Looking for a last-minute getaway over the holidays? Or maybe you’re contemplating where to spend next year’s PTO on a vacation. Italy is always a good idea no matter when you decide to visit, but there’s no better time than the winter off-season to avoid crowds and snag deals on boutique hotels. 

Whether you’re visiting for the first time or you’ve visited before, Italy typically conjures images of the usual suspects: Rome, Florence, Venice. While these cities definitely deserve a return visit, here are three alternatives to explore a different, calmer side of The Boot. 

Lake Como

Dreaming of vacationing like Clooney? Besides its most famous resident, Lake Como is known for being a haven for plenty of other celebrities and power players, but that doesn’t mean a trip here has to eat into your savings. Not only will you take advantage of more affordable lodging costs during off-season (October-March), you’ll also witness the gorgeous snow-capped mountains surrounding the lake, too. 

Where to stay

A beautifully updated 19th century Airbnb house in Cadenabbia. Nestled near Tremezzo, the house is a quick ferry stop to visit the surrounding towns.

If you’re looking to treat yourself a bit more, Filario Hotel is an ultra-sleek boutique hotel located right on the water in Lezzeno. 

What to do

Explore Villa Balbianello to see the luxurious grounds where movies like Star Wars and James Bond were filmed. Villa Carlotta, a famous museum with sprawling botanical gardens housed in a seriously ornate mansion, is also nearby. 

Visit the famed town of Bellagio. Those postcard images of Lake Como? Probably taken in Bellagio. Which means it can get busy (read: ultra-crowded) during peak season, but slows down significantly during the winter for travelers to enjoy the restaurants, shops and picturesque streets in peace.

Stroll down the cobblestone streets of Varenna, a more laid-back version of Bellagio, and climb a system of narrow staircases lined with quaint houses to admire. You can also hike the Wayfarer’s Path nearby for incredible views of the lake.

Rent a speedboat and see Lake Como from a different perspective. Try Boat2Go for 2-3 hour rentals complete with a complimentary beverage cooler. Guests at Filario Hotel can book a boat directly from the property. 

Where to eat

Ristorante Bella Vista

Via Zerboni 6, Veleso

Ristorante Bella Vista offers spectacular views and local food in the mountains overlooking Lake Como. Up a steep mountain peppered with switchbacks, the restaurant can be reached by car (drive slowly). Get their tomato pesto and prosciutto bruschetta, risotto with peas and cream, and polenta. Visit during lunch for the best views.

Da Abate

Frazione Villa, 4, Lezzeno

You’ll find extremely fresh and tender seafood at Da Abate. It’s hidden away down a flight of stairs, where you’ll find an intimate patio packed with diners sipping house wine. You can’t go wrong with any of their white fish options in butter sage sauce. 

Cafe Bistrot

Contrada Scoscesa, 13, 23829 Varenna

A quiet cafe right by the water in Varenna where you can grab an espresso and people watch on a lazy afternoon. Don’t sleep on the bruschette here though, it was one of the best I’ve ever had. Pancetta and peach is an unexpected flavor combo that will make you wonder why you haven’t tried it sooner.

Quick tips

Make sure to book tables for meals in advance to ensure restaurants are open on the day you’re planning to visit.

The best way to reach Lake Como is by flying into Milan and renting a car. The drive is about an hour and a half from Milan to the lake.


If you’ve ever wondered where heaven on earth is, Tuscany comes pretty close to being it. Every hour seems to be golden hour, with glimmering sunlight hitting the endless rolling hills and picturesque cyprus trees like a Renaissance painting come to life. In a region known for its wine and cheese, this is definitely a bucket list trip for all food lovers. 

Where to stay

Querceto di Castellina is a family-owned full service bed and breakfast located in Castellina di Chianti. With a vineyard that produces great wine (try their unique, crisp white blend called Livia) and classic Tuscan cottages featuring updated farmhouse architecture and all the modern amenities you could need, you might never want to leave. The owners also host a multi-course dinner in their idyllic vineyard with wine pairings throughout the year, so be sure to check availability when you book your room. 

What to do 

Experiencing a wine tour is a given. To start, check out Castello di Verrazzano for their Chianti Classico and Vin Santo, and gradually make your way down the Tuscan countryside. 

Drive through Val d’Orcia, a UNESCO World Heritage site with unbelievable views and high quality local wines like Bruncello di Montalcino, Vino Nobile di Montepulciano, and Rosso d’Orcia. 

Have a pecorino cheese picnic near Pienza at Cugusi di Cugusi Silvana, a farm known for its cheese in the valley. They’ll pack up your cheese, cured meat, fruit preserve and wine selection into a picnic basket with cutlery and cups for you to enjoy al fresco on their property.

Take a day trip to Siena, a nearby walled Medieval town known for its cityscape and food. Spend the day wandering around the streets that are seemingly frozen in time. 

Where to eat

Osteria la Porta

Via del Piano 1, 53026 Monticchiello, Pienza

Try local delicacies here like truffle and pecorino over pasta. Make a reservation to dine on the terrace to enjoy your meal with yet another insane view of the Tuscan hills. 

Officina della Bistecca

Via XX Luglio, 11, 50022 Panzano in Chianti 

Have you watched the Chef’s Table episode on Dario Cecchini? If you haven’t, you should. And then promptly book a reservation at his Florentine steakhouse for a simple, fun meal done to perfection.

Quick tips

During late autumn and winter, holiday markets pop up around Carnival for your gift shopping needs. There is also an abundance of designer outlets, with the largest one being The Mall, where you can snag luxury goods for a fraction of their retail price. 

To get to Tuscany by air, fly into Florence and rent a car. From the airport, the drive is about 40 minutes without traffic (but you should expect some traffic). 

Cinque Terre

The five fishing villages scattered along the Mediterranean Sea are collectively known as Cinque Terre. It’s an otherworldly place, each village with a unique personality of its own. The destination has become massively popular throughout the years, causing the local government to warn travelers that a cap on visitors may occur in the near future. Summers are often unbearably crowded, making Cinque Terre another great option for off-season travel. 

Where to stay

Il Giardino Incantato located in Monterosso al Mare is everything you could want in a B&B. Are you someone who likes breakfast cooked to order in the morning and waiting for you in a private lemon tree garden? I am too. Fausto and Mariapia own and manage the beautiful property tucked around an unassuming corner in Monterosso, the main village where inbound trains arrive. 

What to do

Hike the Sentiero Azzurro (the Blue Trail) from Monterosso to the last village of Riomaggiore in time for sunset. The entire hike takes a leisurely 9 hours, including short stops at each village along the way (Vernazza, Corniglia, Manorola). Once you arrive in Riomaggiore, take a moment to enjoy the sunset, and then stop by a local restaurant for a seafood dinner or take the train back to your home base. 

Where to eat

You’ll find that most of the small hole-in-the-wall shops serving focaccia, gelato or calamari have excellent food. To start, grab a cone of fritto misto from Il Bocconcino for some of the freshest fried calamari, cod and shrimp. Vegetarian options are available too. 

Quick tips

Make sure you purchase the Cinque Terre trekking pass beforehand to avoid being turned away due to trail capacity. 

The closest airports are Florence and Pisa. You can take a train to La Spezia and transfer to a direct train to Monterosso. Once you arrive, the best way to explore is by foot and train. 

Have you been to any of these places? Do you have your own suggestions of must-see spots in Italy? Let us know in the comments below!