The Best Bars in the Tuscan Hilltop Town of Pienza, Italy

Pienza is famous for its far-reaching views of the Val d’Orcia – the picture-perfect valley that represents Tuscany on countless guidebook and magazine covers. This pavement-side bar by the city walls puts you by the best of them. Gazing over a sea of pine-forested hills and sage-green meadows, only interrupted by the odd golden stone farmhouse, you’ll sip vivid Aperol spritzes and nibble the crisps and nuts brought out in shot glasses by your host.

On a historic side street that looks like it’s been built from gingerbread, this chic little deli and bottle shop serves tasty wines by the glass, plus generous charcuterie boards, in its small cafe space and tree-shaded garden. The owners are super-knowledgeable about the local food and wine scene, sourcing unusual bottles from all over Italy and Europe, and they’re just as enthusiastic about craft beers. Try one of the Pop Art-bright cans from the Milanese brewery Birra Lambrate.

This low-key, convivial hangout is filled most nights with the lilting chatter of locals – gathered around tiny circular tables topped with pots of herbs outside the entrance, or grazing on honey-dipped cheeses and homemade biscotti in the delightfully tiny, old-fashioned interior. Join them in ordering red wines and slivers of pecorino from late afternoon, asking owners Sara and Giuseppe what’s new in their well-stocked larder.

This diminutive, white-canopied cafe may not look like much from the outside, but it hides a secret-feeling courtyard patio, where you can sit out among vine-climbed trellises and thyme growing from goose-shaped pots. Facing a sleepy back corner of the old town, it’s a sleepy spot to sip a fruity local sangiovese and share a platter of mini-toasts topped with cheese and anchovies. It turns into a fully fledged restaurant in the evening, so come mid-afternoon for the most soporific setting.

Hip, cocktail-focused and filled with artful clutter such as tan-leather Chesterfields, tailor’s dummies and gilt-edged oil paintings, this high-arched, cavernous stone bar is the trendiest in town. Tropical potions are served in ceramic flamingo’s heads or pewter goblets. The town’s smallish young population heads here after dark as the music ramps up. Sit outside for a great view of the Val d’Orcia from the edge of the city walls, where flowering vines are climbing the bar’s exterior behind you.

A wine shop and deli where you’re encouraged to hang out and taste the produce, this pretty, poky redbrick space is lined with jars of homemade pickles, preserves and tapenades as well as pungent wheels of cheese. Select a platter of salami, hams, bread, and cheese slices from the elegant boards on display; then, ask for a flight of local wines to taste with them. It’s a brilliant Tuscan-food induction and the place to pick up a stash of gifts and souvenirs before you depart.

Part of a big gourmet complex that includes a Michelin-listed fine-dining restaurant, a wine cellar and swanky tables set in ancient cloisters, CCB is in the gardens of the 15th-century San Francesco monastery. An illuminated white kiosk serves a scattering of informal tables set among manicured, gravel-paved gardens, where a well-heeled crowd of thirty- and forty-somethings come to clink well-mixed G&Ts, Aperols and negronis and pick at shot glasses stuffed with grissini (breadstick) or cornichons. Come in daylight to see the views from its elevated terrace; stay on after sunset for peak vibes.

There’s an effortless chic to this whitewashed, brick-trimmed enoteca, with its gleaming marble counter and neat pine racks of wine bottles. Sit up at high wooden bar stools to sample the local sangiovese and montepulciano reds as your hosts Gioella and Alessio prepare snacks of pecorino with sliced pear and walnuts. Three-wine tastings start at very reasonable prices, so it would be rude not to go for the five-taster or one of the premium-wine options. This is a thoroughly modern way to drink the fruits of the region.