San Diego
We are a small charter company we offer a personal experience that is flexible to our guests needs. Sailing Is our speciality and we will try to sail our best to shut down the engine and sail by wind power.... More
Private Tour
Private Sunset Sail in San Diego
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North America
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Superb19 reviews5
We are a small charter company we offer a personal experience that is flexible to our guests needs. ....
Private Tour
Sunset Sail on the Tall Ship Matthew Turner in San Francisco Bay
Set sail on the tall ship Matthew Turner and soak in the stunning sunset views of San Francisco Bay, including iconic sights like the Golden Gate Bridge, Alcatraz, and Angel Island. This unique experience combines adventure with t... More
Private Tour
Sunset Sail on the Tall Ship Matthew Turner in San Francisco Bay
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North America
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Superb19 reviews5
Set sail on the tall ship Matthew Turner and soak in the stunning sunset views of San Francisco Bay,....
Private Tour
Sunset Wine & Cheese Sail in St. Margarets Bay
Set sail on a scenic journey through St. Margarets Bay, renowned for its rugged coastline and stunning islands. During this 2.5-hour Sunset Wine and Cheese sail, indulge in local wines and charcuterie as the sun sets over Nova Sco... More
Private Tour
Sunset Wine & Cheese Sail in St. Margarets Bay
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North America
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Superb19 reviews5
Set sail on a scenic journey through St. Margarets Bay, renowned for its rugged coastline and stunni....
Private Tour
Private Sightseeing Charter in Frenchman Bay
Enjoy a 2-hour tour of Frenchman Bay with eagle, seabird and porpoise sightings plus more. Explore the Porcupine Islands and Egg Rock. See beautiful views of Acadia National Park from the sea. Learn some history of coastal Maine a... More
Private Tour
Private Sightseeing Charter in Frenchman Bay
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North America
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Exellent5 reviews4.2
Enjoy a 2-hour tour of Frenchman Bay with eagle, seabird and porpoise sightings plus more. Explore t....
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
Likely to Sell Out 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
Tuesday Night Lights: McCovey Cove Sail
The ballpark season has arrived! Tuesday Night Lights trips are the perfect way to welcome summer on the San Francisco Bay and root for the home team! Depart from Pier39, take a relaxing sail along the city-front, and settle into ... More
Private Tour
Likely to Sell Out Tuesday Night Lights: McCovey Cove Sail
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North America
The ballpark season has arrived! Tuesday Night Lights trips are the perfect way to welcome summer on....
Private Tour
Private Luxury 55ft Yacht Cancun Isla Mujeres up to 17 Pax
Set sail on the Exodos 55ft Sea Ray Sundancer for an unforgettable private yacht experience in Cancun. Ideal for celebrations like birthdays, bachelorette parties, or family outings, this luxurious charter accommodates up to 17 gu... More
Private Tour
Likely to Sell Out Private Luxury 55ft Yacht Cancun Isla Mujeres up to 17 Pax
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North America
Set sail on the Exodos 55ft Sea Ray Sundancer for an unforgettable private yacht experience in Cancu....
Private Tour
Private Couples Sunset Sailing Tour in San Diego
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. Your sunset saili... More
Private Tour
Likely to Sell Out Private Couples Sunset Sailing Tour in San Diego
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North America
A Sunset Sailing Charter on San Diego Bay is an awesome way to spend the day sightseeing in beautifu....
Private Tour
Likely to Sell Out
Private Charter Day Tripper Boat for 14 People
4-Hour Private Cruise Exclusively Reserved for Your Party! Includes a Fun and Experienced Captain, Clean Restroom, Large Cooler, and A Premium Bluetooth Sound System For You To Play What You’d Like! You Can Also Add A Photograph... More
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Likely to Sell Out Private Charter Day Tripper Boat for 14 People
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North America
4-Hour Private Cruise Exclusively Reserved for Your Party! Includes a Fun and Experienced Captain, C....
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Private Half Day Sailing Charter in Penobscot Bay
There are a lot of ways to get out on the water in Maine, but at Sailing Sasa, we make every charter feel personal, relaxed, and genuinely memorable. We’re a small, family-run sailing charter, and Sasa is a thoughtfully restored... More
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Likely to Sell Out Private Half Day Sailing Charter in Penobscot Bay
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North America
There are a lot of ways to get out on the water in Maine, but at Sailing Sasa, we make every charter....
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42 ft Lagoon Catamaran Cancun and Isla Mujeres
Please let us know if you are celebrating any special ocassion! We are certain you will LOVE the many tones of blue that the caribbean ocean offers in our beloved home, we will take you to the most iconic and best spots, and pleas... More
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Likely to Sell Out 42 ft Lagoon Catamaran Cancun and Isla Mujeres
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North America
Please let us know if you are celebrating any special ocassion! We are certain you will LOVE the man....
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Luxury Yacht 58 ft for up to 20 people 4 hrs
Azimut yachts are designed to pamper the most demanding tastes. Feel the pleasure of sailing aboard this luxury yacht along the coast of Bahía de Banderas. You will enjoy every moment and every place in this tropical paradise. L... More
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Likely to Sell Out Luxury Yacht 58 ft for up to 20 people 4 hrs
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North America
Azimut yachts are designed to pamper the most demanding tastes. Feel the pleasure of sailing aboard ....
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Oyster Bay Three Hour Sailing Experience
Set sail on Long Island's Gold Coast with a private 3-hour sailing charter for up to 6 guests aboard WINDSWEPT, a Jeanneau 36i. This charter offers flexible departure times, allowing you to choose a start time that suits your sche... More
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Likely to Sell Out Oyster Bay Three Hour Sailing Experience
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North America
Set sail on Long Island's Gold Coast with a private 3-hour sailing charter for up to 6 guests aboard....
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Luxury Sunset Cruise with Open bar in Vallarta
As the golden hour sets in, step aboard a luxurious 50-foot Beneteau sailboat and cruise along Banderas Bay’s stunning coastline. This sunset sailing experience offers an unforgettable evening of elegance, romance, and breathtak... More
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Likely to Sell Out Luxury Sunset Cruise with Open bar in Vallarta
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North America
As the golden hour sets in, step aboard a luxurious 50-foot Beneteau sailboat and cruise along Bande....
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Private Catamaran Ride in Los Cabos Food and Bar Outdoors
Enjoy a complete catamaran experience combining scenic sailing, snorkeling and onboard dining. Sail in front of the Cabo San Lucas Arch while enjoying open bar and fresh foods such as ceviches, guacamole and fruit. It includes a s... More
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Likely to Sell Out Private Catamaran Ride in Los Cabos Food and Bar Outdoors
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North America
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Superb17 reviews5
Enjoy a complete catamaran experience combining scenic sailing, snorkeling and onboard dining. Sail ....
Free Cancellation
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JFarwell Sip & Sail aboard the Reverie
This private day sail allows you to enjoy happy hour on your own time! Enjoy 1.5 hours of unwinding in luxury with friends, family or colleagues. Step aboard our 50’ Catamaran and be greeted with a perfect locally crafted bevera... More
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Likely to Sell Out JFarwell Sip & Sail aboard the Reverie
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North America
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Superb19 reviews5
This private day sail allows you to enjoy happy hour on your own time! Enjoy 1.5 hours of unwinding ....
Free Cancellation
Private Tour
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Cabo Sunset Sailboat Tour with Open Bar
Our sunset sailing experience stands out for its perfect balance of relaxation, scenery, and personalized service. Unlike larger, crowded cruises, this tour offers a more intimate atmosphere, allowing you to fully enjoy Cabo’s i... More
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Likely to Sell Out Cabo Sunset Sailboat Tour with Open Bar
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North America
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Superb19 reviews5
Our sunset sailing experience stands out for its perfect balance of relaxation, scenery, and persona....
Free Cancellation
Private Tour
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All Inclusive Half Day Sunset Catamaran Adventure
Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter experience from St. Petersburg with fuel, ice, bottled water, soft drinks,... More
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Likely to Sell Out All Inclusive Half Day Sunset Catamaran Adventure
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North America
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Superb19 reviews5
Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and cr....
Free Cancellation
Private Tour
(Saving inf% )
Likely to Sell Out
Sunset Sailing Experience Los Cabos Open Bar and Gourmet Bites
Experience the breathtaking beauty of a Los Cabos sunset on a premium sailing yacht. Cruise along the stunning coastline, passing iconic landmarks like El Arco, Lover’s Beach, and the lively sea lion colony. This small-group tou... More
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Likely to Sell Out Sunset Sailing Experience Los Cabos Open Bar and Gourmet Bites
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North America
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Superb19 reviews5
Experience the breathtaking beauty of a Los Cabos sunset on a premium sailing yacht. Cruise along th....
Free Cancellation
Private Tour
(Saving inf% )