So, yeah, I'm in MA as we all know right now. I leave Saturday.
Now, my experience with Boston proper has always been as a pedestrian, with the exception of my last trip where I flew in and got lost trying to get out of airsport to get to Western Mass. Since I knew I was going to travel inside Boston and knew that I would want to drive around Western Mass with the option of getting lost and needing to find my way home, I bought a GPS prior to my trip. It's worked mostly well, with the exception of Boston having several roads intersect and the GPS getting confused as to whether to turn left or right. Later I found out that 3D mode is better for that so you can really see what's going on where you need to go, but I digress.
I was in the South End visiting a former professor of mine. We talked for a few hours, went out to dinner, talked a little more, then I had to leave to head back to NH to stay with friends.
My GPS told me to go one way (after it took about 2 minutes to calculate the route) and he told me to go another. I decided to take his directions since it kept me off Storrow Drive. As soon as I started on his route, I hear "Recalculating route. Recalculating route. Recalculating route." All while I was on the same road and not crossing over anything.
Now, I've heard GPSs get mad when you don't follow their directions. I've even heard one tell you to make "the next legal U-turn". But NEVER have I heard one have to do three different recalculations in a row without crossing over or missing any turns.
I guess that's one of the cool things about the midst of Boston!