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Help. Needing to pick a Tuscany city tour option.

Looking for advice on which tour to pick. It will be our first time in Tuscany and our private driver for a day trip from Florence gave us the town options below.

  1. ⁠Montepulciano and Pienza (Val d'Orcia area)
  2. ⁠San Gimignano and Siena
  3. ⁠San Gimignano and a couple of small towns in Chianti
Posted by
1859 posts

Off the top of my head:
1: These towns are beautiful and would be a wonderful visit. BUT they are nearly 2 hours away from Florence by car. So it will be 4+ hours of driving and probably more.
2: I found San Gimignano to be lovely but way too touristy to be really enjoyable. Siena deserves a whole day by itself and doesn't require a driver but it does provide convenience. If you do this one I would do a couple of hours in SG as early as possible and then spend the rest of the day in Siena.
3: See above but this will give you the most variety with the least amount of driving.

If you have time to do Siena by yourself via bus or train I would take 1 or 3 and do that. If not I'd probably do 2 as I described above.

Is there a guide or just transportation? Some of the towns really benefit from some background and context that hiring a driver will not provide. I would do some research and delve into whichever towns you decide to visit to get the most from your time.

My $.02, I'm sure others will have other opinions,
=Tod

Posted by
7280 posts

My first thought was: if you won't see Siena any other way, then definitely 2. I wouldn't go to Florence/Tuscany without seeing Siena.

Posted by
6448 posts

Great overview above! I’d do whatever I could not do otherwise, and as a day trip to Siena is doable by bus or train, I’d go with one of the scenic drives.

Posted by
144 posts

I also would pick #1. The drive through the Val d’ Orcia is spectacular and Montepulciano has some of the best red wine in Italy. You will get the Tuscany views you see in photos. Sienna is a very interesting city but can easily be accessed via bus from Florence on your own.