Want to spend about 3 weeks in Italy between late May and mid June, rough plan Rome > Amalfi / Capri > Florence > Cinque Terre > Milan > Dolomites (want to hike Seceda, Alpe di Suisi and Tre Cime) > Venice
I know the logistics of planning all of it, however, my question is how feasible is it to do this spontaneous, i.e. I want to be flexible and not book anything in advance, is this even possible, has anyone done it in Italy? Technically this is still shoulder season so I am thinking it should be possible?
Are hotel prices closer to the dates going to be crazy (they are crazy right now in some of these places) however my thought is that there may be better deals last minute. #travel source