As an almost retired strolling minstrel I would say go for it. Decide which period you like and get a very good costume - not an old curtains job.
You could try going to your local entertainment agency; they will get you bookings at PTA's, fetes and fairs if you like being close to the public, and chatting. I managed to get bookings for myself far and wide - but I never wanted to give concerts, I get embarrassed when people clap.
One way of making contacts is to volunteer to play at a couple of historic events, as discussed in another section of this website. If people like you they will ask for your card and you may get interesting bookings. However you will find that playing your instruments in tune is the least of the problems you will encounter. You will find out the best way to deal with hot weather, rain, bothersome children, and what to do when people get up and dance. People will want to touch your instruments and they will ask questions too, so you will need a fund of short anecdotes to amuse them.
I've learned that zebras are worried by the pipe and tabor, but ducks do not mind at all.