Of course ... many/most of my cycling trips involve picking some random city off a map.

When the weekend rolls around, we'll pick a place somewhere within 100-ish km of where I live, and ride there ... preferably not the same place two weekends in a row. For some variety we might drive out to a place an hour or two or three away and cycle from there. For even more variety, we'll pick a spot even further away, and drive, take the train, or fly there to cycle from there.

Many of our destinations have something to do with an Audax/Randonneuring event ... we'll pick an event and go ride it. If the event is in another country, we'll stay a while and meander around the other country having a look at things.

So yes ... pick a spot and go!