I would like to get input on a Tuscany itinerary I’m working on for September/October 2027. My wife and I are fit 60-year-olds and experienced travelers in Europe. We are interested in architecture, art, history, local cuisine and natural landscapes. We have visited Italy (Rome, Venice, Florence, Cinque Terre) before. We like to see and do a lot when abroad, but we are trying to transition to a slower travel style. We like to walk around each town and soak in the local flavor, visiting 1-3 ‘must see’ sites on each day trip.
The trip I am planning is focused on Tuscany. We will arrive in Rome on a Sunday (we stay busy on arrival day), spend 14 days on the ground and depart on a Sunday. Our night prior to departure will be in Rome. I picked Lucca (6 nights) and Siena (7 nights) as our bases for a couple reasons. As we approach retirement, I want to try out a few towns in hopes of finding where we want to spend more extended periods in the future. Both towns are high on my list for longer stays and I plan to talk with locals and realtors while there. Also, in my opinion, a town’s character is on display before and after the ‘tourist’ rush of the day. By only staying in apartments in two towns, we will have an opportunity to get a small sense of ‘living like a local’.
We plan to do day trips from Lucca by train, and considering Pisa, Florence (1 museum), Collodi, Pistoia and possibly Bologna. We will take the train to Siena and rent a car there for the more remote towns. We can visit one or two towns (if they are close) per day. This may be overly ambitious. Day trips we’re considering are San Gimignano, Volterra, Assisi, Cortona, Montepulciano, Pienza and Arezzo.
I picked the individual towns from years of reading this forum and from RS guidebooks. That said, I welcome suggestions on other places to consider or changes to my travel plan. Thanks!