Bike Across Italy

The bicycle tour of a lifetime, cycling coast-to-coast across Italy.

This spectacular 11-day coast-to-coast bicycling tour across the fabled heartland of Italy winds through lush, sweeping countryside and charming medieval villages.  Our route from the Pesaro to the Costa d’Argento passes through Le Marche, Umbria, Lazio and Tuscany, four regions celebrated for their rich history, distinctive local cuisines and stunning panoramas. We’ll explore the awe-inspiring Grotte di Frasassi, Italy’s largest cave system, and ancient underground Etruscan settlements. Walking tours with top local guides at Urbino and other sites give you an insider experience, while our deluxe hotels ensure each day of your Italian bicycling vacation ends in pampered comfort.

Discover Italy’s most scenic and historic sites from the Adriatic to the Mediterranean Sea.

One of our most popular bike tours in Italy, this coast-to-coast cycling adventure showcases some of the country’s most important monuments. We’ll make a challenging climb to see the Monastery of Fonte Avellana, discover the medieval town of Gubbio with its outstanding amphitheater, and explore Assisi and Spello, home to the famed Roman Gates, the Temple of Minerva and the Basilica of St. Francis. Along the way we’ll have a wine tasting at a family winery, observe the medieval art of paper-making, and learn culinary secrets behind the incredible regional cooking you’ll enjoy throughout the trip. Each day highlights Italy’s best and most scenic bicycling routes, from the incredible ascent to Orvieto to the grand finale of the Tombolo di Feniglia.

“It was such a great tour, I had to do it twice!”
– Eli C., Marblehead, MA


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  • Wander through medieval hill towns, castles, and ancient abbeys
  • Learn about Etruscan and Roman civilization
  • Visit Italy’s largest cave, the Grotte di Frasassi
  • Tate distinctive wines and cuisine from four regions
  • Cycling on historical routes detailing threads of Italy’s past from east-to-west
  • Explore with local guides the quaint towns of Assisi and Urbino

Trip Details

Single Supplement
11 days / 10 nights
Total Mileage
346 miles
Daily Average
35 miles
Rolling to hilly
Start/End Locations
Pesaro/Porto Ercole
Trip Dates
05/11/19 - 05/21/19
06/06/19 - 06/16/19
07/18/19 - 07/28/19
09/05/19 - 09/15/19
09/19/19 - 09/29/19
10/03/19 - 10/13/19

Make this tour Private or for more information, call:




Welcome to the very pleasant and lively coastal town of Pesaro! We meet at noon today in the lobby of our hotel for introductions and a light lunch. Afterward, we change into our biking gear for a quick spin in the area. In the afternoon you’re free to explore Pesaro or just relax at your seafront hotel and spa. Tonight we dine in town and you’ll have your first introduction to the Italian aperitivo.


From Pesaro we ride through fields and family farm plots en route to Urbino, a thriving cultural center and college town whose fairy tale skyline is visible for miles. In the evening, the main piazza is often filled with townspeople, university students, artists, and musicians from around the world.


Today we follow part of the Roman road—Via Flaminia—to Le Marche region. The Via Flaminia was an ancient Roman road leading from Rome over the Apennine Mountains to Ariminum (Rimini). The ride ends in a spectacular gorge that is visible for miles, the Gola Rossa, which winds through wonderful mountainous farmlands, and where underground rivers have carved the immense Grotte di Frassasi.


Today we cross the Continental Divide! We ride through the ‘wild’ territories of the Appennini, crossing from Le Marche into Umbria. This morning we will visit the fascinating Grotte di Frasassi, the largest grottoes in Europe. Following our visit we ride through a beautiful river valley, then we climb up to one of the gentlest mountain passes of the Apennines and our arrival in the well-preserved medieval Gubbio comes after an incredible descent.


We descend from Gubbio to ride through the Appennini towards Monte Subasio—a day of spectacular scenery! Stop at the Roman amphitheater for a great photo-op. A couple of wake-up hills and fun downhills through the lush landscape help you to work up an appetite for lunch, then a rolling stretch with a final ascent brings you to Spello’s town center. Tonight, we’ll have a cooking lesson in Spello at Enoteca Properzio with master chef Marco Gubbiotti.

Spello Rest Day

Today there is an optional morning ride, or you can take time on your own to explore Assisi and Spello. Later in the day, a shuttle will take the group to Assisi for the walking tour with a local guide. Assisi’s sights include the Roman gates of Spello, the Church of S. Rufino, the Church of Santa Chiara, the Temple of Minerva and the Basilica of St. Francis of Assisi. After the tour we’ll visit Sportoletti, a family-run winery that is one of the best in Umbria, and maybe all of central Italy! We’ll walk through their vineyards for an informative talk before sampling their wines.


Ride through rolling farmland to medieval Bevagna, where you’ll learn about paper-making the way it was done in medieval times. Then we climb to Montefalco through olive groves and vineyards. After lunch, we drop down along a tiny road with magnificent views on both sides. After Bastardo we begin to climb again through vineyards, and sunflower and wheat fields.


Despite the long uphill, today’s ride is straightforward, short, and not too tough if you take the hill at your own pace. After descending from Todi, we climb for seven miles along an incredible shaded road. The grade is fairly gentle all the way up. We’ll have lunch in Orvieto and then have a guided visit of private underground caves.


We descend from Orvieto and then enjoy a gentle climb out of this immense volcanic basin as we head towards Bolsena. We’ll enjoy a swim in the Bolsena lake, leaving you refreshed for the climb ahead. The climb to Gradoli and beyond is tough, but a fantastic ride along a ridge is our reward. We are in three regions today: Umbria, Lazio (briefly) and finally Tuscany.

Porto Ercole

Today’s regular road and extra loop split right at the start of the ride; the main loop heads to Pitigliano and then climbs out of it to reach Manciano, whereas the longer ride heads to Saturnia, a town whose thermal springs have been in use since Etruscan and Roman times. The two routes rejoin for a rewarding downhill descent to the Mediterranean coast. The longer loop provides two more climbs to S. Martino sul Fiora and Montemerano. Tonight is our farewell dinner where we’ll continue to celebrate our coast-to-coast adventure!


Around 9 am, there will be one complimentary shuttle to Orbetello-Monte Argentario train station to catch trains to other destinations in Italy. Or, why not spend a few nights on the Costa di Argento exploring footpaths or relaxing on the beach? Buon viaggio!

What's Included

Trip Planning

  • Carbon bike rental equipped with a Garmin Edge GPS
  • Informative tour leaders throughout the program
  • Ciclismo jersey and water bottle
  • Group shuttle to train station on the last day of the tour

On The Tour

  • Van support
  • 1 wine tasting
  • Walking tours of Assisi, Urbino and visit to private underground cave in Orvieto
  • Cooking demonstration with a master chef
  • Visit to Frasassi grottoes and paper maker in Bevagna

Accomodations & Meals

  • All accommodations
  • All breakfasts
  • 2 lunches
  • 8 dinners

Meet the Guides