Tuscany’s Prettiest Villages (some of them anyway)

Tuscany has a wealth of picturesque town’s and quaint villages beyond the main stops of Florence, Pisa, Siena, and San Gimignano. From the vineyards to the hilltops each place has its own special and unique atmosphere while promising classic postcard views of a renaissance landscape and warm streets with flower dotted houses. Here are a few worth checking out…

Montepulciano is a quintessential Tuscan hill town. From regal medieval stone gates to attractive steep streets it has a lot to tempt like wine shops offering tastings of Vino Nobile, quality artisan shops unique only to Montepulciano, and lovely cafes and restaurants with breathtaking views of the Val d’Orcia.

Majestic Montepulciano

Greve in Chianti is a sweet tiny town who’s main attraction is its irregular shaped piazza. And what a nice piazza it is. Vaulted walkways with some tempting food shops and local produce make it a center for village life. Not far from Florence, it makes an easy afternoon day trip.

Sidewalk cafe along Greve in Chianti’s piazza

Montefioralle is a bijoux small hamlet of calming atmosphere with mainly residential houses. Quiet, light stoned streets make it an oasis in the middle of the hills of vineyards.

Quiet streets of Montefioralle

Monteriggioni while very small is worth the visit for its unique walled medieval village. An attractive central piazza and fortress feel to it, it sits magnificently on a small hill often only passed by road, yet it makes for a quick but satisfying stop.

Montalcino is surprisingly low key and sleepy considering it is home to one of the best wines in the world. Needless to say this is a must go for any big wine fan. Obviously most things here are geared towards wine, the tasting, the selling, the bars which makes for a fun time. Start at the Castello for great views -and a bit of wine. A short drive outside of Montalcino is the famous Sant’Antimo abbey, one of the great highlights of the area.

Castellina in Chianti is a little gem of a town. Typically Tuscan, with scenic streets and houses, it also possesses a unique feature of a covered, vaulted tunnel street that even has a few shops and restaurants along it. Sunny and bright.

Street in Castellina di Chianti

Cortona is a popular town, bustling with activity with a lively central piazza. Honey coloured houses and sweeping views over the countryside make it both slightly grand yet typical of everyday Tuscan life. It is hard to not talk about Cortona without pointing out its link to ‘Under the Tuscan Sun’ so this welcoming town does not disappoint.

Arezzo is a classic medieval town though also a small city to those in the local area. Don’t let that deter you, like Florence, the closer you work yourself to the center the more you go back in time. Once you hit the historical center Arezzo is enchanting. Period buildings with ancient shields and heraldry decorate the exterior of the main piazza. For art historians, Arezzo is on the Piero della Francesca Trail and one of his most important works, The History of the True Cross can be seen at the Basillica de San Francesco. For antique hunters Arezzo has some quality shops and weekly fairs worth checking out.

Castiglion Fiorentino is a delightful village on the road between Arezzo and Cortona. This sleepy little town has some photo worthy aspects with arched streets and a splendid church tower, while the vaulted archways on the piazza show off stunning vistas of the countryside.

Monticchiello is one of the most charming villages in the Val d’Orcia. This delightful cluster of houses with a small cafe and very good restaurant is perfection of iconic Tuscan dreams. On the way from Montepulciano to Pienza it is surrounded by pleasant rolling hills and valleys and cypress trees lining the roads.

Charming Monticchiello

Pienza sits proudly on top its hill and was built with ‘ideal’ renaissance town planning and possesses much grandeur in its small space. Elegant streets, flowers in all the house windows, and the famous Via del Amore overlooking the stunning valley below. A must see.

Elegant Renaissance architecture in Pienza