Tuscany can include cities from Florence to Pisa, but we prefer the charm of its small towns. A daily road trip from Montepulciano as your base to nearby villages will deliver an unmatched, laid-back Italian experience. Hilltop medieval villages, stone walls and streets, cypress-dotted landscapes, and red wine – what more could you ask?

Montepulciano as your base

Experiencing the Tuscan countryside requires a plan. You have come to the right place.

We city-hop in Italy via train. Milan to Venice. Venice to Florence. Florence to Rome. The high-speed rail is a safe, convenient way to crisscross the country. Tuscany begs for you to slow down and enjoy the views. The roads are good. The signage is manageable. Even your fellow drivers aren’t as crazy as Rome.

We rent a Mercedes-Benz in Florence, and cruise southeast down to Montepulciano in less than 2 hours. For the next 4 days we travel the uncrowded back roads from village to village before returning to our base each evening.

Montepulciano accommodations

Your choice of lodging is unique. Tuscany has farmhouses called agriturismo, presenting an authentic B&B experience. We visit several, and can highly recommend this approach. Of course, there are also numerous country inns. No chain hotels in this region.

We choose what with think is the best of both worlds. On the reliable booking.com we find Alberto Charming Home, rated an exceptional 9.9. It is a 2-bedroom home, literally across the street from the Basilica of San Biagio, and a walk down the hill from the center of Montepulciano. Clean, spacious, ample parking, and great location for an attractive price – truly fits with Stephen’s “upscale on a budget” philosophy! Charlotte is pictured here outside the front door.

Alberto greets us and answers our questions about places to go in the days ahead. He leaves us with a bottle of Vino Nobile di Montepulciano, the excellent red wine the region is famous for. Let the libations begin.

Montepulciano exploration

The town, built mostly in the 16th century, is one of the larger we will visit. It has a population of about 14,000. That provides us with services such as a fine grocery store that serves up fresh pasta meals, salads, and home-baked breads that make it convenient to prepare dinner in our home instead of a nightly restaurant trip.

That’s not to say that we never eat out. Just footsteps away from our home is one of the town’s finest establishments, La Grotta Ristorante. We enjoy a sumptuous meal there. Once again, sometimes upscale, sometimes budget.

The walled town features a sizeable square (Piazza Grande), ringed with important buildings, such as a town hall and bell tower. The whole town feels like an open-air museum. 

There are numerous stone-covered streets to wander filled with quaint boutiques and places to eat and drink. It should be worth noting that every one of those streets takes you seriously up or downhill. Montepulciano may be the hilliest town we have ever visited. At least it is pedestrian-friendly, with only residents allowed to drive inside the walls.

We turn down one very long street (Via di Gracciano nel Corso) and encounter Torre di Pulcinella. It is a clocktower whose masked puppet figure (Punch, of Punch & Judy fame) strikes his bell upon our noon arrival. Presumably, for several hundred years the clock needed to be wound each evening. Now it is electric (but 4 minutes fast according to my phone).

There are churches to explore and a convent next to a spectacular valley view. As the mood-setting ground fog clears, we can gaze down on the Basilica that is next to our home. At least the walk from here is all downhill!

Montepulciano to Bagno Vignoni and Montalcino

There are numerous roads that radiate from Montepulciano. We explore a different direction every day. Keep in mind that any one of the villages we mention here is close enough to be explored in any order or simply by itself. This is merely the path that we wander. Follow us or choose your own. That is the charm of Tuscany.

We take the highway southwest toward Monticchiello, which becomes SP88, finally turning on SP53. Google Maps doesn’t let us down.

Our destination would only be 30 minutes away, but we are in no hurry. The countryside here features the occasional villa and agriturismo, which means plenty of winding roads marked by cypress trees that are so characteristic of this region.

The enchanting village of Bagno Vignoni has a unique setting. The Renaissance-era buildings of tiny town surround a natural hot springs pool, whose waters flow down to the valley below.

This is the perfect place to relax and enjoy a simple lunch. Later, we stroll around the handful of interesting shops that line the pool. The shopkeepers are friendly, counting themselves among the 30 residents of the community.

It is only mid-afternoon, so we keep traveling. The town of Montalcino is only a 20-minute drive west, taking SR2 to SR14. Montalcino is another towering village dominated by the fortress, built in 1361. It has all the medieval trappings and a population of just 5,000. We think the best photos are from the surrounding hillsides, gazing across at the walled town.

The return trip, on SP146 past Pienza, takes a mere 40 minutes. We are in Montepulciano in time to rest and eat dinner. Who wants pasta and red wine?

Montepulciano to Monticchiello and Pienza

Our wanderings next take us west just 8 km to the ancient hamlet of Monticchiello. We walk in as tourists to a village of fewer than 200 people. We stand out here, which is fine, because we are guided by a local into a gallery that includes scenes and props from their most famous event. Each summer, residents perform a nightly play (Teatro Provero) highlighting their life and heritage. This was even transformed into the 2017 movie Spettacolo.

Everyone speaks to us in Italian and we reply in English. Though little is directly understood, we each get the general idea. It is somehow comforting here.

It can be challenging to write about places like Monticchiello without resorting to cliches like “authentic” and “old world” and “forgotten by time.” Still, as we watch a man roasting chestnuts in a pan as large as himself, we have to wonder how old that tradition might be. How ancient are those stone walls with determined plants pushing their way out of the crevices?

Come for the town, stay for the visuals. There is a peacefulness to the deserted streets and the endless views of the valleys below.

But we want to press on, and the town of Pienza is just another 8 km to the west. Climbing yet another hilltop, we park at the edge of town in almost a suburban setting. Pienza is, by comparison, bustling. A town of 2,000 people, it feels livelier.

If Montepulciano is known for its red wine, Pienza is famous for its pecorino cheese, made with sheep’s milk from local pastures. Multiple stores sell it, others present the perfect charcuterie board.

Pienza turns a perfect gold in the late afternoon sun. We are elated to visit this beautiful town. The 14 km back to Montepulciano on SR 146 also delivers exceptional views. Back home we are hungry, having skipped lunch. Time for pasta, topped with percorino cheese. And of course, red wine.

Montepulciano to Montefollonico to Torrita di Siena

On today’s road trip we venture north for the first time. Just 9 km away, Montefollonico vies for most picturesque. Fewer than 500 people make this 13th century gem their home. We have most streets to ourselves. There is peace and quiet that is almost a little eerie.

Like many other Tuscan villages, Montefollonico sits on a hilltop. We wander to the edge of town, past yet another old church for dramatic views of the valleys below.

Our last leg is a quick 10 km north on SR 15 to Torrita di Siena. We pass through one of the four gateways in the 13th century walls. All roads lead to Piazza Matteotti. It is a classic town square, with a clocktower and buildings repurposed for today.

We are invited to attend an art gallery show with the local artist. It makes for a memorable end to another perfect Tuscan day. The 10 km trip back on SP 135 is not as pretty, but we are home in less than 15 minutes. The cake at the gallery is nice too, but dinner beckons. Who is in the mood for pasta and red wine?

We hope we have shown that you don’t have to venture more than 35 km to discover the quintessential Tuscany experience. Idyllic scenery at every turn of the road. Easy access to quiet hamlets steeped in history. Interesting people going about their lives, such as our video here of father and son harvesting olives. This is a road trip from Montepulciano!

Do you have any questions or suggestions to help others? Feel free to comment at the bottom of this post.