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Well, Boston has a European style street layout, which can be rather maze-like (especially if driving), whereas NYC has a very easy-to-follow grid pattern. On the other hand, Boston is a much smaller, more condensed city, and is very easy to traverse on foot (it is "America's walking city"). It also has a very extensive public transportation system for a city of its size (subway stops are closer together than they are in NYC). You just have to figure out the Inbound/Outbound system on the subway lines.
Overall, Boston is easier to get lost in, but in my opinion it's definitely the more manageable city for pedestrians.
It really depends on where you are in each city, it can be very long and confusing getting around NY (especially on the subway), I personally hate taking the subway and luckily my neighborhood is on the outskirts of NYC and we have no subway service only the bus and Long island Railroad .
Overall I'd say New York is the easiest to get around.
The transit system in NYC is superior. The subways cover a larger geographic area and run 24/7. But Boston is so compact that it's an easier city to walk around in, and really almost everything a visitor would want to see in Boston is within walking distance of the Common.
Boston is only more walkable in the sense that is compact and you could walk most of the attractions in a weekend and get around w/o using public transportation... Not so in nyc...it is massive, plus the public trans options are better...it is just as walkable if you are in a specific hood...but it is much much larger than Boston. If you are not used to walking all day on concrete you are going to be hurting...
New York is considerably easier to get around. I still get lost in Boston sometimes haha. NYC's public transportation is better than Boston's too, so that helps. However, as others have mentioned, since Boston's much smaller than New York, the attractions are closer to one another.
But that may not make a difference if you're walking around and can't find the street you're supposed to be on because nothing about the Boston street-system makes any sense haha.
How easy is it to hail a cab in Boston if you are outside of the downtown area? Can you easily hail a cab areas like South Boston, Charlestown, or Allston?
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