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Petsitting in Tuscany

With our sweet pup Kiddo in tow, we headed for the hills in search of medieval villages, quaint wineries and beautiful vistas.

For three months, we’d been petsitting in Rome, caring for Kiddo, a 9-year old shepherd mix. In that time, we learned he enjoys adventure as much as we do. For our last hurrah in Italy, we decided a road trip was in order. Having visited several places in Italy, including nearby Florence and Cinque Terre, we chose to return to magical Tuscany. After securing a pet-friendly Air BnB in Montepulciano, we picked up our rental car and headed out of town. The traffic-laden capital was soon behind us, and nothing but the serene countryside lay ahead.

Along the way, we stopped in the ancient town of Orvieto, 90 minutes outside Rome. Situated high atop the tuff cliffs, this medieval village feels very much like a working town. The stunning Orvieto Cathedral, a 14th century Roman Catholic church, is a sight to behold. The ornate Gothic facade and striking black and white striped exterior reminded us of the main cathedral in Sienna. As we made our way through the town, Kiddo was in heaven sniffing all the new and different smells. After enjoying an al fresco lunch, we hopped back in the car and an hour later, reached our final destination: Montepulciano.

The picturesque hill town of Montepulciano was the ideal home base for our week in Tuscany.

In off-season, we had the town practically to ourselves. Kiddo loved joining us in our explorations. We started at La Terrazza, the iconic main square featured in the Twilight movie series, then wandered the quiet streets lined with delightful, pastel homes. Locals would smile at Kiddo, “Bellissimo cane!” Of course, it wouldn’t be a trip to Tuscany without one (or several) wine tastings. Montepulciano is known worldwide for its Vino Nobile wine. Da Ricci and Contucci, both in the historic center, offer delicious wine, as well as impressive, centuries-old wine cellars.

While our homebase was Montepulciano, we spent our days visiting different nearby villages, each with their own enchanting personality. In Pienza, we took in breathtaking views of the Val d’Orcia. In Monticello, we stumbled on a whimsical open-air art exhibit featuring oversized sunflowers. And in Montalcino, we wandered through a labyrinth of narrow stone alleyways that opened up onto extraordinary vistas. Kiddo even got special permission to enter former Benedictine monastery, Abbey of Sant’Antimo, and used his charm to join us at Casanova di Neri winery where we enjoyed complimentary tastings of award-winning Brunello di Montalcino wine. Molto buono!

Our Tuscany trip was the ideal way to wrap up our time in Italy. And we can’t think of a better travel companion to share the experience with than Kiddo.

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