Montalcino is the kind of town that immediately feels like it was made for wine lovers. Perched atop rolling hills in Tuscany, its narrow streets are lined with wine boutiques, tasting rooms, and charming shops. It’s a beautiful place to wander, though we did wish there had been a bit more variety beyond all the wine-focused spots. The centerpiece of town is an impressive old castle, where visitors can sample wines or enjoy lunch while soaking in the views. We only had a few hours to explore before heading to Corte Pavone, so we didn’t get the chance to try one of the popular wine boutiques for a meal—but it’s definitely on our list for next time.

Our real highlight came at Corte Pavone. Andrew was eager to tour the vineyard and cellars, and it didn’t disappoint—he loved learning about the winemaking process from start to finish. The tasting that followed was extraordinary, featuring Brunello di Montalcino, a prestigious, full-bodied Italian red made from 100% Sangiovese grapes, locally called “Brunello.” Each wine was paired with thoughtful bites that enhanced the flavors, making the experience both educational and indulgent. It was one of the few experiences we booked ahead of time, and it quickly became one of our favorite parts of the trip. Surrounded by the Tuscan landscape, it felt like a true immersion into Montalcino’s winemaking heritage.

Afterwards, we drove back through the Tuscan countryside toward Siena, where we were staying at an Airbnb. The rolling hills, scattered cypress trees, and golden vineyards created the perfect backdrop for reflecting on our day. Montalcino may be small, and heavily focused on wine, but it’s undeniably charming, and the experience at Corte Pavone made it one of the most memorable stops of our trip.

XOXO