The Hill Towns of Umbria - Self Guided Bike Tour Italy - Van Gogh Tours

Hill Towns of Umbria

From: $1,550 USD

9 Days / 8 Nights
Type: Self-Guided
Level of Difficulty: Moderate

Imagine Yourself…

  • Discovering lovely historical villages on gorgeous, rolling landscape
  • Daydreaming in the gorgeous Cortona, setting for “Under the Tuscan Sun”
  • Cycling past cellars and tombs carved into the soft Tufo stone cliffs
  • Enjoying a meal of fresh, local fish from an island cafe
  • Gazing on one of the most important Italian cycles of painting in a breathtaking church in Assisi


Van Gogh Tours - Hill Towns of Umbria - Italy - Cycle Tour Self GuidedCycling 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 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, the patchworks of wild flowers. 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’ll enjoy visits to the impressive towns of Cortona (in Tuscany), PerugiaAssisi, and Spello with their typical medieval appearance, and exquisite hilltop villages scattered over Umbria’s green hills. You’ll discover century-old farms and churches (notably the unforgettable Basilica of San Francesco in Assisi) and sweeping views over the unspoiled Umbrian landscape. The climate is mild, the food is delicious, and the art is incredible.

Daily Itinerary

  • DAY 1 - Cortona

    You will arrive in the Terontola train station and transfer to your hotel in Cortona, still part of Tuscany and the setting for Frances Mayes’ bestseller “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 massive 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’s a wonderful city for a delightful afternoon’s sightseeing.

  • DAY 2 - Cortona – La Corte del Poggio – 28 miles (45 km)

    You will enter Umbria and pedal by Lake Trasimeno, whose shores shelter migratory birds that nest in the bamboo that surrounds the lake. All around you’ll notice lovely villages surrounded by olive groves. There will be time to take a boat to Isola Maggiore where old ladies still weave traditional lace, fisherman mend their nets, and where you can savor some delicious fresh fish at Sauro’s Fish Restaurant. Discover the Montecorognola view point over the lake, Monte del Lago and San Feliciano fisherman village. Later you’ll continue biking to our destination, a peaceful agriturismo in the lush countryside. Cooking class is possible ($115 per person, including dinner)

  • 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 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 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 (44 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 an impressive choice of this gorgeous craft in Deruta’s shops and workshops. You might like stop in Torgiano, home of Umbria’s finest wines produced by Giorgi Lungarotti. Here, you can visit their wine museum which features medieval machinery. Then it’s easy biking to Assisi. Make time in the afternoon to see this city’s artistic highlights. You can 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, you’ll get an unforgettable view of the facade with its simple, harmonious lines. Inside the lower church are beautiful frescoes by famous artists such as Lorenzetti and Giotto, and the wonderful Chapel of St. Martin is completely frescoed by Martini with scenes of the life of St. Martin. It’s 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’s 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 a well-preserved original exterior.

  • DAY 5 - Assisi – Spello - Bevagna – Assisi – 31 miles (50 km)

    Today you’ll cycle through beautiful olive groves on top of a ridge to Spello, a small, perfectly preserved town still encircled by Roman walls. It’s possible to make a stop in Bevagna on your way back to Assisi. Don’t forget to sample the famous Sagrantino wine. You could also stay in Assisi today and have more time to explore this fabulous “pink” city.

  • DAY 6 - Assisi – Montefalco - Todi – 25 miles (40 km)

    You’ll start by cycling into the heart of 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. Then cut across the Monte Martani mountains before descending towards Todi, a lovely little town perched on the top of a hill. We spent the night in an historical palace.

  • DAY 7 - Todi to Orvieto – 27 miles (44 km)

    Last but not least the road from Todi to Orvieto is winding and turning in a rugged, beautiful landscape, with nice views over the Corbara lake. This Etruscan town dominates the valleys with its brown-red cliffs of soft Tufo stone which, since Etruscan times, have been carved to make tombs and cellars. You should try to make time to visit the Duomo, considered the finest cathedral of its period in Italy with some amazing frescoes by Signorelli. You can take a final stroll up and down Orvieto’s narrow streets where you’ll find many picturesque stores for some last minute shopping.

  • DAY 8 - End of Tour

    Your tour ends today with departure after breakfast.

Dates & Prices

Green = Open | Yellow = Limited | Red = Full




Solo Traveller


$ 1550

$ 1780

$ 1930

  • Prices are per person in US Dollars – inclusive bike rental
  • Choose your own starting date
  • This tour can be guided upon request
  • What's included

    • 7 nights of double occupancy lodging in mostly 3-star, air-conditioned hotels with private facilities each night
    • Daily breakfast 
    • 21 or 24-speed hybrid bicycle
    • GPX files
    • Luggage transfers
    • All taxes and gratuities for the hotel and restaurant portions of the tour
  • Bikes

    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, and optional bike computer. It’s also possible to replace our pedals with your own “clip on” pedals. Helmets are not included, so please bring your own helmet!

    We have a few bike upgrades available on this tour. Here are the supplemental prices (per tour):

    Bianchi Via Nirone Road Bike: $40
    Wilier Carbon Frame: $96
    Electric Bike: $120

    We advise you only to rent an electric bike if you have first tried one at home. They’re heavier than regular bikes and therefore can be difficult to maneuver. In addition, you can rent children’s bikes, child seats, bike trailers, and tag-alongs.

    Van Gogh Tours - Bike Tours - Guided and Self Guided - Italy Van Gogh Tours - Bike Tours - Guided and Self Guided - Italy

  • Meals

    Included in the tour price you’ll receive daily buffet breakfast. For the buffet breakfasts there’s an assortment of cold meats and cheeses, eggs, bread, jams, cereal, yogurt, fruit, coffee, and tea. For lunches you will be in a town so you can find lunch at a restaurant on your own. Dinners will be on your own, and you can choose one of many delicious restaurant options within easy walking distance from our hotel. 

  • Not included

    • Airfare
    • Alcoholic and bar beverages
    • Cooking class ($115 per person, optional)
    • Lunches and dinners
    • Transportation other than scheduled transfers
    • Trip cancellation insurance


The accommodations listed below are examples of those usually used on the tour. Depending on availability, you may be booked in a different accommodation of equal quality.


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