We try to travel during shoulder season. However, we are finding a lot of places are losing their shoulder season or it has been pushed into winter. CT was one of those places. We were there at the end of October. It was far from shoulder season.
If I want to visit extremely touristed cities, like Venice or CT and many others, one of the choices I make is to stay in the city and enjoy the quieter mornings and evenings as opposed to day tripping and hitting the towns at peak. Sometimes people complain about the crowds when they visited at the most busy time of day and didn't venture from the well beaten path.
We also, opt for less desirable weather because our priority is fewer people. We will be in Salerno mid February and if it's sunny and mid 50s, we will day trip to Amalfi town and the smaller cities south of it.