Thinking of going to Boston for the first time, what is it comparable to?

NYC, Philly, DC, or any other cities?

Would I need a car?

Philidelphia reminds me of what Boston could be. It has the same look and feel, but cleaner, friendlier and less traffic.

You won't need a car, just a lot of money to afford to live here

I live near Jacksonville, and frankly, I found Boston to be much like Jacksonville.....kinda flat (except for 4 or 5 buildings), and kinda spread out. I found driving very easy there. We were in the South side of Boston (Jamaica Plain area). It is oozing with history, and I very much enjoyed visiting there.

The first responder is completely wrong. Boston is not flat, and it sure as hell isn't spread out. Boston is a very dense and compact city; everything is very close together.

So, to answer the second part of your question: no, you don't need a car to live here (provided you're within the city limits) and it would actually be more beneficial for you not to own one.

Let me break it down for you by pros vs. cons.

Pros
1. excellent and cheap public transportation
2. beautiful harbor and close to the ocean
3. world-class colleges and universities
4. finest hospitals in the nation
5. distinct New England seasons
6. airport is conveniently located to the city (only 10 minutes by train from downtown)
7. fine sports tradition (particularly baseball) and rabid sportsfans
8. interesting blend of the old and new
9. vibrant nightlife (doesn't compete with New York's, but still good for a city of its size)
10. entertainment and the arts (Boston Symphony Orchestra, museums, etc.,)

Cons:
1. absurdly-expensive housing and property
2. shortage of parks and land
3. compact and dense city; makes for a lack of space and privacy
4. people not as laid back as in other states
5. no street grid system which makes it difficult to drive, navigate and park
6. very touristy, and can get a bit expensive and crowded in the summer months (although on the flipside, this is also the same time when the students have emptied out of the city)
7. having the finest hospitals in the nation may not mean much to you if you can't afford it
8. for newcomers, it can have a "snobby" feel to it, due to all of the higher-learning institutions such as Harvard and MIT
and
9. the job market can be competitive for that same reason

Sean_201 is right; Dan is out of his gourd. Jacksonville??? JACKSONVILLE??

Boston (actually it should be considered Boston/Cambridge) is the most European-like city in the USA. San Francisco or Seattle like attitudes without the hills, (and with better public transportation). But I would most suggest that it is like a small London or a Dublin.

I completely disagree with am, Boston is nothing like Philly, if anything is much much cleaner and safer than Philly. I lived in Boston for years, and used to travel to Philly for business on a regular basis, and Philly didn't remind me of Boston at all. Yes, there is a lot of history, but I never really felt safe, and it always seemed gloomy there. I don't think its really comparable to NYC, Philly, or DC, I think San Fran is a good but not great comparison. Boston is very much its own city. Its very dense, you can walk from one end of Boston to the other in about an hour. Its cleaner than most big cities. It does have great public transportation and a car would not be necessary if you intend to stay in Boston proper. It can be difficult to get around Boston in a car because the streets are very narrow and it is not a grid system. Its a really vibrant and fun city as well.

For the poster that compared Boston to Jacksonville, I think that's a very poor comparison as well. Jacksonville is the largest city in the U.S. (in sheer size not population) and has none of the history or culture Boston has.