There are hilltop sunsets. And then there’s Castelfalfi – where the sun doesn’t set, it lingers. It glows, stretches, and seems to say, “Go on then, have another glass.”

Nestled in the heart of Tuscany, Castelfalfi isn’t just a resort—it’s a restored medieval village turned luxury sanctuary, complete with a castle, olive groves, vineyards, and a golf course that makes you question whether you’ve actually died and gone to Italian heaven.

Setting the Scene: Tuscan Dreams on Tap

My wife and I arrived at Castelfalfi for part of our 25th wedding anniversary trip, and truth be told, we were a little nervous—Belmond had already set the bar sky-high. But Castelfalfi brought its own unique magic. While it didn’t aim to compete with Belmond, it stood out in a wonderfully modern and refreshing way—from its sleek design to the heartfelt hospitality. We found ourselves truly charmed by its luxury and serene atmosphere.

Imagine:

• A sleek, modern hotel with interiors that whisper understated luxury.
• Views that look like someone smudged reality with a Renaissance painting.
• A soft breeze, a Negroni in hand, and silence interrupted only by the occasional bird that’s clearly got a better work-life balance than you.

Meet Lorenzo: Sommelier, Storyteller, Secret Cellar Keeper

On our first evening, I met Lorenzo—Castelfalfi’s sommelier and the maestro of Tuscan wine—a man who could probably pair Chianti with quantum theory if asked.

He welcomed us into the tasting room which looked more like an art installation than a wine cellar. Think glass walls, museum lighting, and racks that showcased bottles like jewels. A temple to wine if ever there was one.

Turns out, Lorenzo knows Gieole from the Belmond, which is like saying your barista is mates with Heston Blumenthal. He excitedly introduced me to a gem I’d yet to discover: Podere Le Ripi’s “Amore e Magia” Brunello di Montalcino 2017—a biodynamic marvel full of ripe cherries, smoky minerality, and just enough “oomph” to make me question my life choices up to that point. We saved it for our final evening. Poetic, really.

Dinner at La Rocca: Views, Vintages & a Very Special Cellar

Before the grand finale, we had one of our most memorable evenings at La Rocca, the fine dining restaurant perched on the castle headland. The menu was as elegant as the setting. I went for:

• Asparagus with white chocolate – weirdly wonderful.
• Raviolini filled with braised baby pork – like eating a warm hug.
• Sirloin, morels, capers, raspberries – a reminder that food is art if the artist has truffles.

But the true star of the evening was Gianmarie, the head sommelier with a excellent knowledge of wine and a gracious, easygoing manner. As one of the youngest sommeliers to qualify in Italy—something he achieved over a decade ago—he now serves as the proud keeper of the castle’s remarkable cellar. A tue seasoned guide.

We enjoyed a flight of wines that danced between flavour and finesse, all within budget (yes, miracles happen). Here’s the roll call:

• Langhe Arneis by Ceretto – crisp and zesty with a floral kiss.
• Il Rosé di Casanova by La Spinetta – the Rosé for people who think they don’t like Rosé.
• Villa Antinori Chianti Classico Riserva 2021 – a velvet glove of a wine.
• Preussen Rheinriesling by Fuhrgassl-Huber – German discipline meets summer orchard.
• Bianca di Valguarnera 2019 (Insolia) – Sicilian sunshine in a glass.
• OGRÀ 2015 by Cotarella – brooding, bold, and brilliant.
• Taylor’s 20-Year Tawny Port – smooth enough to convince you dessert is for amateurs.

The Cellar That Time (and a Few Collectors) Forgot

Just when we thought it couldn’t get better, Gianmarie asked, “Would you like to see the cellar?”

Reader, we said yes.

What followed was an underground journey into the heart of Castelfalfi’s vinous soul. The cellar is vast, historic, and gloriously cool (in both senses). We saw two antique glass vats from the early 1900s that once held 7,500 litres each—basically the dream bath for any wine lover.

Among the bottles, a few legends:

• Poggio al Vento Brunello di Montalcino Riserva 1990
• Il Poggio Monsanto Chianti Classico Riserva 1982
• Pétrus 1992 – yes, that Pétrus.

1,700 labels strong, this cellar is more than a collection—it’s a pilgrimage site. And I’d gladly convert.

The Grand Finale: Amore & Magic Indeed

Our final night saw us uncork “Amore e Magia” on the terrace. It was the perfect end to a week of wine, wonder, and 25 years of shared laughter. We toasted with D’Incanto Vin Santo del Chianti 2009—an amber-hued finish to a golden trip.

The Verdict

Castelfalfi isn’t just a place. It’s an experience, a love letter to Tuscany, and a reminder that the best things in life pair beautifully with a great glass of wine and someone to share it with.

So, if you’re wondering where to go for your next romantic escape, wine-soaked getaway, or simply a break from emails—Castelfalfi is calling. And you should answer.