The other day I was driving through Boston, on my way to visit daughter #1 in Jamaica Plain. Daughter #2 was riding shotgun, and I asked her to keep an eye open for me at the two places on this route where I tend to make wrong turns.
Now, it's not that I get lost. And it's not that I'm unfamiliar with the route. The fact is, Boston's roads are in places notoriously irregular. They used to be both irregular and largely unmarked; now they're irregular and marked only well enough to clue an alert navigator who knows the route, but not well enough for a driver who has to contend with traffic and isn't absolutely sure of all of the lane changes and turns.
We got through both places without incident. At the Kenmore Sq./Fenway exit from Storrow Drive, I naturally wanted to bear right to go right, but my daughter reminded me in time to bear left to pick up the right turn onto Boylston St. outbound. At the intersection of Boylston St., the Fenway, the Riverway, Park Drive, and Brookline Ave., I had to stop at the light, and thus had time to remember that to go slightly left on the Riverway I needed to turn right, move two lanes left, follow the curve left, and then go straight. (None of that is shown properly on Google Maps, by the way. Ground truth is a whole 'nother essay.)
I mentioned to my daughter that even after 30 years of living in the Boston area I always want to cross that intersection and turn left, which is the way that looks like it should be correct, but isn't. My daughter, who had spent a summer working at the Joslin Diabetes and Endocrine Research Center, just off the Riverway, mentioned that she had never been able to make anyone understand how to get through this intersection correctly when asked for verbal directions.
The designers of Boston's streets had extraordinary flexibility, for lack of advance planning. I grew up in Philadelphia, which at its core was laid out on a planned rectangular grid at the time of William Penn, and there the streets are much easier to understand in most places (albeit with a few notorious exceptions near the Schuylkill River). Boston, on the other hand, had much less in the way of planning in colonial times.