San Gimignano - 6 nights itinerary of Tuscany
Ciao Colleen and welcome to our Forum!
Tuscany is a beautiful place, and you’ll be impressed by its beauty, especially as you are visiting it for the 1st time

Renting a car is actually the best way to tour Tuscany, especially if you wish to visit medieval hill top towns like San Gimignano, that cannot be reached by train.
Driving along the winding and scenic roads of Tuscany can be a very pleasing experience, that will give you the opportunity to appreciate the region’s beauty and its wonderful countryside, including its lesser known corners
On this article you can find very useful information on moving around Tuscany by car, and
here all you need to know about
renting a car in Tuscany, that you can comfortably reserve online before departing.
San Gimignano is really amazing, probably one the most famous medieval villages of all Italy.
It is an incredibly and perfectly preserved medieval town, with its unique skyline of towers pointing to the sky.
Walking through its narrow streets and alleys you’ll get the impression to have come back right to the Middle Ages!
Truly an experience
San Gimignano is a perfect base to tour around the area, but it’s a tiny village and can be visited rather quickly. Since Tuscany is large and really has so many things to visit, I suggest you split your holiday and stay at least in another place.
So, I suggest you start basing yourself in San Gimignano for about 3-4 nights. While here you could start a number of day trips, first of all to
visit Florence (at about 1 hour’s drive) and the
Chianti region south of Florence.
The beautiful Chianti villages, like Greve in Chianti, Castellina in Chianti and Radda in Chianti, are all easily reachable in less than 1 hour’ s driving.
Chianti is famous all over the world for its superb wine production, so you may also enjoy taking some
wine tours.
As you prefer staying in country areas, far from the hustle and bustle of city centers, I recommend staying at
Casolare di Libbiano or at
Borgo della Meliana, both very good properties with fantastic surroundings in the countryside near San Gimignano.
Another good option might be the typical Tuscan
farmhouse Il Cellese, east of San Gimignano, in the lovely village of
Castellina in Chianti.
I also suggest a visit to the mighty
Volterra, lesser known than San Gimignano but equally beautiful; famous for its
alabaster manifacturing. High on a rocky promontory, the city is typically medieval and has many lovely and charming shops, selling a wide range of local products.
For the rest of your holiday, I suggest you move to the south of Siena, in the wonderful
Val d’Orcia region. While here you should absolutely
visit Siena, Monteriggioni and all the lovely villages of the Orcia valley, such as Montalcino, famous for its Brunello wine, the ideal city of
Pienza, famous for it tasty pecorino cheese, and the beautiful
Montepulciano, with its elegant Renaissance palaces and the outstanding Piazza Grande.
In the area, I highly recommend staying at
Podere Cunina or at
San Giovanni in Poggio, both beautiful Tuscan farmhouses with splendid and scenic countryside surroundings; perfect for a relaxing and unforgettable vacation!
Finally, some useful tips and suggestions for
a 7 day itinerary to Tuscany, with a list of all the places you absolutely must visit.
In case you need further suggestions, feel free to post again at anytime
Enjoy planning your trip to Tuscany!
Ciao from Florence.