Celebrating Italy in the Off Season

The delights of Italy are universal: clinking Negronis in Rome, spinning a Riva through Venice’s Grand Canal, island-hopping off the shores of Sicily, all interlaced with hefty doses of wine, mozzarella, and art. It’s this limitless allure that has travelers from all over the world descend on the boot with near insatiable fervency, and often all at the same time—at least that’s how it can feel when trying to claim an inch of the Amalfi’s rocky beachfront in July. But in arriving en masse, travelers risk muting the very thing they come to enjoy: the essence of the place, as conjured by the lifestyle that Italians pull off with aplomb.

As such, we are stealing a page out of the playbook of one of our favorite Italian tastemakers, stylist and writer Gianluca Longo, and declaring the off season the new season. These months, usually between September and April, are when the locals reclaim the corners of their country, and move more easily in their daily rhythms. In other words, it is when the most local version of Italy comes alive.

This isn’t just about skipping the crowds. Crucially, it is knowing that the Amalfi coast has extensive hiking trails and vineyards that harvest in autumn, and that Taormina, Sicily’s clogged-all-August resort town, is simply magic at Christmas, and that Lake Como’s foliage in November rivals that of New England’s. Seasonal destinations don’t just go poof! and disappear when the temperatures drop, but are dimensional, with year-round appeal, and the locals will tell you as much. So, we contacted top tastemakers in many of Italy’s most heavily touristed areas to tell us what they love most about their hometowns in less-visited times of the year. And if you need any more convincing, we gathered our top specialists—who know how to connect travelers to a place better than anyone—to share their own tips for pulling it off. Read on to start planning your trip to Italy in the off season. —Erin Florio and Maddalena Fossati

Restaurateur Francesco Panella’s Guide to Eating Your Way Through Rome in Fall

"I like places that are not famous. I'm used to gourmet restaurants, but places like Cesare al Pellegrino—a small 25-seater in Piazza Farnese—reassure me. I often stop at Roscioli's. If they're full, I eat on a stool. That’s how close we are; we've known each other since we were kids. I arrive and ask, ‘Me dai da mangià (Can you give me something to eat)’?" Read more here.

Florence Comes Alive in Fall, According to Italy Segreta Founder Marina Cacciapuoti

"I love weekend walks outside the city center when the air is cold, and you feel the literal and metaphorical warmth of a countryside restaurant upon entering it. The winter light is clearer, starker, and crisper. Maybe we appreciate it more just because the days are shorter and the weather colder, but the sunsets really do turn the sky the brightest pink. On some days, the visibility is so great that the Ponte Vecchio—seen from the Ponte della Trinita—looks like a painting with the hills extending infinitely behind it." Read more here.

How Artist Alessandro Florio Spends Winters in Taormina, Sicily

"Our climate is great year-round, and getting to enjoy the weather without the crowds is a perk. One captivating place is Casa Cuseni, an early 20th-century villa built by Robert Kitson, an English painter who moved to Sicily for love. It’s now a house museum with a delightful bed & breakfast, a wonderful place where some of the most important 20th-century intellectuals and artists stayed, such as Dalì and the futurist Giacomo Balla." Read more here.

Why Portofino Is Best in September, According to Filmmaker Francesco Carrozini

"When I stroll through the square, I can take my time chatting with the vendors. In August they are too busy for that. A favorite spot is Bar Jolly, where I’ll chat with the owner, Mauro, for hours. This place is wonderful—it channels 1950s Riviera with old-school stripes and wood lacquered tables. In August, there is so much glitz that passes through Portofino but in September that’s all gone and the place starts to feel timeless again." Read more here.

The Romance of Como in the Colder Months, According to Hotelier Valentina De Santis

"At this time of year, you either get crisp days when you can almost reach out and touch the opposite shore or romantic mornings when what we call la bruma—a kind of winter mist—rises off the water and everything is hazy and indistinct. You also get the most incredible sunrises and sunsets, and I love to go for long walks with family and friends in the chestnut woods. We always come home with bagfuls of chestnuts. Then begins the fun of roasting them." Read more here.

How Style Editor Gianluca Longo Spends Fall in Puglia

“For me, off-season travel is all about being able to actually connect with locals. One October, I was swimming in Porto Badisco, one of my favorite coves. I noticed these two older women with perfect hair on the shore with their foldable chairs. They were digging into a lasagne. I couldn’t resist chatting to them with the sneaky hope they would offer me a bite. And they did! Plus they had cold beers! We were there alone, just the three of us, chatting together for half the day.” Read more here.

Springtime in Venice Is Unbeatable, According to Author Alberto Toso Fei

“You can take a lesson in Venetian-style rowing along the city's smaller canals. If it's open, go to the island Lazzaretto Nuovo to see where preventive quarantine was developed in the 15th century. Or visit a few historic artisan workshops. Venice has very long traditions of glassmaking, goldsmithing, beadwork, textiles, mosaics, and boat building. In short, one can get into a different mood and tune into the city and its rhythm by finding ways to talk to those who live there.” Read more here.

Le Sirenuse's Aldo Sersale's Winter Guide to the Amalfi Coast

"Many small towns and villages celebrate their patron saints or local products with events that attract both residents and visitors curious to experience the Amalfi Coast like a local. For example, for the Sagra della Zeppola, a festival on Positano's Spiaggia Grande beach in late December, locals prepare the typical frittelle (deep-fried dough), pasta e fagioli, broccoli and sausage paninis, and pizza." Read more here.

How to Do Italy in the Off Season, According to Travel Specialists

“It’s a little bit of a local secret that fall proper is the best season in the Dolomites. Not only is there the changing of the seasons and the colors, but also a sensation of quiet that the locals find very welcome after what was likely a busy summer and early fall. They are keen to promote this time to visitors—over the years, I’ve been told by owners and general managers of hotels that this really is the best time to be here, you’re sharing the paths with fewer people and the air quality is amazing."

Credits

Lead editors: Erin Florio, Maddalena Fossati, Arati Menon, Sarah Allard

Editors: Sarah James, Sara Magro

Adaptation: Jaclyn DeGiorgio

Visuals: Andrea Edelman, Sophie Knight, Pallavi Kumar

Lead social media: Mercedes Bleth

Supporting social media: Lucy Bruton, Kayla Brock

Audience development: Abigail Malbon, Amber Port

Production: Erika Owen

Originally Appeared on Condé Nast Traveler