Please help with 3 Nights and 2 1/2 days in Tuscany.


New member
My husband and I (late 40s/early 50s) will be in Tuscany at the beginning of September. We do not plan to visit Florence or Pisa, and we will have our own car. First, I would like to whittle my list of towns to see down to a realistic plan that allows us some time to just "take it all in." Once that is decided, I need help choosing a home base.

Here are my places to see. I would appreciate opinions on what I can skip, as well as which towns can be combined into one outing. We are not overly into museums and art, etc., and I don't mind things being a bit "touristy" as I am, after all a tourist. We enjoy food, wine and friendly people :) We are okay with spending a bit of money on nicer accommodations if necessary, and prefer to be not too far from town or village activity. Thank you so very much!

San Gimignano


you can imagine most of the towns you mention as being on the edge of a circle, being the Chianti Classico area, with Siena being the southernmost point.

Lucca is a bit further away, above Pisa, to the "north".

From experience, Cortona is a bit further away to the "east"..Montalcino and Pienza are very close but again further away to the south, more than 1 hour's driving from Siena

Greve and Castellina (as well as Radda and Gaiole) are close and can be done together.

So are San Gimignano and Volterra.

However Lourdes will be able to help more as she knows the area much better than me.


The Tuscan Expert ;-)
Staff member
Ciao Duchesse,

Sgrima has done a good job of describing the locations of the towns across Tuscany and which ones can be visited together because close to each other.

If all you have is 2.5 days, time will be limited.... I imagine you're driving from somewhere: from Rome or Milan/Bologna? I ask because it could be useful to know so that we can also offer an idea of the order in which to see things.

So let's suppose you are driving up from Rome. As you drive up, since you prefer wine and food to museums/art (you don't need to visit museums to see art since everything is like a museum ;-), I'd suggest heading west from the A1 to Montepulciano and Pienza and Montalcino. This area is dedicated to red wines (rosso di Montepulciano and brunello di Montalcino) and cheese production (pecorino in Pienza) ;-) You can have lunch at either of the first two, depending at what time you arrive. Remember lunch hours for restaurants are 12.30-2.30 latest, kitchens do close! Then your choices are panini and whatever you might find at bars (coffee shops) which are the "fast food" equivalent for Italy. Then keep driving toward Montalcino - visit the Sant'Antimo Abbey nearby, truly gorgeous! - passing through San Quirico. The landscapes here are beautiful.

Then head up toward Siena for dinner and for the night, I think it would make the perfect base for you. You don't have to stay in the city center given you have a car and don't really want to worry about the ZTL but some hotels do offer the chance to drive up to the hotel to drop off luggage and then park outside. This article has info on parking although take it just as a guidance because it is a bit outdated and needs updating.... I think it is likely they've done away with most of the free parking :/.

In any case, Siena is a perfect base and gives you a chance to really live it better. The next day you can head toward Volterra and San Gimignano. On the way there, you'll pass by Monteriggioni and Colle Val d'Elsa, you can stop briefly.... or not, you can always head back your last day..... I'd suggest spending some time in Siena on your third day and visiting the main square, the Palazzo Pubblico, the Duomo with its nearby monuments (baptistery and climb up the facciata for the view in the museum, at the very least). Siena is lovely and many people spend too little time there. If you dedicate the day, you'll have a chance to enjoy it very much.

On your last day, if you're heading north, you can spend it in Chianti. From Siena, you can pass through Monteriggioni again, then head to Staggia (quick stop to see the castle if you want) and from there head up to Castellina - some of the most beautiful landscapes with vineyards in the area are here. From Castellina, head to Greve, stopping in Panzano along the way. If you have time, visit the tiny hamlet of Montefioralle above Greve, it is where Amerigo Vespucci's family lived. You can spend all day here or head out to your next destination by the time you need to...

There is definitely lots to see just driving around, more than there is generally time for.... so just stay flexible and see what you can fit in!!


New member
Grazie Lourdes!

We will be driving down from Bellagio or Stresa... haven't quite decided which yet. I have narrowed down our lodging to these four options. I would love to hear your thoughts on all or any if you are familiar with them.

Il Casello
Relais Fattoria Valle
Pensione Palazzo Ravizza
Relais Vignale


The Tuscan Expert ;-)
Staff member
Siena would be the perfect base for your itinerary

Ciao Duchesse,

Ok knowing you arrive from the north is very useful! You still only have 2.5days/3 nights, so you want to be in a position where you can easily move about without too much time spent in transit to destinations.

Of the places you found and like, I like the one in Siena the best - also because it has its own free parking!! But particularly because it is central and from there you'll find it quick to move around in each day without going too far in any direction.

As you arrive off the A1, you can exit on Firenze Sud and take the Via Chiantigiana into Chianti.... stop in Greve, Panzano and Castellina as you make your way to Siena on your first day. You can spend evenings and your last morning in Siena, you definitely do want to spend some time there as well.
On another day, from Siena you can head to Volterra and San Gimignano. As you head back to Siena, you could stop and have dinner in Colle Val d'Elsa or Monteriggioni.
On the other day, head south into the Val d'Orcia. Montalcino, San Quirico, Pienza and Montepulciano are your destinations....
if you love food and wine, you won't have any problems in finding either in any place in Tuscany, especially as you pass through Chianti and this area south of Siena.
On your last day, as you head south I imagine you can stop in Cortona ;-).

Just make sure to spend time in Siena as well :) See, aside from Lucca, you've got all of the places you wanted to see covered ;-)