As the enduring appeal of Netflix's Emily in Paris starring an American marketing maven traipsing through Paris in high heels suggests, aesthetic escapism is having a moment. Paris, with its fashion, fantasy and flirtation, is the honeymoon capital of the world for good reason. But when it comes to being the capital of a good time, another contender steps into the spotlight: Italy.
For a dream European escape that includes a scavenger hunt through residential Rome, carnival mask-making in Venice, and lipstick-formulating in Milan, look no further than this curated 7-day itinerary for Italy.
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For the kind of traveller who loves piecing together the perfect trip, this Italy bucket list guide provides ideas for where to go and where to stay. But if you'd rather step off the plane at Fiumicino with everything dialled in, our Chic in Italy: Set-Jet Stays package delivers the best of Italy in one neat package, no spreadsheets required.
Rome
If nhow Roma, your base in the Eternal City, had a motto, it might well be veni, vidi, vino. The stylish bolthole will conquer you in less time than it takes to whisper “mamma mia” as you gaze out over the vast expanse of Villa Borghese, one of Rome’s most elegant green spaces. The final arrow in Cupid’s quiver? The in-suite wine cellar, which seals the deal: Rome is love at first sight.
And if, after all that Chianti, you find yourself craving a bowl of bolognese or carbonara, our
guide to the best pasta in the city has you covered. Then it’s time to meet the charming neighbour who first caught your eye from the window — Villa Borghese.
The cultured park: Villa Borghese
Once the private estate of the Borghese family, one of Italy’s most powerful noble families, the park is a refined blend of formal gardens, wooded paths, fountains, sculptures and world-class museums. Chief among them is Galleria Borghese, home to masterpieces by Caravaggio, Bernini, Raphael and Titian. Also worth a detour: the Pincian Hill, for sweeping views of the city; Cinema dei Piccoli, the world’s smallest cinema hosting children's and regular movie screenings; and the Temple of Aesculapius, where you can drift past a classical lakeside folly in a rowboat.
Rome on three wheels: a retro adventure
Your official introduction to the City of Seven Hills will take place from the comfort of a retro Vespa sidecar. Guided by a local history buff, you’ll follow clues through hidden courtyards with winking statues, before switching gears into an electric vintage Fiat 500 cabrio for a breezy, eco-friendly spin through the Eternal City.
A pit stop for gelato and prosecco primes you for a hands-on Italian cooking class and a crash course in the local dialect, Romanesco, perfect for tossing around at farmers markets should you decide to linger a little longer. While the Chic in Italy: Set-Jet Stays itinerary has you in Rome for just a few days, an extension is definitely on the cards if you're visiting in spring. Here’s why.
Anantara Concorso Roma
Rome is, of course, an all-season delight. But spring is something else entirely: Easter with its Colomba di Pasqua sweet bread, wisteria cascading over Trastevere’s sun-warmed walls and one of the most unique experiences in Italy, the Anantara Concorso d’Eleganza Roma.
For three days each spring, the Eternal City becomes the epicentre of the historic motoring world, staging a
rarefied gathering of classic Italian automobiles. As hand-picked collectors from around the globe present their prized machines, the city’s timeless architecture makes them feel as contemporary as the latest EV. Before the winners are announced on the final day, there’s ample diversion for both die-hard enthusiasts and the aesthetically inclined, from champagne receptions to the
elegant concorso parade winding through Rome’s storied streets.
Stay at the grand Anantara Palazzo Naiadi Rome Hotel for the full concorso experience, book a day pass to pose next to vintage beauties, or don that special gown you’ve been saving and head to a black-tie dinner in a historic palazzo. After all, when in Rome…
And if you need a break from all the chrome and vroom, join one of the
Sketching Rome Tours. Designed for all skill levels, this relaxed, artist-led workshop takes place at
iconic locations like the Roman Forum, Colosseum and Trastevere, offering a quieter, more contemplative way to capture the city’s timeless beauty.
Venice
Arriving at Santa Lucia train station via high-speed train from Roma Termini, you’re just 10 minutes from the elegant Avani Rio Novo Venice Hotel, tucked away in a quiet residential pocket. Nearby architectural icons such as the Rialto Bridge, Piazza San Marco and the Grand Canal have been immortalised in literature, film and fashion shoots. They also feature prominently in every "Italy bucket list" itinerary, inevitably drawing substantial crowds.
Lucky for you, with Chic in Italy: Set-Jet Stays, you’ll get to know the Serenissima by actively participating in local life, far from the madding crowds.
The man behind the mask
Once checked in, it’s off to the Murano islands to explore one of Italy’s most storied crafts. In a secluded garden atelier, you’ll meet Augusto, a master mascarero whose creations have graced productions from Gossip Girl to Batman. With a few strategic touches of gold leaf, feathers and paint, you’ll turn a humble papier-mâché mask into something genuinely special.
Be sure to ask about the iconic bauta mask: a stylised human face with a pronounced nose that allows the wearer to talk, eat and drink without ever removing it. First worn in the 13th century as a way for Venetians to socialise freely across class lines, the bauta quickly became a symbol of elegant anonymity. With only a handful of original examples surviving today, Augusto’s insights into this and other historic designs are as captivating as his behind-the-scenes tales from the silver screen.
Molten moments: crafting glass with a Murano master
For your next adventure, you’ll remain in Murano, making your way across a constellation of islands stitched together by bridges in the northern lagoon. This time, you’ll be the guest of artist Andrea Penzo, whose work has been exhibited at the Venice Biennale and whose high-profile collaborations include the likes of fashion house Fendi.
Though Andrea is known for pushing the boundaries of what Murano glass can express, your workshop will focus on tradition: moulding molten glass into bespoke keepsakes using the centuries-old mouth-blown technique.
You’ll also learn to appreciate imperfections; subtle details like air bubbles aren’t flaws, but signs of authenticity.
Venice recast in candlelight
If you subscribe to the (absolutely valid) belief that there can never be too many candles but also worry about overproduction and harassing bees for wax, NH Collection Venezia Grand Hotel Palazzo Dei Dogi offers an alternative and an experience rolled into one. The hotel itself is worth a visit too, if only for a stroll through its stunning 18th-century botanic garden, complete with rose-lined pathways and a historic ice grotto.
The candles you’ll be making, using recycled soy wax collected from local churches, are part of the social initiative Relight Venice. Each one comes with a one-of-a-kind wooden stand, fashioned from walnut, apple or cherry wood scraps left over from crafting forcole, the distinctive oars used to row gondolas through Venice’s canals.
Row like a Venetian
For those seeking something a touch more athletic, yet no less authentic, consider adding a session of voga alla veneta to your 7-day itinerary in Italy. This centuries-old rowing technique, practised by gondoliers and regatta champions alike, involves standing upright and facing forward, offering both elegance and control, as you glide past faded palazzos and beneath stone bridges.
For a particularly Venetian twist, book a lesson through Row Venice, a nonprofit helmed by expert female vogatrici. Their signature Cichetto Row pairs the pleasure of rowing a handcrafted wooden boat with
well-earned pauses at local bàcari for wine and small bites.
Milan
With your suitcase already bulging with hand-poured candles, mouth-blown Murano glass, and hand-painted masks, you’re en route to Milano, where you might just need to pick up an extra bag. And make it a large one. After all, you’re heading to one of the world’s fashion capitals, home to storied houses like Prada, Versace and Missoni, not to mention some of the best vintage shopping in Europe.
Your Milanese home-away-from-home, NH Collection CityLife, was once a church and still retains its soaring columns and an air of hushed reverence. Nearby, a similar quiet awe awaits at the luxury boutiques of Via Monte Napoleone.
Past perfect: a vintage fashion safari
If your style leans more vintage treasure than fresh-off-the-runway couture, the hotel’s signature Vintage Italian Shopping Tour will make your heart sing (and your banker breathe easy). Laura, a seasoned style scout with an eye for timeless pieces, will guide you through her favourite Milanese haunts. Whether you’re hunting for the perfect leather jacket, a pair of retro sunglasses or something you didn’t know you needed until you saw it, she’s got you covered.
Prada, pastries and a touch of Wes Anderson
Your time with Laura ends on a sweet note with a Prada-branded pastry at the stunning Pasticceria Marchesi, a Milanese institution beloved by the stylish set. Marchesi’s world-famous panettone, now a year-round delicacy, is reimagined for every season: from apricots, lemon and almonds in summer to candied chestnuts, chocolate and figs in autumn.
Reinvigorated under Prada’s fashionable eye, the historic pastry brand is just one expression of the house’s cultural footprint in Milan. Another is the Fondazione Prada, a contemporary art complex that blends high culture with a common touch. It features a library, public gathering spaces and a pastel-hued café designed by filmmaker Wes Anderson as a love letter to Italian pop culture of the 1950s and ’60s.
Colour therapy: a custom beauty lab experience
On your final day in Italy, it’s only natural to feel a touch of melancholy. To lift your spirits and add a splash of colour, the team at Avani Palazzo Moscova Milan has arranged a personalised lip gloss-making session with City Lab Cosmetics. After a strong espresso on the hotel’s sun-drenched terrace, overlooking bustling streets filled with stylish Italians, your creative juices will be flowing.
Once at the lab, you’ll begin with discovering the shades that enhance your natural tones through expert colour-matching. Then, choose the active ingredients, select a flavour and add a pearl finish for extra luminosity. Finally, personalise the packaging with your initials and work side-by-side with a professional formulator to craft your very own lip gloss. The chic and practical souvenir will serve as a reminder that beauty, like travel, is all about self-expression.
There’s a chance, of course, that after completing this 7-day Italy itinerary you’ll be left craving more. And that’s perfectly fine. Because no matter how many times you return, there will always be a new district to fall in love with, a boutique with the softest cashmere to discover and more cobblestoned streets to navigate, whether in sensible shoes or stilettos, like a certain American with a flair for fashion and a knack for social media storytelling.
