This Italian Resort Has Its Own Winery, Lake, and Medieval Village — Plus Tuscany's Largest Golf Course

I was standing on the terrace of a medieval castle–turned restaurant, watching the sun setting over hills dotted with farmhouses and vineyards, when an Andrea Bocelli song planted itself in my head — clearly my subconscious calling me out for being a walking Tuscan tourist cliché. I sipped my glass of Chianti in spite of myself and snapped another photo. Cliché or not, I was loving every minute of it.

Finding unexpected experiences while traveling is exciting, but the truth is, there are some places we visit simply hoping they’ll meet our (very high) preconceived expectations. Every time I’ve been to Tuscany, it has done that for me, but never so perfectly as the days I spent at Toscana Resort Castelfalfi.

The 2,700-acre estate neighboring San Gimignano, just over an hour outside of Florence, houses olive groves, vineyards, a forest full of truffles, hillside trekking paths, and a restored Medieval village. To stay at Castelfalfi is to live out your Tuscan dreams — during even a short trip, you’re likely to find yourself folding fresh pasta dough with an expert chef, digging up truffles with passionate hunters and their pups, tasting wine and olive oil with a local vintner, cruising on a Vespa, and sharing piping hot pizzas and bottles of red late into the night. 

The unexpected does exist here too, in the form of a lake where guests can go fishing, an adventure park, horseback riding trails, and the largest golf course in Tuscany, with 27 holes. When it comes to activities, the sky is quite literally the limit: A hot air balloon will even whisk you over the bucolic landscape, landing just in time for a Prosecco picnic.

And then there’s the hotel, spread over two buildings: the modern main building, where 120 newly renovated rooms and suites open to a bird’s-eye view of the hills, and the historic tobacco warehouse, with 31 more traditional rooms across the street. Guests have access to three pools, a spa, and stylish indoor and outdoor bars. Its six restaurants include a homey trattoria, Il Rosmarino, serving wood-fired pizzas, and fine-dining destination La Rocca. 

Those seeking a private escape can book a villa with its own pool, gardens, and chef, a luxury enjoyed by many a celebrity guest. But for us, what made Castelfalfi a place to remember and return to was the people we met there. It was seeing the enthusiasm behind the Savini Tartufi truffle hunters as they delicately dusted off their latest finds, describing them as “diamonds of the forest” in reverent whispers. It was watching chef Michele Rinaldi deftly mold ravioli into six different shapes in a matter of seconds. It was running late to dinner because firecracker general manager Isidoro Di Franco was taking us on an impromptu golf cart ride, and making new friends over house-made gin and tonics.

Orange sunsets over green hills make for great photos — and here, should absolutely not be missed — but expect it or not, it’s the people you meet who make your experience feel truly Italian.