Hill Towns of Umbria: Self-Guided

Cycling in Umbria is a wonderful opportunity to appreciate both its natural beauty and its artistic treasures and this tour includes visits to some of the major city centers and gorgeous surroundings of this very special region. Umbria is a mystic land and a great serenity can be felt in the air, in the soft colors of the landscape: the grey stone houses, the silvery green olive trees, the soft powdery color of the earth. Biking through Umbria’s sensual rolling terrain with all its sweet power and magic is a gift to yourself you’ll treasure for a lifetime! On this tour you will enjoy visits to the impressive towns of Cortona (in Tuscany) Perugia, Assisi, Spello with their typical medieval appearance; exquisite hilltop villages scattered over Umbria’s green hills; century-old farms and churches, especially the unforgettable Basilica of San Francesco in Assisi; sweeping views over the unspoiled Umbrian landscape, a patchwork of wild flower fields, olive groves and woods; mild climate and delectable Umbrian food; incredible art.

Daily Itinerary

Day 1: Cortona
Arrive in the Terontola train station and transfer to your hotel in Cortona, still Tuscany and the setting for Francis Mayes’ best seller “Under the Tuscan Sun”. Cortona is a small but fascinating city in the province of Arezzo situated on a commanding hill overlooking Lake Trasimeno. Its cyclopean walls, still in great part preserved, are said to be 3000 years old. It was one of the twelve cities of Etruria and in its vicinity many ruins and Etruscan tombs may be seen. It is a wonderful city for a delightful afternoon sightseeing stroll.

Day 2: Cortona – La Corte del Poggio – 31 miles (50 km)
Enter Umbria and pedal by Lake Trasimeno, whose shores shelter migratory birds that nest in the bamboo that surrounds the lake. All around you notice lovely villages surrounded by olive groves. There is time to take a boat to Isola Maggiore where old ladies still weave the traditional lace, fisherman mend their nets and where we can savor some delicious fresh fish at Sauro’s Fish Restaurant. You can also climb to the highest point on the island, crowned by the 14th century Church of San Michele. Later we’ll continue biking to our destination, a peaceful agriturismo in the lush country side. A cooking class tonight is possible.

Day 3: La Corte del Poggio to Perugia – 20 miles (32 km)
Today you’ll bike through lovely, quiet countryside up to Perugia. Perugia is the capital city of Umbria and is the center of major cultural institutions. It was an Etruscan stronghold before it became a Roman colony and was an important walled city in the middle ages, built high up on the hilltop to repel invaders. The streets are precariously narrow. The splendid 14th-century Palazzo dei Priori sits at its highest point and houses the National Gallery of Umbria with its many artistic treasures. The nearby Corso Vannucci is ideal for more strolling and people watching. Don’t forget to try Perugia’s world renowned chocolates! Your comfortable hotel is conveniently located in Perugia’s historic center.

Day 4: Perugia to Assisi – 26 miles (42 km)
As you cycle through the heart of Umbria you’ll pass by Deruta. Deruta is famous for beautiful ceramics that have been produced here for centuries. If you decide to visit you’ll have the largest choice of gorgeous examples of the craft in Deruta’s shops and workshops. Then you might stop shortly in Torgiano, home of Umbria’s finest wines, produced by Giorgi Lungarotti. Here you can visit their wine museum, which also includes medieval machinery. Then its easy biking to Assisi. In the afternoon there is time to see the city’s artistic highlights. Visit the magnificent Basilica of San Francesco, painstakingly restored after the recent earthquake. The basilica complex is composed of two churches built one above the other, the lower one dating from 1228 – 1230 and the upper one from 1230 – 1253. Entering the lower part of Piazza San Francesco, the vision of the façade of the church with its simple, harmonious lines is unforgettable. Inside the lower church are beautiful frescoes by famous artists such as Lorenzetti and Giotto and the wonderful Chapel of St. Martin, completely frescoed by Martini with scenes of the life of St. Martin. It is one of the most beautiful works of the painter and a masterpiece of Gothic art. You can visit the Crypt and the Chapel of the Relics where St. Francis’ belongings are kept. It is the upper church however where you’ll find Giotto’s frescoes illustrating the life of St. Francis and one of the most important cycles of paintings in the history of Italian art. In the Piazza del Commune you’ll see a 14th century pulpit and the Roman Temple of Minerva, with its well-preserved original exterior.

Day 5: Assisi – Spello – Cannara – Assisi – 31 miles (50 km)
Today you’ll cycle through beautiful olive groves on top of a ridge to the small town of Spello, a perfectly preserved town still encircled by Roman walls. You can also make a srop in Bevagna on your way back to Assisi. Don’t forget to sample the famous Sagrantino wine. You also might decide to stay in Assisi today and have more time to explore this fabulous “pink” city.

Day 6: Assisi – Bevagna – Todi – 25 miles (40 km)
You start with an easy ride from Assisi to Bevagna which is known for its medieval market during the month of June. Enjoy a ‘cappuccino’ on the unspoiled medieval market square before you cycle into the heart of the wine country to Montefalco, nicknamed “the balcony of Umbria” because of its spectacular views. Montefalco is also famous for its outstanding wine. Please take time here to admire the dazzling 15th century Renaissance frescoes painted by Benozzo Gozzoli in the huge church of San Francesco. You will then cut across the Monte Martani mountains before descending towards the hilltop town of Todi built by the Etruscans. Visit the impressive Piazza del Popolo, one of the most striking squares in Italy, designed in the Middle Ages so that the square could be defended by closing the narrow exits at each corner. Be sure to see the Palazzo as well, one of the oldest surviving public buildings in Italy. You will spend the night in a historical palace.

Day 7: Todi – transfer to Orvieto – 27 miles (44 km)
Now that you have grown familiar with Umbrian hills you will get a bit more of them; the last day riding along the twisting road above the Corbara lake to Orvieto. This Etruscan town dominates the valleys with its brown-red cliffs of soft Tufo stone which since Etruscan times has been carved to make tombs and cellars. Make sure to leave some time to visit the Duomo, considered the finest cathedral of its period in Italy with some amazing frescoes by Signorelli. Walk up and down Orvieto’s narrow streets where you’ll find many picturesque stores for some last minute shopping.

Day 8: Departure after breakfast.

Getting There

You will be met by a representative in the train station in Cortona. There is a direct train from Rome or Florence to the Terontola Train Station near Cortona. Please let us know the arrival time of your train at least one week before your trip! For train schedules visit the website of the Italian Railways, www.trenitalia.com or www.raileurope.com.


Daily breakfast and two dinners are included

Prices and Dates

Check out “Italy Tours” in our SELF-GUIDED Tour Calendar

Tour Length

8 days/7 nights

      – 7 nights of double occupancy lodging in mostly 3-star, air- conditioned, hotels with private facilities each night
      – Daily breakfast and 2 dinners
      – 21 or 24-speed hybrid bicycle
      – Daily route directions for individual departures in the morning
      – Luggage transfers
    – All taxes and gratuities for the hotel and restaurant portions of the tour

21 or 24-speed hybrid bikes are included in the price of the tour. Bicycles come equipped with: grip shifters, handlebar bag, bell, cage and water bottle, optional bike computer. It is also possible to replace our pedals with your own “clip on” pedals. Helmets are not included; please bring your own helmet!

Level of Difficulty

The daily cycling is on hilly terrain. Level of difficulty is moderate to challenging. Good cycling experience is recommended to deal with up and down hills and periodically difficult Italian traffic.


– Airfare
– Alcoholic and bar beverages
– Lunches and four dinners
– Transportation other than scheduled transfers


Average daytime temperatures in Italy in April and May are 55-75. June, July, and August range from 65-85, and September and October from 60-75. It rains about 7 days per month, with more rain in September and October and less rain in July and August.

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