I live in DC and will be moving to Annapolis in a month or two and living aboard
. I lived in Boston for a couple of years when my wife was in graduate school
From a pure sailing perspective they both have their pros and cons. I grew up sailing around Long Island Sound
and and there are dozens of amazing destinations. The Cape, Martha's Vineyard
, Naushon Island, Cuttyhunk, Block Island, and sailing in Maine
is an experience that everyone should have in their lifetime.
The downside to Boston is that if you're not from Boston, they'll never let you forget it. You'll never feel like you're from Boston. That is largely true of any of the cities on the east coast
that have real neighborhoods and a sense of place.
Washington benefits from the fact that no one is really from there. People come and go based on political winds and so forth, and it is a much more welcoming community in general. It's also much MUCH more diverse ethnically, and much more tolerant and communal in that respect. In short, Washington is friendlier than Boston.
The traffic in DC is rated, as I recall
, as the worst in the country, exceeding even Atlanta which is hard to imagine. That said, the public transportation system is second to none and I know plenty of people who don't even have a car and are extremely pleased with their ability to get around. Outside of rush hour it's a 40 minute drive from Washington to Annapolis.
I also know quite a few people who live in Annapolis and commute to DC for work. Most of them ride one of the subscription bus services that cater to commuters, with very comfortable seats and wifi
and other goodies. The buses depart a few times in the morning and a few times in the afternoon early/evening. They all say the best benefit is that if someone wants you to stay late at work you just say "Gotta go and catch my bus or I won't get home at all. Bye!" lol
Another benefit of the Washington area is that the economy is virtually bulletproof. Between government
spending and the various industries that cluster around the city the job market is always strong. The most recent downturn was pretty much nothing but a speedbump for us.
I think for "getting into sailing" that the Chesapeake is probably a more accommodating place. The Chesapeake is a bay with a fractal outline that gives it about 2,000 miles of coastline. It's semi-sheltered (although the chop when the wind
kicks up can be fierce) and you can get to interesting destinations with a few hours of sailing. The sailing season is longer since it's a bit warmer than Boston and it's not uncommon to get invited out for a sail in November or March.
I don't buy that the wind is worse in the summer than in the NE. I base that on more days than I can remember of being becalmed bobbing around off Nantucket
One huge upside to the Boston area is Cape Code. The beaches are magnificent. It's a three hour drive from DC to the nearest beach on the Atlantic and they don't hold a candle to the Cape's beaches.
Either location has ample sailing opportunities and helpful communities for the beginning sailor. If I were in your shoes I would choose based on which place fit my professional and social needs.