READING: Keyyes Insider: Holiday Like A Ferragamo In Tuscany
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MASSIMO FERRAGAMO HAS CALLED NEW YORK HIS HOME for the past two decades. It was in the city that Salvatore Ferragamo’s youngest son oversaw the expansion of the family’s fashion empire. But Massimo found himself being called back time and again to his original home — the sun-drenched, wine-soaked region of Tuscany.

“It is easy to fall in love with Tuscany,” he notes. “But I grew up there and I lived there for most of my life… Tuscany has always been in my heart.” Today, the Italian native splits his time between New York and the lush, mountainous region he calls home.

Massimo recalls an enviable childhood. The Ferragamo siblings frolicked in the rolling hills where nature was their playground.

“We grew up very much in the outdoors. I would often hide in the woods. I would build my own toys. My older brother helped make a wooden cart in which we could ride downhill,” says Massimo, who thumbs through copies of old family photos as he speaks.

As an adult, he fell further in love with Tuscany. This time, it was because of Castiglion del Bosco — a charming estate in the winemaking capital of Montalcino. “I had no idea that such a beautiful corner of Tuscany still existed,” says Ferragamo, who is the chairman of Ferragamo USA.

The picturesque Tuscany landscape from Massimo Ferragamo’s property, Castiglion del Bosco, is a painting brought to life.
The Ferragamo family on the roof of the Palazzo Spini Feroni in Florence, Tuscany.

He bought the 800-year-old property (complete with its vineyards that grow Sangiovese grapes) in 2003, subsequently transforming it into an upscale resort. The Tenuta produces Brunello and Rossi di Montalcino, as well as grappa and olive oil.

Besides vineyards, the 5,000-acre piece of land is home to fields, forests, and a golf course. The medieval stonewalled village nearby takes visitors on a trip back in time and is a designated UNESCO heritage site.

Keyyes asks Massimo for his best tips for travellers to the region.

If you’re not a wine drinker, what else can one do in Tuscany?

A million things. It depends if you want to relax, or have wild parties. In the summer, Tuscany is all about resorts and the seaside. Think Forte Dei Marmi. Throughout the year, there are plenty of great activities to do in the countryside. I love hiking and biking. Just on our property, we have 250 km worth of hikes.

You can go truffle hunting with dogs in San Giovanni d’Asso, which is very close to Montalcino. You can actually do this all year round because there are always the black truffles, white truffles. The ideal season would be the end of September to November. Generally, the uglier the dog, the smarter the dog is in finding truffles. They are generally mutts, they are street smart. A good hunting dog can be worth 10 to 15,000 euros.

Where should you be based in Tuscany, if you want to explore the region?  

I hate to say it — the best part of Tuscany is in Montalcino. From there, you can visit Pienza, San Gimignano, Siena, Montepulciano. All are beautiful villages. They also have great restaurants. You could be based in Montalcino and go on day trips. Or you could go from one town to another, and stay in nice bed and breakfasts.

You should see San Gimignano. It’s filled with tall towers from the 13th and 14th centuries. They were built to demonstrate who was the richest signore in town. It’s the same concept today. If you want to show you are powerful, you want to build a tower that’s taller. The same in New York, Hong Kong, and Singapore.

What’s the one restaurant you’d recommend going to? 

If you stop in any simple place, you are going to eat well. You are never going to be disappointed. In the countryside, you go to Il Leccio in Sant’Angelo. Hopefully, you like meat. You can have a nice Florentine steak. It has a very good, charcoal grill flavour. Inside the meat is red but outside it’s really well cooked. The texture of the inside with the outside, it’s perfect.

Where would you go for a drink? 

In the main square of Montalcino, there are beautiful 14th-century tower and bars all around. They are all good. You have to judge with your eyes. That’s better than me suggesting. Some have outdoor seating areas, some are more like coffee bars, wine bars. I’m very boring — I drink wine. I would take a very nice glass of red Brunello.

When is a good season to visit?

Always. I’m serious. But I can tell which months you could try to avoid just because it’s cold and rainy — January to the middle of February.

My favourite months are September and October because the climate is fabulous in Italy. There is the harvest. Obviously, it is a very important moment for the winery. It’s cool at night, in the day it is around 70, 75 degrees Fahrenheit. It’s not too hot, but it’s good enough weather to enjoy the pool and other activities.

Rosewood Castiglion del Bosco
Montalcino, Siena 53024, Italy
T: (+39) 0577 1913001

One of the best-preserved estates in Tuscany, Castiglion del Bosco, which is a Rosewood hotel in addition to being a wine-producing tenuta.