Cycling Umbria's Medieval Towns

Cycling Umbria's Medieval Towns

Located just east of Tuscany, Umbria is the birthplace of St. Francis and home to some of Italy's best preserved medieval towns. Join us as we pedal from Perugia to Spoleto through vineyards and olive groves and over gently rolling hills to monasteries, castles, and stone villages virtually unchanged since the Middle Ages. Along the way, you'll enjoy a two-night stay in Foligno and visits to important cities like Perugia, Assisi, Spello and Spoleto. These historic cities, built by Umbrians or Romans and then rebuilt or refurbished over the centuries, are a sight to see as are the small villages we pass through or stay in along the way. Add a visit to central Italy's best known ceramics' town, Deruta and a taste of Sagrantino di Montefalco and other Umbrian wines, and this tour is a classic Italian bike ride.

Tour Dates & Prices

Private Room Fee
Sep 2-8, 2018
Guaranteed to Go!
May 5-11, 2019
 Book by November 15 and save $200!
Sep 1-7, 2019
 Book by November 15 and save $200!

* We are happy to match solo travelers who would like to share a room with someone of the same gender. If no match exists, due to hotel pricing, we will charge 50% of the private room charge. This charge will be collected at the time of the final payment. If a roommate assignment is available it will be refunded at the conclusion of the tour.

Trip At-A-Glance

  • Length / 7 Days
  • Avg. Distance / 37 km (23 miles) per riding day
  • Difficulty / 101
  • Countries / Italy
  • Price / From USD$3400
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  • Tour Summary
  • Daily Itinerary
  • Map
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Tour Summary

Daily Ride Summary


1 No cycling today.
2 24 mi / 39 km
3 23 mi / 37 km
4 26 mi / 42 km
5 16 mi / 26 km
6 28 mi / 45 km
7 No cycling today.
  • Highlights
    Guided tour in Assisi, 2 nights in Foligno, Ceramics in Deruta, Wine Museum, Spoleto and its 5th Century BC walls, Spello and frescoes of Perugino and Pinturecchio, Olive oil tasting, 2 wine tastings
  • Includes
    6 nights' accommodation; 4 dinners with wine, all breakfasts; 2 wine and one olive oil tastings; guided visits in Assisi and Foligno

    The Usual (Included with every ExperiencePlus! tour)

    • Superb tour leaders who are fun, bilingual and avid cyclists.
    • Help with flights, trains and pre/post tour hotels.
    • Comfortable lodging in 3-4 star hotels. 
    • All breakfasts and at least half of your dinners.
    • Use of a high quality 27-30 speed bike.
    • Full van support to carry luggage – and tired cyclists, too! 
    • Special events like wine tastings, cultural visits and chocolatiers.
    • All tips and gratuities at tour hotels and group meals.
    • Unique routes, marked with our famous chalk dust arrows.
    • Daily mileage options.
    • Detailed route map and free use of our traveling resource library.

    What's not included:

    • Transportation to and from the bicycling tour including airfare, or train travel
    • Helmets - we ask that you bring your own to ensure the best fit
    • Meals not listed in the itinerary
    • Tour Leader gratuity

    See the complete list of what's included with every ExperiencePlus! Tour.

  • Countries
  • Begin/End
    Perugia / Spoleto
  • Arrive / Depart
    Rome (FCO) or Florence (FLR)
  • Total Distance
    186 km (114 miles)
  • Avg. Distance
    37 km (23 miles) per riding day
  • Difficulty
    Mostly flatter terrain, but there will be short (and possibly steep, more than 6%) climbs into towns.
  • Terms
Daily Itinerary

DAY 1: Arrive in Perugia

Highlights: Welcome to Perugia and Italy!

Today we'll meet in the well-preserved medieval town of Perugia, the ancient and modern capital of Umbria. Make sure to visit the piazza Matteoti and its Palazzo dei Capitani as the mixture of Medieval and Renaissance architecture makes this square and surrounding buildings a unique architectural blend. Present-day Perugia is famous for Peruginan chocolate, its vibrant old town, and its large Italian language school which serves thousands of foreigners annually. We'll fit bikes this afternoon before enjoying dinner together.

DAY 2: Ride to Assisi

Highlights: Assisi the city of Saint Francis

Short ride today leaving Perugia and heading to Assisi, one of the many lures of Umbria. Our route stops below Assisi in St. Franci's first church which he saved from ruin in the 1200's by selling his possessions and renouncing his family and patrimony, he then lived there as a pauper repairing the chapel. You'll explore a bizarre chapel within a church that was his original Porziuncola and was later engulfed within a massive church (Santa Maria degli Angeli). This was erected in the 16th century to commemorate the beginning of the Franciscan Order. This afternoon we'll explore some of Assisi's highlights and hidden secrets with a local expert.

  • Distance: 24 mi / 39 km
  • Meals: Breakfast, Dinner
  • Lodging:

DAY 3: Assisi to Torgiano

Highlights: Torgiano, Ceramics in Deruta, wine museum

Your ride today first takes you to Deruta where you can enjoy scores of ceramic studios. Deruta is famous throughout Italy for classic Italian ceramics (these patterns are frequently used in a number of Italian restaurants in the U.S.). Enjoy your exploration of Deruta before returning to Torgiano for a dip in the hotel pool. Later this afternoon we'll partake in a wine tasting together at the Lungarotti winery in the center of Torgiano.

DAY 4: Ride from Torgiano to Foligno

Highlights: Roman Spello and olive oil tasting, dinner together in Foligno

We leave Torgiano this morning bound for Spello, a medieval, walled town known for its Roman ruins and its two dozen small churches which are home to important works from the likes of Pinturicchio, a Renaissance super star. Enjoy a visit of the paintings and a coffee in the main square before continuing on to Foligno, our destination for tonight. Along the way we'll stop to visit an olive oil mill where the ripe green Umbrian olives are transformed into liquid gold.

DAY 5: Ride to Bevagna and special winery visit and tasting

Highlights: Guided walk in Foligno, bike ride to medieval Bevagna, wine tasting

We???ll start this morning with a special, guided walk of town to visit Palazzo Trinci and its marvels. A short bicycle ride takes you to the small stone town of Bevagna with its beautiful medieval Piazza Silvestri and the core of town with Palazzo dei Consoli in the same square dating back to the XIII century. From Bevagna, you???ll continue pedaling a short distance to reach the famous wine cellar designed by Arnaldo Pomodoro as the first sculpture in the world in which one can live and work. After a nearby wine tasting of the famous Sagrantino wine as well as a cellar visit, we???ll shuttle back to Foligno.

DAY 6: Ride to Montefalco and Spoleto

Highlights: Vineyards, Spoleto

Our last day we pedal to Montefalco, a hill town now famous for the wine we sampled last night. Riding through Sagrantino vineyards to the top of the small hill and back down, we'll then join a delightful bike path to pedal to the well-preserved medieval town of Spoleto, famous throughout the world for the Festival dei due Mondi, a three-week dance, music and opera festival. Wander and discover the hidden corners of this fabulous town that dates back to Roman times. Don't miss the Cathedral and a walk to the fortress Fortezza Albornoz on top of Colle Sant' Elia. We???ll enjoy a final dinner together.

  • Distance: 28 mi / 45 km
  • Meals: Breakfast, Dinner
  • Lodging:

DAY 7: Spoleto

Highlights: Spoleto

After breakfast, we'll say goodbye. Rome is just over an hour away by train so take time to extend your exploration of Italy.

  • Meals: Breakfast




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