Small group holidays that take in the iconic Tuscan hill towns provide an insight into the history, architecture, cuisine and wine of the Italian region.
Tuscany stirs the heart and mind like nowhere else. It's a feeling that can really only be satisfied by experiencing the history, art, culture and cuisine for yourself – and, if you do, it's guaranteed to be the beginning of a lasting love affair.
The sunburnt patchwork of Tuscany's landscape is defined by its scattering of fortified hill towns; the following five are often on the itinerary of the best small group holidays to the region. Each has a unique personality, but all are characterised by the beautifully preserved medieval architecture, warm-hearted locals and, of course, the unparalleled food and wine culture for which this region of Italy is so renowned.
Montalcino
Situated in the central province of Siena, Montalcino's reputation for producing exceptional wines – including the world-acclaimed Italian red, Brunello – makes it a valuable addition to the itinerary of small group holidays with a focus on food and wine. It's the perfect place to reacquaint or enjoy a first encounter with this superb wine at its source.
With far-reaching panoramic views over the countryside, the ancient streets and charming architecture of Montalcino reveal its history and culture in a very tangible way. For lovers of jazz, the annual Jazz & Wine Festival held in the town every July is another compelling reason to visit.
Cortona
Set in the stunning Chiana Valley in the province of Arezzo, Cortona evokes the storied ambience of medieval times. Steep, narrow stone streets sketch their way through the town, past architectural highlights such as the eleventh-century neo-Gothic Basilica di Santa Margherita. Just beyond the city walls (which date back to Roman and Etruscan times) is Le Celle, a monastery constructed by Saint Francis of Assisi in 1211.
Cortona may be small, but its size is no representation of its importance in history. The best way to take it in is to settle in at a café in Piazza della Republica, order a coffee or gelato and watch the world go by.
San Gimignano
The striking skyline of UNESCO-listed San Gimignano, in the province of Siena, is punctuated by the 13 historic towers (from an original 72) that earned it the nickname "the Manhattan of the Middle Ages". Alongside the well-preserved Gothic and Romanesque architecture, these ancient torre afford the town a unique and very special appeal.
You can take in magnificent views from Torre Grossa, in Podesta’s Palace and, for art lovers, the Collegiate Church of Santa Maria Assunta contains frescos dating back to the fourteenth century. San Gimignano is also famous for its wine, saffron and olive oils – all of which you'll have ample opportunity to try for yourself.
Volterra
Volterra, in the province of Pisa, is a fascinating historical site. Aside from its impressive medieval ramparts and jaw-dropping views, the town's Etruscan Museum is one of the most important in Italy, with artifacts dating back to ancient times. Another building of great significance, the city hall, is reputedly the oldest in Tuscany, with origins from thirteenth century.
The town is also famous for its alabaster, which has been mined in the surrounding areas since Etruscan times. Today you can visit artisan workshops tucked away into the backstreets to watch alabaster objects being created in a centuries-old tradition.
Montepulciano
Montepulciano, also in the province of Siena, is always a highlight on small group holidays for food and wine connoisseurs. The town is home to the famous Vino Nobile di Montepulciano, widely acclaimed as one of Italy's finest red wines.
The main street, il Corso, winds its way from the walls up to the town centre, which features an enchanting blend of Renaissance and medieval features. One of the highlights is Contucci Cantine, the old town jail that's been converted into a vast wine cellar. Stretching the length and breadth beneath the town's main square, Piazza Grande, you can enjoy walking tours around the cellars and, naturally, plenty of wine tastings.
See Tuscany on Small Group Holidays
For those with a desire not just to pay a visit but to gain an authentic understanding of this land, its history and its people, professional small group holidays that comprise an itinerary of Tuscany's iconic hill towns is the perfect way to do it.
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