Driving on daytrip to San Gimignano, Monteriggioni, Siena (and a winery??)


New member
Greetings community!

My name is Luis and I'm from Costa Rica.

On my first time in Florence, 5 years ago, I booked overnight a tour that went on a small bus to Pisa, San Gimignano, and Siena, including a lunch stop on a kind of restaurant with pre-selected menus. The driver was special enough to take us for a few minutes to Monteriggioni on the way back. The tour was worth every penny, as otherwise I would have missed all those special places.

Now, this Thursday April 2, I'm returning to Florence with my wife, and was planning going on a similar tour, though dropping Pisa (because I can go another day by train), and concentrating on San Gimignano, Monteriggioni, Siena, and Chianti, as some tours advertise.

However, as my arrival gets closer, I'm more eager to rent a car for a day and drive there myself, along my wife. I have measured distances in Google Maps, and it yields me about 4 hours driving time, by going through winding roads, rather than the autostrada (which I would like to avoid at least on the way out). If I'm keen on leaving Florence at 8am and returning at 10pm, that would leave me good 10 hours to explore, lunch, and enjoy.

Is that realistic, or am I dreaming too much?

If it is in fact possible, is there anything else you would add, or adjust on the itinerary?

Finally, at this time of the year (providing there is no forecasted rain), would you recommend a convertible car, or should I settle for a Fiat 500 / VW Golf?



The Tuscan Expert ;-)
Staff member
I think it is a doable - rent the car, leave early and spend the day out. Enjoy the drive as well, and don't be in too much of a hurry so that you enjoy it - the biggest difference will be that you will have to find parking, walk into town - on a tour, you are usually dropped off centrally and don't have to worry about parking at all, so that saves some time.

In any case, you can drive from Florence to San Gimignano, then on to Monteriggioni and on to Siena..... the drive back to Florence can be done through Chianti but depends on what time you're heading back. If after sunset, just take the fast road back (Florence-Siena) as you won't be seeing much of the vineyards at that point.

Otherwise, here is the tour that seems you did last time - it includes Pisa:
Monteriggioni Great Place to Eat

I am recommending a great place for you to eat, just off the Monteriggioni exit of the Raccordo SI-FI, the fast road from Florence to Siena.

It is called Bar dell'Orso and has fantastic food and a great atmosphere.

Here is their website:


You won't be disappointed!