Borgo San Vincenzo

Worth getting out of bed for

If you’re looking for postcard inspo that goes well beyond the usual ‘weather nice, wish you were here’ fare, then you’ve come to the right place. For example, you don’t have to cast out very far on your borrowed bike before hitting multiple quirky wineries. Il Conventino offers tastings in, as the name suggests, the picturesque grounds of a former convent, while Icario is all about those endless vineyard views (and the wine itself, of course), as well as regular art and photography exhibitions hosted in a modern space above the barrique cellar. Peer through the glass floor to where the state’s Vino Nobile di Montepulciano matures in great oak casks beneath your feet. La Ciarliana even runs a family-friendly tour with fun flashcards, worksheets and colouring pages for the kids, as well as a juice-tasting session to keep them entertained while parents get down to the serious business of sampling the wines.

Perched atop a hill with a great green patchwork quilt of vineyards spread out beneath it, mediaeval Montepulciano’s atmospheric cobbled streets and squares are chock-full of Baroque and Renaissance edifices, including churches, palazzi and a gothic-style 16th-century cathedral. Don’t miss the Renaissance paintings and monuments inside the cathedral and look out for the comical/sinister Pulcinella figure on the clock tower in the main square. Visitors lucky enough to be in town on the last Sunday of August can also bear witness to one of the country’s weirdest annual spectacles, Il Bravio delle Botti, in which colourfully dressed teams race uphill through the streets pushing 80kg wine barrels in front of them. 

Cheese tasting, oil tasting, cookery classes and, heck, even truffle hunting can also be organised by the hotel’s dedicated experiences team, all but guaranteeing a riveting read for those lucky, lucky postcard recipients back home.

Local restaurants

Montepulciano is very much where it’s at if you’re into moody vaulted cellars, exposed oak beams and traditional Tuscan flavours. Directly opposite the epic Renaissance confection that is the San Biagio church, La Grotta ticks many of the aforementioned boxes. Formerly a 16th-century stable, it’s now a popular dining room serving top-drawer Tuscan fare like pappardelle with rabbit ragu and mussels in white bean sauce with homemade tagliolini and pecorino. A tasting menu is available for those who find choosing just one or two dishes here impossible and there’s a leafy garden for al fresco summer dining.

Osteria del Borgo offers the best of all worlds: a location just off the monumental Piazza Grande, Montepulciano’s main square, an atmospheric pre-Renaissance barrel-vault dining room and a panoramic terrace with – and we don’t use the term lightly – jaw dropping views of the valley and Val d’Orcia hills. The food ain’t half bad either; we’re talking ​grilled Florentine steak, braised beef cheek in vino nobile sauce, tagliolini with porcini mushrooms and – be still my beating heart – homemade tiramisu. The wine list runs to some 600 labels, all hand-picked by this family restaurant’s sommelier brothers, Francesco and Giacomo. Expect local favourites including Brunello di Montalcino, Bolgheri Doc and Vino Nobile di Montepulciano, plus many more fine wines from across Italy and beyond.

Local cafés

You can’t stay this close to Montepulciano without stopping by Caffe Poliziano at least once. This grand dame of Tuscan cafés has been around since 1868 and – with its art deco interiors, potted plants, dainty desserts, and glass cabinets full of delicate china teacups – it wouldn’t seem out of place on the Champs-Élysées or Rome’s Via del Corso. What sets it apart is those sweeping views of the Tuscan countryside, best enjoyed from the terrace with an espresso and a crunchy cream filled cannoli or three.

Local bars

You’re never far from the nearest bottle of wine in Tuscany, and Montpulciano is of course no exception. E Lucevan le Stelle combines those ubiquitous (but never boring) stone arches with arty black-and-white photos and bold, colourful canvases. Peruse a wine list that’s as long as your arm (if your arm happens to be unnaturally long, that is) and sip your chosen libation with splendid views of the Piazza di San Francesco. The bar even hosts occasional live jazz nights.

Nearby Opicifio 16 is an altogether less formal affair. Popular with locals, it’s set on a bustling shrub-lined sidestreet with apertivi and local wines advertised on handwritten chalkboards.