Puglia Day 1: Monopoli
There are places you choose. And there are places that choose you.
Some places you stumble into. Others? They've been waiting for you all along.
Picture this: March 2024, I’m walking barefoot across cold stone floors in a seaside Airbnb, salt air drifting through open windows, and that unmistakable feeling that I was about to make either a brilliant decision or a beautifully reckless one. Spoiler alert: sometimes they're the same thing.
This wasn't your typical vacation. This was reconnaissance.
Before I tell you all about Monopoli, let me back up as I need to give you a bit of back story first.
Years ago, wandering through Perugia in Umbria, I spotted this absolutely stunning dress in the window of an atelier. Without thinking, I turned to my mother and blurted out in excitement, "One day, if anyone ever wants to marry me, I'm getting married in Italy." Classic romantic declaration, right? Well, years passed, the idea of marriage felt increasingly distant, and that little dream got filed away under "nice thoughts that probably won't happen."
Then, years later I got proposed to, meaning that someone actually wanted to marry me!
Suddenly I was staring at the reality of planning a wedding, and honestly? The numbers in Canada were eye-watering. Don't get me wrong — BC has absolutely stunning venues and incredible business owners, but having worked in the hospitality and wedding industry here, I knew the unique challenges that come with being in a tourist destination: seasonal staffing, training new teams constantly, and the premium prices that come with paradise. I was going to say yes to this whole marriage thing only once, and I wanted something completely different — an adventure that felt as extraordinary as the commitment itself.
Lake Como and Tuscany were immediately off the table — stunning, yes, but my bank account had other opinions. That's when my parents, in their infinite wisdom, suggested southern Italy. "What about Puglia?" they asked, with that particular parent energy that suggests they've been researching this longer than you have.
I'd never been to the south. One Google search led to another, tabs multiplying like rabbits, until I was staring at images of whitewashed Trulli, endless olive groves, and coastlines that looked like they'd been painted by Monet. Before I could talk myself out of it, I'd found an incredible wedding planner (the absolutely incredible Salina Oraz) and put down a deposit on a venue I'd only seen in photos.
Bold? Absolutely. The kind of decision that makes you question your own judgment at 3 AM? Maybe. But sometimes you have to trust that the universe is conspiring in your favour.
So I booked a flight to Bari, rented what turned out to be the world's tiniest (and cutest) car, and pointed myself south with nothing but a loose itinerary and an abundance of optimism.
First Stop: Monopoli
First Stop: The Town That Chose Me
The coastal drive was one of those journeys that makes you forget you have a destination — all silver light and winding roads that seem designed for contemplation. I rolled into Monopoli after dark, picked up my keys from a café owner who handed me both a slice of pizza and the apartment keys (southern Italian hospitality hits different), and found myself in Salina's personal Airbnb, literally perched on the water's edge.
Waking up to an Adriatic sunrise? Life-changing. Wandering into town with zero agenda? Even better.
Here's the thing about Monopoli — it doesn't try to impress you. It just is, completely and unapologetically itself. The old town curls around its historic port like a contented cat in the sun, all honey-colored stone and narrow streets that have been worn smooth by centuries of footsteps. The name itself tells a story: from the Greek monos (only) and polis (city) — "the only city" — earned when everyone fled inland during barbarian invasions and this became the last safe harbor.
Dramatic? Absolutely. But also kind of romantic when you think about it.
Monopoli offers the perfect collision of old-world charm and seaside spirit. I started my mornings at Dolce Amaro Café — and trust me, say 'Ciao' to Gianni when you go — it's the kind of spot where the crema on your espresso basically confirms you've made all the right life choices. For sunset? I'd grab wine and wood-fired pizza at Porto Rosso, perched right by the water's edge, watching the day melt into the sea with a pizza crust in one hand and pure gratitude in the other.
There's this walkway along the old fortress walls that gives you uninterrupted views of the Adriatic — in March, it was turquoise and wild, with a wind that felt like it was trying to wake something up inside me. And honestly? It worked.
Where Everything Started to Make Sense
But let's be real — I wasn't just there to wander around looking pensive (though I did plenty of that). I was on a mission to see the place where I'd soon be saying "I do."
Enter Masseria Santa Teresa.
The drive there felt like a pilgrimage through an olive oil commercial. Primordial trees lined the road like silver-green sentinels, their gnarled branches telling stories of years past. The driveway was cobbled and rough — the kind that forces you to slow down and actually arrive somewhere, rather than just ripping in like Lewis Hamilton to a pit stop.
And then I saw her.
Whitewashed walls catching the late winter sun. Wild rosemary blooming along the edges like nature's confetti. Lemon trees heavy with golden fruit. Butterflies dancing between soft green gardens. And there, just visible from the edge of the olive groves, the Adriatic again — because apparently the sea had decided to follow me everywhere.
The food? Like someone's nonna had been cooking just for me. Everything tasted of olive oil and sunshine and that particular kind of love that only comes from ingredients that grew up in the same soil where you're standing. Southern Italy does this thing — it's less polished than the north, more personal. You taste it in the tomatoes, in the hand-rolled orecchiette, in the way even a simple meal feels like an act of love.
I'd been to the hill towns of Umbria, gotten swept away by the drama of the Amalfi Coast, swooned over the elegance of Cinque Terre. But Monopoli? Monopoli felt different. Quieter. More lived-in. Like it had nothing to prove to anyone, which made me want to prove everything to it.
Maybe that's why I chose it. Or maybe — and this is starting to feel more true the more I think about it — maybe it chose me.
This was only the beginning…
This was just day one of what would become a seven-day love affair with southern Italy. But Monopoli had already done its work, planting a seed that whispered: You're exactly where you're meant to be.
Sometimes the most important journeys start with the smallest yes. Sometimes you have to trust your gut even when your brain is asking very reasonable questions about deposits on venues you've never seen. And sometimes — just sometimes — the most beautiful moments happen when you stop trying to control the story and let the story write itself.
Stay tuned for Stop #2 in this seven-day journey through southern Italy. But if you're anything like me, you might want to book a flight to Monopoli first.
And if you’d like to explore which part of Puglia is calling your name—checkout my Complete Guide here.