Hi,

I think it's better you stay in Siena and make a day trip to San Gimignano. It's enough to stay there half day. May you can visit San Gimignano by the way to Siena.

We visit both location and we sure that we come back to Toscany that we visit Siena again. Sure San Gimignano is a real beautiful and you have to visit it.

If you stay in Siena you could also do a day trip to Volterra which is not far from San Gimignano.

Is it possible to do Siena, San Gimignano and Volterra in one day? We also want to stop in Greve Chianti and make a brief stop in Pisa.

And, we want to squeeze in a nice lunch with wine tasting too.

Any recommendations?

We will be arrving in Livorno and have booked a car to pick us up at the port. We have 12 hours.

If you've already stayed overnight in Siena I would recommend staying overnight in Lucca as something that's a little different.

San Gimignano is small and extremely touristy. It's not someplace that I've ever thought I wanted to return to to spend the night. By contrast, I would love to spend the night in Pienza, which is also very small, but for some reason, I would like to spend an evening there.

Lucca, however, is gorgeous. I would love to go back.

With an early start, you could certainly visit Siena, San Gim and Volterra in one long day but you wouldn't do justice to any of them in the relatively short time available. Personally, I can't get enough of Siena, am there weekly sometimes and still want to come back for more. Remember on our very first visit, years back, we spent three nights there, which we felt was about right. But I know visitors, many, who reckon it can be "done" in a few hours. San Gim is usually so crowded you only want to spend a few hours there (assuming you haven't spent a few hours already trying to park as someone I know did last weekend!). But Volterra justifies more than a whirlwind tour. And on top of this you have the driving times between the three towns.

Re staying in Pienza overnight, it's wonderful. Like so many v popular day trip destinations, once the crowds have left you have the small lanes and private corners all to yourself. Wandering on to the village walls at night too and just looking out over the Val d'Orcia and seeing the lights of the distant farms is magical.

We too are doing Florence for 3 nights and then onto Tuscany countryside for the remaining 5 days. I am looking at perhaps Radda or Siena for the Chianti area and Cortona. If you had 5-6 nights, would you stay at ONE place for those nights, or split it up between Lucca area and either Siena/Cortona area?

Thank you for anyone who has been there for a week timeframe - it is our 15th anniversary and first time away without kids for an extended stay (and we are outdoorsy people).