The Best of Tuscany and Umbria - BTUM

The Best of Tuscany and Umbria
Comfort level
8 Days


This 8-day tour is a true full immersion into two beautiful regions that are considered among the greatest places for bicycling vacations. You will see the very best of Central Tuscany and Umbria. These two regions are in themselves historically, culturally and climatically different. Tuscany is known for its hamlets and hill towns, terracotta rooftops, swaying cypress and golden valleys, as well as being the birthplace of the Italian Language, the Renaissance, and the cradle of Italian art. It was a land of wars between hundreds of its towns and villages.

Here you will enjoy the countryside, the rolling vineyards, the poppies in spring and the wild cyclamen in autumn. Most of all, many of the views have changed little for hundreds of years. On our tour you head off into a coffee table book Tuscan landscape of gentle hills, tipped by a lonely pine or oak tree while cypresses line the way leading to the distant farmhouses.

The holy Umbria was a land of peace historically bound to the Church State. It is the land of St. Francis and it is the “Green Heart” of Italy – with its green fields, plains, forests and meadows of the Apennine Mountains. It is known not only for its precious liquid, olive oil, but also for its white and pink Umbrian limestone that was used to build many of its medieval villages.

Umbria is not as famous as the Tuscan landscape, but perhaps more genuine and at least equally beautiful ! You will cycle from village to village, through forests and vineyards, then through the rolling hills between the spectacular hilltop towns of Spoleto, Spello and Assisi in a full immersion in the mythical Umbrian landscape.


Day 1 Arrival at Montepulciano
On arrival at the Chiusi railway station  you will be met by our guide and brought by private transfer to the charming hotel in Montepulciano. After checking in you attend a short bike fitting session and afterwards join an exploratory walk in the medieval town and its environs. Of course we will take our time to see some of the local wineries and why not, taste a good glass of local red wine.

Hotel in Montepulciano – HB

Day 2 Montepulciano to Pienza ride
Today we cycle from Montepulciano through the delightful Tuscan country side to the village of Pienza, a small, perfectly laid out Renaissance town, completely re-edificated under the impulse of Pope Pius II. Pienza is often described as the “ideal city” or the “utopian city”. It certainly is one of the best planned of Renaissance towns, where a model of ideal living and government was attempted. It represented the so-called utopia of the “civitas”, based on the concept of a town able to satisfy the needs of a peaceful and hardworking population. Pienza’s location in the centre of the Val d’Orcia, a wonderfully harmonious valley, helps the town to embody the fundamental principle that humanistic architecture attempted to create a balanced relationship between Man and Nature.

Distance : 40/70 km – Cycling time : 4/7 hours
Hotel in Montepulciano – BB

Day 3 Montepulciano to Cortona
After our breakfast we say good bye to Montepulciano and start cycling towards the Trasimeno Lake, which is the biggest sweet water body of peninsular Italy. We will follow a quiet easy cycling path around the lake, showing us the most beautiful spots of the area. Of course we need to get off our bikes and enjoy a picnic at the lake side. At the end of the day we arrive at Cortona, an important Etruscan settlement with its nicely preserved medieval centre.

Distance : 42/70 km – Cycling time : 3- 4/7 hours
Hotel in Cortona – HB

Day 4 Cortona to Montone & Umbertide
Today’s ride first takes us up into the hills of the pre-Apennine Mountains, and then down again the gorgeous gradual descent on minor asphalt roads towards the Upper Tiber Valley. Here we enjoy stupendous views on the rolling hills and shallow valleys of this part of Umbria. We visit the charming little village of Montone perched on a low hill top and then check in into our nearby hotel.

Distance : 55/75 km – Cycling time : 5-6/7 hours
Hotel in Montone/Umbertide – HB

Day 5 Monte & Umbertide to Assisi
Also today we continue cycling through the Tiber Valley, passing medieval castles and abbeys, on a road flanked by fields and forests to the slopes of Mt. Subasio. A final climb takes us to splendid medieval Assisi, the hometown of Saint Francis. Here we have ample time to explore the city. This little town is full of highlights, among which of course, the Basilica of San Francesco d’Assisi (St. Francis), with its wonderful fresco’s by Giotto, a World Heritage Site. But also the other churches, the Greek temple of the central square and the underground Roman Forum are worth a visit.

Distance : 50/70 km – Cycling time : 4-5/7 hours
Hotel in Assisi – HB

Day 6 Asissi, Spello & Spoleto ride
Our day’s ride starts in the Via degli Olivi (Olive Grove Way) and will take us all around the lower slopes of Mount Subasio. This road affords wonderful views over the plains below. It takes us to the very picturesque old Roman town of Spello, according to many one of the most charming villages in the area. This is an ideal location for a lunch stop en route. From Spello, we may then ride across the Umbra Valley to the foothills of the Montefalco territories, home of the superb Sagrantino red wine, and on to the Roman settlement of Bevagna (extension). Alternatively we immediately head for the major artistic centre of Spoleto with its famous Towers’ Bridge (Ponte delle Torri).

Distance : 65/80 km – Cycling time : 6-7 hours
Hotel in Spoleto – BB

Day 7 Spoleto ride
After breakfast we head off for a short half day ride taking us deep into Umbria. If we wish we can top our last cycling day off with a challenging and epic climb towards one of the most remote areas of Umbria.

Hotel in Spoleto – HB

Day 8 End of the tour
The tour ends at Spoleto after breakfast today. A private transfer takes you to the train station. Departure by train is available to reach Rome, Perugia or Firenze.

Tour details


All nights are spent in beautiful, characteristic and excellent ***hotels. All rooms have en-suite facilities.

3 picnic lunches and 5 dinners are included in the tour price. Other picnic lunches can be prepared for you by the accommodation holders, or materials for picnics can be purchased in the villages where you stay. The evenings you are free from dinner you can go out and find a nice place to eat in the villages where you will be staying.

Nights 1 & 2: The first two nights are spent in a nice 3-star hotel in the wonderful medieval hill top town of Montepulciano. From the cosy hotel the whole of the village is within easy reach.

Night 3: Tonight you stay in a charming hotel in the historical centre of Cortona near the Trasimeno Lake.

Night 4: The next night you stay in a charming hotel near the town of Montone or Umbertide.

Night 5: Tonight is spent in a nice hotel in the famous medieval town of Assisi, birthplace of Saint Francis. From the hotel you can easily reach the main attractions of the town.

Night 6 & 7: The last two nights you stay in a nice 3-star hotel in the medieval town of Spoleto under Mount Subasio.


On our GUIDED TOURS we include almost everything:

  • Private English speaking cycling guide for the duration of the tour (from 8 participants)
  • Tour leader, support van & mechanical assistance for the duration of the tour
  • Professional guiding service during the tour
  • Accommodation: 2 nights Montepulciano, 1 night Cortona,  1 night Montone/Umbertide, 1 night Assisi, 2 nights Spoleto in good ***hotels and agriturismo’s
  • Meals: 7 breakfasts, 3 lunches & 5 dinners; 2 wine tastings
  • Arival transfers from Chiusi railway station to Montepulciano.
  • Deperture Transfer from the hotel to the Spoleto railway station
  • Detailed maps & road book
  • Luggage transport

Not Included

  • Departure taxes
  • Visas
  • Travel Insurance
  • Meals not mentioned in the itinerary
  • Drinks
  • Optional additional tours or activities
  • Tips
  • Items of personal nature
  • Bicycle rental (Fully equipped touring or race bike – typical extra cost of 110 euro per person)


Moderate (3): Mostly moderate rides but with inevitably several climbs, only few of which are really strenuous. All roads are well paved and mostly quiet with little traffic. Extensions or shortcuts are possible on some days.

Fitness: Some experience with bicycle touring and a good general physical condition will certainly make your travel experience more enjoyable. You should be able to cycle for several hours a day also in hot dry weather conditions.


Arrival: The tour starts in MONTEPULCIANO, reached by a short transfer from the Chiusi railway station.

Departure: The tour ends after breakfast on day 8 in SPOLETO. A short transfer brings you from the hotel to the railway station.

Dates & Prices

Please contact us for the latest prices

AvailablePlaces available. You can book this tour with a minimum of 1 person.
GuaranteedGuaranteed Departure. Still some places available.
LimitedThere are a very limited number of available places on these dates. Immediate booking is recommended.
On RequestAvailability and prices on request.
Fully bookedFully booked. Departure closed.
  • Prices are per person and based on 2 people sharing double or twin accommodation.
  • Single rooms (mostly double rooms - single use) are available on all trips. The supplements listed apply.
  • Prices are expressed in Euro's. There will never be a currency surcharge.
  • Actual exchange rates: GB £ - US $ - CAN $ - CHF - DKK - SEK - NOK - Other currencies.
  • A 5 % early booking discount applies for several trips.

Tour variations

It is possible to extend your tour with a few days in Umbria or Tuscany. Details and prices on request. Extra cycling and/or sightseeing options can be provided!

It is possible to book an upgrade in some of the places en route. Details and prices on request.

Also Available

  1. The Best of Tuscany and Umbria (Self Guided Cycling Tour)

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The Best of Tuscany and Umbria
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Small Group Cycling Adventure
8 Days Starting from: €
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