Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 673 Sailing Trips activities in North America. Sort by Popularity. - Page 16Private 2-Hour Day Sailing Experience
As the first and only sailing tour in Central Florida, Sailing Orlando is committed to sharing the joy of sailing with our community and its visitors. From day sailing to sunset cruises or learning the ropes, our private tours off... More
Private Tour

Private 2-Hour Day Sailing Experience
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North America
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Superb40 reviews5
As the first and only sailing tour in Central Florida, Sailing Orlando is committed to sharing the j....
Private Tour
Windjammer Classic Day Sail from Camden, Maine
See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore II! Feel like an adventurer from the 19th century while enjoying state-of-the-art accommodations on a modern windjammer. With wide ... More
Private Tour

Windjammer Classic Day Sail from Camden, Maine
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North America
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Superb334 reviews4.7
See the best of Camden while sailing Maine’s magnificent rocky coast on the elegant Appledore I....
Private Tour
New York City Sailboat Day Cruise to the Statue of Liberty
Experience New York by water on this 2-hour sail aboard Schooner Adirondack, an 80-foot, 2-masted schooner inspired by the pilot schooners of the 1890s. Sit back and relax as the crew raises sail and the boat effortlessly glides a... More
Private Tour

New York City Sailboat Day Cruise to the Statue of Liberty
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North America
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Superb118 reviews4.9
Experience New York by water on this 2-hour sail aboard Schooner Adirondack, an 80-foot, 2-masted sc....
Private Tour
An Unforgettable afternoon Aboard A Classic Sailing Yacht
Book an unforgettable tour with Captain Phil and sail in style aboard, Liberty, a stunning replica of a 1904 gaff rigged friendship sloop. She is an elegant sight under sail, featuring; highly finished woodwork, bronze fixtures, a... More
Private Tour

An Unforgettable afternoon Aboard A Classic Sailing Yacht
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North America
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Superb66 reviews5
Book an unforgettable tour with Captain Phil and sail in style aboard, Liberty, a stunning replica o....
Private Tour
San Diego Bay Sailing Tour
San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. Why not enjoy this natural wonder aboard a beautiful sailing yacht with a knowledgeable and friendly Captain? This group sail is li... More
Private Tour

San Diego Bay Sailing Tour
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North America
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Superb16 reviews5
San Diego Bay is one of the most beautiful bodies of water on the West Coast of the United States. W....
Private Tour
Sail Bainbridge Island & Seattle Waters - Luxury Classic Sailboat
Sailing Puget Sound is an unforgettable experience! We’ll set sail & soak up the panorama of these beautiful & inspiring waters. Departing daily from Bainbridge Island, a 30 min ferry ride from Seattle. This 2hr private sailing... More
Private Tour

Sail Bainbridge Island & Seattle Waters - Luxury Classic Sailboat
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North America
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Superb25 reviews5
Sailing Puget Sound is an unforgettable experience! We’ll set sail & soak up the panorama of these....
Private Tour
1.5-Hour Koa Kai Adventure Whale Watch
Experience an up-close encounter with our winter residents, the Humpback Whale! These beautiful creatures return to Maui every year to birth their young. During this trip, you will get a chance to hear the whale’s unique songs a... More
Private Tour

1.5-Hour Koa Kai Adventure Whale Watch
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North America
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Superb2 reviews5
Experience an up-close encounter with our winter residents, the Humpback Whale! These beautiful crea....
Private Tour
Luxury Catamaran tour to isla mujeres with transportation from Tulum
Excellent service on board Professional crew members Safety measures in all our activities Sanitary prevention protocols for all our guests and staff Once in a lifetime experience Delicious buffet lunch and drinks Beach club (beac... More
Private Tour

Luxury Catamaran tour to isla mujeres with transportation from Tu....
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North America
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Good62 reviews3.5
Excellent service on board Professional crew members Safety measures in all our activities Sanitary ....
Private Tour
Private Luxury Adventure Tours in Cabo San Lucas
Want to go on Whale Watching at your own time and pace? December 15th thru April 15th, you can enjoy this amazing adventure for 2 hours departing at 09:00 am in the morning. Or you prefer more for a special day in the water that i... More
Private Tour

Private Luxury Adventure Tours in Cabo San Lucas
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North America
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Superb8 reviews4.9
Want to go on Whale Watching at your own time and pace? December 15th thru April 15th, you can enjoy....
Private Tour

Sailing Snorkel Adventure
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North America
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Exellent5 reviews4.4
Interactive Sailing Adventure, Snorkeling, Surf Up Paddle, Premium Bar and Incredible views. This Sa....
Private Tour
Private Luxury 42ft Sailing with Snorkeling in Los Cabos
Sail Cabo San Lucas aboard a luxurious 42 feet private sailing boat. Enjoy an unforgettable time Snorkeling with tropical fishes and cruise along the beautiful white beaches. Your yacht and crew will provide you with all the ameni... More
Private Tour

Private Luxury 42ft Sailing with Snorkeling in Los Cabos
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North America
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Superb118 reviews5
Sail Cabo San Lucas aboard a luxurious 42 feet private sailing boat. Enjoy an unforgettable time Sno....
Private Tour
Shared Day Sail along Historic St Augustine Bayfront
Not your average tour, this 2-hour small group sail gives passengers a chance to make new memories on the sea. Our cruise is perfect for all water-lovers: families, couples, and friends. Some guests interact with the USCG licensed... More
Private Tour

Shared Day Sail along Historic St Augustine Bayfront
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North America
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Superb3 reviews5
Not your average tour, this 2-hour small group sail gives passengers a chance to make new memories o....
Private Tour
Snorkeling Adventure in Isla Mujeres
Dare to be part of one of the most enigmatic activities in Cancun and Mexico. The underwater museum is a unique activity in the world since there is no such thing anywhere. This activity is cataloged as mandatory for all traveler... More
Private Tour

Snorkeling Adventure in Isla Mujeres
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North America
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Very Good12 reviews3.8
Dare to be part of one of the most enigmatic activities in Cancun and Mexico. The underwater museum....
Private Tour
Skagway Trail and Sail
This eco-friendly tour of Skagway is like no other experience around! Your tour starts at Klondike Electric Bicycles where you will join us for a self-guided ride to some of Skagway's best sites! You will visit a waterfall, scenic... More
Private Tour

Skagway Trail and Sail
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North America
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Superb3 reviews5
This eco-friendly tour of Skagway is like no other experience around! Your tour starts at Klondike E....
Private Tour
Romantic Dinner on a Spanish Galeon in Cancun
Live this unique experience in one of the most romantic cities in the world! Enjoy a magical dinner with the most wonderful scenary. This is the perfect opportunity to enjoy a delicious dinner while you fall in love with the liv... More
Private Tour

Romantic Dinner on a Spanish Galeon in Cancun
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North America
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Exellent22 reviews4.2
Live this unique experience in one of the most romantic cities in the world! Enjoy a magical dinner ....
Private Tour
The Boat People Cruise Private Harbor Cruises
Join us for an hour and a half picnic cruise with a coastal ambiance on the bow of our sailboat. We strive to create an unforgettable evening with contagious laughter and panoramic views of the Newport Bay. Bring your plus one or ... More
Private Tour

The Boat People Cruise Private Harbor Cruises
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North America
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Superb26 reviews5
Join us for an hour and a half picnic cruise with a coastal ambiance on the bow of our sailboat. We ....
Private Tour
Day Sailing Adventure in the Florida Marine Sanctuary
Escape the ordinary and embark on an unforgettable journey aboard our 50 foot sailboat, “Chao Lay”. Choose a 3-hour Day Sail or our popular Sunset Sail through the Florida Keys Marine Sanctuary in Marathon, Florida. Our sailbo... More
Private Tour

Day Sailing Adventure in the Florida Marine Sanctuary
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North America
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Superb7 reviews5
Escape the ordinary and embark on an unforgettable journey aboard our 50 foot sailboat, “Chao Lay....
Private Tour
Snorkeling Adventure at Isla Mujeres Includes Lunch and Open Bar
Admire the peaceful waters of the Caribbean Sea, aboard a classic or luxury catamaran and enjoy a spectacular day sailing to Isla Mujeres on a fun-filled experience where music, drinks and incredible views will never be lacking. ... More
Private Tour

Snorkeling Adventure at Isla Mujeres Includes Lunch and Open Bar
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North America
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Very Good33 reviews3.7
Admire the peaceful waters of the Caribbean Sea, aboard a classic or luxury catamaran and enjoy a sp....
Private Tour
Pirate Ship Premium Dinner Cruise with Show
While visiting Puerto Vallarta is a must to take the Pirate Sailboat tour. Enjoying magnificent views of Banderas Bay, take unforgettable photos of this amazing experience, while you taste a delicious dinner and have a good time ... More
Private Tour

Pirate Ship Premium Dinner Cruise with Show
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North America
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Exellent31 reviews4.4
While visiting Puerto Vallarta is a must to take the Pirate Sailboat tour. Enjoying magnificent vie....
Private Tour
San Francisco City Lights Sail
The Golden Gate isn’t the only bridge in town! Once the sun sets and the lights come on, join us for a city-front cruise to enjoy the majestic sites of San Francisco in the night sky. See the Bay Bridge lit in all its glory, alo... More
Private Tour

San Francisco City Lights Sail
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North America
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Superb5 reviews5
The Golden Gate isn’t the only bridge in town! Once the sun sets and the lights come on, join us f....
Private Tour