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Back to the Boot (Italian Travel)

Images by Heather Dowd and Gwen Kidera

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Italy has always been there for us, offering passion and panache. The country has also given us some of cycling’s greatest characters, from Coppi to Pantani to Cipo, as well as the gravity defying climbs of the Giro, the instantly classic gravel roads of Tuscany’s Strade Bianche, and the amazing drama found in the final kilometers of La Primavera.


But this country that has given us so much is going to need us when this pandemic is all over. If you’ve been fortunate enough to visit, you get it. Even before you layer on all the cycling mystique, the history and passion, it’s the Italians who’ve perfected la dolce vita. The pursuit of pleasure and indulging in life’s simple luxuries, they’ve made an art of it. The phrase explains what makes Italians seem just so much better at life than the rest of us. They don’t sweat the small stuff; they spend time doing what they love; and they have better food and wine than us. Pretty simple.

In an effort to get back to Italy with our bikes in tow, and to taste a bit of that dolce vita, here are some amazing options to explore what is undoubtedly the best country in the world to pedal a bicycle in (sorry Belgium)—all with guides who know the country like the back of their hands. From the childhood home of Fausto Coppi to the luxurious life beside Lake Garda and beyond, here are three great ways to see Italy like an insider.

Tourissimo’s Special Edition Peloton Magazine Ride

Featured in Peloton no. 74, Beppe Salerno’s Tourissimo ride from Piedmont to Liguria was an experience I’ll never forget. From the back roads that lead to Coppi’s home to hole in the wall bakeries that offer the world’s greatest focaccia to simple seafood in Finale Ligure, the Tourissimo Peloton itinerary hits all the highlights you’d hope for. But some of its greatest gems are the things only an insider could put together. It finishes with the Cipressa and the Poggio before crossing the finish line in San Remo.

What it is: a classically northern Italian adventure that offers cycling history, challenging climbs and loads of la dolce vita with bookings available for later 2020 and summer 2021. Personal highlights included epic sunsets in Gavi and Barolo, racing Beppe up the Poggio and drinking lots of Barolo along with that killer focaccia.

To see more about the tour and booking dates:

Garda Bike Hotel

The folks at Garda Bike Hotel have long been Peloton partners. They offer an array of rides in the region of Lake Garda, but their “Lake Garda & The Epic Climbs of the Giro” ride checks pretty much all of our bucket-list boxes. The Garda Bike Hotel offers cycling-focused amenities and plenty of guided rides, but also serves as a perfect home base for the rider who’d rather go it solo.

After a few days of relaxing and riding around the shores of Lake Garda, a transfer to the hilltop town of Bormio leads you to the mythical climbs of the Giro. The guide group Stelvio eXperience takes it from here and leads daily excursions up Mortirolo, Gavia and Stelvio passes. The food and wine are all Italian hospitality staples, and the accommodations are first rate.

For more info and to book:

Italy Coast to Coast with Duvine Cycling Tours

Almost exclusively, we divide Italy into north and south. Culturally, there are a lot of real differences, but history drives a lot of this as well. Italy’s middle is its heartland in many ways, a breadbasket of profound richness. Emilia Romagna is home to some of Italy’s most important culinary exports, Parmigiano Reggiano, Prosciutto di Parma. Some of Italy’s great pastas hail from here as well. DuVine guide and tour designer Tom Coppock makes a really strong case for the route.

“No one speaks of Eastern and Western Italians, and yet, the Adriatic Coast of the Marche region where we begin the Coast-to-Coast tour has historically been part of the Eastern Mediterranean—its trade and influences far more tied to the great empires in Venice, Istanbul and the Levant, than to goings-on in France, Spain or even the rest of Italy. The Apennine mountains form a huge natural barrier to travel across the peninsula. They are overshadowed by the dramatic topography of the Alps, but in terms of national importance, the Apennines provide the literal backdrop for most of the country. They are also literally a black spot on a typical tourist map of the country, something you must cross to get from Venice to Florence, with no reason to stop. This isolation is what makes them so fascinating now; for two of days we ride through a kind of Italian time capsule—a brief flirtation with the familiar Mediterranean landscapes of olives, vineyards, and hilltowns gives way to a land of rugged village life, gnarled shepherds, and incredible mountain valleys, like the one in Castelluccio.”

You can book this trip, or explore a variety of Italian options at: