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5 full days in Tuscany

I’ll be in Tuscany from Sept.9-15. I’m staying at Il Rosolaccio
Capezzano Basso, 53037 San Gimignano Italy. Do you have any suggestions for an itinerary to make the most of my 5 full days? I’m interested in a “ multi stop wine tour/tasting with lunch or dinner and a driver,” visiting various towns, wandering into the countryside to see the most beautiful views. I will have a car by the way. Any suggestions or recommendations very much appreciated.

Posted by
18091 posts

The closest pretty towns to your accommodations.
Within 10 to 30 min drive:
Certaldo
San Gimignano
Colle Val D’Elsa
Monteriggioni
Barberino Val D’Elsa

45 to 60 min:
Volterra
Siena
Chianti Hills (Castellina, Panzano, Greve)

Chianti Hills and its towns needs most of the day

Siena is a city with lots to visit, and also needs most of the day

Certaldo and San Gimignano can be done both on the same day, and they are the closest to your accommodations (like 10-15 min) albeit in opposite directions. You might be able to add Barberino to those, although it might be a bit too much in a day.

Monteriggioni and Colle can easily be done in the same trip, maybe even Volterra (however I don't like to pack too many towns in a day, and Volterra is a bit of a drive on curvy roads, so maybe it's best to be done separately).

If you are interested in seeing the famous Val d’Orcia (Montepulciano, Pienza, Monticchiello, maybe Montalcino), that area is at least 1h30min away, so doable but it's a whole day trip.

I presume Florence is not part of your intended itinerary. Florence is less than one hour away, but of course in one day you can only see few things as Florence has a lot. If you do, maybe it's best to park at the Villa Costanza parking, along the freeway and take the light rail trolley from there.

I don't have private tours to recommend, I like to use my own car and save. However if you do wine tasting and drive yourself, drink in moderation or you'll end up in a ditch. The Tuscan roads are full of curves.

Posted by
18091 posts

Generally at wine tastings in Italy they serve you 50 to 75ml of wine on average.
A typical glass of wine is 125 to 150 ml.
That means that a flight of 5 or 6 wine tastings is equivalent to at least 2 glasses of wine.
A person of average weight will need about 1 hour to clear one glass of wine, so you might need to wait some time before you can get back to the road and legally drive after a tasting.

Be aware that the DUI limit in Italy is lower than in most US States (0.05% in Italy, while 0.08% in California) and if caught above the limit, the police will seize your US license and your International Driving Permit and send it to the Prefect's office. The Prefect will not release your home license before the end of the suspension period (generally 3 months if BAC is between 0.05 and 0.08). The pecuniary sanctions are heavy and vary depending on the BAC (almost 600 euro at the minimum). It is a penal crime involving prison time if the limit is above 0.08%. So my suggestion is to find a drinking tour, or visit one winery only, then wait at least a couple of hours after the (only one) tasting is over, before getting on the road again.

Minimum drinking age is 18 y.o.