The Best of Umbria and Tuscany

Guided cycling in Umbria and Tuscany is a wonderful opportunity to appreciate the best of both areas and its natural beauty and its artistic treasures. The tour includes visits to some of the major city centers and the gorgeous surroundings of Umbria and Tuscany. This 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 and the soft powdery color of the earth. Biking through Umbria’s and Tuscany’s sensual, rolling terrain with all its sweet power and magic is a gift to yourself that you’ll treasure for a lifetime! This tour includes visits to the impressive towns of Assisi, Spello, Cortona, Montepulciano, Buonconvento, Pienza and Siena with their typical medieval appearance; exquisite hilltop villages scattered over Tuscany’s and Umbria’s green hills; century-old farms and churches, especially the unforgettable Basilica of San Francesco in Assisi; sweeping views over the unspoiled landscape, a patchwork of wild flower fields, olive groves and vineyards; mild climate and delectable food; the wine region of Brunello wines, the barren geometrical cypress-crested mounds of the “Crete” hills and incredible art.

Daily Itinerary

Day 1: Arrival in Assisi. You will be met by your tour leader at the train station and he will drive you to your accommodations for the night. In the afternoon there is time to see some of 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. 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. It is the upper church however where we’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 its well-preserved exterior.

Day 2: Assisi – Spello – Cannara – Assisi – 31 miles (50 km)
Today we’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 we’ll ride through olive groves with no major uphill except for the final climb back to Assisi. You could also decide to stay in Assisi today and have more time to explore the fabulous “pink” city.

Day 3: Assisi – Solomeo – 31 miles (50 km)
As we cycle through the heart of Umbria we’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 we’ll stop briefly in Torgiano, home of Umbria’s finest wines, produced by Giorgi Lungarotti. Here we can visit their wine museum, which also includes medieval machinery. We’ll pedal through soft hills and scenic little villages until we reach either “Il Poggiolo” in Poggio delle Corti, a charming, old fashioned villa. The route today is continuously up and down so we’ll be happy to find a relaxing and peaceful hotel. Dinner included tonight.

Day 4: Solomeo – Lake Trasimeno – Cortona – 31 miles (50 km)
Today we glide 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 for us to take a boat to Isola Maggiore where old ladies still weave 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 and cross into Tuscany while biking to our hotel in Cortona, 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 5: Cortona – Montepulciano – 28 miles (45 km)
Today we’ll cycle in Tuscany through the wine country of Montepulciano. The route leads us past some of the small Chiusi and Montepiulciano lakes. Then we’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 Cantine del Redi with its vaulted cellars in town or have a taste of the “Nobili” wines at Crociani winery, a smaller, friendlier “enotecca”.

Day 6: Montepulciano – Buonconvento – 28 miles (45 km)
You’ll pedal through many wonderful places today. After a visit of the San Biagio Church we 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 by request of Pope Pius II. Walking through the narrow streets of this walled city is a photographer’s delight; the cathedral and the Pope’s residence are well worth a visit. We’ll continue on a small road that will take us to Montichiello, a tiny walled village, in the middle of the incredible “Crete” landscape with its sometimes eerie (depending on the light) barren hills. Later we’ll make a short detour to the ancient spa of Bagno Vignoni. Here we can soak our 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 we pedal on to Buonconvento where we’ll spend the night in a charming agriturismo or in a modern 3 star hotel in the city. Dinner included tonight.

Day 7: Buonconvento – Siena – 31 miles (50 km)
After a steep climb, pedal through the spectacular, eroded hills of “Crete” and then through thick cypress and olive groves as we 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. Century old pines surround the cloister and the walls are decorated with gorgeous, well-preserved frescoes, detailing the history of St. Benedetto and the Benedictine Order. 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 and from there on 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 us 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. Stroll through the famous Piazza del Campo, enjoy a gelato, and find a charming trattoria for your fare well dinner tonight.

Day 8: Walk around Siena and visit some of its museums before departure. It’s a short cab ride from the hotel to the train station in Siena.

Getting There

You will be met by the tour guide in the train station in Assisi. There is a direct train from Rome or Florence to the Terontola Train Station near Cortona. There you transfer by train to Assisi. 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, or


Daily breakfast and two dinners are included

Prices and Dates

Check out “Italy Tours” in our 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
      – Van support OR cycle guide
      – 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 tour price. 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!


For this tour, your group can choose between a cycle guide OR van support. If you choose a bilingual Italian cycle guide, they will bike with you and guide you on the routes and around the towns. There is no van following you! If you choose van support, this is done by a bilingual Italian support driver who transfers the luggage, goes over the route notes and checks on the bikers during the day. They would not bike with you. You have to follow the directions on your own.

The level of difficulty is moderate to challenging, as the daily routes are on mostly hilly terrain. Good cycling experience is recommended to deal with up and down hills and periodically busy Italian traffic.


– Airfare
– Alcoholic and bar beverages
– Airfare
– Lunches and five 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.

Comments are closed.