Giovanni, the author’s virtual guide went along for the ride.

Story and Photos by Lorraine A. DarConte

A dog barks excitedly as I cycle past brilliant green fields of tobacco on my way to the hilltop town of Montone. Several people in a farmhouse step out onto a balcony to see what is causing the commotion (me!). As I ride by, everyone, including me, waves and calls “bongiorno!” It’s a happy, friendly scene straight out of a travel advertisement. The Umbrian people in this mid-central region of Italy are charming, curious and sincerely friendly. Everyone wants to meet me, and when they find out what I’m doing, they cheer me on.

Picturesque landscapes lead mostly up-hill to Montone.

During my ride to Montone, I met an elderly farmer on a dirt road next to his rain-soaked field. We managed to piece together a conversation in Italian and English as I told him I was bicycling from Sansepolcro to Montone to Assisi to Bevagna to Spoleto (with stops in between). His eyes wide with amazement, he patted me on the shoulder and said “Brava! Brava!” I could not disagree with him as my cycling trip through Umbria, and some of its many splendid hilltop towns, required a fair amount of strength and fortitude—both physical and mental—on my part.

I’m not an avid cyclist; in fact, I purchased a bike only a few months before leaving for Italy to prepare myself for this trip. But I’m in reasonably good shape for a 51-year-old—hiking, swimming, and lifting the occasional weight—which turned out to be good enough. If I were younger and/or a cycling enthusiast, the journey would be far easier and faster, but not necessarily better, as I stop often to admire the scenery, chat with the locals, and take a lot of photos.

A Bevagna church with a grand staircase.

One of the best things about this trip was that I didn’t have to do much planning beyond booking my airfare. Zephyr Self-Guided Adventures, www.selfguidedadventures.com, took care of the details including booking my hotels in each town (cozy B&B’s and small hotels that included breakfast), moving my luggage from hotel to hotel during the trip (my bags would be in my room when I arrived in each town), and providing me with a bike and detailed directions to each destination. I also had a choice of easy, moderate and difficult routes (longer and steeper) almost every day. These services and choices explain why 50% of the clientele for Zephyr’s self-guided trips are older vacationers, 45 years or better.

Zephyr offers both small group tours and self-guided tours such as my cycling tour of Umbria. I got to choose the days I wanted to travel, flew into Rome and took a train from the airport to Roma Termini (the city’s central train station). From there I took another train to the town of Arezzo (about 1.5-2 hours ride) and then a bus to Sansepolcro (30 km from Arezzo). This was to be my jumping off point.

In Sansepolcro, I met my “virtual guide” Giovanni and his partner Michaela. They fitted me with a bike, gave me a packet of directions for daily rides, and a Portable Media Player, which featured talks by Giovanni about places I’d visit and highlights along the way. There were also tidbits about the day’s route and an emergency number to call if I needed help.

I was given enough extraneous bicycle gear—spare tires, patches, air pumps, etc.—to make me feel nervous about what might happen as opposed to feeling safe about bicycle breakdowns. As it turned out, other than routine maintenance—air in the tires and adjusting my seat—the only repair I had to make was slipping the bike chain back on. A greasy affair, but nothing I haven’t done before. No tragedies to report . . . that is, if I don’t count the two days I cycled in the rain and some of the mistakes I made along the way, which, I was warned, were inevitable.

An “angel” mime artist in Assisi reminds visitors that Assisi has been a Christian pilgrimage destination since Saint Francis’s time.

The author witnessed four Assisi weddings in less than two hours!

My ride took me through some remarkable country past vineyards and canals, through olive groves and small forests. There were ancient castles and crumbling farmhouses, neat rows of cypress trees and dozens of roadside shrines. Sometimes I missed a turn because I wasn’t quite paying attention, but there were also plenty of times when “semantics” played a role in my misadventures. For example, where my directions said “exit” it should have said “right.” I don’t know if an Italian wrote them or an American, as the company is run from both countries. Then there was the road that was closed for repaving and the sign that had been turned the wrong way, taking me an hour off course . . . up hill. No matter, I managed to find my way to each town thanks to plenty of road signs and the occasional help from locals.

On average, it took me anywhere from four to six hours to get to each destination via off-the-beaten-track roads that were sometimes nothing more than gravel. I chose the easy routes which consisted of rides ranging from 33 km to 56 km. I could have taken the more challenging routes that were often double the distance. But besides the fact that it may have killed me, I was truly keen on exploring the medieval towns, each of which had something interesting to offer, including a steady diet of art-filled churches, expansive piazzas (and pizza!), hidden alleys, cobblestone streets, and assorted museums.

In Bevagna, funerals as well as weddings are part of village public life.

Traveling outside the main tourist areas (Assisi being the only town on the tour that was choked with visitors), my Euros went a lot further. A slice of pizza in Bevagna was equivalent to 80 cents US; cappuccino was $1 or less, and a small gelato or ice cream cone a mere $1.20. In Sansepolcro, I treated myself to a gourmet meal—three courses and wine—for

Most days I stopped for lunch in small “bars”—little roadside cafes that served food and drink, etc. A sandwich, a soda or water and a cappuccino cost $3.30; and it was the same price everywhere I stopped. Hence, I made a habit of taking a mid-afternoon cappuccino break—the perfect pick-me-up to finish the last leg of my daily ride.

Religious art of great history is found in every church and cathedral in Umbria.

I thought I’d traveled far from my home town of Tucson, Arizona until one morning in Spoleto, I encountered a group of cyclists in my hotel lobby wearing Saddlebrook (a small community outside Tucson) racing gear. It turns out that the Saddlebrook Cycle Masters were also on a guided cycling tour of Umbria, proving once again that it is a small world after all.

Umbrians cultivate edible gardens on their riverside lots near Bevagna.

Lorraine A. DarConte is a freelance writer and editorial/wedding photographer residing in Tucson, Arizona. Her work has appeared in numerous publications including, Shutterbug, Nevada Magazine, Budget Traveler, Picture Business, Phoenix Home & Garden, Arizona Bride, and The Rangefinder. Lorraine, who most often writes about photography, is a member of Wedding and Portrait Photographers International, www.ldarconte.com.