From piazzas to canals, here's the insider's guide to exploring Milan and Venice

A twin-city escape from Milan to Venice offers a heady mix of vintage glamour, handmade beauty and culinary joy

From my window, I can see a quiet canal where gondolas drift past like slow punctuation marks.

“Welcome to the graveyard of the rich,” says Sarah, my vintage shopping guide, with a theatrical sweep of her arm. We’re standing in Cavalli e Nastri, Milan’s temple of pre-loved couture, surrounded by rails of Balenciaga, Dior, and Chanel that whisper of better-funded wardrobes. 

I’m transfixed by a pair of cherry-red Gucci ballerina flats with a bow. They’re €200 and they must be mine. Alas, they’re a size four, so unless they also sell time machines to get me back to when I was age eight, I’ll have to leave them behind.

A birds' eye view of Duomo square in the heart of Milan

This is Milan, the insider’s scoop — stylish but not too showy, confident without trying too hard. Over the next two days, the city unfolds like a film reel. First up, a tour with guide Federico Vaccari, the embodiment of Italian charm. 

He’s all easy smiles, immaculate style, and the kind of enthusiasm that can’t be faked. He’s restored his grandfather’s shiny black Fiat 500 to show visitors “the real Milan”, he tells us, patting the dashboard with affection, adjusting his long legs to fold into the driver’s seat.

Federico Vaccari gives unique tours in his grandfather’s restored shiny black Fiat 500, you can book through the Avani hotel in Milan.

At one point, he slows to a halt on a quiet street framed by elegant facades. “What do you think you’ll see in there?” he asks, eyes twinkling, nodding toward a railed garden. I hazard a guess — a fancy fountain? A secret courtyard café? His even better-looking twin? Instead, even more improbably, there they are: A flock of pink flamingos. In the middle of Milan. 

They stand serenely among the greenery of Villa Inverizzi, a turn-of-the-century mansion that hides this unexpected oasis in its private grounds. Romeo Invernizzi, a cheese magnate with a flair for the theatrical, imported the birds in the 1970s, Federico tells us, and they’ve been here ever since. 

It’s surreal, delightful, and oddly moving. It is Milan at its most beguiling, a city that hides wonder behind understatement.

Milan's spectacular Galleria Vittorio Emanuele II shopping mall

That evening, dinner is a masterclass in modern Italian indulgence. Tuscan hand-cut prosciutto, polenta crust with pecorino and truffle, and pappardelle with porcini mushrooms, followed by sliced beef in Barolo reduction. Dessert? Naturally, tiramisu, and a glass (or two) of meloncello, a sweeter, fruitier cousin of limoncello that deserves its own fan club.

The next morning brings a change of pace, from vintage fashion to bespoke beauty, at City Lab Cosmetics. I design my own lipstick, choosing the texture, shade, and even the engraved monogram. I never wear lipstick, yet this one feels like it was made for me — literally. It helps that cocktails are served while we create, because everything feels more glam when you’re blotting your bespoke lipstick before sipping on an Aperol spritz, darlings.

City Lab Experience, where you can design your own lipstick.

We continue the vintage shopping tour, exploring tucked-away boutiques with a mix of designer labels and shabby chic. I snag a Ralph Lauren polo for €4 for my son. Sarah saves the best until last though. She guides us up a tiny stairs to Foto Veneta Ottica, the bottega storica where Lady Gaga sourced her eyewear for House of Gucci. 

There’s an entire cabinet dedicated to Elton John’s most outrageous glasses — wacky shapes, rhinestones, and one pair with window wipers. The whole place is a shrine to style and eccentricity, proof that Milanese fashion is as much about personality as perfection.

Shopping in Milan, one of the world's fashion capitals

That night, at Osteria del Gambero Rosso, the tone turns deliciously local. The restaurant hums with conversation and clinking glasses — salute! — and I learn quickly that “a little truffle” in Italy is never a modest claim. Each course arrives with theatrical timing and an unspoken dare to clean the plate. Challenge accepted.

Our base, the Avani Palazzo Moscova, sits in a former railway station near Porta Nuova, its Franco Boisi Restaurant sets the scene with impeccable Milanese polish. The seafood here, we’re told, is unrivalled in the country. Despite no coast? I ponder. How? Our host shrugs, “Because Milan gets the best.” The tableside tiramisu, made up in front of us with theatrical flair, confirms his confidence.

Tomorrow we take the train to Venice, I’m looking forward to trading the polished thrum of Milan for something slower, softer, and set to the sound of water. But for now, the city still hums in my head: Engines, espressos, trams, treats, and the faint, improbable pink print of flamingos in the shadows.

Venice – a surreal spectacle

The next morning, we glide out of Milan on the train and in under two-and-a-half hours, slide into Santa Lucia Station. We emerge from the darkness of the station and – Bam! Suddenly, almost shockingly, Venice unfurls in full Technicolour. Canals, bridges, boats, the whole impossible spectacle of a floating city. It’s as if someone’s pulled back the curtain on a dream.

Our home for the next two nights is the Avani Rio Novo Venice Hotel, a sleek, design-led property in Dorsoduro. From my window, I can see a quiet canal where gondolas drift past like slow punctuation marks. Venice in autumn glows.

The Avani Rio Nova Venice hotel is a sleek, design-led property

Lunch at the hotel’s 8 Millimetri Cicchetti & Wine Restaurant is an ode to Venetian produce. The standout dish is a San Erasmo Island salad, its greens crisp and peppery, all the ingredients sourced from the nearby island, once a port, now renowned for its market gardening.

Later, we take a water taxi to Murano, the island of glassmakers. The journey alone, sunlight dappling the water, church bells in the distance, feels worth the trip. At Andrea’s glass studio, he and his wife share the ancient lampwork technique, using fine flames to melt and shape coloured glass rods into beads. Watching Andrea work is hypnotic; he turns liquid fire into art with flair. He tells us his four-year-old son recently made his very first bead, keeping the generational trade alive. Well, if a kid can do it…

Esther McCarthy making Murano glass beads in Venice.

I volunteer to try, and I make my own wobbly little creations, imperfect but beautiful, special to me, a souvenir you can’t buy in any shop.

The next day’s highlight is Lunardelli Venezia, a contemporary design atelier that honours the city’s twin materials, wood and glass. “They are worlds apart,” our host explains, “yet they meet at the heart of Venice’s identity.” Wood lies hidden beneath the water, the invisible foundation of the city, while glass captures its shimmering light.

We’re handed small pieces of the old wooden poles, once used to moor gondolas. The wood is worn, pocked with history and time — and worms, I think. We sand it, wax it, and heat it before engraving our own messages into the surface. Mine reads simply, ‘ritorno’ — “I’ll return.” I do hope so.

Canals crisscross Venice in a shimmering tangle

On my last morning, I wander out early with a coffee and no map. Every turn delivers something new: A hidden courtyard, a wonky bridge, magnificent masks, a glimpse of water where you don’t expect it. Laundry lines strung like bunting remind you this is home to the lucky few. A woman walks by with her little poodle on her head. As one does.

Getting lost in Venice is not a mistake, it’s the point.

I come across a free art exhibition by Stefano Lotumolo. I spend 10 minutes in a church, taking in the frescos, the stillness, the respite from the busyness outside. I eat a perfect pizza off Piazza San Marco, in a cafe with a tiny garden, and a fabulous house red.

That’s the beauty of a twin-city trip like this: Milan and Venice are two sides of the Italian soul. They couldn’t be more different, but together they make perfect sense. Milan is energy, the hum of fashion, cool cars, and cocktails. Venice is reverie, a slower rhythm, light caught in glass, footsteps on stone. Both are pure Italy, distilled.

I come home with a custom lipstick that actually suits me, handmade glass beads, a worrying craving for Aperol spritz, and my little wooden souvenir reminding me to return again one day.

Italy, it’s a date.

Escape Notes 

Fly 

Cork-Amsterdam-Milan Linate Airport with KLM. 

Travelling between the two cities is seamless: high-speedFrecciarossa trains connect Milan and Venice, with wifi and postcard-perfect scenery along the way.

The flight home was direct with Ryanair from Venice Marco Polo Airport to Cork.

Where to stay 

Avani Palazzo Moscova Milan Hotel: A chic conversion of a 19th-century railway station near Porta Nuova, blending maximalist Milanese glamour with Avani’srelaxed style. The Franco Boisi Restaurant serves refined Italian classics with flair.

avanihotels.com/en/palazzo-moscova-milan 

Avani Rio Novo Venice Hotel: Modern design meets Venetian soul in the heart of Dorsoduro.Expect canalside calm, creativeinteriors, and stand-out dining at8 Millimetri Cicchetti & WineRestaurant.

avanihotels.com/en/rio-novo-venice

• Esther was a guest of Avani Hotels.