I was born in Boston and have been here my entire life (39 years) – so, I’ll tell you what I know (largely abridged, natch).
Weather
Boston, like all of New England gets all four seasons in (mostly) their truest forms. Winter is snowy, cold and damp. Spring is rainy, cool with lots of budding trees and flowers. Summer is hot and humid with thunderstorms. Autumn is cool and breezy and the leaves change into amazing colors.
The weather can also be unpredictable and change on a dime. If you like variety of weather, Boston is for you.
Food
Simply put, I can’t think of a single style of cuisine that’s not well (and tastefully) represented within 20 miles of anywhere in Boston. Good range of prices also.
Transportation
If you’re not used to it, driving in the city is insane (hint: the roads were not planned a la Manhatten). I love it though. Ya just gotta be a little adventurous.
Otherwise the public transportation is great. The MBTA has trains (red, orange & blue lines), trolleys (green line), dedicated bus routes (silver line), commuter trains (purple line) and a boatload of city buses. You can easily (and affordably) get anywhere in the city and well out into the burbs. There’s even a Boston-Maine train and ferries out to the islands.
Culture
There’s waaaay too many choices to list here, so here’s some of my favorites: Museums (MFA, Gardener, ICA, MIT List, Museum of Science, Natural History at Harvard); Music (Boston Symphony & Pops, Scullers Jazz Club); Recreation (Public Garden, Boston Common); Cool Spots (Harvard Square, Davis Square, Jamaica Plain, East Cambridge, Arlington Square); Movie Theaters (The Capital Theater); History (Downtown Lexington); Odd Combo (Hang out at the Design Center on Drydock Ave in South Boston and watch the planes come and go from Logan Airport across the water in East Boston); Farm (Wilson Farm, Lexington ok, I work there. shameless plug)
Pick up The Improper Bostonian and Stuff at Night to find what’s happening in terms of clubs and events. Both rags are free.
Hospitals
Some of the best in the world and Massachusetts had guaranteed health care years before President Obama (which may be a good or bad thing depending on your perspective).
Politics
Well, as November’s election proved, Massachusetts is still one if the most liberal states in the country despite a vocal conservative group (Howie Carr, etc.).
Colleges
Can’t swing a dead cat without hitting a college or university. Lots of diversity of choice and cost. Some of the best in the country.
Demographic
Almost literally, people from all over the world. Stand in one spot in Harvard Square, Newbury Street or Jamaica Plain and dozens of nationalities will pass you by.
We do have a history of being a bit segregated (residentially) however.
Attitude
Big hearts, bigger mouths. Very sarcastic. Not always friendly.
You need a good sense of humor and a thick skin.
Cost of Living
Pretty high compared to other parts of the country. Living in the city proper is near impossible, but there’s more affordable options in the surrounding suburbs.
Getaways
Boston is within two hours of beaches (Gloucester, Newburyport, Rockport), skiing, islands (Marth’s Vineyard, Nantucket), Cape Cod, Providence RI, and Springfield.
Few more hours by car or train to Maine, Manhatten or even DC.
Anywho, hope this helps. Best of luck.