Cheap Parking Tip in Boston
The only thing I hate just as much as driving in Boston is parking in Boston - which is usually just as chaotic and ridiculously expensive.
Jon and I lucked out immensely during our stay this past weekend when we missed our turn for a parking garage near Government Center and Faneuil Hall. That parking garage would have been about $16 for our night in Boston - which, for a larger city, isn't bad.
But we were able to find on street parking meters which were even cheaper. I asked a bouncer in a bar nearby when the meters were active until (since it didn't say). He told us they were active Mon-Sat until 8pm.
We got there around 6pm and the meter, as it turned out, would only allow us to put in two hours worth of quarters which worked out perfectly. We paid $2.50 for what ended up being about four hours of parking. That's even better than Albany, NY prices in downtown during the day.
The trick with this, however, is you need to get there before all the parking meters are taken and it should be by around 6pm since the meters (where we were anyway on India Street) were only good for two hours. You also need a lot of quarters. The price was 25 cents for every 12 minutes.
Some additional thoughts and tips from friends who used to live in/around Boston:
Rhianna said that in many residential areas the parking metered areas are reserved for residents with permits after 8pm: "Back Bay and South End are two places that I seem to remember getting tickets. Around Fenway was brutal...A little known fact is that the alphabet cross streets in the back bay don't require meter feeding on Saturdays and there are always visitor parking spaces in residential neighborhoods where you don't need permit. But some neighborhoods strictly enforce the 2-hour limit (Porter and Kendall come to mind) so meter feeding will still get you a ticket."
Clementine: "You can find free, non-permitted parking in just about every neighborhood, but there are about 500,000 other people looking for those spaces as well...If you want to find cheap/free spots, drive around and Google garages - some have coupons and specials."