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Adventuring in Italy || Part 3: Siena, Montalcino, and Back to Rome || Destination Elopement Photographer

If you missed part 1 & 2, you can read about our trip (and why I’m writing this series) here: PART 1 & PART 2.

We rented a car to drive from Florence to Siena, something that I don’t know if I’d necessarily recommend. We wanted the car so we could take some day trips out of Siena, but Siena is not even remotely car friendly. We had no idea what we were getting ourselves into.

Siena is a medieval walled city in Tuscany – totally unlike anywhere else we visited in Italy. We literally stayed in a castle just around the bend from Piazza del Campo. The streets are narrow, steep, and winding and a road will just turn into staircase. It rained a lot while we were in Siena, but we still went exploring – eating pasta in the piazza, wandering through the maze of streets, nosing through little shops. I found the perfect pair of boots in Siena.

We took a wine class which was a fantastic rainy day activity. The woman teaching the class wanted to give us the leftover prosecco when she found out we were on our honeymoon, but when she went to get the bottle it was empty. Our class was clearly thirsty.

One of the day trips we took out of Siena was to nearby Montalcino. The road there was winding – and there were no guard rails to prevent you from rolling down the hills. I held my breath the whole drive. John just laughed at me. The drive was totally worth it – Montalcino is not only on the top of a hill, but there’s a huge fortress that you can climb to the top of and the view is just incredible. All of Tuscany just spreads out around you and it’s breathtaking.

We bought wine and olive oil in Montalcino to bring home. We saved one of the bottles to drink on our first anniversary, but when we opened it last October there was a small hole in the cork, and the wine had gone bad.

Driving back to Siena from Montalcino we went into the city at the wrong gate – the one the farthest from our hotel. Our GPS was out of date and kept telling us to drive down a street that was now one way – the wrong way we wanted to go. We drove in circles around Siena for an hour and could not figure out how to get back to the hotel. (Siena is a very small city, so if you’ve been there, you realize how ridiculous this is.) At one point John took a wrong turn and we ended up in the middle of Piazza del Campo where you are definitely not allowed to drive. A police officer came running up to us and had to guide us out of the piazza – we were totally mortified. Finally – FINALLY! – we turned a corner and there was our hotel. As we pulled up, there was a huge crowd gathered in the street in front of the parking area – someone had driven up in a fancy car and everyone wanted to see. We slowly edged our car through the crowd and then – crunch – we hit something. A woman whipped around and looked down horrified at whatever we’d hit. I could only see the top of whatever it was, but it had handles and to me it looked like a stroller. I immediately started yelling, “OH MY GOD WE HIT A BABY!” I locked eyes with the woman in front of us, and her expression definitely was one of, “Yes, stupid American, you hit my baby.” Then the doorman from the hotel appeared – laughing. “It can’t be a baby, the doorman’s laughing!” John declared. We backed up and the woman pulled whatever it was from in front of the car – it was just a shopping cart. Empty. No baby. And not even dented. But she still had a furious expression. We pulled into the parking area, heads low, totally embarrassed, my heart racing from thinking we had just run over a small child. After that we didn’t drive again until we left Siena. Seriously… don’t drive in Siena.

We ended our trip back in Rome, in the same hotel where we’d began our honeymoon. We watched one last sunset from our room. Had one last gelato. One incredible last dinner at Sapore di Mare. And then we were up early the next morning, back to New York City. And it was pretty much the greatest two weeks ever.

  • Haha, the driving misadventures must have been stressful at the time, but fun to hear about after the fact. Very glad you did not hit a baby. The photos are swoony.