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  • Montepulciano is effortlessly civilised and makes a beguiling base should you have a villa nearby. Its appeal lies in the mellow mix of Renaissance palaces and moody wine bars made for sipping Vino Nobile di Montepulciano. Like all quintessential Tuscan towns, it is built on a human scale so designed for strolling and relaxing on a Renaissance stage set, with set-pieces around every corner.

    Architecturally, Montepulciano is “the Pearl of the Cinquecento” so shaped by the Renaissance. The town is Antonio da Sangallo’s masterpiece, just as Pienza belongs to Rossellino. While Pienza was perfectly planned, Montepulciano developed more freely so has an asymmetry and spiritedness that Pienza lacks. Even so, there is a loftiness about Montepulciano that makes itself felt in the noble palaces and equally noble wine. Even the citizens consider themselves superior, somehow above the fray. But ultimately Montepulciano is a smooth operator, delivering the true Tuscan lifestyle.

  • 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.

  • 1. Piazza Grande stage set

    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 doorways. Both styles reflect Montepulciano’s buffeting 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.

  • 2. Il Corso – amble through history

    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.

  • 3. Palazzo Comunale – for scenic views

    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, surveys 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

  • 4. Contucci Cantine wine-tasting

    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: Via del Teatro 1, 53045 Montepulciano (SI)

    Tel: +39 0578 757006

  • 5. Tempio di San Biagio - Renaissance church

    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 interior feels deeply classical, closer in spirit to the Pantheon in Rome than to a small Tuscan church. Sangallo’s bold design skills rival Bramante’s, not just in the church but elsewhere in the city, from elegant stone wells to porticoes.

    Address: Tempio di San Biagio
    Via di S. Biagio, 20, 53045 San Biagio SI, Italia

    Tel: +39 0577 286300

  • 6. Montepulciano Wine Route

    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

  • 7. Country walk to Montichiello

    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

  • 8. Ballooning in Tuscany

    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 Romanesque churches. 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.

    Map coordinates for Montepulciano launch site: 43.0861,11.7642

    Tel: +39 3381462994

  • 9. Fonteverde luxury spa

    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

  • 10. Museo Civico – city art

    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

  • Eating and Drinking

    Whilst in Montepulciano, be sure to sample the wine and local delicacies on offer, from delicious luxuries to mouth-watering staples. Vino Nobile di Montepulciano, a Sangiovese-based wine, represents the heights to which Tuscan reds can aspire. Instead, full-bodied Vino Rosso di Montepulciano goes well with “peasant” snacks that have become healthy fast food for non-peasants. Ever-present are crunchy bruschetta and crostini, coated with fresh tomato and garlic or slathered in olive-oil or liver-based spreads. Also look out for Pecorino cheese flan or panzanella, a typical bread salad with herbs, as well as pici al ragu, homemade local pasta in a beef sauce. Most decent bars will be able to sort you cantucci with Vin Santo, the typical biscuits and dessert wine combination.

    For more eating and drinking recommendation in the area see our travel destinations list.

  • Caffè Poliziano

    This lovingly restored Art Nouveau café–restaurant is set in the historic heart of Montepulciano. Fellini was a fan and likened it to a great Mitteleuropean café that wouldn’t be out of place in Vienna. It remains a landmark so is often full but it’s worth trying to get a table, even if it’s just for a coffee and cake. The reasonably-priced light lunches are perfectly acceptable, ranging from crostini and cold cuts or salads and spicy chicken. Take in the views over Valdichiana from the panoramic balcony, ideally with a glass of Vino Nobile di Montepulciano to hand.

    Address: Via di Voltaia nel Corso, 27, 53045 Montepulciano

    Tel: +39 0578 758615

  • La Solita Zuppa

    This welcoming, rustic, mid-priced inn is set in the heart of Chiusi and looks like a classic Tuscan osteria, with exposed bricks and beams. Reflecting the restaurant’s name, vegetable soups are definitely on the menu, from ribollita to onion soup, as are pasta dishes with beef sauce or garlic and tomato sauce. Main courses may be centred on wild boar or lamb, with an excellent selection of cheeses to follow.

    Address: Via Porsenna 21, 53043 Chiusi

    Tel: +39 0578 21006

  • L’Osteria del Conte

    This friendly, confident, central spot is known for its hearty, Tuscan home-cooking, with portions as generous as the staff themselves. Unusually, there is also a fish-based menu and one just for cured meats and Tuscan canapes, all at middle-of-the-range prices. Highlights are the beef carpaccio, the raviolini stuffed with pecorino cheese, and the pasta in garlic-flavoured tomato sauce (pici all’aglione).

    Address: Via di San Donato 19, 53045 Montepulciano

    Tel: +39 0578 756062

  • La Grotta

    This memorable but pricey place is where locals go for a special occasion. The palazzo was once the home of architect Sangallo, and is right next to his stunningly positioned church of San Biagio. Set in vaulted dining rooms, the mood is romantic but rustic-elegant, with servings of creative Tuscan cuisine underpinned by French influences. Try the artichoke tart, the rack of lamb or the wild boar braised in plum sauce on a bed of spinach (brasato di cinghiale alle prugne sul letto di spinaci).

    Address: Località San Biagio 15, 53045 Montepulciano

    Tel: +39 0578 757479

  • L’Osteria dell’Acquacheta

    Set just off the main square, this ever-popular, rough-and-ready inn serves simple but tasty dishes such as huge steaks or pici (the chunky local pasta) with wild boar sauce (ragù di cinghiale) or tagliatelle with truffles. Wine is sloshed into glass tumblers and your bill might be scribbled on the tablecloth. It's great value and fun so worth sharing a table with others. Book the second sitting for dinner if you want a more leisurely meal.

    Address: Via del Teatro 22, 53045 Montepulciano

    Tel: +39 0578 717086

  • Shopping

    Montepulciano is a place where shopping merges into leisure. The winding road from Pienza up to Montepulciano is lined with vendita diretta signs, tempting you to buy pecorino cheese and wine from the producers themselves. There’s no escaping wine, the most popular purchase in town, especially when it’s generally linked to a relaxed tasting in rock-hewn vaulted cellars or in a modish wine bar that doubles as a wine shop. Most of the bigger winemakers can sort shipping for you.

  • La Dolce Vita

    This well-restored medieval building is stacked with wines, mostly from Tuscany. Carved out of tufa-stone, the adjoining wine bar doubles as a laidback but stylish bruschetteria, where you can pair particular wines with lights snacks. In summer, the tables spill out onto the street, with a moody view of Montepulciano.

    Address: Via di Voltaia nel Corso 80, 53045 Montepulciano

    Tel: +39 0578 758760

  • La Bottega del Nobile

    This is a stylish wine shop-cum-wine bar where tastings can be accompanied by light snacks, such as crostini, cheeses and cured meats. There’s also a vaulted cellar of a restaurant serving simple, rustic meals matched by local wines.

    Address: Via di Gracciano nel Corso 95/Via delle Cantine 13, 53045 Montepulciano

    Tel: +39 0578 757016

  • Parking & Getting Around

    The twisting road from Pienza upto lofty Montepulciano is visible for miles around, with houses clustered on the hillside. Much like Florence and Siena, Montepulciano operates a ZTL, meaning a Limited Traffic Zoning system. Traffic is essentially banned inside the city walls, but you can park outside San Biagio, from where it’s a short but steep walk into town. Alternatively, park in one of the  car parks at Montepulciano’s eastern end and then walk through Porta al Prato to Piazza Savonarola. The most convenient car park is on the adjoining square, on Piazza Don Minzoni (free in winter only), from where minibuses (€1) weave up the hill to Piazza Grande. If walking, from Piazza Savonarola take the princely Via di Gracciano nel Corso up to the main square. When leaving Montepulciano for Pienza, do not resist the Madonna di San Biagio, perched on a platform below the city walls.

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