The Best Places to Drink and Stay in Italy

Pink and purple jellyfish hang from the ceiling near the staircase, and a goggled diver crouches frozen mid-launch by the pool wall: Capri Tiberio Palace commits to its retro bit with real conviction. This boutique hotel runs on a 1950s and '60s aesthetic, vine-covered garden paths, a rooftop terrace, spa, restaurant, and Jacky Bar for nights that go late. The Piazzetta is a short walk, so the oasis is optional.

Perched on the western shore of Lake Garda, this grand old lakeside hotel has been turning its terrace into an argument for doing absolutely nothing all afternoon for well over a century. Vaulted ceilings, antique furnishings, and a spa filled with natural light set the tone inside, while the hotel's own boats offer a way out onto the water when the view from your glass of red wine stops being enough.

The name means "here one heals," which remains a reasonable excuse to book a suite on Capri's most famous street. This grand hotel has been the island's social headquarters since forever, its white facade and orange-blossom gardens drawing the kind of guests who prefer not to carry their own luggage. Pools, terraces, a spa, and the street-side Quisi Bar keep guests occupied from breakfast through whatever hour counts as late on Capri.

Peach-colored walls on a cliff above the Faraglioni rocks, with a pedigree that traces back to Le Corbusier's original design. This small luxury hotel on Capri rewards the climb with sweeping sea views and interiors that blend original tapestries and antique paintings with 1930s-inflected furniture from a recent refresh. The pool terrace is where everyone eventually ends up, staring at the same water they came to Capri to stare at.

Original art by Keith Haring and Arnaldo Pomodoro lines the corridors of this whitewashed resort perched above Anacapri, which makes the gin bar feel like a bonus rather than the main event. Five restaurants and bars, most with sea views, handle the eating. The spa runs a signature circulation treatment called Leg School Therapy, which sounds made up until you're already booked. Helicopters, speedboats, and chauffeurs sort the transfers.

A cliff hotel perched a thousand feet above the Bay of Naples, with views that sweep from Vesuvius to the Sorrentine peninsula and down to water so blue it looks retouched. The Terrace Bar serves oysters and champagne while you absorb the spectacle, and nearly every one of the 55 rooms faces the sea. A statue of Caesar Augustus stands guard on the grounds, eyes fixed on the water, apparently unmoved by the whole thing.

A converted medieval hamlet in the Chianti hills, Borgo San Felice is a 60-room resort where the buildings were once a bakery, an olive press, and wine cellars. The vineyard is still working, the spa leans into grape-must treatments, and two restaurants keep you from ever needing to leave. Siena is close enough for a day trip, but the hot air balloon over the hills at dawn makes a reasonable argument for staying put.

A neoclassical facade on the Lake Como waterfront in Menaggio, with the kind of ornate molding and chandeliers that make you feel underdressed just walking through the lobby. This hotel pairs that old-world bones with freshened interiors and modern furnishings, so it reads more lake house than museum. Balconies look straight out over the water, the spa is properly calm, and the pool is the sort you photograph before you get in.

The low-slung terracotta rooflines and weathered wooden beams were designed to look like a Sardinian fishing village, which is an ambitious premise for one of the Costa Smeralda's grandest luxury resorts. It works, somehow. Private coves, a waterfront pool, and suites with hand-painted furniture and sea views keep things from feeling too theme-park about it. Watersports and yacht excursions are on hand for guests who find lying still professionally difficult.

The design riffs on the 1950s golden age of Italian bar culture, and Cinquanta leans into it without tipping into kitsch. It's a cocktail bar in Pagani where an espresso at the counter is as welcome as a negroni with friends, and the staff seem to mean it. The specialty drinks menu rotates monthly, dusting off forgotten classics alongside more idiosyncratic combinations. Difford's Guide and The 50 Discovery have both taken notice.

Historic photographs of the original café guided the renovation, so the room feels like a Florentine institution that quietly relocated across the street and pretended nothing happened. Giacosa 1815 opens as a coffee-and-pastry spot, then pivots to aperitivo as the evening arrives. The Negroni is practically mandatory, given the history, but the cocktail list keeps going for those who feel like exploring past the obvious.

The toilet is famously larger than the bar, which seats four people at a counter and leaves no room for ambiguity about what kind of night you're having. Backdoor 43 is a reservation-only cocktail bar tucked behind another bar on the Navigli, and the bartender on duty is working exclusively for you. Guests pick the music, the pace, and apparently the vibe. Very small, very Milan.

Two rooftop pools and a cocktail bar on the fourth floor of a building in Milan's Porta Garibaldi district set the scene here: the kind of place that decided glamour and a proper dinner weren't mutually exclusive. Brass, marble, and vintage wood fill the interior while the terraces open onto skyscraper views. The kitchen keeps the Italian menu light and seasonal, and the cocktails have become a standard reference point for the city.

The cocktail bar that decided pizza was the obvious food pairing, back when that was a radical idea in Milan. Dry is a lively, sociable spot on Via Solferino where the drinks are serious and the tables are meant to be shared, sometimes with strangers who are perfectly happy to share them. The room runs warm and international, the kind of place where arriving alone rarely stays that way for long.

Six hundred year old columns greet you in the lobby of this hotel, housed in a Renaissance palazzo a short walk from the Trevi Fountain. The team kept the bones intact, so cocciopesto plaster, Travertine stone, and a monumental marble staircase do most of the decorating. It's the kind of place that makes you feel like a guest of the building as much as the brand, which is a neat trick for a wellness hotel group.

Art nouveau bones, a courtyard that feels borrowed from a film set, and the kind of slightly faded glamour that no interior designer can fake. Hotel Locarno is a historic Rome property steps from the Piazza del Popolo, and it still carries the bohemian mood that drew Fellini and his crowd decades ago. The current owner inherited it from family and has kept it exactly as it should be: atmospheric, a little theatrical, and blessedly unmodernized.

Colorful Mexican-tile bar top, embroidered stools, and a wall of agave spirits that would embarrass most dedicated mezcalerias: La Punta is a tequila and mezcal bar tucked into Trastevere, run by the team behind Jerry Thomas Speakeasy. They traveled to Oaxaca to build the menu, and it shows. Downstairs, a smaller den packs in even more bottles and Mexican paraphernalia. Order slowly; the list rewards it.

A glass roof now covers what was once an open courtyard of a Renaissance-era convent, and the Four Seasons Firenze built its signature cocktail bar around that fact. Pale light, deep sofas, and verdant garden views make it feel less like a hotel bar and less like a museum than you might expect. In the evenings a pianist plays, the bar team reinterprets classics with some invention, and the crowd dresses accordingly.

Emerald walls, a marble bar top, and a grand piano set the scene at this cocktail bar near Milan's Centrale station. The conceit is a fictional bartender named Nik, sailing the world across the decades and mixing drinks inspired by the people he meets along the way. It sounds like a lot, but the room pulls it off with enough charm that you stop questioning the lore and start ordering. A Discovery selection from The 50.

The tenth floor is the whole argument: Cecconi's wraps you in a 360-degree panorama of Rome while serving Italian classics to a crowd that came for cocktails and stayed for dinner. As a place to stay, it leans on the Soho House formula of muted tones, terrazzo floors, and locally made wall hangings, which manages to feel warm rather than branded. The Discovery list from The 50 gives it a nod.

A former boarding school on the northern hillside above Florence, converted into a five-star resort with enough restraint that the frescoes and coffered ceilings stayed put. Original classrooms are now suites with hand-painted walls, stone bathrooms, and small wine cellars, all looking out over the Duomo from a comfortable distance. The Auberge Collection's Italian debut landed a spot on The 50 Discovery list.

Twelve suites inside a centuries-old palazzo that has never left the founding family's hands, which is either a remarkable preservation story or a very long estate dispute, probably both. The rooms range from frescoed ceilings edged in gold to a suite with its own gilded chapel. Boutique hotel barely covers it. Named a Discovery by The 50, it sits on one of Genoa's grandest streets and sleeps like a private museum that finally let you in.

A rooftop pool with the Dolomite peaks arranged around it like they know what they're doing sets the tone at this 14-suite boutique hotel in Castelbello. South Tyrol practically invented this genre of grown-up mountain retreat, and Amaril fits the template with natural materials, a proper spa, and a no-guests-under-14 rule that keeps things quiet. Apartments come with kitchenettes if you're settling in for a while.

Floor-to-ceiling glass and Patricia Urquiola's interiors face the eastern shore, where Il Sereno sits among Lake Como's old money mansions looking conspicuously, deliberately modern. It's a boutique luxury hotel with 40 suites, a 60-foot infinity pool, a boathouse converted into a spa, and a waterfront restaurant that holds a Michelin star. The kind of place where the lake does half the decorating, and the design team handles the rest.

Hammocks, tribal masks, and enough bottles to stock a small nation line the walls of this legendary Milan cocktail bar on Viale Piave. Dario Comino has been quietly pioneering every technique in the cocktail world, from clarification to fermentation, since before most bars knew those words. Drinks here borrow from distant cultures while playing with texture in ways that tend to surprise even regulars who think they know the menu.

Perched at 1,800 metres in the South Tyrol, this spa resort sits close enough to the clouds that the distinction feels negotiable. Floor-to-ceiling windows and stone-accented interiors keep the architecture out of the landscape's way rather than competing with it, and balconied rooms make ignoring the Dolomite peaks essentially impossible. A spot on The 50 Discovery list confirms the pilgimage has a point.

A 16th-century watchtower anchors this resort on Ischia's quieter western edge, part of the Pellicano group but content to let its more famous sibling steal the spotlight. Rooms and cottages sit inside a lush private park, dressed in hand-painted tiles, handwoven wall hangings, and soft creams that feel less like a design brief and more like someone's actual taste. A private bay keeps the crowds at arm's length.

An 800-year-old Tuscan villa set across 200 acres of gardens, wild land, and a working kitchen garden, all of it painstakingly restored by its Danish owners into a boutique resort that somehow feels like a very grand private home. The grounds alone justify the visit, but the interiors match them beat for beat. A Discovery from The World's 50 Best Hotels, and easy to see why once you're standing in the orto at dusk.

The Ferragamo family bought an entire medieval Tuscan hamlet and turned it into a resort, which is a sentence that explains a great deal about the atmosphere. Il Borro's 38 suites occupy centuries-old stone buildings scattered across the property, each fitted with exposed beams, open fireplaces, and antiques chosen by hand. The kind of place where the grounds themselves feel like the amenity, and the village outside your door has been there since the thirteenth century.

The menu at this rum bar in Marina di Ravenna's international port runs to 180 pages, part cocktail list, part coffee-table book on Haiti's distilleries. More than 2,200 bottles line the walls, and the 24 drinks range from Caribbean classics to inventive originals. It holds a Pinnacle Guide pin. Pack patience: a bar this devoted to sugarcane spirits is not a place for a quick one.

A medieval castle in the Maremma countryside, converted into a ten-suite boutique hotel where the kitchen is rustic and the service feels like a neighbor insisted you stay. Marble pools sit among cypress trees, with olive groves and vineyards rolling out in every direction, and the gardens smell the way Tuscany is supposed to smell in other people's photos. It's castle-as-farmhouse, and somehow more relaxing for it.

Tucked under the Procuratie Nuove arcades on Piazza San Marco, Caffè Florian has been around forever, and the gilded, frescoed rooms know it. It's a coffee and drinks bar where tourists come for the theater of the thing and locals duck in for a quick espresso at the counter, which costs considerably less than sitting down in the ornate dining rooms with the orchestra outside. Both options exist; just know which one you're paying for.

Bartenders in white tuxedos hand drinks to bellboys who carry them across one of the more theatrical lobby lounges in Venice, which is saying something. The Dandolo is a hotel bar in the Gothic palazzo next to the Doge's Palace, and the setting does most of the heavy lifting. Classic cocktails are reliably solid; the rest of the menu is less memorable. Come for the room, not the drinks list.

The black-and-white geometric mosaic walls do something clever with the glassware and smoked ceiling mirrors: the light never quite settles. This is the bar inside the Mandarin Oriental Milan, and it runs from espresso at eight in the morning all the way to a proper late night, organizing itself around aperitivo and the slower hours that follow. The outdoor sofas stay calm well into the evening before the room finds its louder gear.

Perched above a Replay store in Milan's gleaming Piazza Gae Aulenti, the Octavius Bar arrives as a nautical surprise, with boat-like design details in a neighbourhood that reads more glass tower than harbour. The cocktail bar draws the after-work crowd that lives in this part of the city, the kind of people who take their aperitivo seriously. Gae Aulenti is Milan's most self-consciously international square, which makes the whole thing feel pleasingly theatrical.

The name comes from the horticultural term for a cutting, a piece of a plant relocated to take root somewhere new, which tells you something about the ambitions here. Talea is an experimental cocktail bar tucked into a slightly unexpected corner of the Navigli area, with a room that feels deliberately intimate. The drinks lean on kitchen technique as much as bar technique, so what arrives in the glass tends to surprise before it satisfies.

The terrace hangs right over the Grand Canal, which is either romantic or deeply unfair depending on your budget. This hotel bar inside the Gritti Palace does the Grand Venetian thing without apology: etched mirrors, red marble floors, white-tie bartenders working through a long menu of classics. The crowd leans tourist, but the setting is so extravagant that nobody seems to mind being exactly where a postcard told them to be.

The terrace hangs right over the Grand Canal, which is the whole argument for sitting here. This hotel bar at the Bauer does its job quietly, with black leather club chairs and scarlet walls they call the Red Room, though the interior is otherwise pretty modest by Venetian hotel-bar standards. Order something cold and watch the boats go by, which is exactly what everyone around you is doing.

Floor-to-ceiling shelves of wine and spirits line the walls of this canalside enoteca near Ponte San Trovaso, which works simultaneously as a wine shop, coffee stop, and cicchetti bar. The family runs the counter together, father and sons pouring by the glass while the food comes from behind a glass display case. A dozen or so wines open at a time, mostly from the Veneto, and bottles leave tucked under tourist arms at a reassuring clip.

A small cocktail bar with an industrial-meets-contemporary fit-out on a residential stretch between Porta Venezia and Piazzale Loreto, where boutique shops outnumber tourists. The team comes out of five-star luxury hotels, and it shows in the pacing and the polish, though the room itself is relaxed enough that nobody feels underdressed. Milanese regulars mix with the kind of international crowd that follows a good bartender from job to job.

Wine labels plaster the ceiling at this old-school Venetian wine bar tucked into a narrow alley near the Rialto, and the cellar below holds over a thousand bottles at prices that feel slightly illegal for Venice. Rough wooden benches, bare planks on the walls, and a glass counter piled with cicheti complete the picture. Locals have been doing exactly this, a glass and a small bite, here for generations.

A handful of bar stools at a grey marble counter, and the rest of the room is tightly packed tables that belong to diners at mealtimes. Harry's is a cocktail bar that trades heavily on its history, and it earned every bit of it: this is where the Bellini was invented, and Hemingway was a regular. It's small, plain, and slightly intimidating to walk into, which somehow makes ordering one feel like an occasion.

A 15-meter bar counter lined with bamboo shelves stacked floor-to-ceiling with rum pretty much tells you everything. Rita's Tiki Room is a cocktail bar on Milan's canalside strip, serving Tiki classics and house originals alongside Polynesian snacks with a Cantonese edge. The same team behind Rita around the corner runs this one, and the vibe is full commitment: proper accoutrements, no ironic winking at the theme.

The sign is easy to miss, which seems to be part of the point. This cocktail bar in Porta Romana pulls you into a low-lit room of velvet sofas, extravagant mirrors, and sparkling lights that make it feel like the '80s never quite ended. The kind of place where you stop checking your phone without deciding to. A neighborhood worth wandering for its trattorias anyway, so the detour is painless.

A corner bacaro a short walk from San Marco, with shutters thrown open and barely a meter of corridor to stand in. The reason to know it is the hours: open until 1am most nights and 2am on Saturdays, long after Venice has gone to bed. Drinkers overflow onto the campo, voices carrying loudly enough to navigate by, which the neighbors have noted and the police occasionally confirm.

The Negroni Sbagliato was born here when the owner grabbed sparkling wine instead of gin and decided to serve it anyway. Bar Basso is an old-school neighborhood cocktail bar in Milan that has barely changed since the late fifties, and the happy accident has been the house drink ever since. Order yours in one of the enormous chalice glasses the original owner designed, a shape you'll start spotting around the city once you know to look.

Surfboards and antique furniture share wall space at this cocktail bar on the far edge of Milan, and somehow the combination works. The room feels less like a city bar and more like a countryside detour, all mismatched art and skating decks, with a plant enthusiast behind the counter shaking what Italians have always called "misture." Five kilometers from the center, which is exactly far enough to feel like you've escaped something.

A windowless room on Via del Moro in Trastevere, done up in dark wood and overhead luggage racks like a very stationary Orient Express car. Jerry Thomas is a classic cocktail bar with 90-minute reservations and bartenders dressed for a century ago, which suits the bottled classics and Champagne on offer. Outside, Trastevere does its rowdy thing; inside, you'd never know.