Cycling in Italy: Ultimate Guide on Where to Go and What to Do
Cycling in Italy is truly all that it’s cracked up to be. It’s by far the most popular cycling destination in Europe and welcoming to cyclists of all levels. Dating as far back as 1909, the inception of the Giro d’Italia, Italy’s strongest cycling tradition lies in the regions of Tuscany, Veneto and Lombardy.
With so many things to see and hundreds of kilometers of pavement to roll over, I know how overwhelming this choice can be.
If you love exploring and taking on new challenges, this cycling in Italy guide is for you. It would be an impossible task to consider any cycling guide complete, but keep reading if you’d like to learn about the most popular cycling regions, Gran Fondo’s and events in Italy.
I’ll take you through the basics — what you need to know about cycling in Italy, on toward 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.
Get the Ultimate Cycling in Italy Guide as a convenient, downloadable PDF.
When’s the best time for cycling in Italy?
While you can ride in Italy year-round in most regions aside from the high mountains, it’s sun's out, guns out from April/May to October. Weather will unlikely get you down in these months, yet Italy is inseparable from drama and emotion.
When it rains, it pours — thunder, lightning, hand gestures, the works. Then the skies clear, the sun makes its reappearance, and it’s business as usual.
It’s a good idea to carry a light wind jacket or vest for long descents except in July and August when temperatures hit 35 - 38° C. If you don’t cope well with heat, Dolomites is your best bet in these two months.
The 15th of August marks Ferragosto which is synonymous with summer vacation in Italy. Essentially everybody outside of tourism is on holiday this week if not the entire month of August. They either gravitate to the mountains but mostly the seaside. It’s a pretty relaxed time except when cycling on coastal roads.
Cycling in Italy Tips
There are fountains nearly everywhere while cycling in Italy. Once you notice, one or two, you’ll start to pick up on them. This is why most Italian cyclists carry just one 500ml bottle of water using their second bottle cage for a tool kit.
Fountains are often in parks (with benches), piazza’s, village centres and also random points along the road. Drinking, however, from fountains marked “acqua non potabile” would be a gamble. If you’re dyin’ of thirst and can’t find a fountain, here’s how to ask somebody… anybody:
Cycling in Italy is generally safe, yet be mindful of an influx of non-local drivers in July and August when tourism peaks. The roads for you are most likely narrower than home, and sadly Italy has its occasional impatient driver who likes to overtake on a solid line. It’s always wise to err on the side of caution wherever you ride.
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 northern Apuane and 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 the least fashionable cycling kit you’ll ever set your eyes on.
Cycling the Island of Elba
The Island of Elba is where Napoléon Bonaparte was exiled and only 10km 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.
Not only for the former King of Italy, had Strava existed in 1956, Fausto Coppi would also undoubtedly be a king of Elba. 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 is Paolo Bettini, and Vincenzo Nibali have filled their water bottles at this glorious fresh, natural spring, too.
If not a vacation spot enclosed by the Mediterranean sea, Elba's the place to achieve mighty goals.
Cycling in Chianti
In North Tuscany rides are sown together by climbs while in mid and South Tuscany it’s hilltop villages. Chianti isn’t only for wine lovers, but light-hearted fun.
Hardly the six o’clock breaking news but 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, Volterra, and if you like meat, the famous butcher in Panzano in Chianti.
Cycling The Lands of Siena
The Crete Senesi surrounding the town of Asciano have no words to describe their beauty; 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 other land of the earth. The Orcia Valley urges introverted quests such as 1934 Nobel Prize writer, Luigi Pirandello, and painters at the Siena School of Art who have brought forth timeless literature and works of art.
Spend your days meditatively pedaling and your afternoons at natural thermals spas like the ancient Roman baths in Bagno Vignoni or Bagni San Filippo and Vivo d'Orcia. Don’t miss town like Pienza, Radicofani, San Quirico d'Orcia, Montepulciano, Montalcino and a photo of the Chapel of the Madonna di Vitaleta.
Grand Tour Val di Merse
A lesser-known, rural area of Tuscany is Val di Merse, west and south of Siena. If you’re yearning for serenity now, these roads could be for you. So quiet in fact, you may not encounter a car, let alone a water fountain or cafe for miles. Grand Tour val di Merse is a 159km signposted route with 2500m of elevation and 12km of strade bianche.
The Grand Tour brings you through Casole d’Elsa, Radicondoli, Chiusdino, l'Abbazia di San Galgano —the church with no roof, Muro and others. In Val di Merse, you're not yet another walking credit card, but the curiosity of gentle souls peering out from wide eyes.
Il Grand Tour della Maremma
Maremma, also off the beaten path is home to ancient, dormant volcano, Monte Amiata. This 1738 m gentle giant can be crested seven different ways but from Abbadia San Salvatore (12km average 6 per cent) is a good place to start.
Another permanently signposted route, The Grand Tour of Maremma is a 370km journey with 5200m elevation, unknown portion of white roads, and the 1.2km muro di Monte Nero.
Taking the grand challenge will introduce you to Etruscan sites and L'Area del Tufo — towns of Pitigliano (Little Jerusalem), Sorano, and Sovana. Tufo translates to tophus which is Latin for stone. They’re unusual villages to visit with fascinating tunnels and caves beneath them.
Cycling in Umbria
As Tuscany’s neighbour, Umbria doesn’t get the attention and respect it deserves, but with smaller economic resources it’s an authentic travel through time. Beauty shines through its kind eyes, wrinkles and scars while areas of Tuscany are photoshopped like a happy family portrait.
The most obvious points of interest are Perugia, Spello and Assisi, yet La Via Flaminia is the route the Romans took through the Apennine to the Adriatic Sea. The old Roman road strings together museum-like towns of Bevagna, Trevi, Nocera and Spoleto being my favourite for its layers of history.
Know Umbria through its rolling hills, Apennine climbs and yet more towns: Vallo di Nera, Orvieto, Città della Pieve, Gubbio, Montefalco and Stroncone. Fewer tourism euros reflect in the quality of the pavement, but it’s no Hilton Hotel replanted in Italy.
Not technically Umbria is nearby Cortona put on the map with Frances Mayes’ “Under the Tuscan Sun” and Civita di Bagnoregio in Lazio — only accessible by foot but worth a Google image search if not a non-cycling escapade.
Cycling in the Dolomites
If you call an altitude training camp a vacation, then this is your destination. Prerequisites being you can’t be afraid of heights or self-inflicted pain — possible benefits: unquantifiable. But you have to be willing to do the work; nobody becomes a climbing machine by sitting in alpine spas all day long.
The best way to optimize your time is an east to west (or west to east) point-to-point tour. This isn’t obligatory, but expect to retrace your tracks. For example, if you base yourself in Bormio, you’re near Passo Stelvio (21km average 7.3 per cent), Passo del Mortirolo (14.3km average 8.3 per cent), Passo di Gavia (25km average 5.6 per cent) and the Umbrail Pass (18.3km average 7.1 per cent).
If you stay in Corvara or Cortina d’Ampezzo you’ll have access to the Sella Ronda loop: Passo di Campolongo (5.8km average 6.1 per cent), Passo Pordoi (9.2km average 6.9 per cent), Passo di Sella (5.5km average 7.9 per cent), and Passo di Gardena (5.8km average 4.3 per cent). Plus also the second half of the Maratona figure eight loop: Passo Giau (9.9km average 9.3 per cent) and Passo di Falzarego/Valparola (11.5km average 5.8 per cent).
An alternative might be the gratifying (punishing), 90 per cent paved Yolomites 5000 — 120km with 2000m of up starting from Val Badia including Passo delle Erbe, Passo Furcia, Passo Fedaia (14km average 7.6%), and more.
cycling the Italian Lakes
Five lakes make up the region that also crosses over into Switzerland, and Lake Como is the most popular. The peak of Passo del Ghisallo is an epicentre of cycling in Italy. The climb itself is used in Giro d'Italia, Coppa Agostoni, and Giro di Lombardia dating back to 1905. Ride it the classic side from Bellagio (9.3km average 5.7 per cent) or the gentler side from Canzo.
Each year thousands of cyclists from all over the world stop by 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.
There’s a cycling museum next door collecting and preserving cycling’s artifacts from antique bikes to the first pink La Gazzetta dello Sport leaders jersey’s. Visit the chapel on a bike ride, but you’ll need to make a separate trip for the museum.
There are many spots in the surrounding mountains with breathtaking views of the lake, like from Pigra on the west side of Lake Como.
cycling in Verona & Lake Garda
The place to be for a well-rounded cycling in Italy trip, fair Verona is anything but tragic. Despite being a little touristy, Verona is a cyclists delight because it has almost everything: rolling hills, scenic mountains, and a picturesque lake — all with a close look into Italian life. Your potential itinerary might look something like this:
bici through the rolling hills and vineyards of Valpolicella, dinner in Verona
bici up Monte Baldo followed by swim in Lake Garda
recovery bici to Valeggio sul Mincio then opera/concert/play at the Arena — one of the best-preserved ancient structures in the world
If this sounds too lax, 18 - 26km 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 has Italy’s highest concentration of Michelin-starred restaurants. The lands are hilly like Tuscany with towns and castles proudly perched on top.
Barola and Barbaresco are Piedmont’s most famous wines grown around Monforte d'Alba, Barolo and La Morra — the Langhe area you’ll want to cycle through, which is also the heart of white truffle season between September and January.
Saliscendi is the name of the game which roughly means take no prisoners. Just kidding, it means up-down. Your cycling destinations in this area are restaurants and villages like Neive, Grinzane Cavour, Diano D’Alba, and Castiglione Falletto.
Moving onto other pursuits of non-mediocrity you have monster climbs like the 40km Colle del Nivolet and 2000m high military gravel roads near the border of France stitched together in the Torino-Nice Rally: Colle delle Finestre, Strada dell'Assietta, Colle Dell'Agnello, The Via Del Sale, and Col de Turini.
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 short, 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.
But don’t rule out the bike too quickly. Your tour won’t be complete without cycling coastal roads and inland through Valle d'Itria to Alberobello’s trulli with visits to white towns of Locorotondo and Ostuni. I don’t doubt 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 your days away in the Adriatic Sea, do not skip the mesmerizing ancient cave town of Matera with a captivating history of redemption.
Cycling in Sicily
An exploration site 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 the stuff thick, dense history books are made of.
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? Discover Siracusa through the world of ideas where Plato once lived and the contrasting material world of the Sicilian mafia.
From the east visit towns Taormina, Castelmola, Noto, Ragusa and 1800m active volcano, Mount Etna. Five 30km climbs lead to respective south and north peaks where the Giro d’Italia has crowned six stage winners.
Get the Ultimate Cycling in Italy Guide as a convenient, downloadable PDF.
8 Beautiful Italian Gran Fondos & Events
Few insider tips to apply for each event:
registration, for the most part, is as competitive as a hot eBay auction (do your homework and use a strong internet connection).
always buy the photo package.
1. Gran Fondo Strade Bianche, Siena (early March)
Emerging as The wish list event, the white roads of Siena piggyback the pro race that started in 2007. In 2016 RCS, organizers of Giro d’Italia, unleashed the Gran Fondo and it seems to have doubled in size each year.
It’s a magical and dramatic event that finishes in Piazza del Campo, where the renowned biannual Palio Horse Race takes place. The weather on the second weekend of March is unpredictable enough that you may get white roads or a grey-brown muddy slip ‘n slide. Either way, it’s a bucket list weekend — one of my faves.
The Gran Fondo stretches 139.2km over the Lands of Siena with 31.4km of gravel. The Medio Fondo is 86.6km in which 21.6 are gravel. The downside of the Medio is cutting out the Crete Senesi, but if it’s raining, ouch, that’ll hurt.
2. Gran Fondo Firenze, Florence (mid-April)
Inspired by the 2013 World Road Championships, Gran Fondo Firenze is the perfect excuse to visit the renaissance city. You would expect yet another Chianti affair, but no, it heads due north up the Fiesole climb where Marianne Vos attacked to become World Champion and into the heart of the Florence Apennine.
Not only will you retrace the path of the World Champion herself, you’ll be in history’s fine company with the race starting from Piazzale Michelangelo near Galileo Galilei’s old stomping grounds.
Take on the Apennine with the Gran Fondo at 135km and 2800m or chop it out at a total of 95km and 1600m of elevation for the Medio.
3. Gran Fondo Nove Colli, Cesenatico, (third week of May)
This race calls themselves The Queen of Gran Fondo and who can argue with a Fondo that started in 1971? They describe the route in Italian 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 - unforgettable emotions.
It starts in Cesenatico and makes its way to the base of the Apennine mountains on toward the border of San Marino. It’s a stunning area. Why chose beach over mountains when you can have both in this race?
The Lungo is 205 km with 3840m of elevation, and the Medio is 130km with 1871m 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, its stunning scenery with a good-sized serving of hurt.
The course forms a figure eight, the first loop being the Sella Ronda with a cool four climbs: Passo di Campolongo (5.8km average 6.1 per cent), Passo Pordoi (9.2km average 6.9 per cent), Passo di Sella (5.5km average 7.9 per cent), and Passo di Gardena (5.8km average 4.3 per cent).
For the full maratona, it’s another round up Passo di Campolongo, Passo Giau (9.9km average 9.3 per cent), and Passo di Falzarego/Valparola (11.5km average 5.8 per cent) totalling 138km and 4230m of elevation. I take it as fine people watching with roadside food and a pizza party to boot.
5. Sportful Dolomiti Race, Feltre (mid-June)
Next to the Maratona, the Sportful is the pretty unnoticed sister. The climbs might not be as steep or as famous, but they are Giro d’Italia climbs and equally as beautiful. At half the size, 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 at 140km.
The 210km Gran Fondo is the 20th stage of the 2019 Giro d’Italia with 4 main climbs: Cima Campo (18.2km average 6.1 per cent), Passo Manghen (22.2km average 7.3 per cent), Passo Rolle (19,9km average 4.8 per cent), and Croce d’Aune (13.5km average 6.3 per cent) but with a downhill finish into Feltre.
6. Gran Fondo Roma, Rome (mid-October)
One of the few chances you’ll get to roam Rome as the Roman’s did. Starting with the Colosseum at your back, roads closed to traffic; you’ll have a green light to the Eternal City for the entire day — less thousands of race faced Italians, of course.
The 118km, 2000m course covers south-east 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? The highly sought after first row starting grid the following year in your new champion jersey. 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. Worthwhile pursuits don’t tend to come with little effort, and here we have Il Muro di Sormano (7km at 9-27 per cent) 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 10km before to visit the Madonna del Ghisallo and pray to what or whomever you believe in that the wind be at your back.
At 112.6km with 2700m of climbing, this ain’t no walk in the park, but race numbers are still selling like hotcakes!
8. Eroica, Gaiole in Chianti (early October)
Not classified as a Gran Fondo, Eroica is in a category of its own. It’s signposted permanently meaning you can ride l’Eroica any day of the week with any bike you’d like. But not for the event. Showing up on say a gravel bike is bad form and not the spirit of the l'Eroica.
You must come with a historically inspired or vintage style bike not newer than 1987 with down tube shifters, strap-in pedals, 32-spoked wheels with rims made of either steel, aluminum or wood, and vintage wool clothing to suit — bonus points for carefully selected accessories.
Founded in 1997, Giancarlo Brocci wanted to reconnect the modern generation of cycling with its historical roots and preserve Tuscany’s last gravel roads. As the Italian Giancarlo is, he defines his participants as “hunters of feelings and emotions.”
You may be frightened by the thought of riding steep, dusty gravel roads on a tank of a bike, but you have options. Routes range from 32km, 46km, 81km, 106km, 135km, and 209km. You’ll have from dusk (5 am) till dawn to ride 209km with impeccable attention to detail including candlelit lined roads before sunrise.
This event translates into memories for life, and by the rate of its expansion, many others would say so, too. In Italy alone, Eroica has added three additional events: Nova Eroica, Eroica Montalcino, and Eroica Dolomiti.
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.
I devoted my mornings and evenings to the Italian language and my afternoons to cycling in Italy. RidewithGPS became my best friend, and so did TrenItalia. My classmates were taking the train to nearby towns, and I thought civilly spending over two or three hours on the train to see one town was for suckers. So I learned to bang them all off in one ride with a single train ride home.
But there are hundreds of thousands of villages and roads to cycle in Italy, and one can only expand their radius 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 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 that uni degree. I’d heard about people doing it whose first language wasn’t even using the same alphabet, so I considered myself a shoe in.
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 as well as it ever was! The vast and particular area of the Apennine from Bologna lit me up like a Christmas tree.
Sadly, all the serenity now I’d achieved cycling in Italy was going to hell in a handbasket when it came to attending university lectures. Finding the classroom was like picking out a needle in a haystack of big doors, small doors, roman numerals, floors, buildings, and hallways.
The good news: my Italian was decent enough to ask for directions, but the downside: it wasn’t good enough to understand the answer. There’s a saying that the way a relationship starts is usually an indication of the way it will be. This was true for my journey in Bologna. An SOS course correction brought my studies and eventual graduation to Pisa then Lucca.
Hindsight showed me that you are as many people as you are languages. To my ignorance, speaking Italian wasn’t as simple as translating English words. I had to find 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 started to make my first real Italian friends. The race schedule was initially a mystery, but it didn’t take long to notice their toothpick physiques where destined for the high mountains and I was suddenly going to be a climber as well.
Italians take their Gran Fondo racing as seriously as I did my pro cycling career. If I wanted even to contest these races, I would need a little 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 enough to discover Italy by bike, and that, my friend, is good news. We have our whole lives to learn new things. Whether or not you cycle in Italy with me on a guided ride or cycling trip, I welcome you to never stop exploring.