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+44 (0)1506 635399 info@hookedoncycling.co.uk

Tuscany to Umbria Bike Vacation

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Homepage > Italy > Tuscany to Umbria Bike Vacation
  • Duration: 9 Nights
  • Difficulty: Level 3 (level 3-4 by taking the longer rides options)
  • Tour Type: Self Guided
  • Availability: Daily from April - October
  • Location: Montepulciano
Tour Details

Welcome to Hooked on Cycling Holidays and our cycling holiday in Italy. This particular biking vacation in Italy is a 10-day cycle tour exploring two beautiful regions that are considered among the greatest places for cycling vacations. You will see the very best of Southern Tuscany and Umbria. These two regions are in themselves historically and culturally 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.

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.

Starting Location


Price Includes

  • 9 nights Bed and Breakfast
  • 3 star hotels and guest houses
  • Information Pack
  • Luggage transfers
  • Welcome meeting
  • Navigation by Smart Phone App

Price Excludes

  • Transport before and after tour
  • Flights
  • Travel Insurance
  • Hybrid Bike Rental
  • E-Bike Rental
  • Racing style Rental Bike
  • City Tax
Trip Info

Travel Insurance

It is a requirement of booking this tour with Hooked on Cycling that you have suitable travel insurance which covers you for the chosen activity and for emergency evacuation and hospital care.


Day 1Arrival at Montepulciano

If you arrive early visit to the town of Montepulciano and some of the local wineries.

Day 2Montepulciano-Monticciello-Pienza-Montepulciano 25-43 miles, 40-70 km

Today’s ride will provide some magnificent views of Tuscan towns and the countryside. You will ride to Pienza, the dream town of Pope Pius II, a place of architectural masterpieces where you can shop for ceramics and sample delectable Pecorino cheese. The ride is rolling with some sections on white roads.

Day 3Montepulciano to Cortona 26-43 miles, 42-70 km

Before you set out on your cycle ride today take a final look around Montepulciano, you will now know why it is one of the most beautiful hilltop towns of Italy. You will take the cycle path around Lake Trasimeno before the final climb up to the historic town of Cortona.

Day 4Cortona to Montone/Umbertide 35-46 miles, 55-75 km

Today you will wonderful views of the Chiana Valley and Lake Trasimeno from the slopes of the pre-Apennine Mountains. Following a gorgeous gradual descent onto a minor asphalt road that you will join the Upper Tiber Valley. Soon you shall arrive at the medieval town to Montone.

Day 5Montone/Umbertide – Assisi 30-43 miles, 50-70 km

Today’s ride continues to follow the Tiber Valley passing medieval castles and abbeys, on a road flanked by fields and forests to the slopes of Mt Subasio where the fabulous Roman and Medieval town of Assisi lies, the home to St Francis.

Day 6 ASSISI-SPELLO-BEVAGNA  25-40 miles, 40-65 km

Today if you decide to ride the core route you can stay longer in Assisi as it is a short ride. The ride is along the Via degli Olivi “Olive Grove Way” will take you around the lower slopes of Mount Subasio. This road affords wonderful views over the plains below. The very picturesque town of Spello is the ideal location for a lunch stop on this route. From Spello, we ride across the Umbra Vale to the foothills of the Montefalco territories, home of the superb Sagrantino red wine, to the Roman settlement of Bevagna.

Day 7BEVAGNA loop  30-60 miles, 50-98 km

Bevagna is a lovely small roman and medieval village, it may be worth also relaxing in town and for those who would like to ride we have selected wonderful rides to the wine areas, ceramics and outstanding medieval hilltop towns.

Day 8BEVAGNA-SPOLETO 25-44 miles, 40-70km

A gentle easy ride on the Umbra Vale with scenic views of the hilltop towns that face it. A Longer route will take you to Montefalco (a medieval town famous for its wines) and Trevi (a gorgeous medieval town also known as the capital town of Olive Oil)

Day 9SPOLETO loop 18-42 miles, 28-68 km

Spoleto is a wonderful roman medieval town with lots of things to see and places to go, our rides will be a short half-day easy ride or a challenging and epic climb towards a remote area of Umbria.

Day 10Departure after breakfast

The tour ends after breakfast. Departure by train is available to reach Rome, Perugia or Florence.

2 persons minimum


How to get there

By Plane
By plane to Pisa, Perugia or Rome airports
There are trains to Chiusi (from Pisa 2.5 hours, Perugia 1.5 hours, Rome 1.5 hours) and then by bus to Montepulciano or a taxi (around 30,00 €)
To return there are direct trains to Rome/Perugia (1.5 hours) and Pisa (5 hours) from Spoleto

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2024 Prices – For a complete tour price breakdown please click the book now button and select your holiday tour date. Prices will then be listed.

 Tour Code Prices From (per person) Book Now
CETUSUMB (9 Nights)  from £1395 Book Now
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