I have lived and sailed on the Chesapeake for the past 30 years. I have also sailed on much of the U.S. Atlantic coast at one time or another keeping boats for varying periods of time in Long Island Sound, Charleston, Savannah, Miami, and Sarasota.
While I am very partial to the Bay and think its one of the best cruising grounds that I have sailed in, it is in no way perfect. As others have noted, the winds tend towards the light side for much of the period from late spring until early fall. It can be miserably hot and humid during summer but certainly not as bad as the places that I lived in the south. I had a friend who worked charter boats in the Med and Caribbean and she would refer to sailing on the Chesapeake as sailing in a mudhole, the water being brown during the summer and comparatively shallow. Just about the time that the winds get good, the temps drop to the point that warm clothing is required. but you can sail almost all year round until the temps drop below freezing and cruising stops (unless you have a boat with a heater). And so, if judged by those criteria, there are better places to sail.
But on the flip side, the Bay offers an amazing number of beautiful and diverse anchorages spread out over an ever changing shore line. They vary from good sized cities like Baltimore and Washington, to a slew of quaint little towns, to rural backwaters where there are almost no signs that man has been here before you. The currents here are relatively benign, the channels well marked, and the bottom usually soft.
With a decent turn of speed there are often dozens of nice anchorages within a comfortable day of sailing. There are great service yards and you can sail almost all year round in the worst years and all year long in the best. There is also very high caliber racing as well as scads of opportunities for casual trots around a race course. To me the joy of Chesapeake is about the diversity of experience that is available and the broad ranges of places to sail to in any given day, week or month on the water.
The area around Annapolis has a reputation for being expensive to keep a boat, but if you keep your eyes open and talk with budget challenged locals, there actually are inexpensive places to keep boats around Annapolis, and there are very good quality boat yards who do work for very reasonable prices. When I have had large projects to do, I have priced them in a variety of locations, on both the eastern and western shores, and have not found significantly less expensive yards than the one that tend to use on Back Creek of Annapolis.
I like that buying marine stuff is relatively easy, and that there are enough, and large enough marine stores you can usually see and touch items before you buy.
In terms of a place to live, I love that Annapolis is less than an hour's drive to Baltimore and Washington, and a couple hour drive to Philadelphia. This allows day trips to wonderful cultural resources. In winter, we take 'land cruises' to enjoy the various museums (most of which are free in Washington) and to concert venues in the area.
In terms of living expenses, downtown Annapolis tends to be more pricey than some surrounding areas, but again, there are very affordable homes within a 15-20 minute drive from Annapolis. When I have compared prices between eastern and western shore homes, there just is not that much of price difference (5-10%) when comparing apples to apples, other than in the prime markets like downtown Annapolis, which is still a bargain when compared to Washington DC. Obviously there are less expensive areas to live like the Carolinas and portions of Georgia, and North Florida on either coast, but these tend to be more rural and so the kind of cultural amenities that I enjoy tends to be harder to come by.
So from my perspective as a glass is half full kind of guy, the Chesapeake is way more than half full even if much of the year its more than half full with mud colored water.
Jeff
