Siena and San Gimignano: A Road Trip in Tuscany

We had a free day in Florence and decided to go on a road trip to Tuscany.  We rented a car for the day and drove through vine-clad hills of Tuscany through the beautiful wine country to Siena and San Gimignano without actually making it into any wineries. The tall cypress trees, windy roads and postcard-worthy landscape of Tuscany kept us busy with our eyes glued to the window that we didn’t miss the wine.   We did stop at a couple of vineyards on the way – just for a couple of pictures and for the kids to see the grapes up close. Although we did make a note of the name of the wineries we passed by, to try the wines later. It was a fun road trip through the Tuscan Hills.

San Gimignano
Just before entering San Gimignano

San Gimignano

San Gimignano is a small walled medieval hill town in the province of Siena, Tuscany, north-central Italy. Known as the Town of Fine Towers, San Gimignano is famous for its medieval architecture, unique in the preservation of about a dozen of its tower houses, which, with its hilltop setting and encircling walls.  The Historic Centre of San Gimignano is a UNESCO World Heritage Site. It was our first stop. The town also is known for the white wine, Vernaccia di San Gimignano, produced from the ancient variety of Vernaccia grape which is grown on the sandstone hillsides of the area. House wines anywhere in Italy, served out of the colorful ceramic little wine pitchers was so good too.  It took us about an hour from Florence to San Gimignano.


Kids enjoyed San Gimignano and the colorful flags.  We had a nice lunch at the city center with Vernaccia Di San Gimignano and enjoyed some gelato later.  I checked out their ceramic store and brought home a wine jug.


We drove then drove to Siena. We sat in this Piazza del Campo which is regarded as one of Europes greatest medieval square marveling and taking in the beauty and architecture. The Palio di Siena (known locally simply as Il Palio) is a horse race that is held twice each year, on July 2 and August 16, in Siena. Ten horses and riders, bareback and dressed in the appropriate colors, represent ten of the seventeen contrade, or city wards. The race itself, in which the jockeys ride bareback, circles the Piazza del Campo, on which a thick layer of dirt has been laid, three times and usually lasts no more than 90 seconds. It is common for a few of the jockeys to be thrown off their horses while making the treacherous turns in the piazza, and it is usual to see unmounted horses finishing the race without their jockeys. We visited the Duomo, marveled at the rich interiors and then sat in medieval square watching D pretend to ride his little Ferrari car we got at the Ferrari store in Rome, around the square.

Siena and San Gimignano

We then headed back to Florence enjoying the panoramic countryside as the sun started to dip on what was a gorgeous day in Tuscany.

We hope to g back to Tuscany for a longer vacation someday to stay in a Tuscan villa and explore Umbria at a much slower pace.  I would love to go when the sunflowers are in bloom.  If you have seen my profile picture you know how crazy I am about sunflowers.  Driving through the Tuscan countryside and visiting Montepulciano and Pienza is definitely on my bucket list!

Popular Tours to Siena & San Gimignano

Have you been to Tuscany, Tell us your experience of this beautiful region of Italy! We would love to go back and spend more time.

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12 thoughts on “Siena and San Gimignano: A Road Trip in Tuscany”

  1. I have been to SG this year and I totally fell in love with this place! Tuscany is a place I would actually would consider living. Great photos 😀

    Thank you for joining #MondayEscapes

  2. I’ve been to Siena, Pisa and Florence as part of a tour, but I’d like to do a proper road trip as I’ve seen so many beautiful photos of Tuscany!!

    1. There is so much to do in the area, we would love to go back and live there for a couple of months! Florence and Tuscany is probably my most favorite place.

  3. Such a lovely area of Italy, I was in San Gimignano many years ago. The horse race in Siena sounds interesting, would be strange to see a horse arriving at the finish line without its jockey! #mondayescapes

  4. This brings back happy memories of a two week holiday we had in Tuscany and Umbria about 20 years ago. I still remember how beautiful San Gimignano was. The skies were just as blue. Must return one day.

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