Van Gogh Tours - Tuscany - Italy

The Best of Umbria and Tuscany

From: $1,540 USD

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

Imagine Yourself…

  • Biking through softly colored, undulating landscapes
  • Sampling the highest quality, DOCG rated wines of Bevana
  • Gazing over a gorgeous lake from your hotel behind the 3,000 year old walls of Cortona
  • Wandering the lovely cloister of the picturesque Monte Oliveto Maggorio
  • Enjoying the famous cuisines of the Tuscan tradition


Van Gogh Tours - The Best of Umbria and Tuscany - Cycle Tour - Bike Tour - ItalyCycling in Umbria and Tuscany is a wonderful opportunity to appreciate the best of both areas and their natural beauty and artistic treasures. This tour includes visits to some of the major city centers and the gorgeous environment of these gorgeous regions. A great serenity can be felt in the air, in the soft colors of the landscape: grey stone houses, silvery green olive trees, the soft powdery color of the earth. You’ll bike through sensual, rolling terrain, a magical gift to yourself that you’ll treasure for a lifetime! This tour includes visits to the impressive towns of AssisiSpelloCortonaMontepulcianoBuonconventoPienza, and Siena with their typical medieval appearance. You’ll discover exquisite hilltop villages scattered over Tuscany’s and Umbria’s green hills, and century-old farms and churches – especially the unforgettable Basilica of San Francesco in Assisi. The hills will give you sweeping views over the unspoiled landscape, a patchwork of wild flower fields, olive groves, and vineyards. The barren, geometrical cypress-crested mounds of the Italian Crete Senesi hills are distinctive and beautiful. The food of this region is particularly delicious, and there are fine wines to be tasted in Brunello.

Daily Itinerary

  • Day 1: Arrival in Assisi.

    You will be met at the train station and driven to your accommodation for the night. In the afternoon there will be time to see some of 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. 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 saint’s life. It’s one of the most beautiful works of the painter and a masterpiece of Gothic art. 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. Unforgettable masterpieces! In the Piazza del Commune you’ll see a 14th century pulpit and the Roman Temple of Minerva with a well-preserved exterior.

  • Day 2:  Assisi – Spello - Cannara – Assisi – 31 miles (50 km)

    Today you’ll cycle through beautiful olive groves along a ridge with delightful views to the small town of Spello, a perfectly preserved town still encircled by Roman walls on the Subasio slopes. Later you’ll ride through olive groves with no major uphills except for the final climb back to Assisi. On the return trip you can visit Bevagna, going through the most famous wine area of Umbria, the Montefalco Sagrantino “Denominazione di Origine Controllata e Garantita” (DOCG). Alternatively, you could decide to stay in Assisi today and have more time to explore the fabulous “pink city.”

  • Day 3: Assisi – Solomeo – El Poggio delle Corti -  31 miles (50 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 and you’ll have a difficult time choosing from the gorgeous examples of the craft in Deruta’s shops and workshops. Then you’ll stop briefly in Torgiano, home of Umbria’s finest wines produced by Giorgi Lungarotti. Here you can visit their wine museum, which also includes medieval machinery. You’ll pedal through soft hills and scenic little villages until you reach “Il Poggiolo” in Poggio delle Corti: a charming, old fashioned villa. The route today is continuously up and down so you’ll be happy to find your relaxing and peaceful hotel. You can choose to take a cooking class in the afternoon ($115 per person, which includes the dinner and wine at night).

  • Day 4: Solomeo – Lake Trasimeno – Cortona – 31 miles (50 km)

    Today you’ll glide 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. You can also climb to the highest point on the island, crowned by the 14th century Church of San Michele. Later you’ll continue and cross into Tuscany while biking to your hotel in Cortona, the setting for Frances 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 massive walls, still in great part preserved, are said to be 3,000 years old. It was one of the twelve cities of Etruria and in its vicinity there are many ruins and Etruscan tombs. It’s a wonderful place for an afternoon sightseeing stroll.

  • Day 5: Cortona – Montepulciano – 28 miles (45 km)

    Today you’ll cycle in Tuscany through the wine country of Montepulciano. The route will lead you past some of the small Chiusi and Montepulciano lakes. Then you’ll head for beautiful Montepulciano, one of Tuscany’s highest hilltop towns and known worldwide for its fabulous red Vino Nobile wines. You can visit the superb Cantina del Redi with its vaulted cellars in town, or have a taste of the Nobili wines at Crociani winery, a small, friendlier “enoteca.”

  • Day 6: Montepulciano – Buonconvento – 28 miles (45 km)

    You’ll pedal through many wonderful places today. After a visit to the San Biagio Church you’ll ride to the perfect Renaissance town of Pienza, an architectural jewel famous also for its wonderful cheese, the pecorino di Pienza. Pienza was planned and built from 1459 – 1462 by the famous Florentine architect Gambarelli at the request of Pope Pius II. Walking through the narrow streets of this walled city is a photographer’s delight, and the cathedral and the Pope’s residence are well worth a visit.  You’ll continue on a small road to Monticchiello, a tiny walled village in the middle of the incredible Crete Senesi landscape with its barren hills that appear eerie in some lights. Later you’ll make a short detour to the ancient spa of Bagno Vignoni. You can soak your feet in the warm sulfurous waters – appreciated since Roman times – that bubble up into a large pool constructed by the Medici family in the picturesque Piazza. From here you’ll pedal on to Buonconvento where you’ll spend the night in a charming agriturismo or in a modern 3-star hotel in the city.

  • Day 7: Buonconvento - Siena – 31 miles (50 km)

    After a steep climb, you’ll pedal through the spectacular eroded hills of Crete Senesi and then through thick cypress and olive groves as you approach the 14th century Benedictine monastery of Monte Oliveto Maggiore, one of the best known Benedictine monasteries in Tuscany. The monastery was founded for hermits in 1313 and was suppressed by Napoleon in 1810  After restoration it was made a national monument, though some monks remain as caretakers. Ancient pines surround the cloister and the walls are decorated with gorgeous frescoes detailing the history of St. Benedetto and the Benedictine Order. You can contemplate the cloister with its magnificent fresco cycle on the life of St. Benedict, then continue on to Asciano, a small town in the heart of the Crete Senesi. From there it’s to Siena, one of the most beautiful cities in Italy. After Florence, Siena (once Florence’s most powerful rival) is by far the most interesting town in Tuscany and offers many treasures. Highlights are the dazzling Cathedral and the Palazzo Pubblico, both gorgeous Gothic buildings, and the Piazza del Campo, one of the most remarkable squares in Italy and the site of the yearly “Palio” horse races in July and August. You can stroll through the famous Piazza del Campo, enjoy a gelato, and find a charming trattoria for your farewell dinner tonight.

  • Day 8: Tour Ends

    You can walk around Siena and visit some of its museums before you depart. It’s a short cab ride from the hotel to the train station in Siena.

Dates & Prices

Green = Open | Yellow = Limited | Red = Full




Solo Traveller


$ 1540

$ 1760

$ 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 3 or 4* boutique hotels, air-conditioned hotels with private facilities each night
    • 21 or 24-speed hybrid bicycle
    • Daily breakfast 
    • 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.


  • 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 cancelation 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.

Hotel Chiusarelli

Hotel Chiusarelli

  • Siena
  • Rooms renovated according to NeoClassical style
  • Walking distance to historical center


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