I have 7 nights to spend in the Umbria/Tuscany countryside and am trying to decide where to stay. I've already been to Florence/Rome several times and do not plan on spending time in either city on this trip. Instead, I'm flying into Rome and out of Pisa. I'll be renting a car and driving directly to a town called Amelia (this is a nostalgic stop) for one night. From there, I could either spend 3 nights in Montepulciano and 3 nights in San Gimignano (using them as "home bases" and taking day trips) OR I could town hop and spend 1 night in each town, working my way north (ex. Amelia > Civita di Bagnoregio > Montepulciano > Siena > Castellina in Chianti > San Gimignano > Lucca). Has anyone ever done a "town hopping" trip like this? I'm trying to decide if doing a trip this way would be fun or exhausting.
I would do montepulciano, Siena and Lucca for two nights each. Too much headache with townhopping.
I would (and have many times) stay in a small town, with a train station, off the tourist map. The towns you mentioned are hugely overrun with tourists.
You can practically close your eyes and jab your finger on a map and see what you come up with. It’ll all be good (as long as there is a train station, although you didn’t mention your mode of transportation). Switching hotels every day is time-consuming and unnecessary when you can just plant yourself in one home base and do day trips in every direction.
Decide the villages you want to see and choose a maximum of a couple of bases from which to take day trips.
Hello madeleine.dibiasi, and welcome to the forum,
I have to agree with the longer stay base town plan. One night stays don't even allow for one full day someplace. Only by staying somewhere for a while do you have any hope of finding a favorite coffee place in a town versus one new one in every town.
The southern cluster of Pienza, Montepulciano, San Quirico d'Orcia, Montalcino and anywhere else you want to see is a good southern location.
For a northern location I would not recommend San Gimignano since it is completely touristed out. I spent a week outside Castellina in Chianti many years ago and it is pretty well positioned. It was very much a town trying to "come up" at the time and I think they have succeeded in that somewhat. Siena, SG, Volterra are all within reach and Greve and Radda in Chianti are close.
For Lucca, Pisa and Florence they are all connected by train so after you drop off the car you can explore these as well before you fly out. You could easily stay in Lucca and train to Pisa - there airport buses or train+tram combo to the Pisa airport - or vice versa.
I only stay in places one night if it is logistically necessary - flying out the next day - because you won't remember any one town. Also I have to say that, for me, part of the appeal and charm of rural Tuscany is the slower pace of life and the seasons. If every day is planned out and accounted for I think too many people rush through the area and miss the charm of lingering and the la dolce far niente.
Practical advice: get an International driving permit IDP for all drivers before leaving the states, read up on ZTLs before you go and check on each town before you drive there, don't leave luggage in your car when parking.
Have a great trip, rural Tuscany is as beautiful as advertised,
=Tod