Our hill town hopping adventure through Pienza, Monticchiello, and Montepulciano was straight out of a Tuscan daydream – and easily one of the coziest, cheesiest, and cat-filled days of our 2016 Italy trip. We started in Pienza, a town known as the first true expression of Renaissance Humanist urban design (because even in the 1400s, Italians had strong opinions about layout). We wandered the charming Piazza Pio II, peeked into Piccolomini Palace, and, of course, sampled the town’s famous pecorino cheese. From there, we made our way to Monticchiello, where the views at Osteria La Porta made us feel like we’d accidentally wandered into an Italian Olive Garden commercial – except with actual wine and charm. Finally, we rolled into Montepulciano, met a very cuddly street cat we named Monte, and explored the town’s wine scene – starting with Contucci Cantina, a medieval cellar straight out of a movie. We headed straight into the atmospheric depths, where we met Adamo, the legendary and endlessly friendly vintner featured in Rick Steves’ videos. Wandering past enormous casks of wine tucked under ancient stone arches made us feel like we’d unlocked a hidden level of Tuscany. We wrapped up the day back at our 12th-century agriturismo, Castello di Spedaletto, a working castle with a real mill and the kind of peaceful countryside charm that makes you wonder if maybe this is where you were meant to live all along.

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