DH and I will be in Boston the last week in March. That Friday is our anniversary, and the current plan is to spend Friday afternoon exploring the North End and have supper somewhere Italian. However, I'd rather not bother with reservations... I'd rather wander into someplace not fancy that looks/feels good and happens to be wherever we happen to be at the moment.
The question would be, is that nigh on impossible? Are we talking "must have reservations" anytime anywhere in that neighborhood on a Friday night? I'm happy to eat at the bar, I'm not happy to wait more than 1/2-an-hour - 45 minutes for a table. I have no idea what time I'm talking about, either, more of a "when the mood strikes" kind of thing... although I guess it also will depend on how much there is to explore and what time it all closes!