The Secret to Seeing Italy Like a Local (Without Planning a Thing)
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Ever dreamed of cycling through Europe, wind in your hair, tiny trattorias around every bend? Same here—and this year, I decided to make my bucket list trip happen. A multi-day ride through Italy was the idea: quiet backroads, slow mornings, charming towns. But once I started planning, challenges arose—I had no idea how to plan cycling routes that wouldn’t dump me on busy highways, I wasn’t about to fly my bike across the ocean, and I definitely didn’t want to haul all my gear on my bike.
Fortunately, I found the perfect solution: a self-guided tour. It offers the best of both worlds—the structure and support of a guided trip (itinerary planning, hotel and activity bookings, bike rental, and luggage transport), with the freedom of independent travel (eating wherever and whenever I wanted, detouring at will, and setting my own pace).
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I booked my trip with ExperiencePlus! , a family-owned company based in Faenza, Italy, that’s been showing travelers the best of the country since 1972. Their local experts have cycled every part of Italy, meticulously designing the best cycling routes for every region.
I wanted a foodie-focused itinerary—because what’s a cycling trip without frequent gelato and pizza stops? I also wanted to avoid major tourist crowds and grueling hills. After chatting with an ExperiencePlus trip planner, I landed on their self-guided Bicycle Romagna—Heartland of Italy’s Homemade Pasta tour . This seven-day adventure ticked all the right boxes—just the right amount of cycling (around 30-40 miles per day) that would still leave plenty of time for exploring, along with overnights in charming small towns where I could experience the true “dolce vita,” the Italian sweet life.
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The best part: everything was seamlessly planned out for me, from hotel bookings to turn-by-turn cycling directions. All I had to do was pack my helmet and just show up. Once on the trip, I lived by ExperiencePlus’ Ride with GPS app. It included my daily map, hotel details, suggested meal stops, activity highlights, and even alerts about tricky parts of the route, like narrow paths or short stretches on busier roads. There were generally multiple options per day for routes with higher/lower elevation changes or ways to extend the ride if I was feeling up for it. Trust me, if I had been trying to navigate these remote Italian roads on Google Maps by myself, I’d still be lost in an olive grove somewhere.
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As a carry-on only traveler, I appreciated that ExperiencePlus provided everything I needed on the tour. I chose a high-end titanium bike, but e-bikes and tandems were available too. Each came equipped with a bag, lock, water bottle, and light. Serious riders could bring their own pedals, shoes, or even seats.
What was notably absent was a firm deadline or time crunch, meaning I could truly set my own pace. My only firm time commitment was to have my luggage packed and ready to go by 9:30 am, so that it could be magically transported to my next hotel, leaving me unencumbered on my bike for the day. I loved being able to decide on the spur of the moment if I wanted to sleep in and savor an espresso before heading out or to get an early start on my day. Every day, I woke up at my four-star hotel and enjoyed a complimentary breakfast before opening up my GPS app to see where the day would take me. I could start at my leisure and ride at my own pace, without having to worry about holding up a group or waiting for slower riders. If something caught my eye along the way, like a castle that begged to be explored or a gelato shop that looked like the world’s best, I could simply pull over and spend as much time as I wanted there, exploring Italy at my own pace.
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While the trip was mostly unstructured, I chose to add two memorable experiences. First, since the route passed through Brisighella, one of the world’s best olive oil regions, ExperiencePlus arranged an olive oil tasting. I learned to look for Brisighello DOP, a label indicating that at least 90% of the olives were locally grown—a true signal that what’s inside the bottle is liquid gold.
They also set me up with a piadina cooking class, so I could master this classic Italian flatbread and recreate it at home.
The tour took me through small towns such as Riolo Terme, Dozza, and Faenza. Visiting in early April, before the start of the popular tourist season, added to the authentic feel. I sat in piazzas enjoying apertivos, and slipped into local trattorias without a reservation (although that may have been more due to my 8 pm dinner time instead of eating at 9 pm like the locals), without having to choose a place that could accommodate a big group. The absence of crowds made it feel like I was living the small-town Italian life, and I wouldn’t have discovered these spots without the expertise of the local tour planners.
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To book a self-guided tour is to give yourself the gift of freedom and time. Being able to stop whenever, wherever I wanted, was priceless. I’ll never forget riding through the small towns and pulling over at a quaint coffee shop along the roadside just to share an espresso with the kind owner, or discovering a medieval castle with no one else inside and having the stunning views of the rolling countryside all to myself.
Editor’s Note: The writer of this story was hosted by ExperiencePlus on its self-guided Bicycle Romagna trip.