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Cycle Tuscany and Umbria

Self-guided cycling Tour Tuscany and Umbria.
From March 1 until November 31 – only from 4 pax or more.
Guided trips from 6 pax or more.

Only need a bike for your cycling holiday in UMBRIA OR TUSCANY

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Road cycling Tour Tuscany and Umbria on a road bike

Cycle a wonderful road bike trip in Tuscany and Umbria. You’ll cycle from the Tuscan village of Lucca all the way to the beautiful Umbrian city of Assisi. Cycle over the green hills of Tuscany and pass as many vineyards as you want! You travel through enchanting towns where nature’s charms combine with the wonders of art and the pleasure of excellent cuisine.

This bicycle tour begins in the medieval town of Lucca. From here you cycle to Florence. This city is world famous because of its art and Italian culture. On your way through Tuscany, you will find characteristic old villages like Gaiole, Radda in Chianti, Montalcino, Luccasolo, Pienza, or Montepulciano. The route brings you to Siena, renowned worldwide for the Palio but which is also home to monuments, churches, and grand buildings. In Umbria, you’ll discover more perfectly paved countryside roads. Orvieto, Todi, Spoleto, Spello, and Bevagna have remained intact over the centuries. The last stop on this bike journey is Assisi, the city has plenty of historical monuments, impressive walls, churches, and beautiful architecture.

Experience Tuscany and Umbria on road bikes!

  • The medieval town of Lucca also known as “the town of 100 churches”
  • Cycling in Italy is great: fantastic scenery, perfect roads, and fine food make Italy a road cycling paradise
  • Florence or Firenze: the birthplace of the Renaissance and capital of Tuscany world famous for its art and Italian culture
  • On your way through Tuscany, you will find characteristic old villages like Gaiole, Radda in Chianti or Montalcino
  • Visit the UNESCO World Heritage city of Siena
  • Discover Umbria and peddle through peaceful medieval villages
  • Challenging routes with hilly landscapes and average distances of 70-100 km a day!
  • Assisi with its hidden treasures like the Palazzo Vescovile, Palazzo dei Priori, and Palazzo del Popolo
Day 1
Check in

Check-in around 14.00 at your charming hotel in Lucca. There will be a briefing, and bike fitting and the tour organizer explains the coming itinerary of this cycle Tuscany & Umbria road cycling tour. Airport transfers from Pisa or Florence airport (on request).

Day 2
Lucca to Florence 105 km

Are you ready for your first cycle day in Tuscany? The route starts at your hotel in Lucca. Before leaving this splendid place, you recommend exploring it by bike, pedalling along its elegant streets. After visiting Lucca, you pedal through the marvellous Tuscan countryside, along the olive oil and wine trails of the DOC areas of Colline Lucchesi and Montecarlo. From Montecarlo to Montecatini Terme the scenery changes completely and you find yourself on an open plain, surrounded by trees and flowers. Montecatini Terme has many thermal baths, spa facilities and wellness centres. Today's tour brings you to Florence on a fantastic journey through the rural area where Leonardo Da Vinci was born and developed his genius. Finally, you reach Florence. An extremely elegant city, Florence is a cradle of art and architecture. Wander around the numerous squares, buildings and markets.

Day 3
Florence to Siena 95 km

It isn't easy to leave Florence but today Chianti awaits you, with a completely different landscape made up of hills. For anyone who hasn't yet stopped to visit a winery, this stretch and the following ones are still excellent opportunities to do so. Chianti is full of authentic and charming little villages, Today in Radda in Chianti you join the permanent circuit of the 'Eroica', which unwinds along the famous unsurfaced roads so characteristic of this region. Following this route, you pass through the Chianti Classico area, with its famous vineyards. You cycle downhill through the vineyards towards Siena, which appears on the horizon. This town of art is known around the globe for the Palio which takes place in the splendid Piazza del Campo. Taste the typical local dishes.

Day 4
Siena to Montepulciano 96 km

This morning, following the Eroica route, you leave Siena and pedal between the rolling hills south of the town. This section has a lot of gentle undulating which is enjoyable on a bike. You continue your way through villages like Radi, Vescovado, and Buonconvento. Soon you arrive in Montalcino, with its old town walls, fortress, Palazzo dei Priori, Duomo, and other religious buildings. You are now on the last stretch in Tuscany. Leaving this beautiful region you’ll remember the gentle ups and downs. The unforgettable scenic views of this area lead you through a superb final Tuscan stretch and into the wonderful and unspoiled region of Umbria.

Day 5
Montepulciano to Passignano sul Lago Trasimeno 73 km

Come down from Montepulciano and cross the Val di Chiana. Here you reach the green region of Umbria. A nice hilly ride brings you to the Etruscan town of Cortona. Leaving this lovely town you cycle up and downhill through a valley. After the last climb, you descend towards the lake. You’ll pass little villages with beautiful views of Lake Trasimeno, nestled between rounded hills covered with olive trees. The finish is at Passignano Sul Lago. From the town center, you can enjoy a spectacular view of the Lake and its three islands.

Day 6
Passignano sul Lago Trasimeno to Orvieto 98 km

After breakfast, you jump on your bike and you’ll leave the cozy village of Passignano behind you. Cycle along the shores of the lake with its bright blue water. A short climb will bring you to Città della Pieve, the birthplace of Pomarancio. Continue the route with ups & downs until you reach Orvieto, an ancient town rich in art and culture. Visit the Duomo, which is a marvelous example of Italian Gothic architecture. Don’t miss the Pozzo di San Patrizio (St. Patrick's Well).

Day 7
Orvieto to Assisi 96 km
After breakfast, you leave for Todi. The uphill stretches are longer today. Todi awaits you with its beautiful town squares and breathtaking views of the Tiber Valley. From Todi, you cycle the last stretch of your Tuscany & Umbria road bike trip. Soon you arrive at your final destination; Assisi. There is much to see in Assisi: the Palazzo Vescovile, Palazzo dei Priori, and Palazzo del Popolo, which now houses the civic museum.
Day 8
Departure day
Time to say goodbye... a good flight back home or else a pleasant stay in Italy. Transfers to the railway station of Perugia or the airports of Pisa & Florence will be made by the Tour guide (on request)


  • Florence International Airport is named after one of the most famous Italians – Amerigo Vespucci. There is no train connection to the airport. From Florence railway station there are good connections to all kinds of cities in Italy. The airport lies only four kilometers away from Florence. Shuttle buses leave every 30 minutes. Florence airport is only 80 km away from the airport of Pisa, Galileo Galilei.
  • Pisa Airport is 2 km from Pisa, 20 km from Lucca, and 80 km from Florence. You can find the train station just outside the terminal. Pisa Airport lies directly on the highway Florence-Pisa-Livorno. Because the airport is so close to the city a ride to the center of Pisa does not take more than 10 minutes.


  • Lucca’s train station is situated on the south side of town in Piazza Ricasoli. Lucca is on the Florence-Viareggio train line, with frequent service to Florence. The ride takes 1 hour and 10 minutes to Lucca from. Also, buses run daily to Lucca as well and leave from Piazza Verdi next to the tourist office.

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Booking Information

Add your start date from March to November
  • All prices are based on double rooms.
  • Departures all days
  • For booking & inquiries please contact us at

Extra Information

  1. Fill out and submit the online booking request or send an email to
  2. We tend and try to send all over within 48 hours.
  3. Please do not make travel plans until you receive our confirmation.
  4. Please be advised that we make every effort to ensure that all the information given on this site is accurate. All statements and information have been researched and supplied by third parties.
  5. The information given is accurate and reliable, to the best of our knowledge. Should errors be found, we will rectify them as quickly as possible. However, we accept no responsibility for errors or inaccuracies.
  • 7 nights lodging in a 3* star boutique hotel (you can upgrade to 4* hotels) standard double room from €1350
  • Daily breakfast
  • Welcome briefing and information about the tour
  • Bike fitting
  • Luggage transport to your hotels
  • Hotline for assistance
  • GPS with all routes if you have your own GPS we will send all the routes 10 days before the arrival date
  • Road book with all routes and instructions
  • Dinners, lunches & drinks
  • Carbon Road bike €295
  • E-Bike €295
  • Insurance & Airfares
  • Airport transfers
  • High season supplement July - August
  • Single supplement on request




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