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Americas Destinations

Chesapeake Bay (Annapolis)

Dream Yacht Charter

Chesapeake BayView Map


Dream Yacht Charter
Americas Getaways

Dream Yacht Charter - USA - Chesapeake Bay - Inset
Dream Yacht Charter - USA - Chesapeake Bay - Inset
Dream Yacht Charter - USA - Chesapeake Bay - Inset
Dream Yacht Charter - USA - Chesapeake Bay - Inset

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Chesapeake Bay


Only a handful of waterways in the world can match the Chesapeake Bay for sheer sailing pleasure. At about 200 miles long, it’s the largest estuary in the United States with thousands of miles of shoreline to explore. It offers sailors protected waters, great anchorages, a forgiving bottom, gorgeous natural scenery, and unique towns and villages steeped in history. It’s perfect for novices just learning to sail, yet challenging enough to keep experts captivated for a lifetime.

The Dream yacht Charter base is at Port Annapolis Marina on Back Creek in historic Annapolis. A sailing Mecca if ever there was one, Annapolis lies at 38 degrees 58 minutes north latitude and 76 degrees 29 minutes west longitude. Maryland’s capital city is the perfect starting point for your Chesapeake Bay exploration.

Before embarking, however, seeing the sights of Annapolis is a must. You can stroll down to “Ego Alley” at Annapolis Harbor, and then grab a sandwich at Chick and Ruth’s Delly on Main Street. A couple of streets over, you can visit the Maryland State House, historically distinctive because it’s the oldest state capitol in continuous legislative use, topped by the largest wooden dome in the nation. Annapolis is also home to the U.S. Naval Academy.

The Chesapeake Bay takes its name from a Powhatan Indian word, “Chesepioc,” which is loosely translated as “Great Shellfish Bay.” Spanish explorer Vincente Gonzalez was the first European to visit the region in 1561, but the Spanish were never able to establish a permanent settlement. The French founded a settlement called Port Royal (now modern day Annapolis) in 1605. English settlers established Jamestown on the James River in 1607. Two Years later, Captain John Smith became the first European to explore and thoroughly map the Chesapeake Bay, writing in his journal that “heaven and earth have never agreed better to frame a place for man’s habitation.”

Throughout the colonial period, development continued on the Western Shore, and the Maryland and Virginia sections of the Eastern Shore. Annapolis became Maryland’s capital and Baltimore a busy shipping port. During the War of 1812, the British invaded the United States through the Chesapeake Bay, but were stopped at Fort McHenry in Baltimore.

Although union forces occupied Maryland during the Civil War and used the Chesapeake Bay to transport soldiers and supplies to forces arrayed against the Confederate Army, it also served as a haven for smugglers, spies and privateers allied with the Southern cause. In March 1862, the first sea battle between ironclad ships-the Union Monitor and the Confederate Merrimack-occurred in Hampton Roads and forever changed naval warfare. Throughout these periods of growth and conflict, Chesapeake Bay watermen continued to fish for Oysters, Blue Crabs, clams, Shad and Striped Bass. Tilghman Island, for example, is home to the last commercial sailing fleet in North America. At one time, thousands of Skipjacks dredged for oysters, but now just nine are left.

With so many delightful creeks, coves, rivers, towns and villages to visit, Dream Yacht Charter has compiled a list of top places worth visiting and can help create an itinerary for an unforgettable sailing vacation.

Southern route ports of interest include: West River and Galesville, Harrington Harbor North and Harrington Harbor South, St. Michaels, Tilghman Island, Oxford, Cambridge and Solomons Island.

Northern route ports of interest include: Rock Hall, Chester River and Chestertown, Baltimore Harbor, Georgetown and the Sassafras River.