Italy has world-class gastronomy, scenic beauty, superb wines, rich history, incomparable art and architecture. But il bel paese is not so good at individual transportation. It is legendary for an erratic driving style, Fiat 500s (How do you get spare parts for a Fiat? Follow another one around), overcrowded autostradas and Vespas speeding past like angry, buzzing wasps.
But in one mode of transportation, it fares well: cheap, quick, fun, environmentally friendly, healthy biking.
So Italy should be known for its modest but thriving urban cycling culture, which was precisely how I decided to visit it. Living in the bikers’ paradise of Minneapolis, where I ride daily among some 225 miles of bikeways, I wanted to leave the beaten track, hit the road less traveled and see upper Italy in high gear.
The plan was to bike from west to east across Tuscany and Emilia-Romagna last October. I wanted to immerse myself in lesser-known historical and architectural treasures, and discover trattorias where it’s possible to eat fine food at reasonable prices. In a life beset with questionable choices, it was one of the best decisions I’ve ever made.
From the city-center piazzas that make striking public living rooms for chic Italians enjoying la dolce vita, to jumbles of twisting hill paths past conical cypress trees, my journey was adventurous, car-free bliss. Pedaling across and between towns, struggling up the steep hills and zipping speedily down the other side was worth every herculean exertion.
Biking put me closer to friendly locals as a kindred spirit on wheels and saved me from bus rides with 30 strangers, my vision of vacation hell. It exposed me to sun and delicious fresh air, silence other than birds singing to one another from treetops, and panoramic olive groves spread below like tranquil green seas. Motorists, take note!
The late fall timing put me outside during a wonderfully temperate Mediterranean autumn. Visiting picturesque hill towns filled with ancient houses and churches of medieval architecture instead of holidaymaker meccas kept me under the tourist radar. It enabled me to visit sublime spaces with no waits.
Some of the biggest challenges were logistical. Having completed a 700-mile bike journey from Portland to San Francisco last August, I felt confident that my tour legs were good enough. But I didn’t want to ship my trusty American bike overseas. It would cost a mint to load it as airline baggage, and could confound Italian bike-shop keepers as an unfamiliar brand if it needed repairs
Luckily, bike tours in Italy are becoming increasingly popular. Rental agencies with models designed for local use are easy to locate and contact online. For those who like the friendship of new acquaintances, many companies offer group tours with bikes and equipment, the services of a guide, accommodations and daily luggage transfers. Since that frustrates my obsessive frugality and itch for serendipitous day trips, I packed my essentials in two pannier saddlebags. With those and my helmet as carry-on, I moved through Florence’s airport like a road racer.
As to itinerary, there are no bad plans in Italy. I headed south on a mainline train to the Chianti region, covering the 85-mile distance in a little over an hour. My base camp for Week 1 was Cortona, a timeworn walled town on the spur of a spreading mountain, chosen because it is far from ugly, modern construction and near Siena and Montepulciano, homes of favorite memories from earlier trips.
I rented my ride without much discussion from a shop in Siena. Italian commerce is largely based on the principle of “Don’t worry about it,” and rightly so. The store delivered a brand-new, brilliantly geared mountain bike/city bike hybrid with shock-absorbing forks ideal for gravel. The price: about $300 for two weeks, dropoff and pickup included. Try to beat a deal like that.
Rolling into Cortona
Cortona is a great place to tour on a roll. With a population around 25,000, it’s more than a village, less than a city, more medieval, Renaissance and Baroque than 21st-century. The streets are narrow, sometimes excitingly steep, pulling you through attractive shopping thoroughfares to the main square, where you have fine vistas of breathtaking old ramparts. In Cortona, preservationist building laws guarantee that a 1990 roof looks like a 1490 roof. The city’s fabric is unchanged, or changed almost invisibly, the present blended with the past, its spirit still suiting the land that inspired it. The good surrounding walls have kept Cortona together since at least the Middle Ages. Visiting it reminds you how amazingly close New World architecture and candy wrappers stand in the spectrum of permanence.
Cortona is a wonderful and interesting place to experience normal northern Italian life without crushing tourist overflows. It offers great cuisine and delicious wines that are almost laughably cheap considering their quality. The main appeal for many visitors is the extraordinary collection of mysterious antiquities from the 6th century B.C. at the Palazzo Casali’s Museo dell’Accademia Etrusca. For others, it’s Fra Angelico’s awesome Renaissance panel painting, “The Annunciation of Cortona,” in the unassuming Museo Diocesano on the edge of town, surely one of the highlights of any art lover’s Italian tour.
I would guess that what draws the most remarkable numbers is the adoration of Frances Mayes. The American author’s popular memoir of rebuilding an abandoned villa in the city made “Under the Tuscan Sun” a bestseller, a hit film, and a PR bonanza for Cortona. She still lives there, walled off from packs of the faithful from Poland to Hong Kong who ask you to snap their picture posed by the gate like euphoric Elvis fans at Graceland.
Unless you’re extremely fit, remember to schedule days outside Cortonese treasures for long, slow returns; climbing the valley on about 12 percent inclines is muscular work. Still, it’s easy to pedal down and north for 90 minutes to Arezzo to see the stunning frescos by the early Renaissance master Piero della Francesca at the Basilica of San Francesco. Or south to Castiglione del Lago on the south corner of Lake Trasimeno to explore the huge Fortress of the Lion, a pentagonal-shaped 13th-century castle built by Holy Roman Emperor Frederick II in order to kill as many neighboring nobles as possible. It’s a quick trip east of Cortona to visit where St. Francis of Assisi ran away from his rich family and built his first abbey, now a gorgeous hermitage.
An hourlong zip southeast by car will get you to Perugia for late October’s huge annual chocolate festival, a heavenly experience of a different sort.
There’s no reason you couldn’t bike there; highway paths are smooth and almost pothole-free, Italian drivers are polite about giving cyclists room, and it’s common to share roadways with squads in skintight multicolored apparel, pedaling like crazed bike messengers. But time is valuable and there will be some monuments and legends you’ll want to access by bus or taxi.
Onward to Cesena
It was another train excursion that took me cross-country east to Cesena, where I switched to a new bike supplier. Cesena is a scenic oasis of rest and relaxation that exists without crowds or hype or many people knowing about it, not even outside cyclists. Multiple bike shops are available, but the local vehicles tend to the vintage, heritage and prehistoric. It’s not uncommon for users to rely on grandfather’s rusty relic from 60 years back, a commitment to history that feels more anachronistic than Cortona’s restrictive construction codes. Since the city is largely flat as a plate of pasta, antique bikes are fine.
Cesena is a festive place to spin around. Its fascinations center on the good life, with handsomely outfitted professionals pedaling to have a morning cappuccino, younger generations rolling to the barbershop for a stylish trim before an evening date, and many in between commuting to work. With about 88,000 inhabitants, everybody knows everybody and before long they know you, too. There are top-notch cocktail bars indoors, delicious weekend food markets and wine harvest celebrations outside, and the sort of street food that will pack on the pounds even if you’re a spin-class regular.
There’s a pinch of formal pomp at the gorgeous Piazza del Popolo, a cobblestoned, fountain-adorned gathering place just outside the turreted, military-style palace that is now the Museum of Natural Science.
The most celebrated highlight is the Malatestiana Library, the oldest intact public archive of books in the world, and surely among the most beautiful. In 2005 UNESCO listed it in its Memory of the World Program Register as a “rare example of a complete and wonderful collection from the 15th century.” Predating printing in Europe, it’s a mind-boggling trove, ranging from huge tomes of ornate filigreed calligraphy to one volume less than half an inch tall and a third of an inch wide, recorded as the smallest book in the world that can be read without a magnifying glass.
For creations like those, and for Giovanni Fontana, the 15th-century Venetian engineer who joined rope, gears and four wheels to make the first human-powered bicycle prototype, I say “Milli, milli grazie.”