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The Chesapeake Bay

When John Smith sailed into the Chesapeake Bay in 1607, he couldn’t have known the precedent he was setting. Ever since that early cruise, the area has been teeming with sailboats—everything from skipjacks dredging for oysters to race boats competing in regattas and flagships strutting their stuff at the United States Sailboat Show. With all of this on-water action, it’s no surprise that a dozen

When John Smith sailed into the Chesapeake Bay in 1607, he couldn’t have known the precedent he was setting. Ever since that early cruise, the area has been teeming with sailboats—everything from skipjacks dredging for oysters to race boats competing in regattas and flagships strutting their stuff at the United States Sailboat Show. With all of this on-water action, it’s no surprise that a dozen charter companies and sailing schools make their home in the heart of the Chesapeake—Annapolis, Maryland—while others dot the quiet towns along the Eastern Shore and the islands to the south.

Among these is Annapolis Bay Charters, with a fleet that features a full range of bareboat, captained or fully crewed monohulls and catamarans. The company is also a part of Dream Yacht Charter, which has 29 locations and over 450 boats around the world. “Annapolis is the sailing center of the universe,” says Annapolis Bay Charters president Scott Farquharson. “You just can’t beat it, it’s so beautiful,” he says, describing such choice destinations as Dobbins Island on the Magothy or Tilghman Island near the mouth of the Choptank River.

Other options within a day’s sail from Annapolis include the peaceful Wye River, the boisterous nightlife of Baltimore’s inner harbor on the Western Shore or, for authentic Chesapeake culture, the ports of St. Michaels, Oxford and Cambridge on the Eastern Shore. Each of these pleasant towns boasts marinas dotted with characteristic Bay-area boats, Main Streets lined with great shops and friendly people, and restaurants with mouth-watering local blue crabs, clams and oysters.

As a testament to the quality of the sailing there, Horizon Yacht Charters (HYC), which has bases throughout the Caribbean, recently opened an office in the Annapolis area, which will also serve as the U.S. arm of Bavaria Yachts. “It is far and away the sailing capital of the United States,” says Kenny Feld, managing director of Bavaria Yachts USA. “The Chesapeake features the best and broadest of all U.S. waters, and for locals, sailing is in their blood.”

At the new HYC base in the Yacht Haven Marina in Eastport, Maryland, guests can charter boats in the 2011 Bavaria Cruiser range. The base also offers a full complement of services, including learn-to-sail programs and comprehensive yacht management programs. In the winter, charter boat owners will have the option of keeping their boats in charter at an HYC Caribbean base.

Farther north is the Green Point Landing Marina in Worton, Maryland, home of Fair Wind Sailing’s Chesapeake base. Fair Wind Sailing offers day, weekend and week-long charters as well as sailing lessons in an area that is replete with prime destinations, including the Sassafras River and Still Pond to the North, and Rock Hall and the Chester River to the south. There’s also plenty of wildlife for the nature-lovers in your crew. At the mouth of Worton Creek, for example, two pairs of nesting bald eagles put on a show for the boats that sail by. “The area is remarkably quiet,” remarks Fair Wind president Dave Bello. “Even in the dead of summer you can anchor out in Worton Creek in peace.”

With more than 200 miles of cruising grounds stretching from the Susquehanna River in the north to the Atlantic Ocean in the south, the Chesapeake will leave even the most experienced sailor spoiled with choices. Both shores are lined with creeks and rivers that wind through the countryside to quiet towns and provide dozens of deserted harbors. Tides are minimal, and the bottom is generally soft mud or sand, which is relatively easy to back or kedge off of. Still, when gunkholing here, it’s wise to consider chartering a shoal-draft monohull or a catamaran.

The conditions in June are rarely too challenging for an average bareboat skipper to handle. Temperatures are in the 80s, winds are in the low teens and aside from the occasion afternoon thunderstorm, sunny days are the norm—just the thing for sailors interested in exploring a close-to-home chartering gem.

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