Wandering the Winding Curves of Northern Italy

Published October 6th, 2023

All photographs by Steph Kesler

The view from the Riomaggiore train station

Of all the countries I’ve explored to date, Greece and Switzerland were easily the most breathtaking. So, when it came time to plan my 2023 summer vacation, I opted for an adventure that’s smack dab between the two—a northern Italy road trip—with hopes of diving into destinations with diverse landscapes.

My itinerary was eight days in total from August 12th to 20th. Round trip from Milan, I hit bustling cities, lazy lakeside towns, oceanfront cliffs, rolling hills and every nook and cranny in between. As for where I called home: Lake Como, Chianti and Cinque Terre.

Embrace the Laissez Faire Lifestyle in Lake Como

You don’t go to Como for the parties; you go for the views, and they certainly do not disappoint.

If you’re not able to afford a private boat rental, you can easily pop on the ferry to reach the many lakeside towns, each with its own character and charm. For those looking for a beach, be sure to wake up at the crack of dawn as “parking spots'' (unsuspecting areas on the side of the narrow road) fill up fast.

What I loved most about Lake Como was the view from my AirBnB in Limonta as I kicked back with my book each morning (Book Lovers, in case you’re wondering). And let’s not forget slowly wandering the streets with a cup of pistachio gelato in the evenings. This lakeside location is simply picture perfect.

Enjoy the Culinary Delights of Chianti

Chianti has a beauty that isn’t loud or in your face. It’s the subtlety of this region that makes it spectacular. The lack of crowds. The laid-back lifestyle. The appreciation for the finer things in life, where wine and dining are always top-of-mind.

To put it plainly, the Chianti culinary scene far surpasses every other Italian region, in my opinion. Every dining experience was magical because it had all the key ingredients: mouth-watering dishes, delicious wine and jaw-dropping views with sunsets that hugged every curve of the rolling hills.

Beyond the exquisite food from restaurants like La Castellana and Il Vescovino and the local wineries like Fattoria Le Fonti and Casaloste, I was able to get the most authentic taste of Tuscany at my home-away-from-home.

The AirBnB I stayed at felt like a rural cottage, hosted by a lovely couple with much-appreciated passions: cooking and ceramics. I took them up on their offer for a three course meal and I have zero regrets; it was everything I’d hoped for and more. 

Take a Dip in Cinque Terre

Cinque Terre is not for the faint of heart. If you hate long walks and steep inclines, this might not be the place for you. But it’s the price you pay for jaw-dropping cliffside views.

I stayed in Riomaggiore, 100 metres or so from the main dock pictured above. What surprised me most about Cinque Terre was how teeny tiny each of the towns were. So tiny, you could explore each one in a couple hours and truly get to know the residents who live there.

Where Riomaggiore has a “beach” of rocks and large seaside boulders (that requires more than a little agility to scale), Monterosso, a neighbouring Cinque Terre town, has a classic sandy beach where I was able to snag a spot to lay my towel and enjoy the day floating in the crystal-clear water.

What made it even better was the beautiful stone statue at the end of the beach reminding you you’re in Italy and everything is exquisite, down to the last detail.

Don’t Forget to Detour

Just because you’re not staying in a destination, doesn’t mean you can’t visit it. That’s the beauty of a road trip. While I stopped in a number of cities throughout the trip (Verona, Parma, Florence, etc.), a couple detours stood out among the rest.

Lake Garda

Lake Garda can only be described as Como’s fun little sister.
The patios are vast, and everyone seems excited to be there.
It’s not as glamorous as Lake Como, but if you’re looking for a little fun in the sun, look no further, and don’t be worried about bringing the family along with you.

Milan

“Why does everyone go crazy for Florence? Milan is way better.” Those were the first words I uttered upon stopping in Milan.
Yes, it was busy, but the streets were so wide, you didn’t notice.
Window shop and explore beautiful architecture, all while being serenaded by buskers around every corner.

Rules of the Road

When it comes to Italy, there’s no wrong answer for how to get around. If you opt to explore the country on four wheels like me, I’ve compiled a few tips to help drive inside the Italian lines.

Go small or go home. At first, my friend and I wanted an SUV, but boy am I happy they gave us a car because I have no clue how we would have fared on the nation’s narrow streets in anything larger.

Tolls will take a toll (on your wallet). Almost every highway in northern Italy is a toll road where you get a ticket upon entry and pay when you get off approximately $7.50EU every 45-minutes, varying by region. Plan accordingly!

Pay attention to parking. In almost every major city, there are ZTL zones with limited or restricted parking. Additionally, the lines outlining parking spots are different colours to signify things like residents vs. pay parking. Always be sure to Google the colours as they change from city to city.

Trust your gut. While making our way to a Chianti winery, Google Maps led us down a narrow, gravel road, which quickly turned into a very steep rocky road our rental car could not handle. Let’s just say we needed a serious car wash to disguise the off-roading from the rental company. Needless to say, turn around if something seems off.

All in all, Italy satisfied all my cravings. I was able to get a taste of a European road trip, embrace a slower pace and be inspired by new flavours.

Most importantly, I left with a full heart, full belly and new pottery to display when I serve up my best attempt at home cooked pesto pasta.

Steph Kesler

At 18, Steph got her first real taste of international travel as a Disney on Ice skater. For two and half years, she toured the world playing every character under the sun while taking in the sights, tastes, sounds and smells of the weekly destinations she’d call home. 

After hanging up her skates, she graduated from the Masters of Journalism and Communication program at Western. Steph now works with travel and consumer clients as a Director at Media Profile, fully embracing the company’s Work Away Benefit to explore as many countries as possible.


She’s always been an energetic and passionate storyteller—only now, her adventures go beyond the fairytales carved into the ice.


Europe, Road TripsSteph Kesler