The Ultimate Guide To Cycling in Italy

La Basilica di Santa Maria Novella, Florence. Photograph: Alison Testroete

La Basilica di Santa Maria Novella, Florence. Photograph: Alison Testroete

Cycling in Italy truly is everything it’s cracked up to be. By far the most popular cycling destination in Europe, it’s welcoming to cyclists of all levels. The history of cycling here dates as far back as the inception in 1909 of the Giro d’Italia and is still going strong today, particularly in the regions of Tuscany, Veneto and Lombardy.

But how does one decide where to cycle in Italy and what to do?

With so many things to see and hundreds of kilometers of pavement to roll over, I know how overwhelming the choices can be.

It would have to be impossible to consider any cycling guide complete, but If you love exploring and taking on new challenges, this guide to cycling in Italy is for you. Keep reading if you’d like to learn about the most popular cycling regions, Gran Fondos and other events in Italy.

I’ll take you through everything you need to know about cycling in Italy, including the regions of Tuscany, Umbria, Dolomites, Italian Lakes, Verona & Lake Garda, Piedmont, Puglia and Sicily. 

The Apennine mountains from Emilia Romagna to Basilicata and including Il Pirata’s Cippo di Carpegna, are extraordinary and cycling-worthy but at the tail end of the bell curve, so I’ve left them out. Sardegna is also a popular cyclists destination, but without enough personal experience, I’ve left it out, too.

Now, without any further ado, here’s to your next cycling in Italy journey. And as always, if you have any suggestions or tips, I’d love to hear them.

When’s the best time for cycling in Italy?

Although you can ride in most regions of Italy year-round (aside from the high mountains), it’s sun's out, guns out from April/May to October.

The weather will be unlikely to get you down in these months, yet the climate in Italy is synonymous with drama and emotion. When it rains, it pours — thunder, lightning, hand gestures, the works. Then the skies clear, the sun reappears, and it’s business as usual.

With the exception of July and August when temperatures can hit 35° to 38 °C, it’s a good idea to carry a light wind jacket or vest for long descents. If you don’t cope well with the heat, the Dolomites is your best bet for avoiding it during these two hottest months.

The 15th of August marks Ferragosto, Italy’s version of the summer vacation. Essentially everybody (outside of tourism) is on holiday this week — if not for the entire month of August. Although many will gravitate to the mountains, most head for the seaside. It’s a pretty relaxed time, except when riding  coastal roads.

Pietrasanta, Northern Tuscany in August. Photograph: Simone Orsucci

Pietrasanta, Northern Tuscany in August. Photograph: Simone Orsucci


Cycling in Italy, you’ll see fountains nearly everywhere. Once you notice one or two, you’ll start to pick up on them. So many that Italian cyclists carry just one bottle of water, using their second bottle cage for a tool kit. 

Fountains can be found in parks (usually alongside benches), piazzas, village centres and random points along the road. Drinking from fountains marked “acqua non potabile”, however, would be a gamble. If you’re dyin’ of thirst with no fountain in sight, here’s how to ask somebody … anybody:

Scusi, c'é una fontana qui vicino?

Cycling in Italy is generally safe, yet be mindful of the influx of non-local drivers in July and August when tourism peaks. You’ll likely find the roads to be narrower than those at home, and sadly, here as everywhere, there’ll be the occasional impatient driver who likes to overtake on a solid line. It’s always wise to err on the side of caution, no matter where you ride.



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Cycling in Tuscany

The powerhouse of cycling in Italy and the ultimate American dream, Tuscany can meet many, if not all of your needs. From north to south and west to east, just about anything’s possible.

Cycling in Northern Tuscany

Ride long climbs in Apuan Alps and central Apennine mountains near Lucca, introduced to the pro-cycling world by former Danish pro, Bjarne Riis. Lucca and these climbs have been training grounds for names like Thomas Dekker, Tyler Hamilton, and how can I forget the show pony himself, Mario Cipollini.

Aside from the pros, Lucca has one of the most vibrant cycling communities I’ve seen. It’s unlikely you’ll be greeted by other foreign cyclists but by club members wearing some of the least fashionable cycling kits you’ve ever laid eyes on.

Olive groves of Lucca with the Apuan mountains in the distance. Photograph: Simone Orsucci

Olive groves of Lucca with the Apuan mountains in the distance. Photograph: Simone Orsucci

Cycling the Island of Elba

The Island of Elba is where Napoléon Bonaparte was exiled, and only 10 km by ferry from the coastal town, Piombino. With clever tactics, a small team of domestiques, and unwavering discipline, you’ll conquer this entire island in three to four days—tops.

Had Strava existed in 1956, Fausto Coppi would surely also be an acclaimed king. In his later years, he wilfully exiled himself to Elba and made famous his favourite fountain, now enshrined as “Fonte di Coppi,” just outside of Rio nell’Elba. Rumour on the street has it that Paolo Bettini, and Vincenzo Nibali have also filled their water bottles at this glorious natural spring.

Beyond its reputation as an idyllic vacation spot enclosed by the Mediterranean sea, Elba's the place to achieve mighty goals.

Island of Elba. Photograph: Simone Orsucci

Island of Elba. Photograph: Simone Orsucci

Cycling in Chianti

Rides in North Tuscany are sown together by climbs, while in mid- and South Tuscany, it’s hilltop villages. Chianti isn’t only for wine lovers, but good light-hearted fun.

Hardly the six o’clock breaking news but, as long as you’re here, you won’t want to miss out on Radda in Chianti, Gaiole in Chianti, Castellina in Chianti, Greve in Chianti, Castelnuovo di Berardenga, San Gimignano, Monteriggioni, and Volterra. Meat-eating fans will want to pay a visit to the world famous butcher in Panzano in Chianti.

The towers of San Gimignano in the distance. Photograph: Poike/Getty Images

The towers of San Gimignano in the distance. Photograph: Poike/Getty Images

Cycling The Lands of Siena

There are no words to describe the beauty surrounding Asciano; you’ll have to define them for yourself. There’s a limit to the number of rides you’ll do before overlapping routes. Use them sparingly and for V02 max intervals.

Val d'Orcia, added to the UNESCO world heritage sites in 2004 is a seekers’ retreat. Blankets of bright greens or browns drape the Terre di Siena unlike any anywhere else on earth. The Orcia Valley urges introverted quests— a haven for great thinkers such as 1934 Nobel Prize writer, Luigi Pirandello, and painters at the Siena School of Art who have used it for inspiration to create timeless literature and works of art.

Spend your days meditatively pedaling, and soak away your afternoons in natural thermals spas like the ancient Roman baths in Bagno Vignoni, Bagni San Filippo and Vivo d'Orcia. Don’t miss out on a chance to explore the succession of quaint, picturesque towns that dot the region, including Pienza, Radicofani, Montepulciano and Montalcino. Wind up your tour of the fortified city of San Quirico by capturing your own image of the iconic Chapel of the Madonna di Vitaleta.

Crete Senesi. Photograph: StevanZZ/Getty Images

Crete Senesi. Photograph: StevanZZ/Getty Images

Grand Tour della Val di Merse

West and south of Siena is the lesser-known, rural area of Tuscany known as Val di Merse. If you’re yearning for serenity now, these could well be the roads for you — so quiet, in fact, you might go for miles without encountering a single car, let alone a water fountain or café. Grand Tour della val di Merse is a 159 km signposted route with 2500 m of elevation and 12 km of strade bianche.

The Grand Tour takes you through such places and sights as Casole d’Elsa, Radicondoli, Chiusdino, Muro and l'Abbazia di San Galgano (the church with no roof). In Val di Merse, you're not seen as yet another walking credit card, but the curiosity of gentle souls peering out from wide eyes.

The man and object of my affection. Photograph: Alison Testroete

The man and object of my affection. Photograph: Alison Testroete

Il Grand Tour della Maremma

Maremma, also off the beaten path, is home to the ancient, dormant volcano, Monte Amiata. At 1738 m, this gentle giant can be crested seven different ways, but a good place to start is from Abbadia San Salvatore (12 km/avg. 6%).

Another permanently signposted route, the Grand Tour of Maremma is a 370 km journey with a 5200 m elevation, unspecified portion of white roads, and Il Muro di Monte Nero — a 1.2 km stretch with sections at 15% to 20%.

Taking the Grand Tour challenge will introduce you to ancient Etruscan sites and L'Area del Tufo, encompassing the towns of Pitigliano (Little Jerusalem), Sorano, and Sovana. Tufo translates to tophus, which is Latin for stone, and alludes to the fascinating tunnels and caves to be explored beneath these unusual villages.

Pitigliano, village of tophus. Photograph: Elena Kharichkina

Pitigliano, village of tophus. Photograph: Elena Kharichkina

Cycling in Umbria

As Tuscany’s neighbour, Umbria doesn’t get the attention and respect it deserves, but with few economic resources, the region offers an authentic travel experience back through time. Beauty shines through its wrinkles, scars and all-knowing eyes, while some areas of Tuscany are photoshopped like a happy-yet-staged family portrait.

The most obvious points of interest to take in are Perugia, Spello and Assisi, as well as La Via Flaminia — the route taken by the Romans through the Apennine Mountains to the coast of the Adriatic Sea. The old Roman road stitches together a string of museum-like towns including Bevagna, Trevi, Nocera and — my favourite for its complex layers of history — Spoleto.

Umbria can be best appreciated through its rolling hills, Apennine climbs and seemingly endless small towns: Vallo di Nera, Orvieto, Città della Pieve, Gubbio, Montefalco and Stroncone. Fewer tourism euros may be reflected in the quality of the pavement; this is no Hilton Hotel replanted in Italy.

Although not technically in Umbria, nearby Cortona – the inspiration for Frances Mayes’ “Under the Tuscan Sun” — is worth a mention on the map, as is the breathtaking hilltop village of Civita di Bagnoregio in Lazio, only accessible by foot. If you can’t make it for a non-cycling escapade then definitely do a Google image search.

The skies about to break loose above Basilica of Saint Francis of Assisi. I highly recommend you also see the inside. Photograph: Alison Testroete

The skies about to break loose above Basilica of Saint Francis of Assisi. I highly recommend you also see the inside. Photograph: Alison Testroete

Cycling in the Dolomites

If you call an altitude training camp a vacation, then this is your destination. Prerequisites: no fear of heights or self-inflicted pain. Potential benefits: unquantifiable. Caveat: you have to be willing to do the work; nobody becomes a climbing machine by spending their days sitting in alpine spas.

The best way to optimize your time is with an east to west (or west to east), point-to-point tour. This isn’t obligatory, but without it, expect to retrace at least some of your tracks. For example, if you base yourself in Bormio, you’ll be near Passo della Stelvio (21 km/avg. 7.3%), Passo di Mortirolo (14.3 km/avg. 8.3 percent), Passo di Gavia (25 km/avg. 5.6%) and the Passo Umbrail (18.3 km/avg. 7.1%).

If you stay in Corvara or Cortina d’Ampezzo you’ll have access to the Sella Ronda loop: Passo di Campolongo (5.8 km/avg. 6.1%), Passo Pordoi (9.2 km/avg. 6.9%), Passo di Sella (5.5 km/avg. 7.9%), and Passo Gardena (5.8 km/avg. 4.3%). The second half of the Maratona figure eight loop includes Passo Giau (9.9 km/avg. 9.3%) and Passo di Falzarego/Valparola (11.5 km/avg. 5.8%).

For the ultra-motivated, an alternative might be the rewarding (and punishing), 90 percent paved Yolomites 5000 that starts from Val Badia — 120 km with 2000 m of up — including Passo delle Erbe, Passo Furcia, Passo Fedaia (14 km/avg. 7.6%) and more.

The spectacular Dolomites. Photograph: Simone Orsucci

The spectacular Dolomites. Photograph: Simone Orsucci

cycling the Italian Lakes

Five lakes span this region that also crosses over into Switzerland, and Lake Como is the most popular. There are many spots in the surrounding mountains that offer breathtaking views of the lake, such as from Pigra on the west side of Lake Como.

The peak of Passo del Ghisallo is considered an epicentre of cycling in Italy. The climb itself has been a part of races dating back to 1905, including Giro d'Italia, Coppa Agostoni and Giro di Lombardia. Ride either the classic side from Bellagio (9.3 km/avg. 5.7%) or take the gentler side, from Canzo.

Each year, thousands of cyclists from all over the world make a point of visiting the Madonna del Ghisallo, patroness of cyclists since 1949. Inside the tiny chapel, you'll find all sorts of cycling memorabilia from the who's who of professional cycling.

Next door to the chapel, a cycling museum showcases historical artifacts — from antique bikes to the first pink La Gazzetta dello Sport leaders jersey’s. You can visit the chapel on a bike ride, but you’ll need to make a separate trip by foot for the museum.

Ghisallo Cycling Museum. Photograph: Alessio Soggetti

Ghisallo Cycling Museum. Photograph: Alessio Soggetti

cycling in Verona & Lake Garda

Another must-see place for any well-rounded cycling in Italy experience, fair Verona is anything but tragic. Despite being a little touristy, Verona is a cyclist’s delight because it has a little bit of everything — rolling hills, scenic mountains, and a picturesque lake — and a journey through here offers an intimate glimpse into Italian life. Your potential itinerary might look something like this:

  1. bici through the rolling hills and vineyards of Valpolicella, capped with dinner in Verona

  2. bici up Monte Baldo followed by a dip in Lake Garda

  3. recovery bici to to Valeggio sul Mincio before taking in an opera/concert/play at the Arena — one of the best-preserved ancient structures in the world

If this sounds too lax for your liking, an 18 to 26 km trip up through Monte Grappa should tame the inner beast, and you’ll be back on schedule in one day flat.

Cycling in Piedmont

Piedmont is the perfect region for those searching for beyond average. South Piedmont is home to the Slow Food movement while the city of Alba, regarded as its “gourmet capital,” boasts Italy’s highest concentration of Michelin-starred restaurants. Like Tuscany, the lands are hilly, with towns and castles perched proudly on top.

Indulge your taste for fine wines as you pass through Barola and Barbaresco, two of Piedmont’s most famous wine-growing regions around Monforte d'Alba, Barolo and La Morra. You’ll also want to cycle through the Langhe area — the heart of white truffle season every year from September to January.

The name of the game here is Saliscendi, which roughly means “take no prisoners.” Just kidding, it means, literally, up-down. Your must-see cycling destinations in this area include local restaurants and quaint villages like Neive, Grinzane Cavour, Diano D’Alba, and Castiglione Falletto.

Moving onto other pursuits of non-mediocrity, you have your choice of monster climbs like the 40 km Colle del Nivolet and the 2000-meter-high military gravel roads near the border of France — the same ones stitched together to form the Torino-Nice Rally: Colle delle Finestre, Strada dell'Assietta, Colle Dell'Agnello, Via Del Sale and Col de Turini.

Gran Fondo Sestriere Colle delle Finestre. Photograph: Alison Testroete

Gran Fondo Sestriere Colle delle Finestre. Photograph: Alison Testroete

Cycling in Puglia

On a ten point scale of cycling in Italy difficulty, you have the Dolomites at an 11, and Puglia between two and four depending on your level of effort and the way the wind blows. In other words, Puglia is for retired people who play golf, chit-chat with the locals and go for leisurely bike rides.

Puglia isn't only for retired folk, though, it’s also for you, me and trullo houses. When you get to Puglia, you won’t want to spend all your time on the bike when you’re surrounded by glorious, sparkly blue waters anyway.

Your tour won’t be complete without cycling the coastal roads and inland — through Valle d'Itria to the trulli of Alberobello — and taking time for visits to the whitewashed old towns of Locorotondo and Ostuni. I don’t doubt that the bike is also your church, yet consider taking spiritual moments of presence at Santuario di Monte Sant’Angelo (which also happens to be a Giro d’Italia climb).

Lastly, before you float all your days away in the Adriatic Sea, don’t skip the mesmerizing ancient cave town of Matera, and learn of its captivating history of redemption.

Ostuni, Puglia. Photograph: StevanZZ/Getty Images

Ostuni, Puglia. Photograph: StevanZZ/Getty Images

Cycling in Sicily

A tempting site of exploration for archaeologists and cyclists alike, Sicily is a step into another time and another world. Colonized by the Greeks in the 8th century BC, Sicily is truly the stuff of thick, dense history books.

While you probably have the most in common with Italy’s organized, precise Germanic North, why not have a wander through a dichotomy of humanity’s highs and lows? As the place where Plato once pondered life that also gave rise to the material world of the Sicilian mafia, the history of Siracusa is full of dramatic contrasts.

From the east, you’ll want to visit the towns of Taormina, Castelmola, Noto, Ragusa, as well as Mount Etna, the 1800 m active volcano. Five 30 km climbs lead to its twin peaks — north and south summits that have witnessed the crowning of six Giro d’Italia’s stage winners.



Get the Ultimate Cycling in Italy Guide as a convenient, downloadable PDF.



8 Beautiful Gran Fondos & Cycling Events in italy

Bonus insider tips to apply for each event:

  1. Registration, for the most part, is as competitive as any hot eBay auction, so do your homework and use a strong internet connection.

  2. Always scan the photo package.

1. Gran Fondo Strade Bianche, Siena (early March)

Fast emerging as THE wish list event, the white roads of Siena piggyback the pro race that started back in 2007. In 2016, organizers of Giro d’Italia RCS unleashed the Gran Fondo, and it seems to have doubled in size each year since.

The Gran Fondo Strade Bianche is a dramatic and magical event that finishes in Piazza del Campo, home of the renowned biannual Palio Horse Race. Typically, the weather on the second weekend of March is unpredictable, meaning that you won’t know whether to expect white roads or a grey-brown, muddy slip ‘n slide. Either way, it’s a bucket list weekend — and one of my faves.

The Gran Fondo stretches 139.2 km over the Lands of Siena, with 31.4 km of gravel. The Medio Fondo is 86.6 km, of which 21.6 are gravel. The downside of the Medio is that it cuts out the Crete Senesi, which might be just as well if it’s raining (because ouch — that’ll hurt).

Gran Fondo Strade Bianche. Photograph:

Gran Fondo Strade Bianche. Photograph:

2. Gran Fondo Firenze, Florence (mid-April)

Inspired by the 2013 World Road Championships, the Gran Fondo Firenze is the perfect excuse to visit this renaissance city. You might be expecting yet another Chianti affair; but no — the path heads due north and into the heart of the Florence Apennine, up the same Fiesole climb that Marianne Vos attacked on her way to becoming World Champion.

Not only will you retrace the path of the World Champion herself but, with the race starting from Piazzale Michelangelo (near Galileo Galilei’s old stomping grounds) you’ll also be spending time in history’s fine company.

Take on the Apennine with the Gran Fondo at 135 km and 2800 m, or not for the Medio at a total of 95 km and 1600 m of elevation.

3. Gran Fondo Nove Colli, Cesenatico, (third week of May)

This race calls itself the “Queen of Gran Fondo,” and with its inception back in 1971, who can argue? In Italian, the route is described as “dal mare alle colline, un mix di bellezza, paesaggistica, sudore e fatica,” meaning “from the sea to the hills, a mix of beauty, scenery, sweat and fatigue.” And Italians are fighting tooth and nail for entry and “emozioni indimenticabili,” or unforgettable emotions.

Starting in Cesenatico, you’ll make your way to the base of the Apennine Mountains and on toward the border of San Marino. It’s a stunning area. Why choose beach over mountains, when this race gives you both?

The Lungo is 205 km with 3840 m of elevation, and the Medio covers 130 km with 1871 m of climbing.

4. Maratona dles Dolomites, Corvara (early July)

The crown jewel of Italian Gran Fondos is the Maratona dles Dolomites starting and finishing in Corvara. For amateurs, it’s the most prestigious race you can win in Italy. For rest of us, 9880 members of pack fill, it’s stunning scenery with a good-sized serving of hurt.

The course forms a figure eight, with the first loop being the Sella Ronda with a cool four climbs: Passo di Campolongo (5.8 km/avg. 6.1%), Passo Pordoi (9.2 km/avg. 6.9%), Passo di Sella (5.5 km avg. 7.9%), and Passo di Gardena (5.8 km/avg. 4.3%).

For the full maratona, it’s another round up Passo di Campolongo, Passo Giau (9.9 km/avg. 9.3%), and Passo di Falzarego/Valparola (11.5 km/avg. 5.8%), for a total of 138 km and 4230 m of elevation. I look at it as fine people watching, roadside food, and a pizza party to boot.

Maratona dles Dolomites. Photograph:

Maratona dles Dolomites. Photograph:

5. Sportful Dolomiti Race, Feltre (mid-June)

Next to the Maratona, the Sportful is the pretty but unnoticed sister. The climbs might not be as steep or as famous, but they’re still Giro d’Italia climbs, and equally as beautiful. Although it’s half the size of the Maratona, you’ll still be starting in a sea of 5000 other cyclists, so the earlier you register, the lower your number will be. Unlike the Maratona, the Medio Fondo might be more manageable here, at just 140 km.

The 210 km Gran Fondo, with four main climbs, is the 20th stage of the 2019 Giro d’Italia. It’s made up of Cima Campo (18.2 km/avg. 6.1%), Passo Manghen (22.2 km/avg. 7.3%), Passo Rolle (19.9 km/avg. 4.8%), and Croce d’Aune (13.5 km/avg. 6.3%), but with a downhill finish into Feltre.

6. Gran Fondo Campagnolo Roma, Rome (mid-October)

One of the few chances you’ll get to roam Rome as the Romans did. Starting with the Colosseum at your back and with roads closed to traffic, you’ll have a green light to the Eternal City for the entire day — along with thousands of race-faced Italians, of course.

The 118 km, 2000 m course covers southeast rural Rome, weaving through castles, Lake Albano, and four official timed climbs for your chance to be The King or Queen of Rome.

What’s the prize? Nothing less than your rightful place in the highly sought-after, first-row starting grid the following year, sporting your new champion jersey of course. Chop, chop! Rome wasn’t built in a day, and your rivals are already training!

7. Gran Fondo Il Lombardia, Como (mid-October)

Also tagging on to the pro race is the Gran Fondo Il Lombarida. The most worthwhile pursuits don’t ever come with little effort, and here we have Il Muro di Sormano (7 km at 9-27%), where I’m pretty sure grown men cry (not that there’s anything wrong with that). If you think this might be you, you’ll have the opportunity 10 km before to visit the Madonna del Ghisallo and pray to what or whomever you believe in that the wind be at your back.

At 112.6 km with 2700 m of climbing, this ain’t no walk in the park, but race numbers are still selling like hotcakes!

No shame in walking this “wall.”  Il Muro di Sormano.  Photograph: Alison Testroete

No shame in walking this “wall.” Il Muro di Sormano. Photograph: Alison Testroete

8. L’Eroica, Gaiole in Chianti (early October)

Not classified as a Gran Fondo, l’Eroica is in a category of its own. It’s permanently signposted, meaning you can ride it any day of the week, and with any bike you’d like. Except, that is, for the actual event, when showing up on, say, a gravel bike is bad form — and not in the spirit of the l'Eroica.

In fact, you must come with a historically-inspired or vintage style bike not newer than circa 1987, complete with downtube shifters, strap-in pedals, 32-spoke wheels with steel, aluminum or wood rims, and vintage wool clothing to suit — bonus points for carefully selected accessories.

Founded in 1997, Giancarlo Brocci wanted to preserve Tuscany’s last gravel roads and reconnect the modern generation of cycling with its historical roots. As the Italian Giancarlo is, he defines his participants as “hunters of feelings and emotions.”

Understandably, you may be frightened by the thought of riding steep, dusty gravel roads on a tank of a bike, but at least you have options, with routes of 32, 46, 81, 106, 135, and 209 km. You’ll have from dawn (5 am) till dusk to ride 209 km — a route designed with impeccable attention to detail, including candlelit-lined roads before sunrise.

The event translates into memories for life, and, judging by its rate of expansion, many others would agree. In Italy alone, Eroica has added three additional events: Nova Eroica, Eroica Montalcino, and Eroica Dolomiti.

Representing Poli Bici from Lucca. Photograph: Alessandro Castellacci

Representing Poli Bici from Lucca. Photograph: Alessandro Castellacci

Click here for Italy’s full Gran Fondo calendar.

Who might I be to write about cycling in Italy?

On April 29th, 2011, I kissed pro cycling goodbye, healed my wounds, saved up some Benjamins and moved to Perugia nine months later. I was searching for the wind in my face and the sun on my back. Italy called me loud and clear, and I followed like a lost puppy.

Perugia was the rational choice for an irrational decision. There’s an affordable international language school, Università per Stranieri di Perugia, and cheap rent. It has a little baggage, but that wasn’t going rain on my parade. The pictures were beautiful, and I heard the riding was nice, too.

View from Perugia on a winter day. Photograph: Alison Testroete

View from Perugia on a winter day. Photograph: Alison Testroete

I devoted my mornings and evenings to the Italian language, and my afternoons to cycling in Italy. RidewithGPS became my best friend, as did TrenItalia. My classmates were taking the train to nearby towns, but I thought the civility of spending hours on the train to see a single town was for suckers. So I learned to bang them all off in one ride with a single train ride home.

There are hundreds of thousands of villages and roads to cycle in Italy, but one’s riding radius can only be expanded so far. Moving to Verona for two months with the same routine was the solution: language in the mornings, bike in the afternoons. After all, the lost puppy had grandiose plans to get a university degree (but at this point was still unable to read an Italian children’s book). I discovered the incredible area of Lake Garda, the Dolomites and Valpolicella with again the help of TrenItalia.

Nine months in, I packed up my things and moved to Bologna to get after that degree. After all, I’d heard about people doing it whose first language wasn’t even based on the same alphabet. I considered myself a shoe in.

Not really.

I remember picking a random university book off the shelf in a Verona library; to say my comprehension and attention span was poor would be a generous evaluation. But my cycling in Italy was going better than ever! In particular, exploring the vastness of the Appenine area from Bologna lit me up like a Christmas tree.

Bolognese Apennine. Photograph: Alison Testroete

Bolognese Apennine. Photograph: Alison Testroete

Sadly, all the serenity now I’d managed to achieved cycling in Italy was going to hell in a handbasket when it came to attending university lectures. Finding my assigned classroom alone was like picking out the needle in a haystack of big doors, small doors, roman numerals, floors, buildings, and hallways.

The good news was my Italian was decent enough to ask for directions; it just wasn’t good enough to understand the response. There’s a saying: that the way a relationship starts is usually an indication of the way it will be, and so it was for my journey in Bologna. An SOS course correction redirected my studies to (and eventual graduation from) Pisa, then Lucca.

Through hindsight, I came to realize that we are as many people as the languages we speak. Speaking Italian wasn’t as simple as learning to translate individual English words; I had to develop a whole new way of relating to the world and expressing myself.

That whole new world opened itself up to me as a vibrant cycling community in Lucca. A local Gran Fondo team welcomed me with open arms, and that’s when I knew I had made my first real Italian friends. The race schedule was initially a mystery, but it didn’t take long to see that their toothpick physiques were destined for the high mountains, and that’s when I was to be reborn as a climber, too.

Team San Ginese and President Andolfi who loves cheese and prosciutto. Photograph: Alison Testroete

Team San Ginese and President Andolfi who loves cheese and prosciutto. Photograph: Alison Testroete

Italians take their Gran Fondo racing every bit as seriously as I did my pro cycling career. If I wanted even to contest in these races, I would need a small army of three to five gregari to take the wind, close the gaps and provide moral support — all for a lousy prosciutto and a bottle of local wine.

Lastly, to fill in the gaps of my cycling in Italy experience, I guided for companies like La Fuga, inGamba, Rapha Travel and others. The thing is, though, as soon as you close one gap, a new one opens.

A lifetime isn’t nearly enough to discover Italy by bike, and that, my friend, is very good news. We have our whole lives to learn new things. Whether or not you’ll ever cycle in Italy with me on a guided ride or cycling trip, I welcome you to never stop exploring.

Alison Testroete