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Sailing Charters in
West River, MD

Classic Sail Charters offers Chesapeake Bay sailing adventures on our thoroughly refined sailing yacht, the Siena. It is exquisitely appointed, safe, and ready for you to call home while you enjoy the mystique and allure of some of the best sailing grounds in the world.

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One - Six People | 3 -Hour Sailing Yacht Cruise | 25% Deposit

Minimum age: 7 years.

Gratuity Not Included







Chesapeake Bay - West River

Welcome to Classic Sail Charters

Looking for a unique sailing experience on the Chesapeake Bay? Our charters are the perfect way to explore the Bay and its navigable rivers. As the largest estuary in the world, the Chesapeake Bay is a natural beauty filled with an abundance of wildlife. Create your own sailing adventure on the Chesapeake Bay as we work with you to define your perfect excursion and then you may leave the rest to us!

The West River is one of our favorite places in the Chesapeake. The West and Rhode Rivers, which feed the Chesapeake Bay, are home to acres of natural landscape that hug the shoreline. As you make your way to Siena, you will be welcomed by the relaxing views of local hayfields and horse farms. Couple your sail with a visit to one of the local waterfront restaurants or dockside bars in Galesville, Maryland to get the most out of your day.

West River Yacht Harbour in Galesville, Maryland is less than an hour drive from Washington, D.C., yet it boasts quiet Chesapeake charm, all within a day trip from home.