Many would argue that spring and fall are the best months to travel to Tuscany: The weather is perfect, the crowds are minimal, and the wine harvest is plentiful. But Massimo Ferragamo, chairman of Ferragamo USA and founder of Rosewood Castiglion del Bosco estate in Tuscany, tells us why you should be planning a Tuscan getaway this winter.

Massimo is the youngest son of Salvatore Ferragamo, who was often referred to as the “shoemaker to the stars.” Over a decade ago, he purchased a 4,200-acre estate in Tuscany and turned it into a truly tranquil escape. Normally closed during the winter months, Ferragamo decided to offer a Winter Villa Escape package at his Rosewood Castiglion del Bosco estate through April 12.

What made you decide to open your villa during the winter?

We wanted to share the pleasures of Tuscany in the wintertime with our guests, and there is no better way to have a truly Tuscan experience than staying in a villa. They offer a real home-away-from-home feeling and are the perfect retreat for reading, enjoying a glass of brunello by the fireplace, painting, and simply indulging in quality time with your loved ones.

What do you love about Tuscany in the winter?

Many travelers associate Tuscany with summer travel or the fall wine harvest, but the Italian countryside is a magical wintertime destination that is worth discovering.  The region offers a number of vibrant seasonal activities to partake in, while also serving as a breathtaking backdrop for deep relaxation and reflection. I love driving around Tuscany in the winter, exploring different Tuscan towns and getting lost in the rhythm of village life.  There is always a new shop or restaurant to discover, and you don’t have to fight the crowds that you sometimes face in the warmer months.  

What can you do in Tuscany during the winter that you can’t do during the warm weather months?

There are so many vibrant seasonal activities: markets, local fairs, and special attractions that are often missed by tourists who consider this time of year the off-season.  Carnevale, for example, starts at the beginning of February and is a month-long celebration that includes masquerade balls, lively parades, traditional dishes, and over-the-top gatherings. Tuscany, Viareggio, Lucca, Arezzo, and Florence are all known for their Carnevale festivities. Benvenuto Brunello, the event at which the new brunello vintage is released, is also something that should not be missed during February, and the exhibition held in the center of Montalcino is open to the public for the first time this year.  

What does your estate offer guests during the winter?

Rosewood Castiglion del Bosco is located in the beautiful Val D’Orcia, a UNESCO World Heritage Site and possesses a rich legacy and deep roots within Tuscan history. The property boasts much of its original stone walls and even medieval frescoes painted by Sienese artist Pietro Lorenzetti, which can be found in the Church of San Michele in Rosewood Castiglion del Bosco’s Borgo. During the winter, we offer travelers the ultimate Tuscan hideaway. During the winter months, guests can enjoy tastings and tours at the on-property winery, one of the largest brunello di Montalcino producers in the region, and play a round of golf at Rosewood Castiglion del Bosco Golf Club, Italy’s only private golf club and home to an 18-hole golf course designed by acclaimed British Open–winner Tom Weiskopf. Unfortunately, our on-site restaurant will be closed but there are many restaurants and markets nearby.

Where do you recommend visitors dine during their stay?

My favorite restaurants in the area are Drogheria Franci and Pizzeria San Giorgio in Montalcino and La Porta di Sotto in Buonconvento. I go to these local osterias because I know I can find simple and genuine Tuscan food like homemade pici pasta, Fiorentina T-bone steak, and wild boar.

What markets and shops do you visit often?

Tuscany is renowned for its high-quality artisan products, from handcrafted leather goods to fresh pasta and locally foraged truffles. Travelers interested in taking home some regional culinary delights should stop by Enoteca Fortezza in Montalcino for an incredible selection of Tuscan and Italian wines and Mulino Val D’Orcia for organic pasta made with ancient, local grains. For fashion lovers, I recommend stopping by Pianigiani Leather Shop in Buonconvento for custom-made leather accessories and Montalcino 564 in Montalcino for a selection of high-quality Italian textiles.

Are there any day trips from Tuscany that you recommend?

Tuscany is filled with charming hillside towns and villages, ideal for day trips and shopping excursions. If I have a moment, I always stop by Seggiano to dine at the region’s only Michelin-starred restaurant, Silene, or visit Pienza to sample some pecorino cheese.

What are some insider tips on how to do Tuscany like a local during the winter?

Though many travelers are aware of Tuscany’s autumnal grape harvest, few realize that the month of February is also a particularly exciting time for wine lovers as well. February is when many producers release their new vintages of brunello di Montalcino. There are two events that are very exciting: the Benvenuto Brunello that I previously mentioned and the Brunello Crossing. The Brunello Crossing is a non-competitive race that takes place over two days, February 11 and 12, in the breathtaking Montalcino countryside.  It includes guided tours of wineries to highlight the connection between sport, land, wine, and food.

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