Hill Towns of Tuscany

Although Florence is one of my favorite cities, and I love spending time there, I was excited to leave the city behind and finally get out into the Tuscan countryside. Today, we traveled to Siena and San Gimignano, two of the most charming towns in Tuscany, both of which had captured my heart many years ago. The weather could not have been better.

Siena is one of the best-preserved medieval towns in Italy and is renowned for its stunning architecture and historic center. Our walking tour took us past all the important attractions in town. We strolled from the Palazzo Pubblico, the political and cultural center of Siena, which sits in the impressive Piazza del Campo, one of the most beautiful medieval squares in Europe, to the stunning gothic Duomo and the city’s other churches.

Piazza del Campo and Palazzo Pubblico

The Churches of Siena

In addition to its architecture, Piazza del Campo is known for hosting the Palio di Siena, a thrilling horse race held twice a year. Throughout the city, we saw colorful flags representing the 17 rival contrade, or neighborhoods, of Siena. These are reminders of a distant past that is brought to life during the Palio.

The main sights of Siena are located within a maze of narrow streets and steep alleyways, and it was nice to simply wander from one to the other, gazing at the distinctive buildings and rich architectural details.

Sights in Siena

It was soon time to leave Siena and drive through the lovely Tuscan countryside.

Beautiful Tuscany

We stopped for lunch at Fattoria San Donato, a small medieval village surrounded by the green hills of San Gimignano. The property is now an agriturismo, a type of accommodation in Italy where guests can stay in a rural property and experience the way of life of the Italian countryside.

The property and its setting were gorgeous with incredible views, and our meal was delicious with all locally grown ingredients. I was ready to check in for a long stay.

Lunch at Fattoria San Donato

Fattoria San Donato Has an Amazing Setting

We than drove to San Gimignano, another stunning, medieval hill town in the heart of Tuscany. San Gimignano is known for its skyline of towers and is often called the “Town of Fine Towers” or the “Manhattan of the Middle Ages.” Our walking tour guide pointed out many of these tower houses, and I admired the preservation of the town’s rich architectural heritage.

Some of the Towers of San Gimignano 

Medieval Architecture in San Gimignano 

After walking through the narrow streets and craning our necks upwards, we stopped at Piazza della Cisterna, a square that is enclosed by beautiful brick houses and more towers. This former marketplace features a unique triangular shape, a patterned brick pavement, and an octagonal well at its center from which the piazza gets its name. 

Piazza della Cisterna

Tim and I, as well as most of our group, finished a long day of sightseeing with a special treat – the world’s best gelato! Gelateria Dondoli is tucked away in this charming town and boasts an amazing collection of awards, due in part to the many experimental flavors that the owner has created. I stuck with a classic chocolate, and it was delicious.

The Best Gelato

We returned to Villa Olmi for our final dinner and prepared to leave in the morning to embark on our cruise.

We Had a Great Group!