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Lived in both cities: 3 years in SF, 6 and counting in Boston. Came to Boston for the job.
In some ways the two cities are similar: seaports which have the ethnic and commercial diversity that comes with their location. However, it's hard not for me to see Boston as another East Coast city like Philadelphia or DC, rather than a unique place like SF. Don't get me wrong: it's not a bad thing necessarily, since in Boston you can get to other major cities very easily (hard to do in SF). But it explains Bostonians' anxiety about their identities: the need to be different comes from being not at all that different at bottom.
So, on to specifics:
- Nightlife
SF by a long shot. There are huge areas even in Boston that have nothing going on (eg, Downtown Crossing).
- Diversity (economy)
Boston. The economy in the city is rock solid. California is much more shaky these days. But that does mean rent in Boston is almost worse than SF. Don't be fooled by the surveys suggesting otherwise: the stats include Dorchester, a huge wasteland and Boston's geographically largest district, where rents are 1/4 of that in the rest of the city.
- Diversity (culture/people)
SF by a long shot. SF might be the most diverse place in the world because there are so few kids. So no one settles down and there is constant turnover, as there's been since 1849.
- Languages spoken
Clos but I am probably saying that because I actually understand some of the (mostly European) languages spoken in Boston, whereas there's no way I am going to understand the Asian languages spoken in SF. But Boston English, though...
- Education (Will be the most anticipated criteria IMHO)
Boston clearly has the universities. Here things get complicated due to the lack of state funding of higher ed. Massachusetts ranks 50th in per capita public spending on university education. This does mean that educational possibilities are oriented toward the wealthy.
- Lifestyle
Hard to say really. So much depends on your social status.
- Friendly people
Surprisingly, I give the edge to Boston because I appreciate the sincerity despite the fact that there are a small minority of incredibly nasty people.
- Climate
SF by a long shot. Boston not only has long winters, but it gets hot as hell.
- Medicine (Hospitals, clinics, health related things)
Boston by a long shot. The treatment possibilities out here are excellent.
- Natural scenery
SF by a long shot. Massachusetts is pretty ugly when you get out of the city. The suburbs are disgusting. Nothing here to compare to the Napa Valley or even Golden Gate Park.
- Shopping
SF. Union Square vs Downtown Crossing ... No comparison.
- Economy overall
Boston by a long shot. SF will always prosper, but the dependence on tourism and fly-by-night operations like some of the dot-coms my wife worked for does not bode well for long-term stability.
- Population city proper and metropolitan area
Tie.
- Benefits from location
See other entries.
- Public Transportation
Close, but I have to give the edge to SF for having a three-tiered structure. Boston's Green Line is the worst subway I've ever seen, but it's Red Line is the best I've ever seen. SF is more consistently ok. But just ok.
- Airports
SFO by a long shot over BOS, which is possibly the worst airport in America. In 2007-08, one of the Logan terminals had only one men's restroom open. You can imagine the lines.
- Skyline
SF by a long shot. Boston was built on the rule that the church steeple had to be the highest structure in town, and it still shows.
- Vibrancy of downtown
SF by a long shot.
- Museums
Boston. The historical museums are especially impressive. And there's even the ICA for modern art, though it's no SF MOMA.
- Theater, Music, & Arts scene
Tie. Boston has very few good rock venues but better bands overall.
- History
Boston by a long shot. No need to explain this one.
- Parks
SF. The Common is pathetic. However, there is nothing more abject than the SF Zoo. GG Park is the tiebreaker.
- Food
SF by a long shot. Boston food is still mostly traditional American - good but not daring.
- Anything else you can come up with to compare these two cities.
Of course there is sports, which is very important to Bostonians, and they would pile on me I gave the nod to SF. But I'd rather watch a game at SBC than Fenway any day! So cramped and the Sox fans are ornery.
So SF wins handily, though if you want a job you should move to Boston.
I don't think you should limit your assessment of shopping in both cities to just Union Square and Downtown Crossing. There are other shopping areas in both cities, such a Copley, or Newbury Street in Boston.
Any of the major cities in the Boston -Washington corridor are superior to San Francisco.
I don't mind Boston pride, but I object to this kind of East Coast provincialism. It is annoying and all too common. True, there are more great cities on the East Coast. But there are also far more horrible places. There are few cities on the Pacific coast (well, ok, except Richmond) that i would find it terrible to live in. But there are quite a few in this "corridor" of yours that are basically Third World, due to much greater social stratification, racism, bad public policy, etc.
I don't think you should limit your assessment of shopping in both cities to just Union Square and Downtown Crossing. There are other shopping areas in both cities, such a Copley, or Newbury Street in Boston.
But Newbury IS in Copley Sq. That's just one other area, and not that great.
Granted, it depends on what you're looking for. Bookstores, for instance: Boston wins easily. But clothes? SF residents care more about their clothes than about their personal relationships. Good clothes shopping in SF.
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