The Tuscan Countryside

We’d heard that ChatGPT can create an itinerary so we decided to give it a try, asking the AI for a “relaxing day trip around Siena (not including Lucca)” where we’ll be heading on Sunday for Sarah’s weeklong painting course. Read to the end to find out how she performed…
Paul rented the quintessential Italian touring car (see photo) and we set off, first stop Monteriggioni! This small walled town is known for its medieval fort and watchtowers, and the castle walls offer views of the surrounding Chianti region. I’m not sure if we’d recommend this stop… it was both touristy and poorly maintained. ChatGPT let us down. Maybe we should have asked for “an off-the-beaten path itinerary”.

After this somewhat disappointing start we headed to San Gimignano, ChatGPT’s next stop (also recommended by HI (human intelligence in the form of trusted friends and family). This hilly village reminded us of the medieval villages in Catalonia; it’s beautiful. The predicted rain finally caught up with us and we were “forced” to browse art galleries and have an early lunch.

Our final planned stop was Volterra… and this was our favorite. Another a walled town, Volterra showcased the most beautiful and expansive Tuscan vistas (enhanced by the dramatic thunderheads circling the region). I’m not sure the video or photos do this justice. A favorite stop here was Palazzo Viti https://palazzoviti.it/ Cheers to the AI for the Volterra rec!

Our final stop was completely unplanned, and of course, these are the best types. Spotted on a distant hill by the intrepid travel guide, the artsy and idillic town Casole d’Elsa beckoned. The route was beautiful via worn single lane back roads and the town surprised us with art and more vistas.
The only slight hiccup in the entire trip was locating the Avis drop-off location back in Siena. Google Maps, Waze and the vague directions on a tiny printout all contradicted one another. I’m sorry ChatGPT wasn’t around to share her two cents.

What a great day!Read more