Cliffside kiosks at 15th-century palaces and street-side spots with live music set the scene in the Medieval commune of Gubbio, Italy, on the slopes of the Apennines Mountains.
The time-worn Perugian town of Gubbio is all knobbly fairytale bridges and potted geraniums trimming chubby stone-built cottages. Take a day trip here from Rome or in tandem with Assisi to immerse yourself in its storied Roman, Renaissance and Medieval sites – from the half-moon amphitheatre with seats now mossy with grass to the clanging bell in the Basilica of Saint Ubaldo’s tower, with its romantic views of the basil-green countryside below. Indeed, every inch of this ancient hillside settlement is incredibly photogenic – and you can pause at these watering holes between photo shoots.
You’ll have to go in search of this smart, antique-feeling cocktail bar not far from Piazza Grande. Enter to find heavily stacked bookshelves, cushioned stone alcoves by arched windows and thick wooden ceiling beams meeting ancient stone walls. Wine is the main event here – ask owner Marco to talk you through the most interesting bottles – but the team is just as whizzy with a cocktail, with rosemary-topped spritzes and icy G&Ts among the top orders.
Outdoor film screenings and live-music sessions hallmark this cute street-side bar, within view of the dainty Chiesa di San Giovanni Battista, with its ivory-coloured bell tower. Gig night or not, music is always playing, and a huge buffet has plenty of veggie options. Grab a table inside to sit amid scarlet walls punctuated with vintage film posters and zebra-print upholstery. The cocktails here go above and beyond the standard, too – try something tall and fruity.
There’s a lovely, parasol-shaded outdoor pavilion at this historical espresso bar, facing pretty public gardens and with views of the churches and houses on the hillside. Pause here between sightseeing stops for a rousing coffee, a scoop of mint gelato or an Aperol paired with filled focaccia. As evening descends, strings of filament bulbs and tall patio heaters create a cosy al fresco scene.
Don Navarro is one of the slickest and most modern hang-outs in town; this temple to hops features exposed brick, beer mats plastered on the walls, hulking metal taps and flags hanging from the ceiling. The lad vibe is strong, but the outdoor tables are set in a quaint courtyard of low, stone-built houses. So, pull up a chair at distressed wooden tables for a frosty pint and a pizza to share in a serene historical setting. It won’t be the cheapest round you’ll order in Gubbio, but it will have the best selection of brews.
Get a fantastic introduction to Umbrian wines at this Medieval-feel enoteca (wine shop and tasting room), set on an atmospheric street of butcher shops and fashion boutiques. Sit on the dreamy patio among potted herbs and succulents to taste whatever the owners point you to, served with free nibbles such as bread, cheese and salami. Also, it’s worth peeking into the tiny shop to peruse the bottles for sale, displayed in a cavernous stone space with traditional ceramics and vintage decanters.
This coffee shop-wine bar has a delightful age-old exterior with a hand-painted wooden sign and chic modern furniture inside its gnarled stone walls. Locals pop in for superior coffee, blasted from its hulking espresso machine, and feather-light baked goods dusted with powdered sugar – but it’s just as atmospheric for aperitivi.
This down-to-earth, international pub is one of the few places in town that rocks on into the wee hours, pouring cold pints of German, Irish, Italian and British beers for its sociable punters. Inside has the feel of a ye olde Irish inn, with polished wooden cabinets, frosted-glass partitions and red-and-gold signage, but there’s a sprawling patio surrounded by charming Gubbio architecture, too. Peckish? This is the place to get a stack of onion rings or a Tex-Mex taco.
Translating as “the Hanging Gardens”, this kiosk with tables and a view is in the gardens of the ornate, 15th-century Palazzo Ducale, with views of sun-bleached stone walls, crenellated churches and rolling green hills from its elevated position. Go at golden hour to sip an Aperol spritz as the fading sun places its Midas touch on hedges and shrubs. The bar’s humble looks in a dazzling location mean it’s a well-kept secret stumbled upon by a lucky few.