"We have an expression in Italy: Buttare il cuore oltre l’ostacolo. It means throw your heart over the fence and the rest will follow.”

Massimo Ferragamo smiles and looks out at the view from our perch on the terrace. Before us the Tuscan hills collide into one another as cypress trees point straight as arrows into cloudless sky. Wildflowers bloom among fescue grass swaying in the soft breeze, swifts dart through the sky in formation, the sun is golden; it’s a watercolour in 3D.

This is Castiglion del Bosco – a one-time dilapidated village and winery in the beating heart of the Val d’Orcia, now transformed into one of Europe’s most unique resorts and private members clubs. Massimo, youngest son of the great Salvatore Ferragamo, purchased the property after falling irrevocably in love at first sight.

Heart flung firmly over fence, the fashion mogul spent the last 21 years transforming the 4,200-acre estate into an achingly stylish playground for the privileged few. The 800-year-old borgo (or village) has been transformed into a Rosewood hotel: 23 suites, a luxurious spa and beautiful dining options.

What can I say? I like to take risks. I like confrontation. I like the challenge!

The tiny church of San Michele Arcangelo, complete with (of all things) a Pietro Lorenzetti wall painting, is now restored to its former glory, and the castle itself (Castiglion del Bosco meaning ‘castle in the wood’) stands as a ruin among newly landscaped gardens – an affectionate reminder of the past.

Elsewhere, the rackety old barns have become 11 private villas sitting in their own quiet solitude, while the unloved winery, belonging to the revered Brunello di Montalcino denomination, has returned to its former pomp. Few wines in the area now match this 100% sangiovese Tuscan red.

The growing group of private members enjoy exclusive access to a golf course designed by architect and former-Open champion Tom Weiskopf, while a wine club, available with a Bond-like vault for storing one’s wine, is on hand for those who wish to combine oenophilic and sporting pleasures. It’s a giant undertaking for anyone, not least a guy who was originally looking for a small plot of land to build a villa for his family and friends, and grow a little wine…

You know that big shiny toy you wanted as a kid? The thing your mum told you was too expensive, but that made you want it all the more? Massimo wears the grin of a man whose mum caved in and bought it for him anyway – the kind of unbridled joy that happens all too irregularly in life: “What can I say? I like to take risks. I like confrontation. I like the challenge!” Well, he isn’t the son of Salvatore for nothing.

Apples don’t fall far from the tree

In 1914, a 16-year-old Italian shoemaker by the name of Salvatore Ferragamo arrived in Manhattan for the first time. The Statue of Liberty back then was still a shining beacon of possibility and, after registering at Ellis Island, the young man set out to pursue his version of the American Dream.

“He had just a few dollars in his pocket, but he was here to follow his passion of making shoes – despite his family’s wishes,” Massimo explains. “In Italy, a shoemaker was the most humble job you could choose, but he didn’t care, he didn’t listen, this was his dream.”

As the movie industry grew in prominence in the 1920s, Ferragamo found himself designing footwear for the icons of the era. He opened the Hollywood Boot Shop in 1923 – Marilyn Monroe, Eva Perón, and later Judy Garland would soon come through its doors, crowning Ferragamo ‘shoemaker to the stars’.

You could call it the dawn of influencers: the biggest names in film wearing one man’s designs. Unsurprisingly, it wasn’t long before the Salvatore Ferragamo name was synonymous for glitz and glamour.

Fast forward to modern day and the brand is a public company that encompasses all areas of fashion, as well as its famed footwear. From one teenager’s dreams to a brand that posted sales of €1.35bn in 2018: it’s a rags-to-riches tale worthy of the silver screen. Massimo and his siblings followed Salvatore and his inimitable wife Wanda – the driving force of the brand after the designer’s death in 1960 – into the family business.

As US chairman of Salvatore Ferragamo, it’s been his role to ensure the company “never forgets America’s part in our history”.

In our exclusive interview, we traverse the world of fashion and travel, wine and golf, to find out more about the Ferragamo name – past, present, and future…

Even within the diverse world of fashion, the story of Salvatore Ferragamo is unique. It must be a source of great pride for you.

I have to say, it’s really a great story and a tremendous thing for our family. I’m on the board of the Ellis Island Statue of Liberty Foundation and recently we opened a new museum at the Statue of Liberty. On the wall when you enter the museum there are 50 stars on the American flag that can be dedicated to a person. There’s some great people on that wall – and we dedicated one of the stars to my father and mother. It’ll be there forever, so it was a very moving and nice thing to do.

My father came to the US 100 years ago. It’s a different story because most brands from Europe don’t begin life in America and then come back to Italy to further establish their company. He was lucky in the moment that the movie industry was just starting and he had an opportunity to make shoes for the set, and that’s how he became famous.

Honestly, I didn’t think I was going to join the family business

His personality and everything convinced these stars to keep on being his customers, so in the beginning he was only making shoes for the actors and actresses of Hollywood.

When my father passed away in 1960, I was only three years old and my mother is probably – without taking anything away from my father because we wouldn’t be here if he didn’t start it – the most important person our company has ever had. Without her, it wouldn’t have had the same continuity.

Only a person like my mother could have done what she did. She was a woman running a fashion company in Italy in the 1960s – an incredibly challenging position to be in, but against the odds she succeeded. My mother passed away 18 months ago at the age of 97. She was just a fabulous lady.

As we grew up, we joined the company – my mother never imposed that we join the family business or what we should do in the company, but everyone found their way into Salvatore Ferragamo. My sister Giovanna is more involved in the creative side and my brothers went into the business.

Honestly, I didn’t think I was going to join the family business, but after I worked for six months at Saks Fifth Avenue we opened an office in America. I did six months there, that became three years, and the rest is history.

When my father started, it was the Hollywood actors who loved his shoes: they were comfortable but also very sexy

I think it has always been a company that is very much family guided and family influenced – and still today we are public and all of us have board positions now we’re not in the day-to-day running of the company anymore. It has to have that DNA to continue the work of its founder and carried on by my mother, otherwise we are just another company.

What would your father think of the world of fashion in 2019?

In my opinion, the best form of advertising – you can choose whatever you want: print, digital, social media – is word of mouth. It’s true for the wine, it’s true for fashion, for brands, for cars, everything. The reason this is true is because it is a person who is convinced who is telling you to do this.

When my father started, it was the Hollywood actors who loved his shoes: they were comfortable but also very sexy. They would talk to each other and that’s how the name started to become famous.

There was no such thing as print advertisement at the time. So to answer your question, my father had a gift: he always saw two years ahead what was going to happen – and I think he would do the same if he was here today. He had an incredible vision and an incredible talent.

I think if he saw what fashion is today, he would not be thinking about it for how it was when he was doing it, I think he would bring a fresh mind.

Today, the fashion world is incredibly interesting with a lot of great aspects, but there are other aspects that don’t belong to the DNA of Salvatore Ferragamo and I don’t think he would want to pursue those aspects. But the fact that the world evolves and digital is so important would have meant he had to evolve, too.

Things like streetwear wouldn’t necessarily be seen to work with the DNA of the brand, and certainly differs to Italian high fashion. Is that something you find interesting?

I’m happy that I’ve never been on the creative side of Salvatore Ferragamo because I’m not creative in that way. But I think it’s important to always be relevant, modern and up-to-date in the eyes of the consumer.

I don’t think we would ever cross certain points in terms of style, but in terms of perception we don’t want to appear too classic or out of date.

A good product is in the combination of emotional triggers and fine craftsmanship

Even if the clothes are the same, what that brand has to trigger in your mind has to be that it is up with the times. It’s about working on the brand: there is a reason why people get an emotion for a Ferrari and not something else, when something might be just as good.

But a good product is in the combination of emotional triggers and fine craftsmanship, so it’s very important to work on what creates that feeling towards a brand.

It seems the way Ferragamo, through newly appointed creative director Paul Andrew, is modernising is by weaving in technology into classical pieces.

My father was truly ahead of his time and we’re lucky at Salvatore Ferragamo because we have a patrimony of old design drawings and shoes that provides constant inspiration.

We take that inspiration and bring it into the 21st century using modern techniques. If you do it well, it isn’t copying the past but it is influenced from the past. I think we’ve always done a great job of that.

What does the future hold for the brand?

It’s hard for me to say now, but I think it’s really about listening to what the outside world is saying and being able to always give the best of what we as Salvatore Ferragamo have done as a brand for a long time now.

I have no doubt there will be interesting challenges for a lot of brands in the future. I’m not talking about fashion only, but other sectors, too.

The car world, for example, is changing dramatically year on year. So how does a brand stay relevant 50 years from now when a lot of the habits that we grew up with and are used to change completely?

Companies need to be looking hard at what’s over the hill – and at the same time they need one eye in their rear-view mirror on where you have come from. It’s about evolving, looking at every facet of the business, and seeing what people want and moving towards that.

Even here: we look around us at this beautiful place – the view and the terrain is largely untouched for hundreds of years, we’ve protected that but still we have to think about what people want today. That’s what Castiglion del Bosco is all about, and Salvatore Ferragamo is the same.

Talk to me about Catsiglion del Bosco. It was some leap of faith you took on this place…

Once you get to this place, that's the problem – it's better not to see it, then you're fine! It's true, I was looking for a smaller place to own some villas and have my own wine. I was born in Tuscany and lived in America for many years, and so to have a place in Tuscany was something I wanted very much.

Between the beauty of this estate and the Brunello denomination, which is one of the most prestigious in Italy, I just fell in love. My friends thought I was crazy – they were probably right – but it was really the fact that wherever you look you really don't see anything that spoils the view.

The combination of land and houses and, most of all, the fabulous vineyard that is perfect for winemaking. The winery was one of the oldest houses of Brunello di Montalcino and also one of the largest, so that was very intriguing, but it had been neglected over a number of years.

It was much bigger than anything I had imagined taking on, but this is my legacy. I couldn't say no – and I’m glad I didn’t.

Did Chiara, your wife, have a lot to do with the decision, because obviously her vision in the interiors of the property has been realised so well.

She was definitely pulling back on the decision! "Are you sure you want to do this, Massimo?" But that's how things work between us – I always want to do things and she is a little more cautious.

After we decided to go ahead with the property, though, she has participated with all her heart and I hope she always gets her mention for what she has done with the interiors. Chiara found a fabulous decorator called Teresa Bürgisser Sancristoforo and together they worked very closely to bring the property to life.

I cannot tell you how much they did. They went all around Europe finding furniture and great artisans to help restore individual pieces. Sometimes they'd come back with a piece of furniture and I'd say "Where are you going to put that? Is that firewood?" and then the perfect Florentine or Sienese artisan brought it back to life.

So you've got this incredible property and then as a non-golfer you make the decision to build a golf course.

That I think is a real positive thing, because you can be totally objective with what you're doing – and a little bit also with the wine. Obviously, I love wine, but I knew nothing about making great wine when I got this place. I knew that I needed to listen to real wine experts and learn as much as I could from them. The golf is the same thing.

In the idea of bringing back the property to life, because that's exactly what had to be done, the idea of having a fabulous wine and great hospitality, we thought golf was really a nice completing factor both from a visual point of view and a fun perspective. We went down the road with that idea and once you meet people like Fred Green, the owner of Queenswood who was a great help to me, and of course our architect Tom Weiskopf you start to get excited.

You've created a golf course that feels very natural and also very Tuscan…

That was the intention. The Val d'Orcia is a UNESCO world heritage site, so the golf course had to remain hidden – it couldn't be in your face. This I say about any golf course I see because it's nice when it blends in with the terrain, but here it was a necessity.

For Tom Weiskopf, he really had a clean sheet here to draw upon and the way he used the natural land was just amazing. He came in and created this piece of property that really feels ageless – it looks like it's been here forever.

The golf course is I think quite challenging, but not to the point that it becomes frustrating. The fescue grass is pretty unforgiving if you're not accurate, but the fairways are large to accommodate for that.

When I go out hunting in the winter, I'll go through these grasses and the creeks that intersect some of the holes. Hopefully when I come back I have a pheasant or hare, but for sure I'll come back with 20 golf balls! It's really funny.

Being at Castiglion del Bosco feels like the extension of a family estate, which seems to be the way of Montalcino. It isn't like Bordeaux – it's quite small, it's familial, it's discrete…

I think you really get the exact feeling. It's true, Bordeaux, which has all my admiration and makes some fabulous wine, has I think 120,000 hectares of vineyards, while Montalcino is 4,000 hectares, so you know it's really a handkerchief in comparison to that.

Of course, the terroir is very particular so it balances for other reasons – a little bit like Barolo, which is also small and hilly, and is always looking for a little piece of field to grow grapes. There's something charming about these smaller denominations.

Here at Castiglion del Bosco also, the idea of Chiara and Teresa when they were designing the villas was when you're staying there you feel like it could be your home. That has to extend to the other areas and so the feeling you get in the clubhouse is almost neighbourly – they all relate to each other even if they are from a totally different part of the world.

If you go to the winery, you go to the hotel, if you go to the restaurants, it has to be something that seems like the same place even if they are completely different activities.

I think it's really about executing what we're doing now well

Terroir in winemaking is the unplaceable quality of certain place distilled into the wine. I wonder if you look at Castiglion del Bosco that you get that same sense of the terroir in the experience?

That's a really good way of putting it, because terroir shouldn't be only for wine but for everything, so the feeling of terroir has to come from all the experience you have in a place. Going back to the wine, the terroir in this case is very very particular.

Only one grape is produced here and sangiovese is the most famous grape in Tuscany, and outside of this region there is not one place yet where I have tasted where I've said “oh wow”. It's one of the most difficult grapes to grow, but in Tuscany and Montalcino in particular it really comes into its own.

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It's really funny, the terroir in Montalcino is not just the land but also the mentality of the people. The Tuscan mentality is very particular. We inflict rules upon ourselves that no one in Bordeaux or any other denomination would dream of doing.

In the Brunello denomination the rules are such that you can only use those grapes, it has to age for five years, it has to be grown at a certain altitude, I could go on.

It's as if we said, how difficult can we make it for ourselves, and let's do that! Having said that, it makes the winemaking process more challenging and fun, because it is an incentive to do well with what you have – growing this grape and really treating it in a way that is so particular.

Even the soil isn't soil, it's crushed rock… and one of the rules of the denomination is you can't water the ground! I remember a couple of years ago it just wouldn't rain, and these poor grapes, I don't know how, go down really deep into the rock to sustain themselves.

The fruit ends up being 20% smaller as they try to survive, but the wine from 2017 so far seems like it's going to be fantastic, just with reduced quantities. It's an uphill process to make a great Brunello with all these limitations, but if you do it well the results are really rewarding.

What is the future of Castiglion del Bosco?

I think it's important to keep doing what we're doing and there are a few other things that we have in our plans that will be a nice compliment to what we have now. Most of all, I think it's really about executing what we're doing now well.

What I think we've done quite well from the beginning is listen to our members and guests, and try to deliver what they like as best as possible. We're building another 20 suites at the borgo, which is great because I never thought that would happen after we opened in 2008 and there was the crash, and we had a wonderful place, wonderful staff and no one showing up. Now, we have the opposite problem, so that's very positive.

Members love the experience of coming here: the wine combined with the golf course. But some have expressed an interest in keeping some of their car collection here – and there's no better place to drive than around here – so we have already started to organise a garage to facilitate that desire. So it's really that combination of executing what you have to do and then building out from there.

Find out more about the history of Salvatore Ferragamo or apply for membership to Castiglion del Bosco.