The Best Bars in the Tuscan Wine Town of Montepulciano, Italy

In a competitive field, this enoteca (wine shop meets tasting room) is one of the most stylish and informative spots to learn about local wine. As well as plummy, potent bottles of montepulciano, you might try lavender vinegar, pecorino cheese with honey, or bread with olive oil, alongside the reasonably priced wines dispensed from techy temperature-controlled cabinets. Factor in a cool, cavernous stone-clad tasting room, and it’s a chic and modern way to sink a few glasses.

Arty black-and-white photography hangs on ochre stone walls at this generously sized bar, which hosts live jazz nights and oyster tastings, as well as serving wines nightly to a well-heeled, older set of drinkers. It’s part of a palazzo-turned-boutique-hotel, Locanda di San Francesco, but there’s none of the stiff businesslike quality of a traditional hotel bar. Instead, colourfully splashed canvases and a buzzy terrace with views of the piazza give it a bohemian, social-hub feel.

This swish old dining and drinking spot has the feel of a European grand cafe, with dainty desserts displayed in glass cabinets, silky upholstery, potted palms and elegant crown moulding on the ceiling. But, really, you come here for the terrace: a wrought-iron balcony with an expansive, panoramic view of the broccoli-green forest and patchwork-like farmland. Sit out in the breeze for a coffee, cake, glass of wine or one of the many old-school liqueurs stacked by the counter.

Most nights in rural Italy, all you want is a pavement-side table on a balmy side street, with a bit of atmosphere – and that’s exactly what you get at this chilled wine bar, its patio trimmed with potted shrubs and hand-scribbled blackboards. It’s a popular aperitivo spot for young locals, who summon ice buckets and mini-dishes of crisps from late afternoon onward. For an unusual souvenir, pop into the shop area for one of its boozy jams, made with gin, vodka or bitters.

Founded by two expert sommeliers from local restaurant Osteria del Borgo, this pretty brick-built wine shop and tasting room has a lighthearted, quirky feel. A huge corkscrew sculpture sits above a counter stuffed with chubby cheese wheels, smiley, helpful staff wear matching aprons, and wonky wooden beams and peeling stable doors add a sense of history. Choose from the selection of clear, accessible “flights” to taste a few in one go. Not into wine? You can sample Italian beers here, too.

With wine-red canopies, elegant lettering and pretty planters filled with herbs and flowers, this restaurant and bottle shop is an inviting prospect. Head into its library of neatly shelved and labelled bottles, peppered with wooden crates and rare jeroboams, to taste a few. In the centre is a cylindrical chiller furnished with a set of gleaming wine glasses: you can load up a reusable card to dispense your own. Come to the tasting room for an aperitif, then sit outside for dinner, requesting your favourite wines to go with the meal.

Taste the Italian “sweet life” at this echoing, brick-clad tasting room, with its smooth arched ceilings and spiral staircases. It’s well known as a swish restaurant, but you can stop in for a tasting, or buy a bottle in the shop to drink on site, too. More than 3,000 wines are stored in the local volcanic rock to keep them at the optimum temperature, and the wine list is hugely diverse in terms of price point – whether you’re here on a shoestring or splashing out.