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.

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Tour Style: Classic Hold-A-Space/Questions Request Custom Date Download Itinerary Tour Map
  • Trip At-A-Glance
  • Tour Summary
  • Daily Itinerary
  • Travel Information
  • Map
  • Reviews
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Trip At-A-Glance

Trip At-A-Glance

  • Length / 7 Days
  • Total Distance / 186 km (114 miles)
  • Avg. Distance / 37 km (23 miles) per riding day
  • Tour Level & Tour Style / 1.5 Classic
  • Countries / Italy
  • Begin/End / Perugia / Spoleto
  • Price / From USD$3400
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Tour Summary

Tour Summary

  • 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; and the usual (see below).

    Learn more about what is included and what to expect on your Classic tour at the Classic Tour Style page.
  • Arrive / Depart
    Rome (FCO) or Florence (FLR)
  • Overall Tour Level
    1.5 difficulty level 1.5

    There are short (and possibly steep, more than 6%) climbs into towns.

  • Daily Ride Summary




    Day Level


    Test ride
    39km / 430m
    difficulty level 2.0
    34km / 234m
    Rolling hills
    difficulty level 1.5
    42km / 241m
    Mostly flat
    difficulty level 1.0
    25km / 160m
    Mostly flat
    difficulty level 1.0
    Today's ride is an optional loop ride
    45km / 539m
    difficulty level 2.5
    Last day

Terrain Legend

Gentle Gentle

Rolling hills Rolling hills

Hilly Hilly

Very hilly Very hilly

Mountainous Mountainous

Daily Itinerary
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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: 39km (24mi)
  • Gain: 430m (1410ft)
  • Terrain: Hilly
  • Day Level: difficulty level 2.0
  • 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.

  • Distance: 42km (26mi)
  • Gain: 241m (790ft)
  • Terrain: Mostly flat
  • Day Level: difficulty level 1.0
  • Meals: Breakfast, Dinner
  • Lodging:

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: 45km (28mi)
  • Gain: 539m (1768ft)
  • Terrain: Hilly
  • Day Level: difficulty level 2.5
  • 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
Travel Information

Travel Information

Day 1: Arrival Information

Arrive in Perugia

Meeting time 2 p.m. - on Day 1, meet your fellow cyclists and Tour Leaders at the Day 1 Hotel specified on the itinerary.

The below information will help you plan your arrival. For more tips or other routes, you might like Rome2Rio. The fare and timing information listed below is approximate.

The airports closest to the tour start are Rome’s Fiumicino Airport (FCO) and Florence’s Amerigo Vespucci Airport (FLR)

If you arrive at FLR and continue to Perugia

  1. Vola in Bus Airport Shuttle from the Airport to Florence S. M. Novella train station; runs every 30 min from 5:30 a.m. to 8:30 p.m. Purchase tickets: inside the airport, or on board (20 min/EUR 6) or taxi (15-20 min/fixed rates (plus luggage EUR 1/piece): Weekdays EUR 20; Weekend EUR 20; Night EUR 23)
  2. Train From Firenze S. M. Novella to Perugia (2 hours 10 min/fares vary)

If you arrive at FCO and continue to Perugia

  1. Leonardo Express train to Roma Termini station (32 min/EUR 14) or taxi (Authorized taxis are white and have license id number on the doors, back and inside the taxi. Taxi sign is on the roof.) (1 hr/EUR 48)
  2. Train from Roma Termini to Perugia (2.5-3.5 hours/fares vary)

From Perugia train station to Day 1 Hotel

  • Mini metro from the Perugia train station to Day 1 Hotel; station Piazza Italia (15 min/EUR 1.50; departs every 2 min)
  • or Taxi from the Perugia train station to Day 1 Hotel (15-20 min/EUR 15-20) 

Look up Italian train schedules at or Questions? See our information on taking trains in Europe here or ask us.


As you are planning, remember that the hotels listed in our itineraries are our primary hotels and are - in rare cases - subject to change. Before you make arrangements, check with us if your tour departure is guaranteed. If your tour departure is out further than 6 months, please also check with us as there might be slight changes to the itinerary.

Day 7: Departure Information


Your trip ends on the final day after breakfast.

The below information will help you plan your departure. For more tips or other routes, you might like Rome2Rio.

We recommend flying out of Rome’s Fiumicino Airport (FCO) or Florence’s Amerigo Vespucci Airport

Flying out of FCO

  1. Taxi from the Ending Hotel to the train station (10 min/EUR 12-15)
  2. Train from Spoleto to Roma Termini (not all are direct) (1 hr 20-1 hr 50/fares vary
  3. Leonardo Express or taxi from Roma Termini to the airport (see arrival instructions). 

Flying out of FLR

  1. Taxi from the ending hotel to the Spoleto train station (see above)
  2. Train from Spoleto to Firenze S. M Novella (not all are direct) (3.5-4.5 hours, fares vary)
  3. Vola in Bus shuttle or taxi to the Florence Airport(see arrival instructions)

Look up Italian train schedules at or Questions? See our information on taking trains in Europe here or ask us.

Pre-Trip Planning Checklist

To Do Today!

  • Read through your Reservation Confirmation Email, it has important information to help you plan your trip!
  • Check the date on your passport. The expiration date should extend three months past your date of return to your home country
  • Complete the Customer Information Form online at
  • Apply for trip cancellation/interruption insurance within 15 days of booking. Find details at this page
  • Download the bicycle training program found on the Training Program Blog Page at

3–6 Months Prior to Departure

  • Reserve your flights after you know you have a confirmed tour departure. Please check with our office if you do not know if your trip is confirmed. As you make your plans refer to the Getting To and Away sent to you in your booking confirmation email it provides meeting times and the starting and ending hotels and shuttle information when applicable.
  • Book your pre and post-tour hotel nights. Please refer to the Getting To and Away sheet you received in your Reservation Confirmation Email.
  • 12 weeks before your tour begin your training program found on this page.
  • Final payment is due 90 days prior to the tour start. Please refer to your Deposit Payment Invoice and the Final Payment Reminder e-mail you have received for detailed instructions.

6 Weeks–2 Weeks Prior to Departure

Day of Your Flight

Get as much sleep on the plane as you can. Pack your Getting To and Away information and one day of cycling gear in your carry-on. See you soon!

What to Expect on Tour

Classic Tour Style

Learn more about what is included and what to expect on your Classic tour at the Classic page.





  • Sailing the boat, every afternoon relaxing on the boat after biking and swimming, lovely dinners, hearty breakfasts, bee keepers, traditional dinner out, rides through the islands (up and down!), guides, fellow passengers, crew on the boat-- really it was ALL great.

    Cheryl A., Colchester, VT - June 2021
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