Sailing Trips in North America
Top 10 Best North America Sailing Trips
Found 672 Sailing Trips activities in North America. Sort by Popularity. - Page 272 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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Superb2 reviews5
This 2 hour sailing excursion may take place in Pensacola Bay, passing by areas of Sabine Island, De....
Private Tour
Full-Day Boat Tour to Isla Mujeres from Cancun with Lunch
Spend the day sipping drinks and snorkeling aboard a modern catamaran during this full-day tour to Isla Mujeres from Cancun. Relax in the sun and enjoy the sea breeze (and the open bar!) as you travel to a coral reef to snorkel wi... More
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Full-Day Boat Tour to Isla Mujeres from Cancun with Lunch
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North America
Spend the day sipping drinks and snorkeling aboard a modern catamaran during this full-day tour to I....
Private Tour
Isla Mujeres Sailing Adventure from Cancun
Join the experience of sailing through the Mexican Caribbean Sea from Cancun to Isla Mujeres onboard of an exclusive catamaran...!! This tour is recommended for those who like to have fun, with music for all tastes and open-bar on... More
Private Tour

Isla Mujeres Sailing Adventure from Cancun
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North America
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Very Good6 reviews3.7
Join the experience of sailing through the Mexican Caribbean Sea from Cancun to Isla Mujeres onboard....
Private Tour
Land's End Tour in a Glass Bottom Boat
This is a bucket list level experience! We provide the best tours at the best prices. If you find a better tour for less please let us know and we will do what we can to do better. Private tours available.... More
Private Tour

Land's End Tour in a Glass Bottom Boat
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North America
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Very Good3 reviews3.7
This is a bucket list level experience! We provide the best tours at the best prices. If you find a ....
Private Tour
Private Catamaran: Snorkel, Swim and Dolphin Watching
Show up in style aboard a catamaran with a fun local avid sailor that wants to share his passion with you. Let Captain Kip take you to some of the best spots the area has to offer while you are visiting the Emerald Coast. ... More
Private Tour

Private Catamaran: Snorkel, Swim and Dolphin Watching
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North America
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Very Good3 reviews3.7
Show up in style aboard a catamaran with a fun local avid sailor that wants to share his passion wit....
Private Tour
Live this unique snorkeling experience. El Cielo in Cozumel a magical tour.
If we tell you that you can be near the sky while you are at the paradisiacal Caribbean Sea, could believe us? On this tour that is completely possible! Adventure with us through the coast of the Cozumel Island, visit three of th... More
Private Tour

Live this unique snorkeling experience. El Cielo in Cozumel a mag....
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North America
If we tell you that you can be near the sky while you are at the paradisiacal Caribbean Sea, could b....
Private Tour
Chesapeake Bay Private Cruise
This private cruise for up to 6 persons is great for family outings, friends in town, a girls or guys day out on the water, or just to have the cruise to yourself! Enjoy the peaceful sounds of the waves gently breaking off the hul... More
Private Tour

Chesapeake Bay Private Cruise
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North America
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Exellent6 reviews4.3
This private cruise for up to 6 persons is great for family outings, friends in town, a girls or guy....
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
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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
Luxury Sunset Tour in Sailing Catamaran
Cabo San Lucas is a beautiful town with an always busy and vibrant Marina, from where this beautiful tour departs. This is your best option, to enjoy a beautiful boat ride sunset cruise aboard a luxury sailing catamaran, no crowde... More
Private Tour

Luxury Sunset Tour in Sailing Catamaran
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North America
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Superb3 reviews5
Cabo San Lucas is a beautiful town with an always busy and vibrant Marina, from where this beautiful....
Private Tour
Private Charter
The captain works with the guest to design a custom outing based on his 30 years of cruising experience in the local area. With knowledge of the local sea conditions and coastal ecology. you build a custom experience. Typically, G... More
Private Tour

Private Charter
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North America
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Superb12 reviews4.8
The captain works with the guest to design a custom outing based on his 30 years of cruising experie....
Private Tour
Sailing Adventures 3-Hour Activity in Destin
There’s nothing like seeing the clear emerald waters pass under the hull while sailing on the Stiletto Catamaran. Harnessing the power of the wind as we sail along these beautiful waters is magical. You might even get to experie... More
Private Tour

Sailing Adventures 3-Hour Activity in Destin
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North America
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Superb4 reviews5
There’s nothing like seeing the clear emerald waters pass under the hull while sailing on the Stil....
Private Tour
Private Sailing Experience on Galveston Bay
See the Texas Gulf Coast in a whole new way. Feel the sea breeze, explore the Texas Gulf Coast, and discover a new way to travel aboard our luxury charter yacht. We offer the perfect blend of comfort and adventure, making it the ... More
Private Tour

Private Sailing Experience on Galveston Bay
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North America
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Superb4 reviews5
See the Texas Gulf Coast in a whole new way. Feel the sea breeze, explore the Texas Gulf Coast, and....
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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Superb188 reviews5
With this amazing experience through the Bacalar Lagoon you will live unbeatable moments for 3.5 hou....
Private Tour

Half Day Sail Orcas Island
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North America
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Superb12 reviews5
Lessons are private and designed so you can brings friends and family with no extra charge. Up to 6 ....
Private Tour
Key West Christmas Cruise with Live Band and Drinks
Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our live band and celebrate the holidays and Christmas in Key West. E... More
Private Tour

Key West Christmas Cruise with Live Band and Drinks
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North America
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Superb3 reviews5
Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christ....
Private Tour
Two Fantastic Islands To Discover: Tour To Contoy & Isla Mujeres
Begin your adventure with hotel pickup and a light breakfast at our private marina in Punta Sam. From there, set sail to the charming Isla Mujeres, a Pueblo Mágico (Magical Town), where you’ll have an hour to explore its vibran... More
Private Tour

Two Fantastic Islands To Discover: Tour To Contoy & Isla Mujeres
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North America
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Superb3 reviews5
Begin your adventure with hotel pickup and a light breakfast at our private marina in Punta Sam. Fro....
Private Tour
Cabo San Lucas Private Sailing, Snorkeling and Whale WatchingTour
We offer an upscale service, and our crew is bilingual, knowledgeable, and very accommodating! It is your very own private boat to enjoy snorkeling & sailing with a captain and mate who will treat you to one of the best experience... More
Private Tour

Cabo San Lucas Private Sailing, Snorkeling and Whale WatchingTour
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North America
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Superb70 reviews5
We offer an upscale service, and our crew is bilingual, knowledgeable, and very accommodating! It is....
Private Tour
Crystal Boat Tour with Snorkeling and Drinks in Cozumel
Dare to live this incredible experience aboard our Transparent Boat! Sail the Caribbean Sea and discover the emblematic sites of Cozumel such as the first port gate, the diver's monument, sunken ships and natural landscapes. Marv... More
Private Tour

Crystal Boat Tour with Snorkeling and Drinks in Cozumel
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North America
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Superb5 reviews4.6
Dare to live this incredible experience aboard our Transparent Boat! Sail the Caribbean Sea and dis....
Private Tour
2 Hours Sunset Private Charter on Heart's Desire in Casco Bay
This two-hour sunset private sail is the perfect way to experience Maine's sunset on the coast - complete with lighthouses, seals, and seabirds. Ride aboard Heart's Desire: designed by famed yacht designer - John Alden, measures 5... More
Private Tour

2 Hours Sunset Private Charter on Heart's Desire in Casco Bay
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North America
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Superb5 reviews4.6
This two-hour sunset private sail is the perfect way to experience Maine's sunset on the coast - com....
Private Tour
Private Day Sailing Experience in San Diego up to 12 guests
This private day sail, is a excellent if you are looking for a more exciting sail! Day sailing is best to go see our San Diego landmarks along downtown where we will see the US Midway, Sea port Village, the Rady shell and we might... More
Private Tour

Private Day Sailing Experience in San Diego up to 12 guests
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North America
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Superb45 reviews5
This private day sail, is a excellent if you are looking for a more exciting sail! Day sailing is be....
Private Tour