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As an outsider, driving in Boston is crazy. The drivers are almost as aggressive as New Yorkers, then you factor in wild road layouts in some parts of town. Oh and The Big Dig moved most of the freeways underground which can play havoc with your GPS...I always get pencil-and-paper directions for the last leg of my trip once I get into town! Parking can definitely be a pain. Even when I go with my friend who grew up just outside Boston and knows the area well, we all just park at the hotel and use public transit for intra-city travel and even try to use commuter rail into the suburbs since it takes just as long to wait for a train as it does to wait for the valet to get your car out of the hotel garage!
Getting around with public transit is easy though with the T subway/rail system and the buses. It's one of the nicer public trans systems you will see in the US.
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