Montepulciano was one of those places we almost talked ourselves out of visiting. While planning our honeymoon to Tuscany—with a toddler in tow—we kept hearing people rave about it, and that made us nervous. Would it feel overrun? Too commercial? Another “Instagram town” that didn’t live up to the hype? But from the moment we arrived, those worries completely melted away. Montepulciano felt authentic, historic, and deeply charming, the kind of place that pulls you in slowly and then doesn’t let go.

The medieval architecture alone was enough to win us over. Every street felt layered with history, from the worn stone buildings to the tiny details tucked into doorways and windows. Shortly after arriving, we sat down for lunch at Porta di Bacco, and it ended up being one of the most memorable meals of our entire trip. I ordered a truffle pasta that was rich and comforting, and Andrew—who is a chef—claimed his ragù was the best he’s ever had. That’s not praise he gives lightly. The server recommended wines to pair with our dishes, and they were absolutely perfect. The owner was incredibly kind and welcoming, even chatting with us long enough to know exactly which suburb we were from back in Phoenix—something that still amazes us. As we wandered the town afterward, we were pleasantly surprised by how diverse the shops and restaurants were, offering so much more than just the typical tourist fare.

As if Montepulciano itself wasn’t beautiful enough, the views of the Tuscan countryside in the fall took everything to another level. Rolling hills stretched endlessly into the distance, softened by the season and the overcast sky. Even without sunshine, the landscape was breathtaking—moody, romantic, and unforgettable. Montepulciano may have been a stop we approached with hesitation, but it ended up being one of the places that truly captured our hearts.

XOXO