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14 Days in Tuscany- recommended itinerary

My spouse and I are heading to Tuscany in mid September and are looking for recommendations on towns to visit and suggested length of stay. We're skipping the major spots like Florence and Pisa as we've been there on previous trips. We are considering San Gimignano, Volterra, Montepulciano, Pienza and Assisi as primary destinations while using Siena as a "hub" since we will be using mostly public transport. Our primary interest is "cultural" - history, arts, museums, architecture so I thought these places would be suitable. Which of the above could be done in a day or so, and which would require 2 or 3 days to explore, including surrounding areas. Are there other places you would substitute? I had considered Lucca but it is a little out of the way from Siena.
Our final intended stop is Assisi and from there south to the rest of the country.
Thank You for any tips you would care to share

Posted by
8150 posts

Virtually every farm in Tuscany has apartments and rooms for rent as a source of extra income because their farms are relatively small. Have you considered finding a really nice agriturisimo as a base of operations--doing day trips from. To fully enjoy Tuscany, it's best traveled by rental car because public transportation doesn't go everywhere. Tuscan roads are well marked, well paved and not too busy.

We stayed between Certaldo and San Gimignano in a 2 bedroom apartment--above a winery. We found Poggibonsi to have two great and modern grocery stores, and we were able to cook one meal per day. We went to Siena, San Gimignano, Certaldo and Volterra on our day trips. A few miles east, you'll also find Montalcino to do winery tours from.

When we left, it was 4 lanes and controlled access highways all the way to Orvieto--another great hilltown. That's a little south of Assisi. There, we turned our Hertz rental car in across the parking lot from the train station and hopped on the train for a 70 minute ride into Rome Termini.

Posted by
27138 posts

Pienza is tiny. On Google Maps it looks as if it's about 3000' long and 1500' at its widest--roughly 1/4 of a square mile. One of my sources said you can walk every street in town in less than an hour.

San Gimignano is very small. I assume you'll be ready to leave long before the day is over. Because of its odd shape, it's difficult to say exactly how much ground it covers. Its population is more than 3 times that of Pienza, so I'd guess it does have a larger footprint.

Volterra is larger and has a number of sights (museums and such) worth going inside of. One of my guidebooks says it's worth a full day. I would expect to want somewhat more time than that; I'm slow in museums and am interested in the local alabaster carvings. Volterra's about 50% larger than San Gimignano in population.

In terms of population, Montepulciano is about twice the size of San Gimignano and 50% larger than Volterra.

Edited to add: I forgot Assisi! It's worth at least a full day, I think, and more if you're religious or otherwise want to see the sights in the lower town. I visited on a day-trip but felt it didn't give me as much time as I wanted. You can spend hours wandering around the non-touristy upper town, and the basilica is huge.

I think you may get tired of spending as much time on buses as will be necessary if you stay in Siena. (I realize you aren't necessarily planning to spend all your nights there.) I've been working on planning notes for a trip to that area. This is what I've found about bus service to your targets from Siena (info from Lonely Planet 2021, not verified on bus companies' websites):

San Gimignano: 10/day from Siena (none on Sunday), 1hr to 1 hr 30 min. From San Gimignano to Volterra there are 4 buses per day (Monday-Saturday only); 50 min. with a change in Colle di Val d'Elsa.

Volterra: 4/day from Siena (none on Sunday) with change in Colle di Val d'Elsa. Not sure about total time, but the two components add up to at least 1 hr. 20 min. without any allowance for the layover. I'd probably opt to spend 2 or 3 nights in Volterra and day trip to S.G. from there.

Montepulciano: 4/day from Siena (none on Sunday), 1 hr. 30 min. Buses to Pienza 8/day, 20 min. I'd stay 2 or 3 nights in Montepulciano--mind you, I've never been there--and day trip to Pienza from there. But I'd definitely check the times of those four buses back to Siena. How many of them are convenient?

Pienza: 2/day from Siena (none on Sunday), 1 hr. 10 min. I don't know the bus departure times, but anytime you have only two buses a day to a tiny town, you have a problem. You will probably have 8 or so hours to kill. How will you fill them?

I don't know whether you could (at least theoretically) shave a few minutes off any of those travel times by taking a train from Siena to the station nearest one of the towns and switching to a bus there. I'm doubtful, because Siena doesn't have great train service. Even to a sizable place like Assisi, a bus will probably be faster than a train. But at least there are trains--and a fair number of them run on Sundays; I haven't checked on Sunday bus service to Assisi.

As you can see, Sundays are impossible for visiting a lot of the small towns by bus.