Top Ten Things to Do

This painterly hilltop town deserves leisurely exploration, with stops to take in the medieval and Renaissance architecture and to sample the famous Vino Nobile di Montepulciano wines.

The Piazza Grande is Montepulciano’s showy stage set, in all its historical splendour. This is the chief setting for summer festivals, open-air concerts under the stars and even the occasional film set. The main square sits at the town’s highest point, both culturally and geographically. On one side is the 15th-century Palazzo Comunale (Town Hall), a miniature version of the Palazzo Vecchio in Florence. On the other side stands Sangallo’s impressive mansion, the 16th-century Palazzo Contucci. Florentine design has shaped the grand façades on Piazza Grande, but earlier Sienese Gothic touches are present in the interiors, double arches and door¬ways. Both styles reflect Montepulciano’s buf¬fet¬ing between the two city-states and the eventual supremacy of Florence. Between the two palaces stands the Duomo, which contains a sombre, barn-like nave redeemed by an altarpiece from the Siena School, the huge Assumption triptych (1401) by Taddeo di Bartolo.

Montepulciano’s main street changes its name but not its character on its climb up the eastern ridge of town. Lined by lofty, green-shuttered mansions, Il Corso is dignified and reserved, much like Montepulciano itself.  En route are snapshots of history, from solemn Renaissance mansions at the lower end to recycled Etruscan artefacts. The Renaissance Palazzo Bucelli, at no. 73, is decorated with a mosaic of Etruscan urns and pots, a reminder of the city’s ancient origins. The Corso starts at Piazza Savonarola, which is guarded by a statue of the Marzocco lion, the symbol of Florentine supremacy. The name-changing Corso then becomes Via di Gracciano, Via di Voltaia, Via dell'Opio and Via di Poliziano, before climaxing in Piazza Grande, the town’s summit and centre.

Dominating the Piazza Grande, the 15th-¬century Palazzo Comunale (Town Hall) has a Florentine Michelozzo façade adorning Sienese crenellations. After admiring the severe travertine façade, take the lift and twisting stairs to the top. The tower, modelled on that of Florence’s Palazzo Vecchio, sur¬veys the whole province, embracing Val d’Orcia, Monte Amiata and Siena, with further vistas across to Lake Trasimeno in Umbria. The view also takes in Piazza Grande, where they filmed part of the Twilight vampire series – Montepulciano stood in for Volterra.
Address: Comune di Montepulciano, Piazza Grande, 53045 Montepulciano
Tel: +39 0578 7121
Web: www.montepulciano.org/palazzo_comunale_it.html

Montepulciano is about both wine and heritage but this wine dynasty combines both, from its ancestral stronghold on the main square. Visit this historic palace for a wine-tasting and cellar tour with a local aristocratic family. The Contucci family has lived in Montepulciano since the 11th century and has been making wine here since the Renaissance. If you’re lucky, a family member will be leading the tour through the mysterious maze of tunnels under the palazzo. Apart providing from a guided wine-tasting of Vino Nobile di Montepulciano, this is a taste of noble life in Tuscany. If you are a fan of any of the wines, then take advantage of the estate’s efficient shipping service.
Address: Palazzo Contucci, Piazza Grande 13, 53045 Montepulciano
Tel: +39 0578 757006
Web: www.residenzecontucci.it/palazzo-contucci

Just below Montepulciano’s city walls, at the end of a long line of cypresses, lies San Biagio, the Renaissance church most at ease with its setting. Designed by Antonio Sangallo, this domed masterpiece was begun in 1518. It’s an eye-catching sight, the honey-coloured travertine, matched by a perfect dome and great purity of line. The airy in¬te¬ri¬or feels deeply clas¬si¬cal, closer in spirit to the Pan¬the¬on in Rome than to a small Tuscan church. Sangallo’s bold design skills rival Bra¬mante’s, not just in the church but elsewhere in the city, from elegant stone wells to porticoes.
Address: Via di San Biagio, 53045 Montepulciano
Tel: +39 0578 757 7761

The wine route is worth exploring on a locally-booked tour, not just because it lets you appreciate the various wine estates without worrying about driving. Vino Nobile di Montepulciano, a smooth red wine with a hint of violets, was “ennobled” in 1549 when Pope Paul III’s sommelier proclaimed it “a most perfect wine, a wine for lords.”  If drunk too young, Vino Nobile can be disappointing so trust your palate and ponder going for a pricier vintage. For everyday drinking, consider settling for Rosso di Montepulciano, the town’s gutsy but affordable red, which goes so well with rustic Tuscan cooking. To see what appeals and to gain an insight into local culture, call into the Strada del Vino Nobile di Montepulciano on the main square to check their tours. This reliable wine association runs half-day trips to the best wine estates, as well as city tours, visits to historic gardens and thermal spas.
Address: Strada del Vino Nobile di Montepulciano, Piazza Grande 7, 53045 Montepulciano
Tel: +39 0578 717484
Web: www.stradavinonobile.it

A leisurely hike is a way of getting under the skin of this lovely area and is ideally done with an affordable local guide from Montepulciano. Guides do it the soft way, bringing you back to base by minibus. One of the most accessible walks is an 8km gentle, half-day ramble from Montepulciano to the walled hamlet of Montichiello. Naturally, it involves a winery stop for a tasting of Rosso di Montepulciano DOC and Vino Nobile di Montepulciano DOCG - hence the handy minibus back.
With a good hiking map, plenty of water and a picnic lunch, the more intrepid could consider going it alone, walking along the cypress-lined avenue and country lanes to Montichiello for a picnic lunch, and from there onto the Val d’Orcia and Pienza. This 13km hike (8.5 miles) should take around four hours to Pienza. That said, local knowledge means that a guided walk is likely to be more memorable.
Address: Strada del Vino Nobile di Montepulciano, Piazza Grande 7, 53045 Montepulciano
Tel: +39 0578 717484
Web: www.stradavinonobile.it

Stirring views of Tuscany from the basket of a hot-air balloon are guaranteed. The views may reveal wild boar and startled deer, as well as vineyards and villages, churches and abbeys. From the local ballooning base in Montisi, north of Montepulciano, the dawn ballooning adventure ends with a light breakfast, with sparkling wine. Every flight is different but you should see the Val d’Orcia and maybe even Sant'Anna in Camprena, the Benedictine monastery where The English Patient was filmed. Keen guests can help with the inflation or deflation of the balloon and explore Montisi after the flight. Montisi, once a Cacciaconti fortress, commands a view over two valleys, and has earthy inns and two tiny Roman¬¬esque church¬es. Montisi is the main launch site but there are others outside Siena and Cortona. Bear in mind that ballooning is only available between May and mid October.
Address: Balloning in Tuscany, Via di Circonvallazione, 53020 Montisi
Tel: +39 3381462994
Web: www.ballooningintuscany.com

As arguably Tuscany’s most beguiling destination spa, Fonteverde is a favoured hideaway for Italian personalities who lap up the laidback luxury, rolling hills, and the seemingly remote setting among Siena province’s rolling hills. Fortunately, you can sample it on a day spa basis, and wallow in the hot pools while gazing over a sea of greenery. As for treatments, the spa is one of the best in Italy, and is equally strong in Mediterranean and Oriental treatments. The rural drive provides pleasure in itself.  A scenic route, the Via della Montagna, goes from Montepulciano south, via Sarteano and Cetona, to the spa town of San Casciano dei Bagni. Set on the edge of the village, Fonteverde is a sybaritic spa resort, centred on a Medici villa and upmarket restaurants at the heart of the resort.
Address: Fonteverde Spa Resort, 53040 San Casciano dei Bagni
Tel: +39 0578 57241
Web: www.fonteverdespa.com

Montepulciano’s modest, under-visited museum is set in a remodelled 14th-century mansion, complete with charming courtyard, loggia and well. The recent reattribution of a portrait to Caravaggio has brought the museum more attention. Portrait of a Gentleman is explained by means of an interactive, touch-screen interpretation, letting visitors explore details of the painting, its restoration and new attribution. Among the fusty minor art from Siena, Florence and Bologna, the della Robbia terracottas stand out, along with a school of Duccio Madonna and Child, and Etruscan works. Also on display is the original of the eye-catching Florentine lion symbol whose copy stands on Piazza Savonarola.
Address: Via Ricci 10, 53045 Montepulciano
Tel: +39 0578 717300
Web: www.museocivicomontepulciano.it