You’d think that someone who travels for a living, writes about travel and guides hundreds of people around Europe every year would have magnificent organizational skills. You’d think that everything would always go as planned. You’d think there would be nothing but sunshine and perfect days. You’d be wrong.

Misadventures are the real stuff of travel. It’s what happens when it all goes sideways. I’ve had a pretty colorful life with many misadventures, and I still have them now. I find that, even if it’s awful, scary or disappointing in the moment, they are usually the parts of a trip that are most memorable in the long run. Or maybe that’s just how my brain works- the smooth stuff fades but the insane stuff seems like yesterday.

I had a misadventure yesterday. I actually felt pretty proud of myself that I made it to my hotel in one piece in the end. It all started out so well. Quiet Sunday morning, a cute little silver car and the gorgeous sun-drenched roads of Tusacny. Rolling hills painted in spring green and the sunshine yellow of the canola fields. The scent of newly blossoming wisteria. A little piece of paradise, all for me…although I was actually there for work.

I’d decided to work extra hard this week to create a little gap of time on Sunday to visit a few of our recommended Brunello wineries. I love wine and Brunello is one of my favorites. I just had the Montalcino chapter to do, checking hotels, restaurants and sights. After that I had a small task list of quaint little villages to pass through on my way to the wineries. Maybe lunch in some adorable little piazza and a few minutes for taking pictures. It was going to be the best day ever.

I got to Montalcino and plowed through my list. I stopped by my favorite bar there, the old timey Fiaschetteria Italiana, and chatted with the owner. He offered me a nice glass of Brunello and some snacks. Last time I was there, many years ago, I enjoyed a plate of melted pecorino with pine nuts, drenched in honey. It was perfect with a fabulous Brunello. Despite that great memory, I declined. I needed a clear head and I had places to go. No, grazie.

I was super efficient and got back to the car to make calls and decide which wineries I wanted to hit. I didn’t contact them earlier because I didn’t know if I would be able to make the time to go. As it turns out, you can’t really drop in on many wineries in Tuscany on a Sunday. Most are closed and available only to private tours. Bummer.

There was one listed in our book that appeared to indicate that they might be open on a Sunday, so even if I couldn’t get them on the phone, I drove out there. The road to get up there was gravel and people seemed to stare at me as I drove by, not a good sign, although there was another car in front of me. I and the other car, with an American couple, arrived at the same time at the winery but we were both disappointed. Closed and no answer on the phone. Double bummer.

Change of plans, no wineries were possible. Deep breaths and great disappointment. It was 2 pm and I’d eaten only a cappuccino and an apple. Time to go see Bagno Vigoni, a very pretty village with thermal baths. I imagined myself sitting on a piazza with my tablet, basking in the sun and eating well while working. Google maps said it was only a 20 minute drive past the winery.

Following the Google maps vocal directions, I drove on. The road past the winery wound down and down, changing from gravel to rocks and gravel to….weeds and bigger rocks. But Google said it was the fastest route, it must be so! I drove past a scruffy house with barking dogs that seemed a little forbidding and I started to get nervous. A few minutes later, the road dropped sharply and became rougher. Backing up was impossible so I forged ahead, down the steep and very uneven road. After that hill, the road dove into forest and turned more into a hiking path. Still no place to turn around, so on we go. Then, after bumping along for a good 15 minutes, the road ahead turned into…a creek. No more road. Water.

After some panic I assessed my options. There was only one, turning back. So, I pulled up my big girl pants and did what had to be done, turning around carefully without driving over the cliff and going back. My little rental car was not really up to the task, but I have driven crappy cars all my life and I know how to make a car bend to my will. I gunned the engine and made a run at the steep hill, channelling my best Mad Max road rage face. After some strategic driving and skidding, I made it. Getting out of that canyon was an act of sheer defiance of circumstance. I don’t think I’ve ever been so happy to see pavement again. 

By the time I rescued myself and got to the spa town, I was dying of hunger and a little shaken. Must have food. I parked in the lot. No change in my purse to pay for parking. No change machines in sight. Police on active patrol because it’s Sunday and really busy in touristy places. Great. There must be a Tobacco shop in town to make change for me. Nope. Take out pizza? Nope. Ok, fine, I’ll risk a parking ticket, I want food now. Nope. Won’t anyone take my money? It was 2:55pm. Here in Italy, restaurants close at 3 and reopen at 7. There was not a place in the village that would feed me anything other than gelato, no matter how nicely I asked. Ok, fine. A quick check of the text in the book to make corrections and I’m gone.

I went further to a check another quaint village, one on a rocky promontory nearby. Too afraid at this point to drive beyond pavement, I left my car in the lot far below (which was thankfully free) and hiked up and up and up. I got to a lovely little piazza and the restaurant we recommend there. The owners were having lunch but took pity on me and gave me a small bowl of soup, a glass of wine and a little dessert. So sweet! So grateful. Until bill came. €21 Euro, about $23. Nice. 

At this point I really needed a drink. I also realized that I may not be the only American wandering around Tuscany on a Sunday without reservations at a winery and feeling deeply disappointed. I did a little research and found that one of the big producers, Banfi, is open every single day, and open late. That’s a great find for our readers.

So I went out there, another 45 minute drive, and did a tasting. The cantina was much more quaint than I had expected and the wines were excellent. It was fairly inexpensive, and the tasting room was convivial. Finally I got a break! And some good info for our book. Sadly, I could not drink much wine as I had a two hour drive back to Florence. Va bene.

I figured my misadventures were over. Exhausted, I checked in at a hotel near to the airport. My bag had turned into a huge mess in the car and I schlepped everything up to my room in plastic bags. Then I went to drop off the rental car. I stopped at the only place that was convenient for food. McDonald’s. Yep. You heard me right. There was even a drive through and the fries were piping hot. Unfortunately the lid on my drink was not secure and my Big Mac was totally soaked in Fanta by the time I got to eat it. But I didn’t care. It was the best hamburger ever.

The car rental drop at the Florence airport used to be right in front of the terminal, which is why I decided to drop it there. So easy. But it moved since the last time I rented there. I circled for 30 minutes trying to find the rental car drop off at the Florence airport but could not find it. I eventually called and had the lady at the office guide me there. It’s a good thing I speak Italian, the signs to the lot were barely visible.

The rental car shuttle took me back to the airport where I was supposed to pick up a taxi back to my hotel. Once I got there, the taxi line was empty, but there were at least 40 people in line. I know how these things go in Italy, that was a solid hour of waiting for a cab. I decided to walk back to the hotel. It wasn’t that far, Google said 35 minutes but I’ve got really long legs, so I figured 20. It was dark, but Italy is totally safe, right?

As it turns out, the neighborhood near the airport is lacking in sidewalks but has plenty of car dealerships, Chinese casinos and relaxed prostitutes hanging out along the road. I didn’t know that. Interesting information. Again, pulling up my big girl pants, I forged ahead, walking in that way that makes you look bigger and scarier than you are. I’m really tall, and with my hood on, I could be mistaken for a large man. At least that’s what I told myself. I adjusted my scarf and walked on with the air of “Yeah, I totally know where I am. I totally meant to walk down this street”.

I did make it back to my nondescript hotel and immediately took a hot shower. Needed to wash the day off of myself. I think I shampooed my hair about 5 times. As I did that, I realized that I could let this day defeat me. It was a disaster. It was inefficient, disappointing and a little scary. But on the other hand, it was kind of funny. And no matter what kind of dark cloud hangs over a day on the road, it’s sure better than sitting at a desk.

I have noticed that in travel, disasters eventually become hilarious anecdotes with a bit of time and perspective. I’ve become aware that you can speed up that time if you look at it the right way. Nobody died or was injured. I got all of my work done, even if not in the way I had planned. That’s what counts. And now I have a story to add to my collection of harrowing tales of travel misadventure.

The point is, don’t be afraid of travel disasters. It will happen, it happens to everyone. Cultivate some perspective about it and maybe, someday, you will find it funny too.

Oh, and also, never trust Google Maps.

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