I am back for another rambling adventure. This year, with a little coaxing from my sister Karen, I am breaking out of my U.K. obsession and hiking for two weeks in Italy. Rambling Hank is transformed! I am become Enrico Vagante. I think it makes me sound like a character from a Fellini film. (My pal Vince proposed the translation; for all I know there is a subtle connotation that I am an idiot…)

The plan, as is often the case, involves a blend of walking with company and walking alone. This time, Karen joins my for the first week for a gentle ramble through the hill of Tuscany. Frequent readers of this blog will know what that means: lots of sweaty elevation gains and losses. On my U.K. rambles the towns are often set near rivers. But in Tuscany, the towns are almost all perched on the hilltops, the better to protect all that incredible Tuscan wine. That means that the days often start with a drop in elevation and end with brutal uphills stretches. There is a town where, I kid you not, we end at the town elevator, which takes us up to the part of town we are staying in. I am grateful in advance to the town planners who approved that construction boondoggle.

One weird truth about walking trips is that, while you can get into some difficult situations when you are walking (like being lost in a field of carnivorous ferns, cf. my Wales trip last year), just getting to the starting point is often more exhausting and stressful than anything you encounter on the trail. And so it was this time.

But before the walk always comes the flying. And this time, the gods decided to tease me a bit. My Chicago overnight flight to Frankfurt left almost two hours late, and my connection time in Frankfurt to get to Pisa was just a little over two hours. The plan had been that Karen and I would meet in the Frankfurt Airport (she’s coming from Pittsburgh) and fly the 8:30am connection to Pisa together. I texted from O’Hare that I was concerned. Her flight was also running a bit late. We agreed that anyone who could would get to Pisa and we’d connect there.

She made it. I didn’t. My flight landed at 7:55am, and unloaded us far from the terminal, to be taken in by bus. We were assured that we had been rescheduled onto the 4:30pm flight to Pisa, the only other flight to Pisa on Friday. Not trusting, I called United, to be informed that my supposedly rescheduled ticket had been “cancelled after acceptance,” which puzzled both the United service agent and, when she suggested I talk to someone on the ground, a Lufthansa agent who heroically tried to sort out the doings of Air Dolomiti, a small regional carrier with which United and Lufthansa have some sort of code-sharing agreement. Lufthansa agent said I was on a standby list, and it was a short list so she was optimistic. I don’t trust the optimism of customer service agents, she worked with me on a backup plan. If I didn’t get on that flight, there was a 9:30pm flight to Florence. I could stay there overnight and catch a train to Pisa to meet Karen and make it to my scheduled taxi pickup at 11:45am. The last thing I said before leaving this hero of Lufthansa customer service was “Hey, I have a checked bag. They’ll know to get it on whatever flight I end up on, right?”

“The bag will be waiting by the aircraft, and if you don’t get scanned onto the 4:30 flight, it won’t be put on and will be loaded when you board the plane to Florence. Our baggage handlers here in Frankfurt are excellent.”

Gentle reader, you know what happened.

I killed eight hours in the Frankfurt Airport, which is not as fun as it sounds, and went to the gate for the 4:30 flight to Pisa. I was not the only United passenger from Chicago in the same situation; I overheard or recognized at least six others looking a bit stressed. But whatever “cancelled after acceptance” really means, we all made it onto the plane, and I sighed a big sigh of relief. Until I used my phone and the Apple AirTag stored in my checked bag to see if it, too, was on the tarmac and ready to go to Italy. Much to my dismay, it was still somewhere in the terminal. And off we went.

On arrival, I didn’t even stop at the luggage carousel; I went straight to Lost Luggage and informed them that my bag was still in Frankfurt. After filling out paperwork, I was informed that the bag would come on the Saturday morning flight, and I could come back at 9:45am to get it, or I could have it delivered. Delivery required a 72-hour window. So I committed to coming back in the morning and headed into town.

I had no particular plan to visit Pisa (to get to the starting point for our hike, you can go through Florence or Pisa; I opted for Pisa because the ticket was cheaper somehow), but it’s a lovely little city.

Really lovely.

And I ate spaghetti carbonara to celebrate at least being in Pisa, if still in clothes I’d been wearing for 30 hours and not 100% sure I’d get my bag, with ALL my hiking clothes, in the morning.

Look how happy (and sweaty and tired) I am at the sidewalk cafe.

In the morning, we ate delicious pastries (pistachio cream-filled for me. Yum.) and drank cappuccinos and took the very efficient tram from the central train station to the airport. The key here is that we had to catch an 11:30 train from the central station to meet a waiting taxi in Pontedera to take us to Volterra, our real starting point for the hike.

We got there before the plane landed, and I waited in line while a man explained, from what I could overhear and translate using my non-existent Italian, his entire life story and his genealogy going back six generations to the lost luggage person. When I finally got my turn, I was informed that yes, my bag was on that plane, but I should come back in 20 minutes. Forgetting how time works in Europe, I returned in 20 minutes, only to wait another 25 minutes, during which I could check the “Find My” app and see my bag was about 20 yards away. Finally, it was returned to me, and Karen and I made it back to the train station and made our train with time to spare.

It’s only a 15 minute ride from Pisa to Pontedera, so what could go wrong. Hahahahahaha. We stopped in mid-journey for five minutes, with much puzzlement and resignation on the faces of all the train passengers, then got underway again. The notes for our taxi pickup said the driver would wait five minutes, and if we missed it we would have to call and make a new arrangement. The gods, I thought, had one last trick for me. We made it to Pontedera, and saw a waiting ambulance, which explained our stop–a passenger had a medical emergency, and they had, I guess, determined that the best thing to do was get him to the station. But no taxi driver holding a sign, as promised. So I called, and after I explained I was Sartin for a pickup and the train was late, the first thing the driver said, to my puzzlement, was “I think I am looking at you.” I figured this was some language problem. Then I looked around me and saw a man standing by a van waving at me. Karen and I walked over and he apologized for being five minutes late (not sure he’d actually understood my whole explanation about the train being delayed). He found two other passengers also booked through our travel company, Mac’s Adventures, and off we went toward Volterra.

Volterra is a stunningly beautiful walled hill town with Etruscan archaeology, Roman ruins, medieval walls and gorgeous buildings that have been added to and renovated and rebuilt and linked together over hundreds and hundreds of years. Just gorgeous. I’ll end with some photos in a slideshow and the wildly optimistic statement that, after all that trouble getting here, the walking is going to feel easy! (I know already that is a lie-remember my early caveat about hills…)

See you tomorrow after our first day’s hike, which is a true ramble that brings us back to Voltera for a second night in the same hotel.