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Chianti Region

Chianti Region

A few miles south of Florence lies what many consider to be the heart of Tuscany – the Chianti region. When most people picture Tuscany, they think of gently rolling hills covered in olive groves and vineyards. That is the perfect description of the Chianti region. Driving the area is exhilarating, with every turn revealing another tiny medieval hilltop town that calls out to be explored. Some of our favorites are described here.


Siena is a huge attraction in Tuscany, second only to Florence. With its rich history and terracotta colors, the reason is easy to see. The lively shell-shaped central piazza, Piazza del Campo, twice a year becomes the locale for the famous Siena Palio horse race. The rest of the time, it’s just a fun spot for dining, shopping, strolling and people watching. The main cathedral is a beautiful building constructed of black and white marble, with windows at the top that reflect the sky.

Siena. Tuscany, Italy

San Gimignano

San Gimignano is smaller than Siena but packs a great deal of charm within its walls. Climb the tallest tower for perhaps the most spectacular views of the Tuscan countryside. During the summer months, it can be a bit crowded with tourists but is worth the trip.

Medieval Hill Town, San Gimignano


Greve in Chianti is one of several small wine-focused towns in the heart of Chianti. It has a tiny central square that looks very simple and non-descript. Looks can be deceiving. The best Tuscan wines can be sampled and purchased here, as well as delicious food.

Greve in Chianti, Italy - April 21, 2018: The statue of a black rooster, the symbol of Chianti, Tuscany, Italy.

Greve in Chianti, Italy


Monteriggioni is a beautiful tiny town surrounded by a fortress wall, giving it the look and feel of a medieval castle. Once inside, a great afternoon can be spent strolling the cobblestone streets, shopping and dining at any restaurant- they are all great.

Monteriggioni, Tuscany


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