Florence meant a lot of things to me. It was the home of the Italian language, the city of Dante, Petrarch and Boccaccio where for centuries students — including me — have come to practise their r’s and drink cheap wine. It was the place where I first developed an interest in art thanks to its abundance of masterpieces, from Caravaggio’s Medusa to Botticelli’s The Birth of Venus. And it was the setting for many poignant family memories — where my sister, then aged six, persuaded our parents to take us for a ride on one of those horse-drawn carriages lined up outside the Duomo (mortifying for teenage me), and where my dad, sister and I came to stuff ourselves with gelato the summer after Mum died.
But despite all the treasured vignettes and return visits, I’ve never considered the Tuscan capital particularly, er, cool. This was a city of learning, history and spectacular (traditional) food. Edge, of any description, has been hard to come by.
It’s a theme common to most Italian cities. Once in a previous role I was tasked with putting together annual rankings of the world’s coolest neighbourhoods (it was a tough job, honest). Each year we felt we should include somewhere in Italy, given it was such a magnet for tourists, but we struggled to identify any area, in any city, that met international criteria of hipsterdom — fourth-wave coffee shops, natural wine bars, factories turned multidisciplinary arts spaces and so on. We would usually rotate the Italian entry between the lively Navigli canal district in Milan and whichever part of Naples had the cream of that year’s viral pizzerias. Florence never got a look-in.
So when I heard about the opening of W Florence last summer, I thought: “Perhaps something has changed.” This Marriott brand is known for its brilliant, colourful design; placing more emphasis on cocktails than dinner (sustenance — boring); and DJ sets that start early and end late — a refreshing change from the mostly tired-looking tourist stays that dominate central Florence. Five minutes’ walk from the Duomo, the hotel was the ideal base for a weekend during which my fiancée Morwenna and I would attempt to uncover where else — if anywhere — was in vogue in the city.
What you need to knowWho will love it? Cultured hipsters who want art, good food and nights outHow much does it cost? Room-only doubles at the W Florence are from £364Insider tip The city’s most delicious gelato can be found at La Carraia. Order the cheesecake with frutti di bosco (forest fruits) flavour
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There are few buildings in the centre like this 1960s rationalist-modernist behemoth, formerly the Grand Hotel Majestic. The stone and bronze façade with slit windows has an industrial feel, contrasting outrageously (and to my eyes, pleasingly) with the ornate palaces and gothic basilicas the city is famous for. Inside, after the W renovation, things feel rather glam. The murals at reception depicting the views from the hillside terrace at Piazzale Michelangelo across the River Arno and the menagerie of the Renaissance dynasty the Medicis — tigers, toucans and all — are stylish rather than tacky. And the 119 rooms, centred on a partially covered courtyard reflecting the Piazza dell’Unita Italiana outside, feature marble floors, red velvet curtains and OTT light installations that mimic the arches of the Medicis’ pad, the Palazzo Pitti.

W Florence, formerly the Grand Hotel Majestic, has had a glam makeover
The vibe in our spacious double is luxury but fun — and extremely comfortable. A semicircular drinks cabinet opens as wide as an albatross; inside are premixed negronis and cosmos. The low water pressure in the rainfall shower produces an authentic, gentle drizzle. And the melon Davines Momo products make me smell sensational.
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We crash on the kingsize bed for half an hour before heading out. Surmising that the internet’s edgier types might help me out, I leave a question on the /florence subreddit: “Where do hipsters hang out?” “I don’t think Reddit can answer that one,” is the first, frank response. Undeterred, we seek out a couple of offbeat attractions we’ve heard about nearby.

A spacious double at W Florence
Only in Italy, where literary institutions are generously supported by the state, would you find the Giunti Odeon, a bookshop in a cinema where most of the stalls have been replaced by shelves of detective novels, comics and art books. The main draw is the evocative 1920s decor, particularly the tapestries, mosaic floors and fountains in the foyer — cool in a way that reminds me of “dark academia”, the Oxbridge-meets-goth TikTok aesthetic. But if you fancy seeing a film, you can catch screenings (both new releases and retrospectives) after the shop closes in the evening (tickets £10; giuntiodeon.com).
Another reimagined historic building that caught my eye is the Marino Marini Museum, a tranquil haven five minutes on foot from the main shopping streets, Via Roma and Via dei Calzaiuoli. This gallery was built in the 1980s within the shell of the former San Pancrazio church and holds several of the Italian sculptor’s rugged bronze Horse and Rider sculptures, casting eerie shadows across the nave (£13; museomarinomarini.it). Like at the Odeon, though, the clientele comprises a handful of cultured visitors with outsized backpacks rather than edgy young Florentines.

Giunti Odeon is a bookshop in a cinema
IGUANA PRESS/GETTY IMAGES
DJs and unusual cocktails
We retire to the hotel for the evening. In the W Lounge, a DJ blasts classic Italian pop and Peggy Gou’s Starry Night. As should be expected in any self-respecting hipster hangout, we feel out of place among the sophisticated couples who line the blue lava stone bar. My drink is an invigorating Pisco Saro un Fizz (green Chartreuse, apple, basil and tonic), paired with unconventional but delicious aperitivi of caperberries and plantain crisps (cocktails from £10; marriott.com).
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Dinner is at the hotel’s contemporary Italian restaurant Tratto, run by the same team behind the Michelin-starred Trattoria Contemporanea in Lomazzo near Lake Como. The squid concertinaed onto a skewer and slathered with ’nduja is succulent — and an impressive feat of engineering. But the standout dish is a gloriously rich jumble of pasta with potatoes, mussels and caciocavallo podolico cheese, topped with breadcrumbs and parsley oil (mains from £17; trattoflorence.com).
In milder weather Tratto, alongside the hotel’s Japanese and Korean restaurant Akira Back, will spill out into the internal courtyard. And the Zefiro Rooftop bar, which soft-launched last year and is due to open seasonally when the weather warms up, promises live music and epic views over the city. We vow to come back to the W one day for another night out.
Come morning, we follow some Reddit leads — of which we now have many — and explore Santo Spirito, a laid-back neighbourhood brimming with bars and art galleries, 15 minutes away across the Arno (although with one end of the Ponte Vecchio disgorging visitors here, it’s still very much on the tourist trail). Our destination is the restaurant Il Santo Bevitore, probably the trendiest place we’ve been yet. It’s partly the interior, all terracotta floors, vaulted ceilings and shelves groaning with art books on Fra Angelico and Anselm Kiefer. Then there are the beautifully simple pasta dishes such as the intense, tangy pappa al pomodoro and the wholesome cavolo nero orecchiette. The most alluring thing about this low-key restaurant, however, is that most of the bookish patrons are dining solo — surely the definition of cool (mains from £8; ilsantobevitore.com).
Away from the tourist hordes
But the real revelation of our trip? That’s our next stop, Sant’Ambrogio. We’re introduced to this eastern neighbourhood, about 15 minutes’ walk from the Duomo, by a mysterious Redditor named Available_Cod_2. You notice the change where Via Fiesolana meets Via Pietrapiana. Suddenly, the tourist hordes thin out. Continue along Borgo La Croce and you’ll encounter the buzzing nightlife you never thought existed in central Florence.
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At Birreria Art. 17, open every day until 2am, a chalkboard lists regularly changing craft beers from across Italy — my favourites are a citrussy Bianca Piperita from Opperbaco brewery, a tart Osè from Elvo and a buttery Mostruosa from Agua. Tattooed, baseball-capped regulars stream out from the taproom-style space onto the pavement (drinks from £5; articolo17birreria.it).
Second on our Reddit-approved agenda is Le Murate, a 15th-century convent turned prison turned arts space and restaurant frequented by students, where we enjoy a steaming bowl of mussels and an energetic Balkan-influenced trio on guitar, drums and bouzouki (mains from £7; lemurate.it). And we finish the night at Nugolo, which offers a more refined kind of evening out — veg-heavy dishes made with ingredients from its own garden and the Sant’Ambrogio market, served in a room that feels like an upmarket hotel’s greenhouse, but with only locals for company. The five-course set menu with wine pairings is great value at about £100; if you’re lucky it might include our highlight, the tender pork fillet with cabbage and carrot cream (mains from £21; ilnugolo.com). A buzzy birreria, a repurposed prison, an unpretentious restaurant that dazzles: Sant’Ambrogio upends our same-old-Florence preconceptions.

The café at Le Murate was formerly a convent, then a prison
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On our final morning, inspired by the mural in the W lobby, we climb up to the Piazzale Michelangelo, the viewpoint in the southeast of the city where you can take in a panorama stretching from the Boboli and Bardini gardens to the hill town of Fiesole. The rose garden and lawns up here are immaculate. And the atmosphere, soundtracked by a busker playing ambient guitar music, is pleasant.
I can see why the crowds flock here. But now I know that down there to our right, where Borgo La Croce slices across the centre, they could discover a far more exhilarating — and yes, cool — side to this city.
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Huw Oliver was a guest of W Florence (marriott.com), which has room-only doubles from £364. Fly to Florence

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