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Should you plan a winter city break to Italy in spite of the cold and short daylight hours? Family physician and society personality Iroshini Chua shares her experience and offers some practical tips.
On the back of the global travel resurgence, especially in tourist hotspots like the major European cities, many are already planning their next vacation. Demand for hotel rooms have sky-rocketed, while air tickets are getting snapped up quickly. Unless you’re gunning for a ski or snow-based getaway, the choices for a year-end trip to the continent aren’t great. The main gripe is, of course, the gloomier weather and short daylight hours.
However, Iroshini Chua discovered the charms of a quieter, sleepier Italy during her family driving holiday in December last year. Travelling with her other half Kevin Chua, and teenage children Jorim and Aiyana, she flew into Milan for a two-week jaunt that covered the Dolomites, Venice, Tuscany and Florence. She tells us more about their winter escapade and how to do it cleverly.

First Impressions
Italy was less crowded and more subdued, but we were warmly welcomed and extra attention was extended to us regardless of region. The overall sentiment was positive with the majority of people wearing masks. The scenery was such a change from urban Singapore! A regional itinerary was perfect – to be able to experience snow-capped mountains in the Dolomites to rolling hills of Tuscany, navigating the ancient waterways of Venice to the Renaissance architecture of Florence, all in the same trip. The cuisine varied subtly in each location, and we were able to enjoy the different offerings at each stop.

Winter Upsides
Winter is devoid of crowds in popular destinations like Venice and Florence. You can explore the cities at a slower pace like a local and have a truly immersive experience. In December, there is always the magic of Christmas with fairy lights everywhere and street festivities. For those who want to squeeze a little action in, the snow-capped mountains and skiing activities are only a few hours away. The spectacular cloudless sunsets alone are worth the journey in winter!
Health And Safety
The pandemic may look like it is in decline, but in fact it is now endemic with increasing reinfections and newer sub-variants. Although it may appear that international tourists and destinations are more relaxed now, you still do not want to risk falling sick – Covid-19 or not – during your much-anticipated break. Get your vaccinations and travel insurance in order. Familiarise yourself with the medical care available and stock up on travel meds. You should apply the same hygiene habits: avoid crowded spaces, wear a mask, wash your hands regularly and avoid touching your face. The main thing is to always be mindful about your behaviour and surroundings. During our holiday, we chose to self-drive in a rental car to avoid public transport, and stayed at properties that cocooned us somewhat, to be honest. Our experience was very private, devoid of crowds wherever possible.
The New Norm
There really was no need to check in any earlier than usual. For the several trips I have taken in the past half a year, I needed a couple of extra documents, such as the required Covid test results for some destinations, and proof of vaccination. I also heard from friends arriving at various destinations that immigration officers had asked about their purpose of visit. We had to wear a mask on board at all times except when dining. We also sanitised our hands more often. The business class experience generally remained the same, except that some carriers such as Singapore Airlines now have an online menu instead of a paper copy.

Smooth and Seamless Travel
I pick hotel brands that suit my travel style, and I have been travelling with Leading Hotels of the World and Aman Resorts for years. Their concierge services have been flexible with my itineraries, which are catered to my specific requests, and they had proven to be agile with any sudden change in plans. Let someone else handle the nitty gritty and allow yourself the time to enjoy the journey.
Favourite City
Definitely Venice. Everyone should see La Serenissima (the name for the former Republic of Venice) at least once in their lifetime. Better yet, do it onboard Aman Venice’s exclusive private boat, where you could go island-hopping and discover the lagoons’ best-kept secrets. We visited Murano, the centre of Italy’s artisanal glass-blowing industry since 1291, where I bought a chandelier for my new home); Burano, which is eponymous for its delicate handmade lace; and Torcello, for a terrific meal at Locanda Cipriani, where the likes of Queen Elizabeth and Elton John have dined. One of the charms of Venice is to get lost in its cobbled streets although it’s harder these days with Google Maps. Nevertheless, Venice is even more romantic during winter sans the crowds.
Amazing Aman
Imagine an intimate retreat with the warm, unassuming hospitality of a gracious private home. Now imagine this home being one of the eight monumental palazzos on the Grand Canal of the floating city of Venice! What greeted us as we stepped into Aman Venice: Rococo artworks juxtaposed against Jean-Michel Gathy contemporary interiors and two private gardens.

Our family was swiftly checked by very polished Aman staff into two types of suites: the 527 sq ft Palazzo Chamber Affresco overlooking the manicured gardens below, and the 613 to 957 sq ft Palazzo Stanza Canal Grande overlooking Venice’s famed Grand Canal. “We might as well have stayed in a museum; this place is so sumptuous and sensuous!” – I found myself thinking, as I soaked in the free-standing bathtub gazing up at a beautiful historical fresco lit up by a glittering Murano chandelier.
Ancient frescoes and gigantic chandeliers were everywhere – in the opulent dining venues, the leather-wall-clad library, hanging over the grand piano and in our spacious suites. We found plenty of lounges with ornate marble fireplaces to retreat to, and only ever crossed paths with other guests at the lobby. Staying at a palace in winter is magical to say the least, but to indulge in Christmas-themed dinner with my family in Aman Venice’s ballroom – which we had all to ourselves – with its gilded mirrors and stunning ceilings was unforgettable.
Most Memorable Sights
Florence is one of the world’s most captivating cities as it’s literally an open museum. A treasure trove of ancient art lies peppered around the city’s multiple piazzas. The vast dome of the Cattedrale di Santa Maria del Fiore, also known as the Duomo, is said to be visible from the Tuscan hills beyond, and always made me gasp in wonder each time I saw it. If I had to pick my absolute favourite sight in the city, it’d be Michelangelo’s statue of David displayed at the Accademia. As a doctor, I could appreciate the anatomical precision with which the single marble block was carved to replicate David’s muscles and sinew as he tenses up, ready to face Goliath.
During winter, Florence is also illuminated with a myriad lights and soaring Christmas trees. The setting of the Christmas markets, offering Italian crafts and traditional festive treats like panettone, are a delight for the senses. You can really get into the Christmas spirit by discovering the many sacred artworks and frescoes depicting the life of Jesus.
Superb Service
There is impeccable service, then there is Inimitable service. Italian roads can be narrow and tricky, especially in Florence. After the final stretch of the drive to our hotel Portrait Firenze, we parked our car as close as the GPS would guide us without breaking any traffic laws, and walked the last 200m there. Upon arrival at the property, which is conveniently located a few steps away from the Ponte Vecchio, the hotel staff immediately saw to our welfare and comfort without hesitation. They solved our parking dilemma, hauled our luggage out of the car, showed us into our beautifully appointed 624 sq ft Family Suite with panoramic views of the Arno River, and even returned our rental to the airport – all within half an hour.
One of The Leading Hotels of the World, Portrait Firenze is part of the Lungarno Collection hotels created by the Ferragamo family. What really shone for us was its service, a very important aspect of our long-awaited journey. Travelling during a pandemic can be chaotic, no thanks to sudden changes of plans – from date alterations and cancellations to rebookings, and restaurant venue changes to updates in Covid test requirements or arrangements. The hotel managed all this even before we ever stepped into its Ferragamo signature-scented reception lobby.
The staff planned, anticipated and customised our stay with practiced perfection. If bespoke hospitality was an art, Portrait Firenze had made a masterpiece out of it. In keeping with the Salvatore Ferragamo heritage, the hotel is stylish with contemporary interiors and artworks from the family’s private collection.
We were provided with plush robes in the bathrooms, crisp white linens in the bedroom, and we found touches of Hollywood glamour and footprints of the Ferragamo brand in the entire suite. We couldn’t have been better located in Florence with the city’s fashion district being just a short distance away and the city’s highlights and food institutions closer still.
Winery Recommendation
Driving through the rolling hills under the Tuscan sun and tasting some beautiful 100-pointer vintages from Casanova di Neri is highly recommended. We had bottles shipped cellar-to-door and its flagship Cerratalto label, a Brunello di Montalcino DOCG, was our top pick.
Dine And Lounge
Have you ever had a bad meal in Italy? It’s impossible! Our favourites include Enoteca Pinchiorri in Florence not just for its three-Michelin-starred fare but also to feast your eyes on their extensive cellar. Despite the low temperatures in Venice, we couldn’t resist Gelatoteca Suso and eating streetside fritto misto (fried seafood).
Nothing beats capping off the end of each day with a beautiful sunset. The rooftop bar of Aman Venice gave us a bird’s eye view of the city’s famous roof tops. Our suite at Forestis in the Dolomites presented a picturesque view of the snowcapped mountains basking in an ethereal orange glow. At our resort-of-choice in Tuscany, Rosewood Castiglion Del Bosco, the poolside was the perfect spot to catch the candy-floss pink skies over the vineyards.

Pack Smart
I always decide on a specific colour palette for my trip so that I can easily mix and match items. I also pick pieces with mileage. For example, my Chanel boots can be worn as ankle boots with a gold heel, or as knee-high and waterproof footwear for the slopes. Packing for winter is a bulky affair to begin with and this helps me to manage overpacking. Besides, visiting major shopping havens in Europe allows travellers to purchase new pieces to add to their travel wardrobe. As soon as I landed in Milan, I headed to the shops for outfits in the current trends. Look for key pieces such as jackets, boots, scarves or hats to update your style for the winter.
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