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’s knowledge of all you 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 papermaking, 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


  • 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, Urbino and Orvieto
  • Learn more about Slow Food with lunch in le Marche region

Trip Details

Single Supplement
11 days / 10 nights
Total Mileage
350 miles
Daily Average
35 miles
Rolling to Hilly
Start/End Locations
Pesaro/Porto Ercole
Trip Dates
08/24/17 - 09/03/17
09/07/17 - 09/17/17
09/21/17 - 10/01/17
10/05/17 - 10/15/17
05/11/18 - 05/21/18
05/24/18 - 06/03/18
06/07/18 - 06/17/18
06/21/18 - 07/01/18
07/19/18 - 07/29/18
08/23/18 - 09/02/18
09/06/18 - 09/16/18
09/20/18 - 09/30/18
10/04/18 - 10/14/18

Make this tour Private or for more information, call:




Welcome to the very pleasant and lively coastal town of Pesaro! We meet in the lobby of our hotel at 12 pm for introductions, a light lunch, bike fitting and a quick spin in the area to get our body warmed up for the days ahead. After the ride, opt to take a walk in town and visit the the many sights or enjoy an aperitif before a well deserved dinner featuring the local fresh catch of the day.


From Pesaro we ride into fields and family farm plots en route to Urbino, a thriving cultural center and college town whose fairytale skyline is visible for miles. Today you'll feel as if you've been transported back in time to the Middle Ages, discovering more of Urbino on a walking tour with a local guide, surrounded by historical buildings and a unique atmosphere.


Today we set out for the roughly hewn Le Marche region. Lunch is at a Slow Food establishment in Cagli featuring local fresh food. The ride ends in Gola Rossa, a spectacular gorge that is visible for miles and winds through a wonderful mountain farmland where underground rivers have carved the immense Grotte di Frassasi. The extra loop to the monastery of Fonte Avellana offers a spectacular, challenging climb for those interested. Tonight, stay far away from civilization, at a place with a great spa - perfect for relaxing after a satisfying ride.


This morning we will visit the very fascinating Grotte di Frasassi, the largest grottoes in Europe. Following our visit we'll bike through a beautiful river valley, then climb up one of the gentlest passes of the Apennines to arrive, after an incredible descent, into the well-preserved medieval town of Gubbio.


We begin our bike ride today with a descent from Gubbio as we cycle along the hillside. Stop at the Roman Amphitheater for a great photo op! Then it's a couple of wake-up hills and fun downhills through the lush landscape to work up an appetite for lunch, followed by a rolling stretch with a final ascent to Spello’s town center. *On our May 11 departure, this day is spent in Gubbio to witness the Festa Dei Ceri, an annual event considered to be one of the most unique in Italy!*

Spello Rest Day

Today, there is an optional morning ride, or you can spend time on your own exploring Assisi and Spello. A shuttle will take the group to Assisi for our walking tour with a local guide. Assisi's famous 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 in Assisi. After the tour, learn about wine making at a local family-run winery and then partake in a wine tasting.


Ride through rolling farmland to medieval Bevagna where you will 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. From Bastardo, we begin to climb again through vineyards, sunflower and wheat fields. The approach to Todi is spectacular - a memorable descent toward this medieval hill town's soaring steeple.


Despite the long uphill, today's ride is straight forward, short, and not too tough if you take the hill at your own pace. After descending from Todi we climb for 7 miles along an incredible ascent. We will have lunch in Orvieto and then tour the underground Etruscan ruins. Make sure to look out in the distance to check out the awesome view.


We descend from Orvieto and then enjoy a gentle climb out of this immense volcanic basin as we head towards the charming village of Civita and then onto Bolsena. Lunch followed by a swim at Bolsena will leave you refreshed for the climb ahead. The climb to Gradoli and beyond is tough, but a fantastic bike ride along a ridge is our reward. We are in three regions today: Umbria, briefly Lazio, 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, Italy’s oldest city. The two rejoin for a rewarding downhill to the Mediterranean coast. The longer loop provides two more climbs to S. Martino sul Fiora and Montemerano. The last stretch of the grand finale is through the “Tombolo di Feniglia”, a shady forest that connects the Argentario peninsula to mainland Italy.


Around 9 am we will shuttle you 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 Garmin Edge Touring GPS
  • Informative tour leaders throughout the program
  • Ciclismo jersey and water bottle
  • Group shuttle to train station on last day of tour

On The Tour

  • Van support
  • 1 wine tasting
  • Walking tours of Assisi, Urbino and underground Orvieto
  • Cooking demonstration
  • Visit to Frasassi grottoes and paper maker in Bevagna

Accomodations & Meals

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

Meet the Guides