Re: Chesapeake sailing--western or eastern shore?
So many issues:
1. Maryland vs. Virginia;
2. Northern/Middle Bay vs. Southern Bay;
3. Urban/suburban vs. rural;
4. Northern vs. Southern; and,
5. Bay vs. Ocean.
Annapolis is one of the premier sailing locations on the East Coast, with an active racing calendar and plethora of sailing related enterprises. If you are interested in racing and are willing to live in Maryland, the Annapolis environs is probably your best bet. There are also many nice cruising spots within a day sail of Annapolis. Baltimore is a decent size city with a major league football team, baseball team, historic downtown and sprawling suburbs.
The western shore of the Bay from Annapolis all the way to Solomon's Island is fairly well-developed and covered by subdivisions. South of Solomon's is less populated and more rural. Outside of Flag Harbour, there are few places to keep a boat south of Herring Bay and north of Solomon's directly on the western shore, although there are many beautiful waterfront communities.
Solomon's Island is a great, small harbour and sailing town with a number of marine businesses. South of Solomon's Island is predominantly rural until you reach the Tidewater area of Yorktown, Hampton Roads, Norfolk and Virginia Beach.
It is not unusual sailing south of Solomon's to see few if any other sailboats on the water on a given day, particularly on a weekday.
Virginia and Maryland are quite different states, culturally, religiously, economically, politically, and socially. It is no coincidence that the Mason-Dixon line delineates the North from the South, although Northern Virginia is quite similar to the Maryland suburbs of D.C.
The northern Bay on the Western shore is rather hilly and becomes flatter and flatter as you go south toward Tidewater. The Bay opens up and becomes saltier as you head south, with the widest portions just south of the Potomac River. If you desire to sail in the Atlantic Ocean, the southern Bay offers easier, quicker access than points north of the Potomac River. Somewhere north of Solomon's, it is almost always faster to travel north to the Chesapeake & Delaware canal and down the Delaware Bay to sail in the Atlantic.
The Eastern shore is predominantly rural, with agriculture, particularly chicken farming, as it primary business and some light industry. There are a few historic tourist towns like Chesapeake City, Chestertown, St. Michaels, Oxford and Cambridge, scattered in the northern stretches of the Eastern shore. The Eastern shore of the Bay south of the Choptank River becomes more shallow and marshy and sparsley populated, outside of a few towns like Crisfield and Cape Charles. Much of the fishing industry on the Eastern shore has been decimated by the poor health of the Bay. The Eastern shore offers easy driving access to the beaches of the Atlantic, including Bethany, Rehobeth, Ocean City, and Chincoteague.
If you want to retire in a college town, there are a few to consider in the Bay area, including Baltimore, Chestertown (Washington College), Annapolis (Naval Academy and St. Johns), St. Mary's City, or Williamsburg (William & Mary).
There are so many great books to read about the Chesapeake Bay area and sailing. Some of my diverse favorites for understanding the region are "Beautiful Swimmers" by William Warner, "The Floating Opera" by John Barth (fictional slice of life in Cambridge, Md. in the '50s) [or even Barth's "The Sot Weed Factor" for a satirical historical view], and "Cruising the Chesapeake" by William Shellenberger. One day I will probably get around to reading Michener's book, although I have so far been intimidated by its hefty size.
You could very easily spend several months, or several years, enjoyably exploring your options for relocation by cruising the Bay aboard a sailboat. There are only a few months in the Winter when it is too cold for comfortable sailing.
Last edited by jameswilson29; 07-12-2013 at 06:57 AM.