Chesapeake Bay is one of the best recreational sailing grounds, maybe in the world. Lots of destinations within a day's sail of each other, weather conditions that can change day by day (or even hour by hour), plenty of open water, but protected from the REALLY violent weather (worst I've ever been out in was maybe beating into 4 - 5 foot waves coming down from the north) and lots of neat little anchorages and towns to visit -on both the Eastern Shore and the western shore. I've done two 2-week trips entirely around the Eastern Shore (Baltimore down to Norfolk, out into the Atlantic, up the coast stopping at Ocean City, into the Delaware Bay and through the canal back into the north end of the Chesapeake, and back down to Baltimore). For a sailor, it's pretty durn close to heaven. Worst part is, it's only worth sailing in maybe 7 months out of the year - but I guess we need some time to get those boat projects done.
The Bay is probably why many consider Annapolis to be the sailing capital of the world.
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