The Best Bars in Cortona, Italy

This sprawling terrace of casual metallic tables and chairs has a tropical feel, courtesy of big glossy ferns, palms and hanging baskets. Inventive cocktails might come in a hipflask with a wax seal, or feature toasted marshmallows or a macaron as their garnish. An on-point aesthetic draws in younger locals and the most fashionable Tuscany road-trippers each night. Later on, head inside to snap pics of yourselves partying in the cellar-like interior, a stylish clutter of mismatched vintage furniture, low lighting and, of course, a giant globe.

An enoteca is an Italian wine shop that usually offers tastings and tables for drinks – and this elegant wooden-shuttered number is a lovely spot to people-watch in Cortona. Perch yourself on swirling wrought-iron chairs at its couple of streetside tables, and pick from the library of ruby bottles that line the walls inside. There is a deli counter of local cheeses and meats to nibble through as you go, and afterwards you can stock up on a few bottles of your favourite find.

A classic enoteca with the wood-panelled aesthetic of a bohemian Parisian café, La Saletta has conversation-starting art on the walls and old-fashioned tablecloths out front. By day, it’s a coffee shop serving espresso with its own powdery biscotti. As night falls, you can get quality aperitivi with sharing boards of olives, crisps and crunchy crostini. The local Chianti with a paper-wrapped stack of ciaccia fritta (fried triangles of pizza dough) is a moreish combination.

Right in the main square, close to many of the best restaurants, this hip, vintage-style tapas bar is a design-lover’s dream. Hexagonal terracotta floor tiles, richly upholstered wooden benches and crystal glassware all give the feeling of a 1950s salon, but the food and drink are cutting-edge: fried liver with herby valerian and pomegranate vinaigrette, or Japanese-style nigiri topped with Tuscan cured meat. The house negroni is worth ordering, but wine fans will find knowledgeable staff and a comprehensive list of local bottles to browse.

With a name meaning “Cortonese brewery,” it’s no surprise that this is the beer-lover’s choice, with its own range of craft ales, as well as beer-based ice cream on the menu. Colourfully labelled bottles of unusual brews line the cream shelves around the interior, and little alcoves are filled with jars of pickles and preserves. In daylight, bag an outdoor table for film-set views of a sloping old-town alleyway, trailing down the hillside. Hungry? This place does a mean wild boar pappardelle, too.

The tall glass cabinets and gilt-framed oil paintings have a stately-home feel at this venerable old Italian caffè, where locals come for morning-long coffee sessions with the papers, and a friendly aperitivo hour with generous snacks. Sit up on the mezzanine level to look down at the convivial scene below, or pause on browsing the antiques and gift shops in the area for a glass of wine outside. Owners Massimo and Daniela are both members of the Italian Association of Bartenders, so the cocktails here are top-notch.

A cosy spot with peach-painted walls, gingham cushions, shelves of jams and baskets of lemons, La Fett’Unta exudes an air of grandma’s farmhouse kitchen. Scoot in to share a bottle of fruity Montepulciano, and perhaps nibble on a homemade gorgonzola bruschetta or fig tart, with the mellow chatter of older locals dining around you. Like what you tasted? Pack up a takeaway hamper of the wines, cheeses and pickles, on sale at the counter.