Mastrojanni Relais

Look, I’ve stayed at a lot of places in Tuscany over the years, but Mastrojanni Relais just hits different. It’s tucked away in this tiny hamlet called Loreto e San Pio – and I mean tiny, like you’ll-miss-it-if-you-blink tiny – about fifteen minutes outside Montalcino proper. The first time I drove up that winding road through the vineyards, honestly, I thought my GPS was having a breakdown. But then you crest this little hill and there it is, this gorgeous stone building that looks like it’s been sitting there forever, completely at home among the cypress trees and rolling hills. The whole approach feels almost secretive, you know? Like you’re being let in on something special.

What really gets me about this place is how they’ve managed to keep that authentic Tuscan farmhouse vibe while actually making everything work perfectly. The rooms – well, they feel like rooms someone actually lives in, not hotel boxes. Thick stone walls that keep things cool even in August, windows that frame the Brunello vineyards like living paintings, and beds that are just the right kind of firm. The bathrooms are modern without being sterile, which is harder to pull off than you’d think. I always ask for a room facing the Val d’Orcia if they have one available – the sunsets from there are absolutely ridiculous. You can hear the church bells from Castelnuovo dell’Abate drifting across the valley in the evenings, and honestly, it doesn’t get much more romantic than that.

The thing is, staying here isn’t just about the hotel itself – it’s about being dropped right into the heart of Brunello country. You’re literally surrounded by some of the best wine estates in Italy (the Mastrojanni winery is right there, obviously), and the owners actually know the local producers personally. They’ll hook you up with tastings that aren’t on any tourist maps. Montalcino town is close enough for dinner – maybe twenty minutes if you take the scenic route through San Angelo in Colle – but far enough that you feel like you’re really in the countryside. The breakfast spread uses ingredients from their own garden and local farms, and the staff… well, they’re not putting on some rehearsed hospitality show. They’re just genuinely proud of this corner of Tuscany and want you to fall in love with it too. Fair warning though – once you’ve watched the morning mist roll across those vineyards from your terrace, everywhere else is going to feel a little ordinary.