A Motorcycle Trip Through the Italian Countryside

A Motorcycle Trip Through the Italian Countryside

Photographer and friend of Alps & Meters Joel Caldwell and his wife Hailey originally wrote this Italian travel journal piece for META magazine, and when we read it we knew we had to share. Enjoy!



It’s something I’ve dreamt of for years. And it nearly happened once. A year into planning the “Big Trip”—taking my thumper all the way south to Argentina— I fell in love, resolve fell apart, and for more reasons than just her, it didn’t happen. I’ve never managed to leave the continental United States on a motorcycle of my own. Not until today.

I love leaving this city. Snaking through the madness, millions of people going about their routines, oblivious to my big adventure. Up and over the Brooklyn Bridge. Splitting lanes on the FDR north— lancing through the ubiquitous snarl of traffic. The process of learning to comfortably ride in New York— where cabbies drive like a river of whitewater, aggressively merging, heedless— will serve me well in the coming weeks.

It rains like hell in Montreal. First time to French Canada and I’d looked forward exploring North America’s oldest city. Not to be. I hang my riding pants and shoes directly in front of the fan, set to ‘High’, and hope my things will dry before I pack them away for tomorrow’s flight.

I ride through a saturated Montreal. The rain has stopped and I’m following a route uploaded to my phone the night before. My morning run went long and my concern about being late turns to near panic when the GPS track directs me straight through a golf course. I burn a frustrating hour searching for Air Canada cargo. When I finally arrive, Pierre is waiting for me and performs the Dangerous Goods Assessment in the time it takes me to disconnect the battery.

And that’s that. With a glance over my shoulder at the bike, I toss one of my saddlebags into Pierre’s car and we make the short drive to the terminal. I receive a few curious glances going through security; helmet and jacket in hand. At the gate I strain out the window in the hopes of seeing a motorcycle sized crate being loaded into the hull of the massive Airbus. Nothing. The pre-takeoff acceleration forces me deep into my seat. Somewhere down below, I hope, my favorite machine accompanies me.

At 95 mph on a naked motorcycle, the most comfortable position for me is leaned forward, chest resting against the tank bag, elbows on knees. On the Autobahn BMW, Audi, Maserati— all brand new— scream passed at speeds totally foreign to me. The road is perfect. A belt of dark, seamless asphalt continuing endlessly. Seven hours, down through Bavaria, passed Munich, and into the Alps. The scenery is so consistently beautiful that it doesn’t really make sense, like some sort of alpine hallucination. It’s twilight when I hit a roundabout, turning onto a small road towards Innsbruck.

With a few suggestions from my Austrian expat host, I put together a route that makes today my single best day of road riding, ever. High-speed, twisty-turny, single lane roads have me, for the first time, looking forward to the straightaways. Three mountain passes, culminating in the famous Passo Dello Stelvio— 48 hairpins in northern Italy— each turn stacked one atop the other, until reaching the summit. Dragging pegs, dodging Porches, I make it to the top. Sipping a beer I take in the view, south into Italy, while a few interested Europeans examine my Oregon license plate.


Checking into my B&B, I pull a bottle of wine out of my saddlebag and make for the front porch. Overlooking the Lake Como, fishing boats bob in the placid waters below and I spot at least one ferry steadily making its way to the far shore. Southwest, towards Milan, the shoreline disappears into clouds rose-tinted by the setting sun. I rip off a hunk of bread, slathering it in a nameless Italian cheese. Everything tastes better after a long day of riding.


Tomorrow I pick up my girl!



I am coming off a week of crazy work in New York and arrive to my gate at JFK as the flight is boarding. I’m traveling light. A backpack, a leather jacket, and a shiny new helmet. As everyone else is fiddling with the onboard entertainment, I get a fat glass of airplane cabernet as we hit 30,000 feet and go to sleep.


I’m not a biker chick. I have not (yet) learned to ride motorcycles and my only solo attempt resulted in a scooter crash in Baja at age twelve. (The scooter was hot pink - we called it the barbie bike.) But, I love being a passenger. Riding on the back of a motorcycle is akin to something between meditation and adrenaline. The roar of the wind in my helmet puts me into some sort of trance and I have some of my best, most expansive thoughts at 80 miles an hour, clinging to Joel and watching the countryside rush past.

I land in Milan midday, dry-mouthed and sleepy. I sip a tiny americano and wait for Joel on the curb, my new motorcycle sneakers shining up at me. I see him after a moment or two, waving wildly and running down the parking island. My heart flutters. And so it begins.

A few hours later we are hurtling towards Venice and hit a storm. I squeeze Joel hard when a bolt of lightning hits a hilltop to our right. We are instantly soaked. I can feel warm rivulets of rain running down my shin and into my sneakers. I’ve fogged up my helmet so badly that I can just make out the impression of passing cars and road signs. We stop at a gas station and wait for the heavy rain to let up and for some crazy reason I’m grinning, hard. Look, I’m a bit of a whiner. I’m not the consummate ‘good sport’. But this! This feels like adventure. We are escaping a storm! We are wet and cold but we are out in it! I look at Joel. He is pacing the carport, practically giddy. And I’m not sure what does it but I go a little weak in the knees. He’s just so… free.

By the time we reach Venice, the sun is shining. I lay on a bench with the saddle bags, baking dry while Joel parks the bike. We board a water taxi and speed towards Piazza San Marco and hot showers.

Venice is a wonder. It is surreal to be there. In our pretty little bedroom over a pretty little courtyard. We drink cappuccinos and wander for hours. Night falls and we buy a bottle of wine, a block of cheese, and the Italian equivalent of Ruffles potato chips—a fine picnic. I fall asleep before nine o’clock.



“Sonofabitch!” I swear under my breath. Yet another dead end. Venice is a veritable maze of canals and tangled pathways all heading God-knows-where. It’s getting hotter too, and the long walk from Piazza San Marco to Santa Croce, where we left the bike, was maybe not my best idea. Obstinate, I’m not ready to admit that Hailey’s idea of a water taxi was the obvious choice. Now I’m paying for it, shoulders aching under the load of the saddlebags, trying not to bash the kneecaps of passersby as I maneuver through the claustrophobic passages.

Venice is a major tourist destination for good reason; there’s no place like it. Spread over 117 islands, the seat of major empire from the thirteenth to seventeenth centuries, Venice is a decadent floating city (though in reality sinking), resplendent with the Doge’s Palace, it’s crown jewel. Birthplace of Marco Polo, staging area for the crusades— as a history lover Venezia boggles my mind. And at the moment, I cannot wait to leave.

The water taxi— yeah, finally— delivers us to Santa Croce and my mood begins to lift. Leaving Hailey at an outdoor pizzeria I climb the five flights to the top of the parking garage to retrieve the bike. On goes my helmet, I turn the key, and an ominous, empty click emits from the ignition.

Beads of sweat bursting from my forehead, helmet still on, I push the bike slowly, tortuously up the incline. Eventually reaching the top of the spiral ramp descending to the floors below, I swing my leg over, turn the key on, and shift into 2nd. Coasting downhill I pop the clutch. Too soon. The back wheel locks up and I fishtail, nearly colliding with the parking garage wall. Teeth clenched, I let out an audible growl and try again, letting myself gain a bit more speed. It works! The engine turns over reluctantly, and I hear each piston fire and then catch.

Engine purring, I exit the parking garage and am nearly side-swiped by a fast moving Porsche.  The driver slows long enough to flip me off and say something I take to be unfriendly in Italian. Shaking my head, I collect Hailey and our things, and get the hell away from Venice. To Ravenna!



It’s a beautiful thing to pack light—I can wear my black shirt or my blue shirt and those are all the options. I have exceeded everyone’s expectations and packed just the right amount for my sleek little saddle bag. A pair of running shoes, two t-shirts, a dress, and a long sleeve shirt, and a sweater. Not bad.

Leaving our rambling ranch house accommodation outside Ravenna isn’t easy.  I eye the shimmering water of the swimming pool as I shrug on my leather jacket. A little country cat meows sweetly at our feet as we tip back a final shot of espresso.

We plan to head inland to Urbino, a walled city and UNESCO World Heritage Site, famous for its Renaissance culture and Palazzo Ducale. As we ride south, however, the sky turns black. We stop at a roadside cafe and eat egg sandwiches and talk about our options. Three hours of riding if we go to Urbino for lunch, an hour and a half of riding without the stop. We decide to go for it. Hopefully if we head inland, we’ll bypass the roiling thunderclouds to the south.

An hour later we are sitting under the awning of a country gas station as torrential rain pounds the metal roof. I am a heap of wet leather, my only consolation a snickers bar and the smell of rain on the surrounding coriander fields. And Joel. He reaches over to hold my icy little hand and says the thing we always say when things are a little iffy, At least we’re together. Amen.

We reroute, heading straight towards Monte Conero and our Airbnb. Urbino can wait until next time.

What follows is the freakiest riding I’ve ever experienced. Joel is a cool cucumber, as always, but I cling hard against him as we ride south through the storm. Semis pass us at 80 kilometers, and sheets of water gather along the median. At one point we hit a narrow rut full of water and fishtail. We are still an hour from our destination and I am so cold my hands have cramped into claws. I start singing Tracy Chapman inside my helmet, loud.

Never, ever has a bath felt as good. We huddle in the jacuzzi tub together, staring out the bathroom window at the view. We are staying with a young Italian couple in a beautiful old farmhouse in Monte Conero—a national park that ends abruptly in a dramatic white cliff above  the Adriatic. The 17th century house is made of the same white rock, illegal now to quarry but classic to the old structures of the Marche region. After the long hot soak, we meet our hosts downstairs for a glass of wine. Wine turns into an impromptu three course dinner. Gimi and Laura are warm and funny and we talk late into the night about Italy and politics, their wedding, our travels. Just before bed, we step out onto the wet grass and look out at the view. From the top of the hill we can see the lights of Sirolo, then further down the coast to San Benedetto de Tronto. The sky has cleared and the stars twinkle.




”Fifteen!” I yell through the howling wind to Hailey, locked on tight behind me. We’ve been making incredible time on the coastal highway south of Sirolo and just passed through our fifteenth tunnel. Italian engineer’s proclivity to drill massive holes through the earth is unlike anything I have seen.

A few moments later we emerge into daylight and I take an exit to fuel up. Hailey walks off towards the cold drinks while I begin the now familiar credit card roulette— a baffling game in which the gas pump selects one of my cards at random to approve. A couple hundred more kilometers in the tank, I walk over to find Hailey completely passed out on a bench. I can tell she’s dreaming. This girl dreams more in the space of a twenty minute catnap outside an Agip gas station than I do in a six month period. Inside, I buy an Americano and sit down next to her sleeping form. We’d been traveling hard. Maybe too hard. So far we hadn’t stayed more than a single night anywhere and each day’s ride had been several hours. Already, in Italy alone, we had ridden more miles together than everything combined beforehand. She hadn’t complained once. And even better, seems to be enjoying everything as much as I am.

Dream girl.


Turning off the highway we enter an entirely different landscape altogether. Arid, scrubby, this far south the Adriatic coast resembles the Baja peninsula. Fifteen kilometers from our destination the road narrows into a single diminutive lane, tiny for a car, perfect for a Ducati. Pocked and tarred, a roller coaster of sharp turns and steep inclines, the peculiar road leads us through a series of olive groves, the shimmery leaves softening in evening light. We catch our first glimpse of our destination— Peschici— the white city perched atop the sea.

I will always remember entering Peschici. The uniformly white buildings and cobbled streets. The sound of the engine echoing off the narrow passages, the walls seem to lean in as they rise above. Our route is taking us straight to the heart of the old city, past the castle, and to the edge of the cliff. We climb off the bike and walking straight into a petite ristorante cantilevered over the Adriatic — Porta di Basso. Seagulls cry out, swooping below us against the sheer rock face. We sit next to each other at the tiny table—same-siders staring out at the horizon. And the wine flows…




As we set out, the sun breaks through the clouds and the water is glittering. Smudges of white smoke rise from the groves and skinny dogs skirt the crumbling shoulder of the road. Today will be our longest day of riding—across Italy to the Mediterranean, to Amalfi. I am suddenly aware of the extreme heat. I am, quite literally, broiling. I unzip my jacket to my belly button and position my arms for maximum airflow. I breath deep and controlled, like the way you do in a yoga class. A hot dry wind is blowing hard as we loop onto the highway.

I can even begin to explain this day. It is wonderful and terrible. It deepens my understanding and my love of motorcycle travel. It makes me a believer.

For what seems like forever, we are in the bread basket, wheat and hay and dairy fields as far as the eye can see. The wind is howling now and the bike shudders every so often in the gusts. Stuck behind a hay truck, shards of golden grass ping off our helmets. Our route cuts through lonely little agricultural districts and Joel slaps my knee when we see what looks like a windblown prostitute on the side of the road.

At some point we take a skinny country road through miles and miles of olive groves. The air is dusty and the leaves shimmer silver in the heat. We pass a stone villa, once resplendent but now burned out, all broken windows and graffiti. I am desperately thirsty.

We stop for a moment. Without the wind of the ride, the heat is nearly unbearable. The road is now only wide enough for a single car. I wrestle my jacket off for a moment and pee behind a gnarled olive tree. Joel eats a nectarine that has been baking in the backpack. The scene is so washed out, so void of color, so incredibly hot. I am nearly panting.

The rest of the day is a single minded push to the finish line. We hear later that this is one of the hottest days of the summer and even in the more forested, hilltop towns of the west coast we are baking. Occasionally we drop into a cool spot, a low hairpin that cuts deep into the shade of the forest, and I can smell clean, cool, air for a moment. It is like heaven.

We reach Vietri Sul Mare at six in the evening. We stop for a snack and a long look at the Mediterranean. We order four cold drinks—a beer, a water, and orange Fanta, and a little bottle of campari soda—and drink them fast.  I am a puddle. My thick pants are nearly soaked through with sweat and my hands tremble. My braid, whipped by the wind all day, has solidified into a single dreadlock. But as I prop my feet on the low railing of the cafe and look out over the ocean (and two italian men shouting at each other over a minor traffic incident), I am euphoric.

The last hour is treat, like flying. The air is cool and salty and we are moving slow enough to open our helmet shields. The road is a motorcyclist’s dream—winding dramatically high above the sea. I look down at the mediterranean, dotted with sailboats and shining in the late afternoon light. In some places, the cliffs are terraced and I squint up at the trees growing in skinny stacks—lemons! Beautiful, lush lemon trees heavy with fruit.


We climb up into the hills to our tiny cassetta. It is perched on a cliff with nothing but ocean to the west. We sit outside for a long time watching the sky fade, quiet, tucked beside each other like two puzzle pieces.



Two Vespas shoot passed us on a blind hairpin, leaving us to choke in their two-stroke exhaust trail. The road, winding along the Amalfi coast, clings to the cliff face, sometimes narrowing down to a single lane, or, twisting into a ninety degree turn without warning. Locals, mostly on old patinated scooters make harrowing passes, forcing oncoming traffic ever closer to the cliff’s edge. It’s insanity. Tourist buses lurch around corners, disproportionately huge, forcing traffic to a standstill. Emboldened, I begin making passes as the locals do, having a bit of fun. Hailey squeezes me hard with her thighs, reminding me that there’s precious cargo on back.

We wind our way down to the beach at Positano. It’s so packed I can barely find a spot for the motorcycle, stuffing it halfway into a bush and calling it good. Stripping off our gear, we making a small claim for ourselves on the rocky beach. The sea feels wonderful and I’m amazed at my ability to float, scarcely needing to tread water.

Entering Rome is surreal. We buzz through the city with a swarm of scooters, flying over the slick cobbled streets and dodging pedestrians. The wide promenades are lit by the evening sun and I can see the dome of St. Peter’s Basilica looming in the distance. Hailey wraps her arms tight around me and my heart thumps.



Roma. A day without riding. We wake up late and drink coffee on our tiny balcony, looking out across the orange tiled roofs and watching seagulls screaming and swooping in the morning sun. We take turns reading Wikipedia pages to each other—about Rome, Caesar, Nero, the Colosseum.


Joel and I have been together a long while. We’ve truly been through thick and thin. We’ve moved penniless to New York together, been through the death of a parent together, been stranded in foreign countries with no money together. But this trip feels different—more grown up, happier. We’re in our thirties and now have enough wherewithal to book accommodation in advance and carry more than one credit card. Traveling with him this time has been a breeze. I’ve been hugging onto him for many hours a day and sharing every meal yet the trip has been nothing but laughter and happy shouts through our helmets when the road reveals some beautiful vista or hilltop castle. So perhaps what happens today in Rome is inevitable.

We set out late morning for the Forum. The city is packed and hot. Tourist shuffle on busy streets like cattle. We dip into cathedrals, stop in at the Monumento Nazionale a Vittorio Emanuele, traipse through the Roman Forum. By the time we reach the Colosseum, the dark cloud descends. I am hot, I am exhausted, and most of all I am desperate need of lunch.

We decide to head the direction of home, and towards cafes and markets that I sense are back the way we came. Joel insists we take a ‘new’ route. One that I’m sure will take us the the fast moving multi-lane promenades along the Tiber. I fight him for a moment but then relent. Twenty minutes later we are in a virtual cafe desert, walking along the shoulder of a busy road in the blazing sun. Joel is droning on about some solo road trip he thinks I should take and I find myself thinking; clearly you don’t know me at all, I would never take that trip and I actually might hate you a little bit. By the time we reach lunch I have fat crocodile tears running down my cheeks. I chug a glass of prosecco as Joel tells me that I can be such a drag. DRAG? I hiss, I AM THE FUNNEST PERSON YOU KNOW MOTHERFUCKER.When the waiter arrives with our check we are both turned out to the street, arms crossed, not speaking. I’m not even sure what the fight is about but I am so hurt and so angry and when we get home we fall immediately asleep like tired puppies.


The cleansing fight—the kind you need to have after spending every waking and sleeping moment with one person for days on end. We laugh about it when we wake up and had a lovely evening at the vatican and sharing spaghetti like the dogs in Lady in the Tramp.

The next morning we are hung over from wine and emotions. A big fight like that always makes you cling to one another in the afterglow. I squeeze Joel hard as we wind our way into Tuscany.

8C2A6548 copy_preview-1.jpg

The countryside is bucolic and green and I’m sucking in nosefuls of summer smells—rich soil and jasmine. We reach the walled hamlet Montepulciano in the early afternoon. I’m not sure if it is the cloudy weather, or the fight, or the culmination of so many days on the road but we are exhausted. We reach out sweet little bed and breakfast and I nap so hard I don’t know where I am when I wake. We spend the rest of the day camped out in a cafe with a big view, reading and watching a cold front wash over the hills below.

As night falls we wander through the narrow streets and passageways, looking for dinner. We pass the festive orange glow of packed restaurant and for a moment I mistake if for a private gathering, someone’s home. We push in and ask for a table. It is, hands down, the best meal of the trip. We watch a nonna in the back room kneading spaghetti. The restaurateur brings out huge cuts of raw beef for diners to inspect before cooking. There are only two options for wine—white and red. And best of all - everyone sits at large rough hewn tables together, family style. The mood and jovial, raucous even.


That night we facetime with our families and I can see my face in the corner of the little screen - red-cheeks from too much wine and smiling so hard it hurts.



Starting the bike, we pass through the ancient portcullis and descend into the rolling hills. The dark skies provide startling contrast to the manicured fields— row upon row of deep green vines abut blonde wheat. The road—deserted and perfectly smooth—meanders across hill tops. Shield up, I let the cool breeze wash over my face and through my zipped-down jacket.

Acid or no, Petriolo hot springs is pretty psychedelic. Multicolored mineral deposits form natural baths of varying temperatures, and cascade into a small river. Famed for it’s healing properties, these baths have been used since Roman times and the ruins of a Medici family castle from 404 AD stands sentry. Incredibly beautiful, yet totally unpretentious, Petriolo is completely free and open to the public.

A cast of bizarre characters have made themselves at home around the pools. Cautiously at first, we adjust to our new surroundings and perspective, and explore the baths, swim in the river. One fellow in wet, translucent tighty-whiteys keeps making eye-contact with Hailey. We casually scoot away and then laugh until we can’t breathe. At some point I am swimming in the river and look up to see Hailey slip on some moss, scream wildly and slide into the river in an undignified splash. I fall asleep for a while by the river, lulled by the murmur of trickling water and the low chatting of fellow soakers.


We had planned to stay an hour and instead we stayed five. We drag ourselves from the pools, stinking of sulphur and incredibly dehydrated. An Italian hippie is selling food and drink from the back of his van and we scrounge 4 Euro in cash for a beer and a Coca-Cola. Leaning up against the ruins of the castle with my girl in my arms, I can’t remember feeling this happy.

The rest of the day passes like a dream. Back on the bike we take our time, winding towards Siena. Skies, still leaden, have parted in places to allow visible, crepuscular rays of light to illuminate individual hillsides and passing fields. Unbeknownst to us until later, it is not only the summer solstice, but also the first time in fifty-odd years that the solstice and full moon have shared a 24 hour period. The Strawberry Moon.




Pulling up to the curb at Malpensa International Airport, Joel cuts the engine and coasts to a stop. It’s been twelve days since he collected me not a hundred meters from this very spot. Twelve wonderful, whirlwind days. The beauty of motorcycle travel is the simplicity—it is about the road, the rush of wind, the cold beer at the end of the day.  It wasn’t easy or comfortable but none of the good stuff ever is.

And Joel. We travel constantly, incessantly—we’re addicted to it. But no trip, no ride has been quite like this. We have, quite literally, been spooning for well over a week and somehow it has settled us into each other’s rhythm, as if he has more of me and I have more of him. When I climb off the bike my heart is aching. A kiss goodbye and a long hard squeeze and he is gone.



It’s hot as hell when I pull into Knopf Motorrad in Heidelberg, Germany. Strolling into the office three hours late, I meet Beate behind the desk. She laughs warmly, comparing me to her youngest and least responsible son and directing me to the garage. I give the bike a loving and much deserved sponge bath before rolling her underground, a old WWII bomb shelter converted to motorcycle storage.

I’ve scored a night on the Knopf Family’s couch, as all the rooms are booked and I lie awake, thinking about the trip, the places, about Hailey. Three weeks. More than four thousand miles. Seven countries. Already I’m dreaming of our next trip, where we’ll go and what we’ll see. The thing is, our exploration of the world is only limited by our imagination. And our perception of what’s possible has cracked wide open. This is just the beginning.


Follow Joel and Hailey on Instagram here.