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
May 5-11, 2019
Sep 1-7, 2019

* 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.

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Trip At-A-Glance

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

    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.

  • Arrive / Depart
    Rome (FCO) or Florence (FLR)
  • Overall Tour Level
  • 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

    Tour Level Note: Mostly flatter terrain, but there will be short (and possibly steep, more than 6%) climbs into towns.

    **We use Ride With GPS ( to calculate elevation and mileage information. Due to variance between mapping technologies, totals may differ slightly across devices and applications

Terrain Legend

Mostly flat Mostly flat

Rolling hills Rolling

Hilly Hilly

Very hilly Very hilly

Mountainous Mountainous

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: 39 km (24 mi)
  • Gain: 430 m (1410 ft)
  • Terrain: Hilly
  • Day Level: Day 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: 42 km (26 mi)
  • Gain: 241 m (790 ft)
  • Terrain: Mostly flat
  • Day Level: Day 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.

  • Distance: 25 km (16 mi)
  • Gain: 160 m (525 ft)
  • Terrain: Mostly flat
  • Day Level: Day Level 1.0
  • Meals: Breakfast
  • Lodging:

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: 45 km (28 mi)
  • Gain: 539 m (1768 ft)
  • Terrain: Hilly
  • Day Level: Day 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

Lodging: Hotel La Rosetta

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.

What's Included

For a full list of what's included before, during and after your bike tour, visit our What's Included page.

Pre-Trip Planning Checklist

To do right after you booked!

6 to 3 Months Prior to Tour Start Date

  • Check the online itinerary of your trip and review the arrival and departure information under the "Travel Information" tab to see meeting place and time, if a reservation on a complimentary ExperiencePlus! Shuttle (if applicable) is required, and other important information to help you plan your arrival and 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.
  • Book your pre and post-tour hotel nights.
  • 12 weeks before your tour begin your training program:
  • 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 to 2 Weeks Prior to Tour Start Date

Day of Your Flight

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

What to Expect on Tour


Your bike will be equipped with: a men's or women's saddle, a quick release style seat post adjustment, rear rack and expandable pack, pump, patch kit, spare tube, cable lock, cyclometer, rear lights, a water bottle cage (or two) and a water bottle (or two) and in some cases a bell. If you would like to bring your own pedals and shoes we recommend doing so—your tour leaders will install them during the bike fitting. We have flat pedals with or without cages available. For safety and hygiene reasons you are responsible for bringing a helmet.


Each day you'll receive a daysheet with information on the day's activities, meals and ride. These also include Tour Leader phone numbers, hotel information and interesting historical and cultural information about sites that you may want to stop and see along the route. Your Tour Leaders will also post daily announcements in the hotel lobby with information about sightseeing in town or restaurant recommendations for dinners on your own as well as important information about breakfast, luggage down and "arrows down" time.

Navigating on Tour

Each day we will provide you with a route map with the day's ride highlighted route. Of course, we also mark the route every day with our signature chalk dust arrows. Our arrows make navigating very easy—you may never need to look at the map! The arrows also allow you to ride at your own pace. There is no need to "keep up" with the group—this is your ride!

But what if it rains? What happens to the arrows? In a light rain, the arrows actually "set up" and become more permanent. In a heavy rain, they do wash away. If that happens, we'll re-group to cycle together for those who want to continue cycling while those who prefer to stay dry can shuttle.

For the tech-loving riders out there we offer the opportunity to download GPS tracks of most tour routes to your personal GPS device using Tracks are available upon request approximately three to four weeks prior to the departure.

Van Support

The van carries luggage and supports cyclists. It also has water, fruit and snacks. Though the van has snacks, we encourage you to stop and enjoy markets and find your own favorite local specialty.


We have carefully chosen all of our accommodations for their charm and location. They are typically small, family run hotels that offer you a glimpse into the local culture.

We prefer hotels near interesting sites in the center of town located along the best cycling route in the area. Because many of the hotels are small not all of the rooms will be exactly the same. We keep this in mind and do our best to distribute rooms fairly by the end of the tour. Our itinerary lists our primary hotels. On rare occasions, listed hotels are subject to change.

Meals and Restaurants

Breakfasts: we work hard to arrange complete breakfasts but some hotels still serve continental style breakfasts; cycling is energy intensive so we do recommend you plan for a morning or mid-morning snack on the road at a local café or market.

Water is OK in almost all hotels and in country fountains; if there is a problem, we will advise you.

We'll recommend lunch locations en route and most itineraries include a few group picnics. We limit the number of picnics so you don't feel pressured to be at a certain place in the middle of your ride.

Dinners together are often pre-planned and pre-ordered. We'll ask you prior to your trip if you have special dietary requirements. Preplanned meals allow us to provide a variety of regional specialties and facilitate efficient service. Water, wine and beer are included.

Tipping Your Tour Leader Team

If you feel your tour leader team has demonstrated great expertise and service, common practice within the travel industry is to tip. Tipping is voluntary and greatly appreciated, and gratuity amounts vary widely. Should you decide to leave a tip, as a guideline, we suggest 5% of the tour cost per traveler – this for the entire tour leader team, not each Tour Leader. If you’d like to show your gratitude for your Tour Leaders’ excellent service you can give the tip to any member of the tour leader team, as they share it evenly. In order to avoid social tensions, we encourage you to tip as individuals and not as a group. If you feel your Tour Leaders did not quite meet your expectations, then we would like to know about it. You will also have the opportunity to leave your comments in our evaluation survey which we email to you after your trip.


By reserving space on tour, you agree that ExperiencePlus! Bicycle Tours may use, re-use and reproduce any images, photos or videos that you send to us, or that are taken by our guides and/or other travelers of you individually or in a group, in any medium, including but not limited to print, electronic media, or Internet, free of charge and without your right to inspection, for promoting and publicizing our travel products and services worldwide. If you do not want us to use any images of you that are taken by us or other participants during the tour, you must inform us or your tour leader in writing at the start of the tour.





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