The Best Laid Plans: Adventures In Italy
If you’re anything like me, you carefully plan your vacation. I make lists, watch travel vlogs, utilize AI for ideas, keep notes, and carry a notebook with all collected data on said vacations. You may be a traveler who chooses a destination, buys the airfare, and thrives on spontaneity. Possibly, you are somewhere in between and enlist the help of a travel agent to iron out the details once you choose the destination. Whatever type of traveler any of us is, regardless of all of the meticulous planning (or lack thereof), sometimes things don’t always go as expected.
About a year and a half ago, my amazing husband and I started planning my “Retirement Trip.” Travel vlog watching commenced, lists of ideas for exciting destinations started, and the notebook filled up. Our big trip began with a carefully plotted cruise through Norway, Iceland, and beyond. Then, a last-minute offer added a Mediterranean cruise to our itinerary. With a significant shift in plans, we had to rethink our travel routes.
With a week between cruises, we opted for an ambitious but scenic route—train through Italy, cross into Switzerland via the Bernina Express, explore Switzerland, and then fly to the Netherlands for our next cruise. It was mapped out down to the last detail.
Let the adventure begin!
Civitavecchia Charms and Mediterranean Dreams
We flew into Rome, where catching the next train to Civitavecchia was easy. We quickly fell in love with this charming port city. (If you haven’t read my post about Civitavecchia, you can check it out here.) After two relaxing days, we boarded our ship and set off on a two-week Mediterranean cruise.
Near the end of the cruise, we re-examined our travel plans for disembarkation day, when we needed to get to Tirano to catch the Bernina Express. Getting to Tirano in a single day required precise timing: a train from Civitavecchia to Rome, then Milan, and finally Tirano—on a Sunday, no less, when many trains outside of Rome don’t run. Our Bernina Express tickets were for the following morning, so everything was planned to the minute.
That is, until the night before, when my dear husband proposed a “more adventurous” route.
The Husband Had an Idea (I Had a Wine)
My handsome, darling husband and I have been traveling together for ten and a half years. In that time, I’ve grown accustomed to his last-minute second-guessing. I’ve learned it’s best to humor him and review every detail—sometimes more than once—until he’s satisfied we’ve made the right call. This usually involves a few deep sighs on my part and at least one glass of wine.
So, the conversation began. He was certain there had to be a way to reach Tirano without passing through Milan, which also meant bypassing portions of Italy that we had already seen on a previous trip. I sighed and ordered a glass of wine. We pulled up the travel apps—Rome2Rio, Omio, Trainline, Rail Europe, and Trenitalia—and after some digging, he was right.
There was another option—two extra stops, and we’d end up in Edolo, where we could grab a taxi or Uber up the mountain to Tirano. We’d get in later, but see more of Italy, which made my sweet husband happy. After two glasses of wine and a lot of back-and-forth, I agreed. I was a little uneasy about finding a ride from Edolo on a Sunday night—the bus wasn’t running, and we couldn’t schedule an Uber without knowing exactly when we’d get there. But my charming husband promised it would all work out. So, I took a deep breath and let it go.
We disembarked as planned the next morning, reached Rome by 10 AM, and began our adventurous day of train-hopping. From Rome, we rode to Verona Porta Nuova, changed to a train bound for Brescia, and finally hopped on the last train to Edolo. These were commuter trains, filled with people heading to or from work, caught up in the rhythm of their daily lives. It was a beautiful day, and the scenery was fresh and different from what we’d seen on past trips. Success!
When the Station Clears Out and You're Still There
When we arrived in Edolo, I noticed it was a small town with a small train station. It was, indeed, a commuter stop. We got off the train, and I saw a few people in their cars waiting to pick up their loved ones and get home to Sunday dinner. Greetings and hugs, and very quickly, the train station was empty, except for us.
Sitting at the train station in Edolo, Italy / Photo by Whaldo Digital Content
We found a bench to sit on, and I tried to find an Uber ride. I waited, but there were no Uber driver cars on the map. I hoped that maybe someone was at home waiting to see if any orders came in, and once they saw us, they’d accept the job. We sat there for about half an hour, both of us trying to get an Uber driver to take the job and drive us up the mountain. No takers.
Wishful thinking aside, we needed to get past our Uber dream and devise another plan. Neither of us had noticed any taxis. None had driven by, but we were getting some curious looks from the few locals driving by. I spotted a sign at the station showing a taxi company and phone number. I called but received no answer. I was starting to feel anxious.
The Kindness of Strangers (and the Power of WhatsApp)
My dear husband decided to walk around and see if he could find a business open to get assistance hailing a cab. It was nearly 5 p.m., and again, it was a Sunday. I decided to contact the hotel in Tirano. Maybe they knew of a taxi company that I could call. The hotel was a small, family-owned hotel and restaurant. When I called, a woman answered, told me her name, and explained that she was the manager of the reservations. She spoke English very well, thankfully, because my Italian is sub-par, to say the least. I explained where we were and our predicament. She was very kind and immediately empathetic to our situation. She offered to find some taxi cab names and phone numbers and get back to me quickly. She took my number and WhatsApp contact information to text as well. I sat on the bench outside the train station and waited.
Shortly after, I received a text from her containing a couple of taxi companies to try. I got right on the phone. The first number did not answer; however, a man answered the second number I tried. He said he was done working for the night but would find someone else to drive us. I gave my WhatsApp info and waited.
My husband returned from his walk, where he had had no luck finding anything open, as I suspected. I shared that I was waiting for the taxi company's reply, but had not secured a ride up the mountain. While we were waiting, the hotel manager messaged me several times over the course of an hour. She explained that she had tried to reach a friend to ask if they could come to pick us up, but that person wasn’t available that night.
Since I hadn’t heard back from any taxi company, I contacted the one that had responded earlier. He seemed surprised that I hadn’t heard from his partner and gave me the partner’s name and number so I could try contacting them directly. Clearly, he didn’t want to hear from me again. When I called, a woman answered the phone. After explaining how I’d obtained the number, she yelled to someone in the background. She then asked if I’d pay 100 euros in cash for the ride. At that point, I would have paid 200. I agreed, and she said she’d drive us herself and would be there in half an hour.
I was still texting with the hotel manager, who told me she would not stop checking on us until we were safely in Tirano. I felt very grateful for her empathy and attention. About an hour later, the woman who was to drive us had not shown up.
While waiting, a shuttle bus stopped and let a few people off. I watched with envy as their people then picked them up. The driver stepped out of the bus for a smoke break, so my spouse wandered over to talk to him. I could hear he was trying to convince the driver to drive us up the mountain. Again, I called the number where the woman had answered previously to ask if she was still coming. Again, she said she would be there in half an hour—deep sigh.
Three Hours, Two Tired People, One Bench, and Zero Ubers
It was now nearly 8 p.m. on a warm, balmy July night. I looked around and resigned myself to the fact that we would probably be sleeping on a bench at the train station in Edolo, Italy. It wasn’t ideal, but walking up the dark mountain road for 20 miles, pulling our luggage, was not feasible.
As I sat there, imagining the best items from our luggage to use for semi-comfortable sleeping on the bench, my husband approached me to explain that the shuttle bus driver had received permission to drive us to Tirano if we paid 200 euros in cash. Just as I was processing this information, a van pulled up around the bus and stopped right in front of me. A woman exited the van, opened the sliding door, and looked at me expectantly. I looked at her quizzically, and when she spoke to me, I recognized her voice and knew she was the woman from the phone who would “be there in half an hour”, over two hours ago. She asked if we still wanted a ride. I tried my best to smile and affirmed that we needed the ride!
We declined the shuttle bus driver's offer and loaded our luggage into the woman’s van. I felt guilty turning the shuttle bus driver down, but honestly, he seemed relieved not to have to make the trip. I messaged the hotel manager to let them know we were on our way.
Tirano at Last—Pizza, Gratitude, and a Hug Goodbye
The drive up the mountain was nerve-wracking. It was a steep, narrow road with hairpin turns and no lighting except the van's headlights. Our driver knew the route and drove it expertly, but I kept my eyes down and grasped my patient husband’s hand so tightly that he had to remove it a few times to stretch his fingers. We came upon a small ski town along the road where our driver pulled over so that we could use the ATM to pay her in cash.
When we reached the top of the mountain, I was impressed and struck by the beauty of Tirano. The van quickly came to a stop, and our driver pointed at a building across the square. That was our hotel. I was so grateful to be up the mountain and in one piece that I tipped her beyond the 100 Euros. We gathered our bags from the van, and I shocked her by hugging her goodbye. We pulled our luggage across the cobblestoned square to the hotel, and the manager was pleased to see that we had finally made it.
Although it was later than desired, my loving husband and I dined alfresco in the cobblestoned square, enjoying drinks and delicious pizza at Pizzeria Leti. After our anxiety-filled afternoon/evening, back in our spacious, comfortable hotel room, we each had a cool shower and promptly fell asleep in a soft bed.
Dinner in Tirano, Italy at Pizzeria Leti / Photo by Whaldo Digital Content
The following morning, we headed to the train station in the same cobblestoned square as the hotel. There was no rush or fuss. We had plenty of time to board the Bernina Express to begin the next leg of this epic journey.
Travel Truth: The Best Memories Aren’t on the Itinerary
In the end, we didn’t just take a train through Italy—we took a delightful detour into the unexpected. We met kind strangers, gathered stories, and created memories we’ll laugh about for years.
We’ve learned that even the most carefully crafted plans are really just suggestions. When things go sideways—and they sometimes do—it’s the detours that bring the most color to the journey. As long as we’re safe, we can roll with it. Maybe even laugh about it. Eventually.
There are still many places to see, and yes, I’ll continue to try to organize the perfect itinerary. But I’m learning to greet the curveballs with a little more grace—and a backup bottle of wine.
After all, isn’t that what travel’s really about?
Stay flexible and safe travels.
J.S. Whaldo
