Packing up after our lovely four days in Rome, I was feeling good. I had been concerned about how my little son would take to Italy. He’s not good with change or dealing with frustrating situations, and Italy is all about that. I was kind of hoping that this trip would help him develop skills for coping with difficulties. Rome had gone well and appealed to him, he was content. It was smooth sailing as far as the eye could see. Famous last words.

Our next move in the vacation plan was to pick up our rental car at Termini train station. I had booked through always-reliable AutoEurope, a Smartcar for two weeks. We were planning to head into Umbria, staying at a farm house with a pool and wandering the countryside looking for fun. It was August 14. That doesn’t mean much to you, most likely, but here in Italy that day brings vacation Armageddon, the massive, unending holiday that is Ferragosto.

Lines at the rental car counters were super long. Nico tried to be patient and we made it to the desk eventually. Whipping out the paperwork and anxious to get moving, I waited for our car. The surly woman at the desk looked at my license and balked. I had just renewed it and they gave me the temporary one, which the DMV assured me would be just fine. But no. It wasn’t laminated. I gave her my old one and she wouldn’t take that either. Ok. Well. Huh. What now?

Nico burst into tears and we headed to a cafe to figure out what to do. I called AutoEurope and they were able to change my reservation for a few days later, with the hopes that the laminated license had reached home and could be FedExed to me. I was relieved to find out that they would deduct the days I couldn’t use, as I had prepaid for the car in advance. Our hotel, the elegant Altarocca Wine Resort near Orvieto was a bit of a problem. It’s in the countryside, with no bus nearby. They assured me that I could get a taxi there, but on Ferragosto all bets are off.

Luckily, my bacon was saved by a good friend, tour guide and winery owner Cecilia Bottai. We took the train to Orvieto, had lunch and then met her for our ride to the hotel. The hotel was a lovely one, Nico gasped when he saw our room. He kept exclaiming about how fancy it was! How nice it smelled! He was like a little king in his castle. It really is a cool place, super romantic and scenic, if you’re into that sort of thing. At least some of what I had in mind for our day had worked out.

After stress and confusion, Nico and I hit the pool. He was pleased to find some kids his age to play with and was a happy camper. I, on the other hand, was concerned to say the least and seeking a stiff drink. We only had one night booked there and they were full the next night. Our next hotel was another farmhouse, way out in the middle of nowhere in Tuscany. I know the owner, so I called her to figure out a plan. She was willing to come and get us at the train station, but it was Ferragosto and she was really busy, it was a kind gesture but a major inconvenience for her.

So, what to do? I went into tour guide mode. If there is one thing that a tour guide is good at, it’s fixing problems on the fly. The most logical place for us to go was to Florence. I had no intention of taking my son there, it’s not a real kid friendly place, but it was the only thing that made sense. Florence is also a place where I have loads of contacts, so I called on my most reliable people and got a room booked and things sorted out.

Nico and I had dinner at the hotel’s elegant restaurant. He dressed up in his finest and was full of proper manners. He is an excellent date, full of chatter and funny observations. I tried to get him to speak a bit of Italian, but, as he would do throughout the trip, he was suddenly a shy child. Seeing mommy speak a foreign language was a little weird for him as well. His description was something like this “Momma, when you speak English you’re all la-la-la (high pitched voice) and when you speak Italian, you’re all blwah-blee-blew (low, guttural voice)”. Sorry kid, that’s the way it is.

After dinner, we watched some TV, real Italian TV. That’s quite a spectacle if you’ve never seen it. Lots of talk shows and ladies with big hair and cleavage, often in bikinis. As Nico watched the Italian version of American Idol, I contemplated the rest of our trip. I had no idea if we’d ever get my license. The rest of the trip depended on having a car. I had called all of our friends that we had planned to see and they all volunteered to drive us and make it work, but would it?

The next day was August 15, a dead zone in the Italian calendar, much like Christmas in the US. We needed to get to a train station to head for Florence but there were no taxis. The train line that usually has hourly trains to Florence had four departures all day long. My friend offered to pick us up, but not until 4. So we killed time, swimming all day. It was not what I had planned to do with my day, but Nico couldn’t have been happier. Sun, swimming, mommy to himself. Not bad for a kid. Even if I was stressed about the trip not being perfect, his happiness was really the point of everything and happy he was.

We made it to the train station and had a slice of pizza and gelato because, you know, gelato fixes all ills. I was worried about the trains being full, but they were empty. Everyone in the country was at the beach except us. Nico settled into the train, making a nest for us with his blanket and stuffed animals and said “I’m glad we don’t have a car. If we had a car, I wouldn’t get to snuggle with you.” (Mother’s heart melts and mother feels silly for being so preoccupied about things not going perfectly.)

We arrived into a safe harbor in Florence, the Hotel Accademia. This is a classic Rick Steves hotel, the owners are practically like extended family. We were welcomed by the owner Tea, who hugged Nico and handed him a cold Coke. Our room had a big bathroom with a tub, and Nico again exclaimed about how nice the hotel was. There’s a bathtub! If only my tour clients were always this enthusiastic!

Tea’s husband Angelo owns a restaurant nearby, Giglio Rosso, which I eat at frequently with my groups. We were welcomed like family, all of the waitstaff came over to meet Nico, who hid behind me and tried to crawl under my skirt. So timid! That’s what they all said about him. If only they knew how he is at home. We were given the royal treatment, pasta and bistecca alla fiorentina, finishing with a visit from the dessert cart. Our next day, the only full day in Florence, was pretty mellow. Our crazy pace had taken a toll on both of us and we could not get motivated to do much of anything.

I had made a lunch date with a local guide I know, the venerable Antonia Lanza, tour guide to professors and princes. She’s a fascinating woman and I wanted Nico to meet her. We had a nice lunch, but Nico was shy again, hardly talking. He loosened up a little when Antonia suggested that she treat us to a gelato.

From there, she asked Nico what the one thing he wanted to see was. He said the Duomo, the cathedral of Florence, so away we went. Antonia is an encyclopedia of Florentine knowledge and walked Nico about, telling stories as she went. I absolutely relished the moment. Watching Nico listen to one of my favorite colleagues, it was a little like a private tour, a little like having him set a foot into my secret world amidst the art and history. That was sort of the point of this trip, to let him get a view of my world, my workplace on the other side of the world.

In one sense, those days were a total disaster. In another sense, it couldn’t have gone better. Nico learned to be flexible and that everything will be okay if you remain calm and think it through. And an even better lesson, sometimes when plans go awry, opportunities pop up that you hadn’t considered. Important lessons learned. That’s the beauty of travel.

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Coming soon, Episode 3: Slovenia Isn’t Far Away, Is It?