As someone who’s stayed at not one, but two Belmond hotels, I can confirm: the second time is just as magical. Castello di Casole, nestled in the rolling hills of Tuscany, didn’t just meet expectations—it elevated them in local olive oil, served up with warm, pillowy focaccia on the side, and delivered the whole experience on a sun-drenched terrace overlooking vines.

A Hotel Steeped in Stories and Stone

The castle itself is a thousand-year-old relic of Tuscan history, yet somehow it never feels dated. From Bronze Age artefacts tucked behind glass to rustic beams that have no doubt seen a few feasts in their time, Castello di Casole is where old-world charm meets new-world luxury. Every inch has been lovingly restored—modern comforts like rainfall showers and plush bedding sit beautifully alongside terracotta tiles and heavy wooden doors. It’s the kind of place that inspires both poetry and a good nap.

Missed the Wine Tasting, Found Bliss by the Pool

Let’s get the heartbreak out of the way first: I missed the wine tasting. Yes, I know. Me. A man who runs WineGuide101. But in my defence, it’s hard to keep track of time when you’re floating under the Tuscan sun with a glass of something chilled and golden in hand.

The missed the hotel tasting. Next time, I’ll bring an alarm clock. Or at least set a reminder on my phone.

A Room Fit for a Renaissance Prince

The room we were given was more suite than sleep-space. Think wood-beamed ceilings, stone walls, hand-plastered finishes, and a bathroom you could host a yoga class in. Seriously, the place was so charming I half-expected a local duke to show up with a lute.

An Unexpected Reunion in Wine Country

Ran into my old friend Savio Moschetta here in Casole d’Elsa, completely unplanned and absolutely perfect. We first clinked glasses in Mallorca last year, where he had been a sommelier in Pure Salt Hotel, and here we are again, reunited over a stunning sunset and an unforgettable bottle of Guado al Tasso.

If that isn’t wine magic, I don’t know what is.

The Team: A Masterclass in Hospitality

From the moment we arrived, the tone was set. A young gent welcomed us with a calm warmth that whispered, “You’re in good hands.”

• Alesio at the bar served up our first round and made the best impression since my first sip of my Manhatten. The boar ragu tagliatelle deserves applause.
• Naomi gave us the spa tour—regretfully, we didn’t get to indulge. One more reason to return.
• Roberto & Angelo kept the morning cups of coffee flowing while we relaxed in a courtyard so peaceful, even the fountain seemed to whisper.
• Carmelo shared the secrets behind his focaccia, complete with a backstory on the hotel’s ancient oven. If bread could win awards, his would take gold.
• Antonella was ever-present and always helpful. The kind of presence that makes everything smoother.
• Matteo & Andrea ran the bar like symphony conductors. Andrea even schooled us in the art of the Negroni.
• Elena was a guest experience powerhouse. She tracked down painkillers for us when needed—above and beyond.
• Alessandro, though elusive, clearly ran a tight ship. Thanks for the anniversary bubbles!
• Ruben & Alberto handled dinner with charm and grace. The veal Milanese? Bellissimo.
• Ramsey served up smiles and breakfast with equal ease on our final morning.
• Gioele, Amedeo, Elena, and a kind unnamed gentleman in Tosca made our last dinner something special. The pairing, the pacing, the care—unforgettable.

Perfect Launchpad to Wine Country

Location-wise, you couldn’t be better placed. From Montalcino to Florence, you’re perfectly perched for a Tuscan wine adventure. But honestly? You may never want to leave.

An Evening to Remember at Tosca

Our final night was a symphony of flavour and elegance. At Restaurant Tosca, we indulged in the four-courses of the tasting menu, and it was a triumph. Each dish—especially the roasted rabbit and lamb—was a story in itself. But the real magic came from the wine pairing, curated by the brilliant Gioele.

Gioele’s wine flight was as inspired as the dishes it accompanied—bold, surprising, and beautifully matched. Each glass felt like an encore from the chef. While Tosca doesn’t carry a Michelin star (yet), it easily rivals many that do. The entire team radiated chemistry and charm: Amedeo, Elena, and Gioele delivered flawless service and genuine warmth. There was also another young gentleman whose name I missed—but whose gracious presence left a lasting impression.

To the whole restaurant team, thank you for creating a perfect finale to our Tuscan escape.

The Wine Flight at Tosca – Uncorking Genius

The wine pairing by Gioele was nothing short of extraordinary—each bottle thoughtfully selected to elevate the flavours of the tasting menu.

1. Podere Le Ripi ‘Cielo d’Ulisse’ Brunello di Montalcino 2020
Biodynamic and bold. Wild cherry, dried rose, and earthy finesse in every sip.

2. Donnafugata ‘Ben Ryé’ Passito di Pantelleria
A luscious Sicilian gem. Apricots, honey, and spice wrapped in a golden hug.

3. Altura ‘Ansonaco’ 2021 – Isola del Giglio
Orange wine from a tiny Tuscan island—apricot, herbs, sea air and soul.

4. AnimOso 2019 – Agricola San Lorenzo
Natural Sangiovese in amphora. Juicy red fruit, herbs, and earthy elegance.

5. Avignonesi ‘Occhio di Pernice’ Vin Santo di Montepulciano
Aged over a decade. Figs, cocoa, orange peel and pure velvet.

6. Calvados Morin XO – 20 Ans
A Normandy digestivo to finish. Baked apple, vanilla and oak-aged warmth.

7. San Polo ‘Vignavecchia’ Brunello di Montalcino 2020
Classic, rich and structured. Leather, cherry and refined tannins.

8. Gaja Barbaresco 2010
Iconic Nebbiolo. Truffle, rose, and cherry in one unforgettable glass.

Gioele, this was a masterclass in pairing. Bravo!

Final Thoughts: Go. Stay. Soak. Repeat.

We soaked up sunsets, swam in serenity, and drank in the beauty—literally and figuratively. Castello di Casole isn’t just a hotel. It’s a state of mind.

Belmond, you’ve done it again.