Umbria or Bust: Exploring New Bits of Italy by Bike

Italians always find poetic ways to express even the mundane. One example is long weekends that include a weekday holiday and which are called a “ponte,” or bridge. The ponte born from a weekend plus the Festa della Repubblica on June 2nd generated an idea: a 600 kilometer/ 375-ish mile bike tour from the province of Emilia-Romagna into neighboring Umbria.

Said idea had always been for my boyfriend, Leonardo, and I begin cycling in Faenza on May 29th with our friend Ermanno. On the 28th, Leo leaned across his sunny kitchen table in Pontassieve, Tuscany. “Maybe we should ride to Faenza instead of taking the trenino,” he said, referring to the little tourist train that crosses the Apennines between Faenza and Florence. This meant two climbs (one of which was a substantial pass) and an additional 104 kilometers/64 miles. Of course we had to do it.

Bike tourist in Tuscany on a sunny day.
After the first climb and before the second…
A small Tuscan town called Ronta, which is nestled in the green Apennine mountains.
Ronta, Tuscany

After arriving in Faenza, we inhaled dinner, repacked and tried to sleep so we could shove off at 9 a.m. Leo and I are chronically late, and doubly so together, so I texted Ermanno early on to request leaving at 9:30 a.m. In the end, we left at 10 a.m.

Three bike tourists taking a break on a shady bench in Cusercoli, a small town in Emilia-Romagna.
Cusercoli, Emilia-Romagna

We spent the first part of the day in the flats before a gentle, rolling climb towards Santa Lucia. Italians hail this topography saliscendi, or climbs and descents. I prefer the slang version: mangia beve. It attributes mangia (or eating, which presumably requires more effort) to climbing, and beve (or drinking), to descending.

We paused at a park bench in Cusercoli to wolf down prosciutto and cheese sandwiches from a local grocery store. An hour later, we hung a left in Santa Sofia and headed for Passo del Carnaio (or Pass of the Meat-lover, a hilariously befitting name for a pass nestled in the corner of meat-adoring Romagna). Sweat dripped and weird cyclist tan lines became quite defined as we rode through one of the first real hot days of summer. We were accompanied by panoramas and fields splashed yellow by late-spring blooms. And roads that were, thanks to the Giro d’Italia’s passing not long before, freshly painted and lacking the surface-of-the-moon potholes usually found on such roads.

Descending on a smooth paved road from Passo del Carnaio.
Descending from Passo del Carnaio.

That night, we rested our heads under tents on a level spot of earth close to a very outspoken rooster. We were in Remedia outside of Sarsina, above the E-45, a main highway in a narrow, forested valley that connects Tuscany to Umbria and not much else. Our host was my good friend Cristina’s sister, Monica. Also present was her partner, gruff but warm-hearted Maurizio, Cristina, her wiry friend Gui and a host of dogs and cats.

A small tent with a view of the moutnains behind it.

Once we settled in, Monica took us on a tour of Remedia. We wandered past gardens and rooms where staff processed harvested plants into high-quality essential oils, creams and countless other products. Exiting, I was hit with déjà vu: I’d been in that exact spot two days shy of a year prior on the solo bike tour I planned during Italy’s three-month lockdown. I was filled with joy as I looked at the people and animals around me, illuminated by a pinkish-orange sunset.

The next day, Ermanno, Leo and I rode to Bagno di Romagna. We found it still resplendent in Giro d’Italia pink and white. The window boxes overflowed with rosy flowers and bikes spray painted pink were tied to fences of the same hue. Even the kids had drawn a mass of bike-related pictures, which were still tacked to a bulletin board near the school.

Two grinning bike tourists standing in front of Bagno di Romagna, still decorated with bright pink umbrellas in the sky for the Giro d'Italia.
Bagno di Romagna, Emilia-Romagna

After Bagno di Romagna, Leo had to head home, so he went right and climbed over winding Passo dei Mandrioli as I had done the previous year. Meanwhile, Ermanno and I went left towards Verghereto. It was new territory for me and for Ermanno, a joyful return to his native stomping grounds of Umbria.

A friend of his had recommended we take a “short cut” on the old E-45, which was technically closed due to a landslide. As anyone who rides a bike knows, this translated to no cars and the natural re-transformation of highway into wild and peaceful road.

Two bike tourists on the closed E-45 highway outside of Bagno di Romagna. Nothing but sky and trees.

After lunch in Pieve Santo Stefano’s quiet, shady square, we enjoyed more mangia beve near a turquoise lake sharing the town’s name. I chose the verb “enjoyed” because a strong wind was pushing us towards our destination, Cittá di Castello. Thankfully, because it was another long day (92 kilometers or 55 miles in total) and hotter than a young Brad Pitt.

A bright red poppy-filled field in front of mountains and a lake in the distance.

In early evening, we rolled up to our home for the night: a bar/restaurant called “Il Sasso” across the street from a sizeable river. I started laughing because what I imagined to be a chill, remote scene was anything but: there were hordes of tanned children escaping their parents, scooters roaring by and a restaurant brimming with squawking Italians. By nightfall, however, the crowds disappeared. What remained was bone-chilling humidity and a sea of discarded plastic cups atop the flat field where we would pitch our tents.

As we waited for the calming effects of nightfall, we piled into Gui’s car and backtracked to Cittá di Castello for aperitivo (like American happy hour). We wandered the cobbled streets with a happy buzz, enjoying the colorful medieval streets the town is famous for.

In the morning, Gui and Cristina returned to Faenza and Ermanno and I headed for Umbertide to meet up with his kids. Later, we would catch a train to Perugia where Ermanno had gone to University. But before we could get there, we needed to understand how exactly to do so. In short, I was about to find out that crossing into Umbria meant entering another world.

At Umbertide’s train station, the screens that showcase the arriving and departing trains were off. Also absent were the ubiquitous glass-covered boards listing each train by hour, number, platform and destination. We reverted to the nearest human, who pointed us to a trainless platform.

“Should be that one,” he said as Ermanno and I exchanged amused glances.

A graffiti-covered train and a bike at a deserted train station in Umbertide, Umbria.
Waiting for the train in Umbertide, Umbria.

The train that arrived was slathered in a thick sheen of graffitti, which obscured its windows like tired eyelids. Another shellacked train inched up to it so that they were nose to nose. Which one would win the award for semi-on time departure?

“Train 9702 to Perugia is ready to depart from track one,” announced a tinny voice from a crooked speaker as the two trains connected with a metallic groan. We approached it, but its doors wouldn’t open.

Up train, the conductor leaned his head out the window and waved his hand, the international gesture for, “Wait.”

Again, the tinny voice insisted, “Train 9702 to Perugia is ready to depart from track one.” This message would continue even after we were again waved into the unmoving train and had eaten most of our sandwiches. When it did depart, we had to babysit our wobbling bikes, which were taking up the entryway because Umbria doesn’t believe in designated bike zones. We had long ago given up hope on making our next connection, which may or may not have existed anyway.

Perugia, like most classically medieval strongholds, was perched on a hilltop. Its main train station was located, again classically, but in the modern sense, in the flats underneath the town. At one point, a train did climb up to Perugia, but each person we asked told us something different: that it didn’t exist anymore, that it might, or that it never had.

As we pondered this, our train flew along, despite that its paint job had seen better days and its chairs had been literally sculpted into butt-shaped indents. It also chugged like a car; shifting gears produced a powerful lurch and stopping necessitated that one of us leap into the entryway to keep our bikes from getting off without us.

“It’s a diesel train,” Ermanno explained after the first stop. In neighboring Emilia-Romagna and Tuscany, all the trains had been converted to placid electric trains. In Umbria, just an imaginary boundary away, it seemed like we’d gone back in time.

A message on the train in Italian that means, "Don't tell me that you, too believe that happiness is only found in another person."
Train wisdom: “Don’t tell me that you, too believe that happiness is only found in another person.”

In Perugia, a pot-bellied bus driver informed us the train that once went to Perugia’s center had existed but was now “cancelled forever.”

His big, modern bus had just enough room in its belly to accommodate Ermanno’s bike.

“We’ll just throw the other one inside,” he said, simultaneously puffing a cigar and opening the bus’ rear door. I carried Penny up the steps and parked her in the handicapped area. There was, incidentally, nowhere to buy a ticket and/or the bus driver didn’t care about such things.

So far, my time in Umbria was bafflingly charming — like certain moments in Vietnam, Laos and Thailand. Despite the fact that almost nothing worked properly, it was always accomplished through good humor and ingenuity. Like when our luggage was lost, but then arrived piece by piece in the following days on the back of one of the hotel staff or family members’ scooters.

I asked for a bathroom at the nearest bar, but the tall brunette behind the counter shook her head. “It’s not open.”

“Why is that?” Ermanno asked, raising an eyebrow.

“Because of Covid, right now we’re not allowed to serve inside, so…”

“She just didn’t want to clean it,” I said as we retreated.

“This is part of why I moved away from Umbria,” Ermanno said to me with an eye roll.

However, the following visit to the Basilica of San Pietro provided much more than a bathroom. It was a well-preserved complex now housing the University of Perugia’s Department of Agriculture, Food and Environmental Sciences.

Due to Covid it was closed to the public, but Ermanno’s friend worked there and gave us a private tour. We followed his suspenders and wayward hair through the courtyard, painted a carefully-chosen shade of pale green. It represented how the Basilica, and apparently most medieval buildings, would have originally appeared (they wouldn’t have been gray or brown as they are today).

We headed to the top floor for views, through gardens tended by the students and into the magnificently ornate basilica. Just before saying goodbye, our guide pointed to a gouge in a column and explained it was caused long ago by a cannon blast.

The view from the abbey which included, far in the distance, Mount Subasio towering over Assisi.

Before a roaring descent back to the train station, I trailed Ermanno through Perugia’s sloping maze of medieval streets. Thanks to his studies there, he knew to point out a Roman aqueduct, a temple once used by the Knights Templar and the most panoramic of views. He also found us a mouthwatering torta di testa, a Perugian sandwich made with unleavened bread.

Back in the flats, we found our train despite mismatched signs and because of a kind stranger who waved us over minutes before it arrived. I watched the sun-kissed Umbrian hills passing by the open windows of another lurching diesel train as we headed east. We got off in Foligno, a small town nestled against the Apennine mountains and along the Topino river.

Ermanno’s friend, Enrico, gave us a ride up to Pale (pronounced pah-ley), perched by a popular trail and housing a waterfall, an abbey and several caves. It would’ve been a 10 km climb from the station, and I noted the air was suddenly cool when we shuttled bikes and gear into the house.

Enrico’s companion, Urana, met us at the door sporting a leopard print shirt, a big smile and a hug. Over dinner we shared travel and cycling adventures and our hosts told us about their lives as professional street artists. I sensed immediately the sort of kinship that guarantees future interactions (in fact, I watched acrobat Urana perform in Bologna about a month later).

The next day Enrico, a native of Foligno, took a turn as tour guide. We packed plenty of water and money for roadside snacks and zoomed back to the flats. From there, a maze of side roads, cycle paths and sections of single track guided us towards Assisi.

“What’s that?” I asked, pointing towards a cluster grayish-white buildings on a nearby hilltop.

“Spello,” Enrico. “Our next stop for a coffee. Later, I’ll take you through the old center.” He grinned, his smile lighting up his dimples while the sun did the same on his one gold earring.

Four coffees, stacks of coins to pay for them all and underneath, somebody's bike shoes.

The sun was high in the sky when we reached Assisi, the birthplace of St. Francis. After a short descent to the Basilica the only way was, of course, up through cobbled streets just beginning to be crowded with tourists again. We climbed up to a church housing a Roman cistern and then to the oldest part of town with its narrower streets and gray stone houses. Finally, to the cheers of a gang of motorcyclists, we arrived at the fortress looming above.

The rest of the afternoon saw us circling Mount Subasio, the treed 1290 meter/4230 foot peak that guards over Assisi. Enrico took us through tiny villages inhabited by more second home owners than residents, each one prettier than the last.

As promised, before returning to Pale, we revisited the labyrinthine streets of Spello, stopping for pictures by a Roman gateway with a formidable arched doorway and opposing towers.

And then, after a stout climb back up to Pale, the reward:

After a lingering breakfast the next morning, Ermanno and I descended from Pale to catch another remarkably on-time train. We changed trains in Florence where Leo was able to meet us for a quickly-melting gelato. On the trenino, Ermanno and I looked at each other and grinned. We were exhausted but satisfied and, after six days of biking, starting to become good friends.

Amicis con bicis (friends with bikes)!

I realized something that evening when I was unpacking my bags: I always make fun of Italians for their charmingly amusing habit of discussing food while they’re eating. But as I shook out my tent and put my helmet away, I was already dreaming of my next bike adventure. I guess I’ve got nothing on them really.

5 Replies to “Umbria or Bust: Exploring New Bits of Italy by Bike”

  1. Thanks for so delightfully sharing your bike trip. LOVE it, wish we could join you, but it isn’t happening…all the best…

    1. Thanks again so much for reading and commenting… I am also happy that you liked the latest installment about Umbria! Well, when you can come over here again, you’re always welcome to look me up. It will happen!!!

  2. Love the pictures and the descriptions. Looks so fun, I feel like I’m vicariously traveling with you!

    1. And I love that you feel like you are vicariously traveling with me 🙂 I wish you REALLY were, but we’ll have some adventures together soon enough!! 🙂

  3. I echo your mom on that. And how I miss the wonderful food of Italy. Keep on writing and peddling Silva.

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