When in Tuscany it is easy to get blinded by the beauty of the main cities. After all, there are so many of them in a relatively small area and each one demands a good few hours on a visit. If you find yourself with a little more time, however, or indeed if you book onto a tour that takes you from Florence to Siena, you may have the opportunity to discover one or two of the smaller, yet equally beautiful, towns.

The drive from Florence to Siena (the Chiantigiana road) is a spectacular one and as the landscape rolls past, so do several stunning towns, all worthy of a visit.

San Casciano in Val di Pesa

A short 15km from Florence, this hilltop town is a pretty place that often goes unnoticed. Surrounded by charming churches and fortresses, it is a lovely spot for a morning coffee. If you have a spare hour you can check out the Pieve of San Pancrazio, the Pieve of Santo Stefano and the Pieve of Santa Cecilia. Famous castles close by include Bibbione, Gabbiano, Pergolato and Montefiridolfi. Also near San Casciano is the hamlet in which the Italian writer and politician Niccolò Machiavelli was exiled. It was during his exile that he wrote The Prince and The Mandrake.

Certaldo

A little further from the Tuscan capital is Certaldo, a place full of history. The hometown of Giovanni Boccaccio, writer of The Decameron, Certaldo’s most visited attraction is the author’s former house.

The highest building here is Palazzo Pretorio or Vicariale, which once belonged to the Florentine governing magistrates. Built originally in the twelfth century, it was rebuilt 300 years later.

If you find yourself here in summer you may catch the Mercantia festival; this is a true spectacle that includes music, magicians, theatre and dance.

San Gimignano

A more famous stop off, San Gimignano is a delightful hilltop town distinguished by its 14 stone medieval towers. Today its centre is a designated UNESCO World Heritage site that boasts a huge variety of Romanesque and Gothic architecture. It is also well known for its Vernaccia di San Gimignano wine and a visit to the Wine Experience museum is a highlight!

Colle Val d'Elsa

Known internationally for its production of crystal glassware, Colle Val d’Elsa has a long and interesting history. The oldest part of the town, known as ‘Colle Alta’ is home to the medieval Palazzo del Campana, the Castello, the Duomo and the Palazzo dei Priori. The streets are lined with artisan workshops and craft shops and if you want to buy some of the locally made crystal, the opportunities are endless.

Monteriggioni

A pretty walled town set high on a hill, Monteriggioni was a historically significant stop off along the Tuscan part of the Via Francigena. The walls are as imposing today as they have always been, but once inside this delightful place is as welcoming as any other in the region. The Monteriggioni Medieval Festival and the Slow Travel Fest are held here annually.

Hopefully when planning your trip from Florence to Siena, you will be tempted to make a stop or two. Most organised tours will certainly include the option to take in at least one of these towns. Remember that when you book an organised tour, it is best to go with a local and reputable operator.

Author Plate

Mauro Bramante is the Director of WalkAbout Florence, an independent business offering unforgettable tours and excursions around Italy including day trips fromFlorence to Siena. Whether you want to ride a Vintage Vespa, try the famous Chianti wine or get cooking with fresh local ingredients, Mauro's company promises excitement, adventure and above all, fun. If you're keen to experience the magic of Italy with the help of some passionate and knowledgeable tour guides, look no further than WalkAbout Florence for your next getaway.