Lessons from a Solo Cycling Trip Through Puglia

“Who are you going with?”

My husband looked up from what he was doing.

“No one,” I replied.

His expression shifted almost instantly.

First, surprise. Then concern. Then quiet acceptance.

After thirty-five years together, he knows me well. Once I’ve decided something feels right, there isn’t much point in trying to convince me otherwise.

I was looking for an adventure.

Truthfully, I wasn’t looking for permission. I was looking for evidence—evidence that the woman I remembered being was still there.

I’ve always believed travel has a way of revealing parts of ourselves that everyday life quietly buries. That’s one of the reasons I love it so much.

Puglia had been on my list for years. I love Italy, and I’m determined to see all of it.

The ancient olive groves. The whitewashed villages. The Adriatic Sea. The fresh pasta. The quiet country roads.

It felt like the perfect place to spend five days on a bicycle.

Alone.

I had cycled before—with my husband, friends, and family—but this would be my first solo cycling adventure.

Five days. One bike. One GPS. One suitcase. One slightly nervous Canadian hoping she hadn’t completely overestimated herself.

Getting there was part of the adventure: delayed flights, arriving at dusk in the winding streets of Bari, dragging my suitcase over uneven stone, and trying to find my Airbnb tucked behind an ordinary wooden door that looked like every other ordinary wooden door.

I have this habit when I travel, especially when I’m alone. I walk with purpose, even when I’m completely lost. I’m convinced that if I look confident enough, everyone else will assume I know exactly where I’m going.

I believe it’s a safer way to be.

Eventually, I found it.

One more climb—up a narrow staircase—led me to my host and a rooftop terrace overlooking the city. Church bells echoed through the warm evening air while swallows swirled overhead.

Below me, families lingered over dinner, children played in the streets, and Vespas took advantage of the quieter roads to go even faster. Life unfolded at a pace that already felt different from home.

I hadn’t even started riding, yet somehow I could already feel myself adapting to my new environment.

I only had a short time in Bari, so I tried to soak up as much as I could. I was especially impressed by Castello Svevo di Bari. I’ve been inside many castles, but this one offered something completely different.

Through projections, art, and sound, the rooms became an immersive experience that transported me hundreds of years into the past.

As I was leaving for the train station, I found myself encouraging people debating whether to buy a ticket.

“I promise it’s worth it,” I told them.

After a short local train ride, I arrived in Putignano to meet my fellow cyclists.

There were older couples and younger couples. Friends. Experienced riders who looked perfectly comfortable in fitted cycling gear. This would most likely be the only time I’d see them, as we each had our own journey and accommodations ahead.

Then I met my bike.

It was… substantial.

I was grateful it was white, with minimal rust. I’ll admit it wasn’t the usual calibre of bike offered on these rides, but it was a new tour company. Lifting it to test the weight was my first clue that this ride wasn’t going to be as effortless as I’d imagined.

Still, I smiled.

This was exactly why I’d come.

The route through Puglia was everything I’d hoped for.

Ancient olive trees stretched endlessly across the countryside, their twisted trunks looking more like sculptures than trees. Dry-stone walls lined narrow roads connecting individual family farms, where time seemed wonderfully unconcerned with hurry.

Laundry fluttered on clotheslines—all practical, everyday clothing.

I had packed a small speaker, imagining I’d spend my days cycling to a carefully curated playlist. Instead, I left it in my bag and listened to my tires rolling over pavement, birds hidden in the olive trees, and my own breathing.

Somehow, that became the soundtrack I needed.

As I pedalled, the scent of wild herbs drifted through the warm air. Every corner seemed to reveal something worth slowing down for.

Until the chain came off.

I shifted gears approaching a hill, determined to win this challenge without getting off and walking.

Click. Click. Click.

Silence.

I unclipped from the pedals quickly, climbed off swiftly feeling determined… I held the bike upright, and somehow managed to lift enough of its weight to guide the chain back into place.

My hands were covered in grease. Feeling somewhat accomplished… I looked around.

Nobody.

Good.

I didn’t need an audience.

A few kilometres later…it happened again.

And again.

And again.

FUCK!

This is supposed to be fun, I told myself.

Then I shifted my internal mantra to, “I can do hard things”—thank you, Glennon Doyle.

By the fourth time, I was becoming surprisingly efficient at roadside bicycle repair.

I still never thought to lay the bike down. Apparently, making things harder than necessary has been one of my hidden talents.

Not long after, another challenge appeared.

I had just walked to the top of a very long hill. Sweat was dripping. The chain was back in place. I looked at my grease-marked legs and the unusual tan lines forming beneath my bike shorts.

I took a quick sip of water and clipped in my right foot.

Then I heard barking.

Three dogs came racing at me over my right shoulder from a nearby property.

They were not happy to see me.

No fence. No gate.

Then two more dogs appeared.

Oh, shit.

Their four-legged neighbours wanted in on the action too. They were entirely convinced I didn’t belong on their road.

I wasn’t about to argue.

I pedalled with only one foot, yelling, “No! No! No!” while keeping my left foot unclipped in case I needed to kick whichever dog got closest.

I looked straight ahead and didn’t stop.

Secretly wishing to myself that I learned “Go Home” in Italian on my Duolingo app.

Eventually, they gave up.

My heart took considerably longer to return to a healthy pace.

Later that afternoon, I called my husband.

Not because I wanted rescuing, but because sometimes hearing a familiar voice is enough to remind you that you’re okay.

And then I made a decision.

I was going to stop punishing myself.

I was getting an e-bike.

For so long, I had measured myself by how much I could carry, how much I could endure, and how much I could sacrifice.

At first, it felt like cheating.

By lunchtime, it felt like freedom.

Instead of concentrating on surviving every hill, I finally had enough space to notice where I actually was. I could admire the magnificent rows of olive trees instead of seeing only the ones in my peripheral vision.

I could stop for a pistachio gelato while I watched and admired the cliff jumpers in Monopoli.

I had given myself more time.

Little lizards darted through the dry leaves as I passed. Cars approached from behind, their horns gently announcing they were about to pass.

Back home, unexpected sounds have a way of making me jump.

Out there…

Neither seemed to bother me.

I noticed them. Then I kept riding.

Looking back, that small shift feels strangely significant.

One morning, I found a quiet stretch of rocky shoreline overlooking the Adriatic. The water shimmered in every shade of blue imaginable. The sun was warm, inviting me to soak it up—and perhaps correct my cycling-short tan lines.

I accepted the invitation.

I changed into my bathing suit, found a warm rock, and decided I wasn’t riding another kilometre until I had simply sat still.

My phone buzzed.

There was a message from one of my oldest friends. She had made me a playlist.

Its title made me smile before I even pressed play.

Finding Lisa.

At the time, I thought I was searching for a new version of myself.

Looking back, I know now that wasn’t the journey at all.

I wasn’t finding someone new. I was remembering the woman I had always been.

The title told me she already saw me, even while I still felt lost. Song after song, memories from our childhood mixed with lyrics she knew would speak directly to my heart.

I laughed and I cried.

Mostly, I sat quietly, listening to the waves.

It was exactly what I needed that afternoon.

Years later, when I wrote my story Finding Lisa ( Action Speaks Louder Vol 2) , I realized that playlist had become part of the journey. Not because it changed me, but because it arrived at exactly the right moment.

I tucked my phone back into my bag, climbed onto my bike, and kept riding.

Over the next few days, something shifted.

The bike and I stopped arguing.

The kilometres became less important.

I lingered in beautiful towns. Admired weathered stone architecture. Talked with strangers. Shared wine with strangers. Shared meals with strangers.

One afternoon, drained from the heat and proud of my ride that day, I stopped at a tiny convenience store for some celebratory chilled white wine.

The owner looked at me for a moment before disappearing inside.

He returned carrying a banana.

“Potassium,” he said, smiling as he handed it to me.

He knew exactly what I needed. In that moment, he was my Italian father figure.

We sat outside together—an Italian shopkeeper and a Canadian cyclist. Two people with very few shared words, but somehow an easy understanding.

I just remember how safe I felt.

Moments like that rarely appear on an itinerary. They’re simply gifts travel sometimes gives us.

People often ask me what my favourite part of Puglia was.

Was it staying in a trullo? The food? The wine? The Adriatic? The ancient olive groves?

They were all wonderful.

But my favourite part wasn’t something I could photograph.

It was how I felt—and what I learned about myself while I was there.

I stopped trying to prove I could do hard things.

I already knew I could.

The lesson was learning that I didn’t have to make everything hard.

Choosing the e-bike didn’t diminish the journey. It gave me more of it. More time to look around. More energy to explore. More room to notice what was happening around me—and inside me.

Maybe that was the real lesson of Puglia.

Not pushing harder.

Making room.

Room to pay attention to the subtle clues that appear in unexpected places. Room to hear the answers that everyday noise can drown out. Room to remember what feels good, what feels true, and what feels like me.

I boarded the plane home with bruised legs, grease-stained cycling shorts, a strange tan, and a phone carrying a playlist called Finding Lisa.

Puglia didn’t give me answers.

It gave me something more valuable.

It gave me room.

Room to breathe deeply. Room to laugh. Room to trust my instincts. Room to dream about what might come next. Room to stop proving. Room to simply be.

Because somewhere along the way, many of us become so busy making room for everyone and everything else that we stop making room for ourselves.

Maybe that’s why I keep travelling.

Not to escape my life.

But to create enough space to hear my own voice again—and return home more fully myself.