Jetting off on an Italian multi-leg city break to discover the most cinematic cities in Europe feels like an obvious choice for a holiday, and whilst there are obvious reasons to prompt the trip – i.e. delicious food - we’ll admit that TV’s fave fashion expat Emily Cooper’s move from Paris to Rome might’ve been an influence on our Mediterranean adventure. Thanks to the show’s relocation in series 5, Rome is having a moment, so that’s exactly where we begin, embarking on a chic whistle-stop tour from Rome to Milan to Venice, that’d make the fashionista proud.
It sounds like an undertaking hitting three destinations in six nights, but it’s surprisingly easy (and affordable) to city hop in Italy, thanks to their impeccable train network (no offence National Rail, but you’ve got nothing on Trenitalia). Each city has its own distinct personality - Rome boasts buildings that are over 2000 years old, Milan is a famous fashion hub, and Venice, well, Venice is magical, built on lots of small Islands connected by stunning canals - so it’s hard not to go into this trip without high expectations, but boy, do they exceed them IRL.
If you’re looking to experience the beauty of each destination but need tips on how to do it right, here’s our rundown.
ROME
Where to stay in Rome
This hotel injects playful touches into every aspect of our stay. Neon signs hang above the desks (shaped like chariots) selling mantras like “hacking the empire”, while Roman statues line the reception wearing Beats headphones and high-top trainers. To reach our block of guestrooms, we walk through a small games room where you can play retro arcade games and table football, before hopping in the lift to find a karaoke screen. The whimsical details continue inside the rooms. The curtains are printed with Roman architecture pattern interspersed with Pac Man motifs, and forget boring white waffle slippers, nhow Roma offer bright yellow and purple fluffy thong-toe flip flops. For all its fun eccentricities, the hotel feels very calm, situated in a serene neighbourhood north of the city, just outside the Villa Borghese park.
Where to eat, drink, and what to do in Rome
For sit-down dinners, La Matriciana dal 1870 is everything we dream of in a Roman restaurant. All wood and white linen tablecloths, lots of black and white photographs on the wall and well-dressed, attentive waiters weaving amongst stylish diners. The menu is delicious, Roman classics front to back. Sipping on Negronis to begin, we order red shrimp carpaccio, followed by Cacio e pepe, Mezze maniche alla gricia (pasta with pork and pecorino cheese) and grilled scallops with artichokes. Run by brothers Fabio and Mauro, it’s a gem of a restaurant and a highlight of our trip. Reservations appear a month in advance, and if the hungry crowd gathered outside is anything to go by, plan ahead.
For more culinary delights, Flavio Al Velavevodetto is situated in the foodie neighbourhood of Testaccio (where the Romans go to eat). The menus are printed with ‘In this tavern there is no word “hurry”’, explaining the relaxed dining experience, but happy not to rush, we slowly make our way through mouth-watering traditional pasta dishes and great-value natural wine.
For dessert on the go, grab a tiramisu cup from Two Sizes. We spot more people than we can count digging spoons into takeaway tiramisu pots, as we people-watch over an Aperitivo (when in Rome, eh), learning later that the hole-in-the-wall dessert spot has gained viral status.
Immerse yourself in culture: it’s a given in Rome that every corner you turn is another rich tapestry of history and culture, from its 900+ churches to Renaissance art. It feels unbelievable that a city is fully functioning amongst the impressive ruins. Booking first entry tickets to the Colosseum, we commit to a crack of dawn wakeup call - worth setting the alarm to wander the grounds in the peaceful morning light. We pose for selfies in front of the Trevi fountain (and 20 million tourists), but on a second passing in the wee hours, fewer people are throwing lucky cents and instead, a clearer view of the fountain is illuminated and glowing, atmospheric against the night sky.
For drinks, The Hole Trastevere, located on the cobbled streets of the bustling, bohemian neighbourhood, is the Roman’s take on an Irish pub, serving a great Guinness amongst charming, eclectic décor. To catch live music and artsy locals, we head to Rome’s Monti neighbourhood for Blackmarket Hall, an underground speakeasy sporting kitsch mismatched furniture and serving creative cocktails.
MILAN
Where to stay in Milan
NH Collection Milano CityLife
Housed in a former 1930s church that’s been reimagined to create an impressive 13-story hotel, NH Collection Milano CityLife is striking. The neighbourhood is modern and residential, blending skyscrapers with parks and culture, and the hotel is just 100 metres from Portello metro station, which takes us directly to the city centre. The lobby, flooded with natural light, is as grand as you’d expect from the exterior, and the bedrooms are ultra-modern, featuring high-end amenities including a power shower and a king-size bed. The friendly concierge sits across from the bar and restaurant, Tailors, who serve Milano classics for dinner, and where we feast on a generous breakfast buffet, toasting the midpoint of our trip with a morning prosecco mixed with blood orange juice. The hotel’s secret weapon? Their rooftop pool and bar. With panoramic views surrounded by white pillars, it feels like we're in Ibiza, but sadly, as it's not-so-sunny January, we’ll save a dip for next time.
Where to eat and what to do in Milan
For authentic Milanese dishes, head to Osteria El Binari. A romantic restaurant that’s considered an institution for locals, flaunting exposed beams and rustic fireplaces. The space has individual dining rooms, including a green iron-glass conservatory and a lush ivy-covered outdoor dining garden. It serves classics like the saffron risotto; however, we opt for Tortelli stuffed with ossobuco – a speciality of Lombard cuisine – and Agnolotti with braised beef and truffle.
For vintage shopping, we’re in the right place. Milan’s treasure chests of vintage are tucked away and scattered across the fashion capital. We have limited time for retail therapy, so I prioritise two of the city’s highly celebrated secondhand stores. Cavalli e Nastri is a mecca for designer and archive gems from across the decades. I still think about the pair of Gucci Mary Janes that sat in the window display. Five minutes around the corner is Franco Jacassi’s Vintage Delirium, hidden away in a courtyard; it feels more like a designer-obsessed grandma’s attic than a shop.
VENICE
Where to stay in Venice
Avani Rio Novo Venice
Within the heart of the Dorsoduro district - a quieter, trendier part of Venice, where you’ll find arty locals who actually live in the city – Avani Rio Novo is a welcoming hotel with a contemporary, relaxed vibe. The lobby’s mini library stocks books and magazines on the history of cinema and invokes a sense of community. It’s just a 10-minute walk from Santa Lucia train station, where we’ve arrived from Milan, which is a major plus in a city that’s segregated by many canals. The rooms are bright, offering plenty of amenities, including cosy dressing gowns, ample toiletries, and a yoga mat; still, the best feature is the full-length window overlooking the Ponte de la Sbiaca bridge and Rio Dei Tolentini canal. We wander the local streets, interspersed with boutiques, bars and authentic restaurants, feeling a sense of solitude – rare in Venice – until we reach nearby Campo Santa Margherita, the area’s bustling piazza.
Where to eat and drink, and what to do in Venice
Lunch with locals at Antiche Carampane. Every inch of wall space is covered in an antique mirror, painting, or an old photograph, giving this hidden eatery a homey atmosphere. It’s a true Venetian dining experience serving to-die-for seafood dishes and wine amongst a buzzy crowd staying for long lunches and cosy conversation.
For drinks, there are countless picturesque canal-side bars to mention. The 20+ craft beers on tap at Il Santo Bevitore are what pull us into this lively watering hole, but it’s the cool decor and great noughties soundtrack that keep us staying for three more. We walk across to the hip Vino Vero, to find the best-dressed Venetians wrapped in chic coats, huddled outside the canal footpath, sipping tasty natural wines and biting into Cicchetti (a traditional Venetian bar snack that puts a scotch egg to shame). For a late-night aperitif, it's back to Campo Santa Margherita square, where students gather in hordes, to grab a cocktail – mine was a marg - at Chet Bar.
Paint your own Venetian mask at Carta Alta’s workshop. We hop on the waterbus over to Giudecca Island to visit Augusto's artist studio, where shelves are stacked high with vibrant eye coverings and the more unusual and impressive (sometimes creepy) designs are mounted on the wall. We select our own embellishments and start our hand-painting session whilst Augusto talks us through the history of Venetian masks. FYI, they've made custom designs for 50 Shades of Grey and Gossip Girl, so no pressure. It's a cute, relaxing experience, and we leave with the coolest bespoke souvenir to remind us of the best trip.
Sophie Leen is the Bookings Editor for Cosmopolitan UK and Women's Health UK. She specialises in creating fashion and shopping content across both digital and print platforms, as well as producing all of our fashion editorial photoshoots, which have included our digital cover with Olly Alexander and our curve influencer’s letter to the high street story. Sophie also looks after our Try Before You Train franchise where our team have tested and reviewed over 100 gymwear items.
