Elba Island: The Trip I Didn’t Appreciate as Much as I Should Have

I went to one of the most beautiful islands I’ve ever seen and spent most of the week wishing it was something else.

This is the story of my trip to Elba Island, my pathetic excuses for why I didn’t enjoy it as much as I should have, and how it changed my view on what it actually means to travel well.

Travel is wonderful. It’s exciting, motivating, and one of the few things that genuinely gives me energy. But sometimes, I can overdo it.

There are too many places I want to see, too many ideas, too many little additions that seem crazy not to include at the time. Plans start evolving like a never-ending game of “yes, and,” and before I know it, I’m exhausted before I’ve even reached the destination.

This is what happened after we moved to the Netherlands.

We were so excited to be in the EU, where we could easily travel by car. Mehmet and I were both working mostly remotely, and we couldn’t wait to just get out and explore. As soon as we moved to Amsterdam, we were barely there.

About a year into living there, good friends from the US planned a visit. They wanted to spend a few days Amsterdam, and then head somewhere else, so we decided we’d all go to the South of France together.

But, me being me, I couldn’t let it end there.

We’d drive to Nice and spend time there with our friends, and then after they left, we’d continue into Italy. And because I can’t help myself, when I saw an Airbnb with a beautiful view on an island not too far away, I convinced Mehmet that we had to add that to our plans too.

And so, a visit with friends became a three-week trip through the South of France and Italy, by car, with Bindi.

Because I had been too busy with work, traveling, and adjusting to life in a new country, I barely did any research. I booked everything with a very casual “it’ll be fine” attitude, which is very, very unlike me.

Spoiler: it was not entirely fine.

Once our friends made it to Amsterdam, our days were packed with boat rides, meals, drinks, and an unexpected amount of drama between our visitors. There were constant arguments, pointed looks, and passive aggressive remarks flying across tables.

Things didn’t get much better when we all made our way from Amsterdam to Nice. Thankfully, we were traveling separately, but it was not exactly the joyful reunion with our good friends we had imagined.

To say we were ready to move on to the rest of the trip on our own would be an understatement.

After Nice, we continued into Italy. I had booked eight nights at that beautiful apartment with the view on Elba Island. Since we were working while traveling, I wanted to make sure we had enough time to actually enjoy it. A full week on a Mediterranean island sounded like a dream come true.

To get to Elba, we had to take a ferry from Piombino, Italy. This was our first experience with an Italian ferry, and let’s just say, there’s a learning curve.

We pulled up to the port and a chaotic scene immediately ensued. There were multiple boats leaving for various destinations. We had no clue which one was ours. Everyone working there, and everyone else trying to board seemed just as confused and stressed as we were. People were shouting at us in Italian, waving in various directions, and we were doing that extremely unhelpful thing where you nod confidently while understanding next to nothing.

Eventually, we just followed the car in front of us onto a boat and hoped for the best.

We figured we were probably not going to get very far using English on this trip, so we sat in the car during the crossing listening to a “learn Italian” playlist on Spotify, as if one hour of basic phrases was really going to make any difference.

Thankfully, the crossing was short. Less than an hour later, we were off the boat and on our way to the Airbnb with the spectacular view that had convinced me to book this whole adventure in the first place.

We popped the address into the GPS and started driving.

Now we, and by “we” I mean Mehmet, have driven in all sorts of conditions all over the world. Through the mountains of Bariloche, the chaotic streets of Istanbul, the winding roads of the Amalfi Coast. But this was, without question, the scariest drive I have ever experienced.

Maybe it was my exhaustion, but my fear of heights had kicked in, big time. We were still at least 30 minutes away from the Airbnb, which I had not researched enough to realize was on the complete opposite side of the island from the port, and I was almost in tears.

The road was impossibly narrow to be two-way. It was so winding you could barely see more than a few feet in front of you. And we seemed to be the only people on the island aware that there was exactly zero margin for error between arriving at our destination and plunging off the side of a cliff into the sea.

Things didn’t get much better when we reached our accommodation.

Like I said, I was very quickly persuaded to book this place because of the view. The reviews were good, it had parking, allowed dogs, and that seemed good enough at the time.

While we aren’t the type to book luxury accommodations, we have a certain standard we like. Generally, that standard includes a shower, with a curtain, that is not directly over the toilet.

Our hosts were lovely. They warmly greeted us, expressed some confusion that we were American, because I guess not many Americans make it to Elba on their Italy trips, introduced us to their dog, and gifted us some homemade jams.

They were nothing but kind. But I was already spiraling, and all I could see was that we were spending eight nights somewhere very different from what I had imagined.

As Mehmet came down with the bags, I asked if maybe we should book somewhere else instead.

He pointed to the view and said something along the lines of, “No way. Look at this.”

And to be fair, he was right. The view was incredible.

Unfortunately, I was not yet ready to be fair.

I was working remotely at the time, and while I didn’t necessarily lie about traveling while working, I definitely did not give the full picture of where I was going or how long I would be gone. But honestly, no one at my company really did. As long as you showed up and did what needed to be done, very few questions were asked. Plus, it was summer, half the company was out anyway, and I figured no one would really notice.

What I had not counted on was the almost complete lack of Wi-Fi.

Sure, it existed in theory. But when we tried to use it, we could barely load our email, let alone spend the day on video calls. Mehmet and I attempted to rearrange our schedules so we wouldn’t both need to be on calls at the same time. We switched constantly between the Wi-Fi and our phones’ hotspots, trying to get the best connection. But it was all pretty pointless.

I was convinced my new boss was going to fire me, because all I was contributing to meetings was a series of increasingly panicked “can you hear me now?”s.

Since I had done little to no research, I also wasn’t prepared for the lack of restaurants near our accommodation. Per my usual routine, I woke up the first morning thinking, let’s go get some coffee.

But you see, we were up on a hill. And everything most tourists would want was waaaay down below, at sea level.

We wandered around for a bit, assuming there must be something nearby, and eventually found a small place. It was less of a coffee shop and more of a woman with an espresso machine and a few stools, but it would have to do.

We stumbled through our order, managed to find enough coins to pay because of course it was cash only, and she motioned across the street. There were a few tables set up in a parking lot with a panoramic view over the sea.

It was beautiful.

However, my head was stuck in a state of feeling disappointed, and I was still wishing for a proper coffee shop, and dare I say, some oat milk.

This is embarrassing to admit now, but that was the mindset I was in. I was on a beautiful Italian island, drinking coffee with a view over the Mediterranean, and somehow I was annoyed that it wasn’t the exact version of charming I had pictured in my head.

And that’s how most of our days in Elba went.

Walk Bindi. Stop for coffee. Attempt to work. Fight with the internet. Figure out dinner.

Since I had no desire to get back on those roads unless it was absolutely necessary, and the walk to the seafront restaurants was about 40 minutes - not so bad going down, much worse coming back up - we ended up buying groceries at the one store in town and cooking in the apartment most nights.

It took my nervous system almost the full week to reset.

From reeling from the drama with our friends, to the scary drive, to fearing I had put my job in jeopardy for an Airbnb with questionable plumbing, I could not fully be present in the place I had dragged us all this way to see.

Then, on one of our last days, something finally shifted.

What had I spent the whole week being disappointed about? I’m sitting on an island in the Mediterranean. I was so lucky to be in such a beautiful spot, and I had to make the most of the time we had left there.

We hit the coffee shop then continued down to the beach, one of the most natural, pristine, beaches I’ve been lucky enough to see. We had seafood pasta and aperol spritzes for lunch, we were in Italy, on an island, this is magical.

We went out for dinner that night despite the treacherous walk. We’ll never know exactly what it was that we heard growling at us as we made the walk back in the pitch black darkness of night time, I’m going to assume it was a wild boar.

On the morning of our departure, we enjoyed our final cappuccinos in that parking lot, Volare playing out of someone’s parked car, never taking our eyes off the view. I felt a bit ashamed for how much time I had spent wishing this trip was something else, and sad that I didn’t appreciate it for what it was. Sad, too, that I had wasted so much of the trip comparing it to the version I had invented in my head.

The problem was that I kept wanting it to be something it just wasn’t. A version with stronger Wi-Fi, flatter roads, and oat milk flat whites.

But that’s not really travel. That’s just trying to relocate your existing life somewhere prettier.

And I think that’s the lesson that has stayed with me. Travel is not always about ease. It’s not always about being comfortable, or getting the exact experience you thought you booked, or finding the perfect little coffee shop that already understands your order.

Sometimes it’s about letting a place be what it is before deciding whether or not it has disappointed you.

And sometimes, it’s about drinking the damn coffee, shutting up, and enjoying the view.