You know, the OP did not ask about cost of living, nor about how crowded the area is; he asked about sailing.
I have sailed the Chesapeake, (didn't live there; just cruised it a half dozen times) and frankly I found it pretty boring. Certainly a lot of lovely anchorages and great places to anchor, moor or dock after a day on the water, but it seemed conditions are pretty mild if it's not a blustery day. If there isn't a front coming through, then what you go out into is pretty much what you'll be sailing that day. Mostly?
The Sacramento and San Joaquin Rivers add to the diversity of Bay sailing giving an untold amount of inland cruising grounds.
Bay sailing is year round, and it's not got those hot, sticky and windless summers of the mid-Atlantic states.
First of all sailing anywhere is a great experience.
Boring...you must be quite easily bored. I would think youd get more easily bored in the small confines of Bay area vrs the huge diversity of the Chesapeake with the many historical rivers to enjoy. You dont have to spend you day dodging tankers, sightseeing boats and ferries either.
Most of the Bay is not crowded at all just around Annapolis and Baltimore. Part of the fun of sailing the Chesapeake is going up the Rivers like the Chester, Wye, Choptank, Pauauxet, Potomac,Rhappahanick to name a few.
The weather conditions in the SF Bay are definately more varied unless you are down near the mouth of the Chessie near the Atlantic. No fog on the Chessie either.
The nice thing about the Chessie is that you are also close to New England, Long Island Sound and North Carolina so there are many of new places to go to if you want to expand your horizons some. We travel to New England every year when its hot in the Chessie In SF you can do some ocean sailing, but going north along the coast is difficult and south the options are few and far till you get down near Long beach/ Catalina
Both are great places to sail. I have sailed in SF Bay a number of times and loved it.
We are looking to retire in a few years and are also thinking about changing and have visited areas in the last two years and sailed like SF and San Diego. We have decided to stay here in the Chesapeake and cruise south to the carribean/ Florida when winter comes for 5 months.
For me personally I prefer to sail in peace and quiet though and not feel I am on the Freeway. And when my feet hit land...I dont have to worry its going to move under them.