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Boating on Chesapeake Bay, Chesapeake Bay, Maryland

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Maryland, United States, North America: Sailboats dot the Chesapeake Bay in Maryland.
Chesapeake Bay , Maryland
Concierge.com's insider take:

Even if you don't know a schooner from a skiff, you'd be remiss if you didn't take at least a short cruise on the Bay. Maryland's history and economy hinge on the 200-mile-long Chesapeake, and the nation's largest estuary is considered a paradise for pleasure boats. Annapolis has a variety of day-sail options, including the Schooner Woodwind (410-263-7837; www.schoonerwoodwind.com), a 74-foot wooden yacht that's repeatedly won the annual Great Chesapeake Bay Schooner Race. The state capital is also home port for several sailing schools; the hands-on courses at J World Annapolis (213 Eastern Ave., Annapolis; 410-280-2040; www.jworldannapolis.com) will have you tacking in no time. Watermark (410-268-7601; www.watermarkjourney.com) offers Bay cruises to historic lighthouses or to St. Michaels. On the Eastern Shore's Tilghman Island, Captain Wade H. Murphy Jr. makes day sails aboard the skipjack Rebecca T. Ruark, a national historic landmark first launched in 1886 (410-886-2176; www.skipjack.org). From Memorial Day until mid-October, Smith Island Cruises (410-425-2771; www.smithislandcruises.com) operates a daily ferry from southernmost Crisfield to the state's only inhabited island, which was settled in 1686 and is home to watermen who still speak with a unique, lilting English accent.

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