Tuscan Roadtrip: Montepulicano

A lively hilltop town, Montepulciano offers a mix of architecture, history, food, and wine with lots to do to keep little ones busy. 

After a lovely afternoon exploring San Gimignano, we set off a 2 hour drive to Terra Antica in Montepulciano. The plan was to use Montepulicano as a base for the next three nights with day trips to other towns. Exhausted from our long travel day, we had an early dinner at a local trattoria and went to bed early, dreaming about the food and wine of Val d’Orcia.

Rise and Shine at Terra Antica

Beautiful vineyard views at Terra Antica from the “Acquaviva” Suite, a spacious studio room directly overlooking the infinity pool. Blue skies and sun, albeit frosty, gleeful to be in beautiful Tuscany. 

Terra Antica is a gorgeous wine farm, perfect for large groups of friends and family in suites or villas. Whilst it is self-catering with complimentary use of laundry facilities, buffet breakfast is included. Terra Antica has a large infinity pool and hot tub as well as three sauna/steam rooms, all with amazing views to the countryside. It is truly a relaxing place only a short drive from the main hill top town of Montepulciano. Each day, we took a half-day excursion to explore the nearby towns of Montalcino and Pienza. Then it was some down time chilling out at Terra Antica for quality family time.

Things to Do in Montepulciano

Like all the hilltop towns in Tuscany, Montepulicano is charming but slightly bigger. It is an ideal base if you have children in tow. It is pedestrianised and there are several playgrounds at the opposite ends, plus the beautiful fort. We had a leisurely itinerary and sort of went with the flow. From late afternoon onwards, we drove to Montepulicano parking at P1, entering the hilltop town from Porta al Prato. 

Stroll the Streets & Historic Churches

One of the best things to do in Montepulicano is strolling around the narrow and picturesque streets. My favourite view point is Vicolo dell Mura with a view of Bivio di San Biago just below town. Bustling Il Corso takes you to Piazza Grande, a beautiful grand square flanked with the Cathedral of Montepulciano (Santa Maria Assunta). Soak up the lively atmosphere, marvel at the wonderful architecture, go souvenir shopping, taste some fine Tuscan wines, and enjoy Tuscan delicacies.

Tuscan Food & Wine

We had a lovely meal at La Vineria di Montepulicano, a cute little wine bar. We ordered all the Tuscan dishes – slow-cooked wild boar, pici pasta, and Italian roast veggies. Around the corner from Piazza Grande, there is a tiny pizzeria called Re Al Quadrato Montepulicano, a great spot with kids in tow. Famous for the Vino Nobile di Montepulicano, there are plenty of wine shops all around town. Cantina Ercolani is a great wine shop with a secret underground cellar to explore. 

Natale a Montepulciano

If you are lucky to visit Montepulciano in the winter then do not miss the Christmas market which is open until Epiphany. Piazza Grande and the surrounding area turns into a magical Christmas market with over 70 wooden stalls selling ornaments, chocolates, gifts and food. Further up to Fortezza is home to Castello di Babbo Natale aka Santa’s Grotto, a multi-story interactive experience taking you through to various rooms of Santa’s castle. There is a wonderful playground at the fort too. We had a lovely time, enjoying an extra bit of Christmas. 

Next up: Pienza and Montalcino!