In May 2016 we took our longest road trip yet through Italy. It was a challenge to plan, given three participants on two continents, all with their own scheduling constraints, but we pulled it off to great success.
1st Leg, Regensburg to Piombino Dese to Siena
Piombino Dese
Sarah flew to Venice and met up with Rachel, who flew in from Boston. I (Cliff) drove down from Regensburg early on a Sunday morning. It was a 6-hour solo drive, and I was a little nervous about that after not solo-road-tripping for so many years, but it worked out just fine, with great weather and light traffic all through Austria. When I came out of the mountains in Northern Italy, things started to get cloudier, but the rain was yet to come. Sarah and Rachel took a train from Venice’s big station (Santa Lucia) to Piombino Dese, and I arrived just a half an hour earlier than predicted, scooping them up at the tiny train station and checking in Ca’ de Memi, a fantastic agriturismo bed-and-breakfast we first visited about four years earlier when attending the radicchio beauty pageant. Looking to experience Venice without breaking the bank? Consider taking the train from Piombino Dese. You can walk to the train station from Ca’ de Memi and for about five Euros and 35 minutes of your time you can arrive at Santa Lucia without the hassle of parking locally or paying Venice hotel prices.





Siena
Siena was a new place for us to explore. We stayed two nights in a bed-and-breakfast offering a free parking spot. Upon arrival, we discovered that the “free parking” meant the freedom to hunt for a spot in the surrounding neighborhood. But that was the only hiccup. We found a spot pretty quickly around the corner from the digs and left the car there for the duration of our stay.
We found Siena to be very walkable, despite or because of the narrow streets and steep hills. Our bed-and-break hostesses recommended several different restaurants for dinners and lunches, and they were right on the money: good food, good prices, friendly service.
The weather was not super cooperative the first day in Siena, but after a bit of rain, and a Proseccopause under a large umbrella at a café on the main square, the city was sparkling and ready for us to explore more.
Not to be missed in Siena: the Duomo. We opted for the “Opa Si Pass” to afford us some views from the top of the cathedral and even climb up to the Facciatone for some impressive views.
2nd Leg, Siena to Rome via Pienza and Lago di Bolsena
Pienza
We took our time getting from Siena to Rome. Our Frommer’s Italy guide from 2005 suggested a visit to Pienza for its cheese, so we stopped off there for pizze for lunch at Pummarò. They were delicious. Parking was not easy, but we got lucky on the edge of town.

Lago di Bolsena
After lunch, we got back in the car and headed for Lago di Bolsena, hoping for cool breezes off the lake. Unfortunately, we jumped at the first large parking lot our GPS found (having hunted in Pienza for longer than we wanted) and we ended up parking too far away from the lake to benefit from it. But we had a nice coffee break.
Up next: Part II, Sleeping and Eating in Rome.
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