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Tuscany Travel Podcast: The Places We Keep Going Back To

We spent years living in Italy and Tuscany is one of those regions we kept returning to again and again. In this Tuscany travel podcast, we split the conversation into two episodes because there was simply too much to fit into one.

Part one is about the hill towns we know best, including Cortona, Montepulciano, Montalcino, San Gimignano, Volterra and Siena. Part two moves beyond the classic medieval towns into places like Lucca, Pisa, Chianti and Tuscany’s thermal springs.

Part 1: The Hill Towns We Keep Going Back To

Our Tuscany story really starts in Cortona. Years before we moved to Italy, Under the Tuscan Sun had already planted the idea of Tuscany in our heads, and Cortona became one of the first places that made the region feel real to us. We went back more than once for the views, small streets, food and the kind of slow day that works perfectly in a Tuscan hill town.

Montepulciano is another place we keep recommending, especially if wine is part of the reason you are visiting Tuscany. We talk about walking through the old town, stopping for tastings along the way and why it remains one of our favorite wine towns in the region.

The episode also takes us through Montalcino, San Gimignano and Volterra. Some of our best memories came from festivals rather than traditional sightseeing, including Carnevale in San Gimignano and Volterra’s 1398 medieval festival, when the whole town seemed to step back in time.

We finish part one in Siena, a city we think deserves far more attention than it sometimes gets. We talk about the Duomo, Piazza del Campo, the Palio and, of course, pici, one of our favorite Tuscan pastas.

Part 2: Beyond the Hill Towns

Part two looks at a different side of Tuscany.

We start with Lucca, which immediately feels different from the smaller hill towns. It is a true walled city, much of the center is car-free and you can walk around the perimeter of the walls. We visited for Lucca Comics, but the city itself gave us plenty of reasons to want to return.

Pisa comes up too. Yes, we talk about the Leaning Tower, because it is impossible not to, but our experiences there were never really about spending a full trip checking off one famous landmark.

We also get into Chianti and Greve, an area close enough to Florence to work well when you want wine country without committing to a much longer drive into southern Tuscany.

And then there are the hot springs. Tuscany has an entirely different side once you leave the cities and vineyards behind, and Saturnia is one of the places we talk about most. We cover both the spa experience and the natural thermal pools that make the area worth adding to a longer Tuscany trip.

Planning a Trip to Tuscany?

If you’re planning your own Tuscany trip, these guides can help you go deeper:

Tuscany Travel Guide → our full guide to exploring the region
Volterra Travel Guide → more from one of our favorite Tuscan hill towns
Cortona, Italy Travel Guide → our guide to the town where our Tuscany story started

If you enjoyed these episodes, follow The GetawayZ Podcast on Spotify or Apple Podcasts for more of our European travel stories and advice.