My husband and I have 19 nights to plan from getting from Riccione to Milan starting from May 20, 2023. We are flying out of Milan, so definitely the last 3 or 4 nights will be spent there. We've been to Venice and we'll have already visited Bologna (Emilia Romagna region) and do not wish to go to Rome at this time. Our goals are to slow down and not be rushing all the time. We enjoy great food, wine, history, architecture, and getting off the beaten path (if possible with train travel in Italy!) We'll just be relying on train transportation, understanding that limits a lot of the exploring in Tuscany. We definitely want to go to Florence, Tuscany (maybe Siena), Cinque Terre, and Lake Como.
I have one itinerary:
5 nights Florence
3 nights Siena
3 nights Cinque Terre (although maybe staying a bit north rather than in one of the towns. Also want to hit up Genoa for pesto! And trying to time dates when no cruise ships are in La Spezia)
3 nights Lake Como
4 nights Milan
(1 night unplanned, so we can add to any place)
Another thought is to add Assisi, as it looks like we can get mostly there by train from Riccione and maybe that is a good 1 night stop before heading to Florence.
From my research so far, it seems like Siena is the easiest base to do some Tuscany exploring without a car.
Any thoughts on the locations and/or number of nights? Are there other locations in these areas worth making a home base?
Thanks for any tips!