Villa Rentals near Montepulciano

What to See & Do in Montepulciano

Many visitors enter Montepulciano through the Porta al Prato and stroll uphill along the length of the town’s Corso (main street). You pass several Renaissance palaces en route, including Vignola’s Palazzo Avignonesi in High Renaissance symmetry. Right opposite is a column topped with the Marzocco, symbol of Florence. Andrea Pozzo and Michelozzo also built along Montepulciano’s main drag. It is a treat for architecture fans.

At Montepulciano’s highest point is Piazza Grande, another harmonious ensemble of buildings. On its west side, the Palazzo Comunale was built in the late 1300s then revamped in 1424 by one of the Medici’s favourite architects, Michelozzo, in homage to Florence’s Palazzo Vecchio. (This square actually stands in for Piazza della Signoria in Netflix’s Medici: Masters of Florence.)

The Palazzo Comunale roof terrace is usually open to visitors, the best perch for seeing the lie of the land around Montepulciano. Directly opposite, the Palazzo Contucci is still occupied by one of Tuscany’s best-known wine-making families.

On the south side is the never-finished façade of the Cattedrale di Santa Maria Assunta, Montepulciano’s 16th-century cathedral. The dark is illuminated by a golden “Assumption of the Virgin” in classic Sienese style.

Just outside the town gates is one of the most photographed churches in Tuscany. Fronted entirely in travertine, San Biagio was designed by Antonio da Sangallo the Elder on a perfect Greek cross pattern. The Florentine architect settled here for the last 15 years of his life, designing several buildings and palaces before his death in 1534. If you approach Montepulciano from Pienza, there’s a memorable view of the church as you round the final bend before town.

When you stay in one of our villas near Montepulciano, another of Italy’s great drives is right on the doorstep. With rolling hills punctuated by stone farmhouses, crumbling castles, and cypress-studded ridges, the Val d’Orcia is one of Tuscany’s most scenic landscapes, shaped by centuries of interaction between farmers and the fertile terrain. (For this unique cultural history, the valley is protected by UNESCO.) Looming over it all is Monte Amiata, a 1,738m/5,702-ft. mountain formed from a long-extinct lava dome.

The Val d’Orcia is a photographer’s dream, in almost any season, with vast emerald-green expanses in spring cooked to straw by the summer sun; chestnut groves and trellised vines wearing their autumnal colours; lonely chapels framed by cypress stands dusted in snow during a winter cold snap.

For more on what to see and do in Montepulciano, you can read our Montepulciano travel guide.

Why Stay near Montepulciano

Southern Tuscany is much quieter — you could even say more relaxed — than the equally sublime hills around Florence and the Chianti. Skies are bigger, spaces are emptier and most of the southern Tuscan hill-towns are free from tourism most days of the year.

Of course, if you turn up in time for Montepulciano’s Bravio delle Botti, or a wine festival in Montalcino, you will experience these towns in full party mode.

If you can drag fellow travellers away from your private swimming pool, you will never run out of day-trips from our Montepulciano villas. Just 9 miles to the west — the journey is a stunner — lies the tiny town of Pienza. It is such a perfect miniature of Renaissance architecture that the entire pedestrian centre is recognized by UNESCO, for the “new vision of urban space” it represented in the mid-1400s.

Pope Pius II’s madcap (and unfinished) plan to build a Città Ideale (“Ideal City”) here put Pienza on the tourist trail. It’s a favourite with photographers, and stands in for Florence in several scenes from Netflix’s Medici series — appropriately, because the Palazzo Piccolomini is the masterpiece of a renowned Florentine architect, Bernardo Rossellino.

Chianciano Terme, south of Montepulciano, is known for its thermal waters, said to be beneficial for the liver. (“Spas” in Chianciano are medicinal, rather than for pampering.) The town is also linked with Nobel Laureate Luigi Pirandello, who set two novellas here.

The sights of Siena are around 50 minutes away by car, including the Campo, Palazzo Pubblico and Duomo. Siena is a Gothic-period town almost unchanged in appearance since medieval times. Dante could still find his way around without Google Maps.

For travellers interested in archaeology, especially the Etruscans, you have a unique opportunity to explore one of the most important painted tombs in Etruria. It lies just outside Sarteano, 13 miles from Montepulciano. Only discovered in 2003, the Tomba della Quadriga Infernale is 19m/62 ft. long and has walls still covered in paintings from the 4th century BC. The preservation of its vivid “Demon Charioteer” image is extraordinary.

Detailed guides to the best daytrips from our Montepulciano villas include:

• Montalcino travel guide
• Pienza travel guide
• Sarteano and Chiusi travel guide
• Bagno Vignoni and San Quirico d’Orcia travel guide
• Cortona travel guide

When to Visit Montepulciano

Spring temperatures are pleasant over much of Tuscany, including the countryside around our Montepulciano villas. Pack for an average daytime high of 23℃ (73℉) and lows of 11℃ (51℉) overnight (by late Spring).

In May, Italy’s country-wide Cantine Aperte (Open Cellars) wine event is a big deal around wine towns like Montepulciano. For oenophiles, May is the perfect time to stay.

Summer in Montepulciano is almost always warm and sunny. The daytime temperature often rises beyond 30℃ (86℉), with 17℃ (62℉) overnight typical. This is the season for relaxing by your private pool, especially in the heat of the early afternoon. Stroll through the town in the morning or late afternoon — it’s deserted in the heat of the day.

Montepulciano’s big annual festival happens in August, on the last Sunday of the month. Montepulciano’s eight contrade (neighbourhoods) face off in the Bravio delle Botti. Rival contestants push heavy botti (wine barrels) up the centre’s historic Corso (Main St.) to win the Bravio — a cloth depicting Montepulciano’s patron saint.

Despite cooler temperatures, autumn and winter are still lots of fun around Montepulciano. The sun shines most days, with an average daytime high of 13℃ (55℉) and overnight lows of 4℃ (39℉). But watch the forecasts: it’s not unknown for the entire Val d’Orcia to wake up to a covering of midwinter snow.

For a month-by-month guide to travelling in Tuscany, see: When is the Best Time to Visit Tuscany.

About Our Handpicked Villas near Montepulciano

If you are interested in learning more about what makes us different, you can read the Tuscany Now & More story.

Concierge service
Everyone renting a villa near Montepulciano with Tuscany Now & More gets free use of our award-winning concierge service. To order shopping stocked in your fridge on arrival, or book a private chef to cook for a special occasion, you should contact our concierges directly. They can help. Making your holiday lettings extra-special is all part of our service.

While you are in Italy, our dedicated, experienced ground staff are available by phone or WhatsApp.

Checking in & out
You should check in at your Montepulciano holiday rental between 4pm and 7pm. We can accommodate different arrival times, if you communicate this in advance to our office staff.

Montepulciano is approximately equidistant from the two major airports serving central Italy. Allow just over 2 hours to drive from Pisa Airport to Montepulciano. Rome’s main international airport is approximately 2 hours, 20 minutes away by car.

If you are not in a hurry, the town is best approached via the SS2, exiting this road at San Quirico d’Orcia to join the eastbound SS146 via Pienza. Views from this road, south over the expanse of the Val d’Orcia, are unforgettable. You’ll find yourself pausing for a photo every mile or so.

Upon arrival, you will inspect the property alongside our villa owner or caretaker. They can also demonstrate appliances, equipment and utilities.

Check-out is 10am on the final day of your holiday rental. The villa owner or caretaker will arrive at 9am to settle outstanding payments, if you have any. If you wish to depart earlier, you can let us know in advance.

Cleaning
Both the luxury villa and your private swimming pool are cleaned prior to arrival. Some of our holiday villas around Montepulciano have additional cleaning or pool/garden maintenance scheduled during the week. Maid service included with Tuscany Now & More vacation rentals involves cleaning and tidying, but not making beds, kitchen cleaning, laundry or ironing. Extra services can be organised via our travel concierge team.

Bed linen & towels
Our Montepulciano holiday rentals include bed linens, bathroom and swimming pool towels for all guests. These are provided weekly. Extra services and/or changes can be organised through our concierges.