Trip Inspiration: A Winter Escape to Italy

Dreaming of an Italian getaway without the crowds? Try a winter escape.

You saw it on my Instagram account first: I’ve got Italy on my mind. This month, the hubs and I are heading back to the land of vineyards, gelato, and cliffside lemon groves. We’ll stick to Rome and the Amalfi coast, but you can bet narrowing down the itinerary was hard work. What part of Italy isn’t worth seeing?

The best time to visit Italy

There’s only one downside to Italian holidays — the crowds. That’s why my favorite time to visit has always been shoulder season, in the spring or fall. But these years of planning trips for others have opened my eyes to how each destination offers something different through the seasons. For instance…

Italy in winter? Pure magic.

Imagine a dust of snow over rolling Tuscan hills,. The warmth of candlelit tables spilling light onto the twisting alleyways of Positano. A romantic mist rising off Venetian canals. Not to mention Italy’s own corner of the Alps, where were designated a UNESCO World Heritage site in 2009.

A winter Italian escape is the perfect glimpse of the quieter, intimate side of a country that will be gorgeous no matter when you choose to visit. If you’re up for a European winter vacation and haven’t considered Italy before, here are my insider tips.


What could be more festive than cozying up to blazing fire (sparkling wine in hand, of course) at an Italian holiday market? The holidays usher in dozens of Christmas markets across the country. Each one offers local handmade gifts and pastries. I’ve heard the street markets in northern Italy, and especially the Trento street market, glow with Christmas charm.

And then there’s New Year’s Eve. Hello, Franciacorta and Prosecco. I’m dying to plan a NYE itinerary in a bustling Italian city — like Turin, at the foot of the Italian Alps (a perfect way to kick off a luxury ski trip, am I right?) or Rome, where the height of celebration takes place in Piazza del Popolo.

Depending on the region, winter getaways can extend a couple months into the new year. Valentine’s Day in Italy is known as ‘La Festa Degli Innamorati,’ the ‘feast of lovers.’ Romeo and Juliet’s hometown of Verona even hosts a festival, Verona in Love. Spending Valentine’s Day in the ‘Land of Love’ with your sweetheart — how much more romantic can it get?


Italy is a popular summer destination because of its beaches, sunny Tuscan countryside, and — yes, I’ve already mentioned this — creamy gelato. It makes perfect sense in the summer. And while I’m convinced it’s a perfect winter destination too, it’s important to know that certain regions are more winter-friendly than others. My recommendation?

The Dolomites. These mountains have a lot of competition with the Alps so nearby, and yet skiers keep coming back for more. Dolomite rock has pink undertones that glow in the sunlight, creating brushstrokes of rosy light in the sky. Aside from being gorgeous, the slopes are perfect for hiking, skiing, and snowshoeing your way to the evening après-ski scene.

Rome. Rome in winter still has all the activity without the flocks of camera-clad tourists. If you’re hoping to get a more up-and-personal look at one of the most iconic cities in the world, you’ll love winter in Rome. Temperatures are cool without the Alpen bite. Especially in January and February, popular sites like the Colosseum will seem almost empty. It’s a photographer’s dream.

Why you should visit Rome in the winter

Sagre. A series of events rather than a location, Italy’s sagre are food festivals that pop up all over the country. Sagre, though year-round, are particularly welcoming in the winter months. Each village hosts these local foodie celebrations on different dates, so it’s important to have a well-planned itinerary. The January festival in Naples includes dozens of celebrations around community bonfires, where participants indulge in  hearty soups and stews. I can’t imagine a more authentic Italian experience than spending a winter holiday traipsing between villages, sampling some of the best local Italian fare the villages have to offer.

Sicily. If you want to experience Italy’s winter magic without the chill, I recommend Sicily. From November-February, the island gives you perfect sweater weather! Another advantage is enjoying a different season of fresh seafood than most visitors to Sicily (I’ve heard the sea urchins are best in February!). If you’re a history buff, winter is the time to check out the archaeological sites without the usual crowds.

Venice. If you’re already a Venice traveler, you’ll know about the intricate, ornate masks behind the glass at boutiques across the city. It’s nearly impossible to duck down an alleyway and not come upon a selection of costumes for Italy’s own mardi gras. So why not stop in during the height of it all? Carnivale is scheduled according to the Lenten calendar, so it does vary from year to year (typically between February 3rd and March 9th). There will be parties and parades, with celebratory food and drinks for everyone. It’s an exciting winter festival that manages to be both traditional and thoroughly modern. If you’re the adventurous type, why not plan a trip to attend some of the most lavish masquerade balls in the world? And don’t forget — you can look forward to unwinding in your luxury suite at one of Venice’s historic hotels or boutique private apartments when the celebration is over.

Why you should visit Venice in winter

As I’ve said before, paradise is personal. There’s no way to cover all Italy’s winter escapes in one article, so I’m hesitant to give specific recommendations until I hear from you first! If you are interested in exploring this eternally mesmerizing country (seriously, is there anyone who doesn’t want to visit Italy?), let me know if I can help. And if you’re dreaming of a different winter destination, don’t hesitate to get in touch about that too! Now is the perfect time to get started on early 2020 travel — and it’s not quite too late to dream up a luxury trip for the festive season either.