Van Gogh Tours - Tuscany bike tours - Italy

Umbria the Easy Way

From: $1,390 USD

8 Days / 7 Nights
Type: Self-Guided
Level of Difficulty: Moderate

Imagine Yourself…

  • Wandering the narrow, windy streets of ancient hilltop villages
  • Enjoying local fish caught fresh on Isola Maggiore
  • Cycling to find the perfect picnic spot near the hilltop monastery St. Francis prayed
  • Learning the secrets of Italian cuisine with a cooking class
  • Sampling Umbria’s finest wine in Torgiano


Van Gogh Tours - Umbria the Easy Way - Cycle Tour - Self Guided ItalyCycling in Umbria is a wonderful opportunity to appreciate both its natural beauty and its artistic treasures. This tour includes visits to some of the major city centers and gorgeous surroundings of this very special region. Umbria is a mystic land with a mild climate, and a feeling of serenity in the air and in the soft colors of the landscape: grey stone houses, silvery-green olive trees, the magic powdery color of the earth. Biking through Umbria’s sensual rolling terrain is a gift to yourself that you’ll treasure for a lifetime! On this tour you will enjoy visits to the impressive medieval style towns of Cortona (in Tuscany), PerugiaAssisi, and Spello. You’ll visit the exquisite hilltop villages scattered over Umbria’s green hills, pass century-old farms and churches (especially the unforgettable Basilica of San Francesco in Assisi). As you bike through this unspoiled landscape you’ll enjoy sweeping views over patchworks of wild flower fields, olive groves, and woods. Umbria is also famous for deletable dishes and some incredible artworks.

Daily Itinerary

  • DAY 1 - Cortona

    You will arrive in the Terontola train station to be transferred to your hotel in Cortona, still in Tuscany, and the setting for Frances Mayes’ bestseller “Under the Tuscan Sun.” Cortona is a small, fascinating city in the province of Arezzo situated on a commanding hill overlooking Lake Trasimeno. Its immense walls, still in great part preserved, are said to be 3,000 years old. Cortona was one of the twelve cities of Etruria and in its vicinity many ruins and Etruscan tombs can be seen. It’s a wonderful city for a delightful afternoon sightseeing stroll.

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

    You’ll enter Umbria and pedal by Lake Trasimeno, whose shores shelter migratory birds that nest in the bamboo around 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 the traditional lace, fisherman mend their nets, and where you 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 you’ll continue biking to your destination, a peaceful agriturismo in the lush countryside. 

  • DAY 3 - La Corte del Poggio loop – 22 or 31 miles (35 or 50 km)

    Today you’ll have many options for what to do with your time. You could relax for the whole day in your small and charming B&B, or you could take a short bike loop to Panicale. In the afternoon you can take a cooking class ($115 per person, which includes the dinner and wine at night). If you’re feeling more energetic, you can explore a longer loop to visit Deruta, famous for its intricately painted ceramics.

  • DAY 4 - La Corte del Poggio – Perugia - 22 miles (35 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 in the middle ages was an important walled city 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 5 - Perugia to Assisi – 22 miles (35 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 be able to see a wide variety of gorgeous examples of the craft in Deruta’s shops and workshops. Then you might stop 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 it’s easy biking to Assisi. In the afternoon there will be time to see the city’s artistic highlights. You could 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 6 - Free day in Assisi

    Assisi deserves an entire day to enjoy and your inn has a lovely swimming pool to relax by. However, if you want some exercise today you can take a half-day hike to Eremo delle Carceri, a small monastery, located on the spot where St. Francis was fond of praying in solitude. At the top of the trail, 500 meters from the Eremo, is a nice picnic spot with tables and benches.

  • DAY 7 - Assisi – Spello – 31 miles (50 km)

    Today we’ll cycle through beautiful olive groves on top of a ridge to the small town of Spello, a perfectly preserved medieval town still encircled by Roman walls.

  • DAY 8 - Tour Ends

    Your tour ends today, with departure after breakfast.

Dates & Prices

Green = Open | Yellow = Limited | Red = Full




Solo Traveller


$ 1390

$ 1590

$ 1750

  • 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
    • Cooking class ($115 per person, optional)
    • Alcoholic and bar beverages
    • Helmet
    • 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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