Umbria, Tuscany and Marche on road bike

Discover in these 3 regions all the nature, culture, and history on your bike

Grade

Difficult

When

April - Nov

Accommodation

3* Hotels

Price 3* Hotel

€657

Road Bike Hire

€195

Half Board 3* Hotel

€185

Wine tasting

On request

Tracks for Gps

On request

Single room

€218

Gravel Bike Hire

€205

From: €657

Description

Umbria, Tuscany, and Marche

Self-guided cycling Tour Umbria. Self-Guided: Every day of the week from 1 April till 31 October (except 10/08 – 24/08/2025).
For guided options from 4 persons or more send us an email.

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Self-guided cycling Tour Umbria, Tuscany, and Marche on a road bike

This cycle tour is perfect for those looking to personally experience the unique and unspoiled region of Umbria with its beauty and hospitality. Umbria, nestling between Tuscany, Marche, and Lazio, is maybe one of the smallest regions of Italy, but it has a wide range of different landscapes: from harsh gorges to sweet green hills, wild woods to fertile plains transformed by varied cultivations; oases of fresh, crystal clear spring water and enchanting lakes. This cycle tour combines the beauty of nature with sightseeing in quiet little medieval towns.

The trip starts and finishes in the surroundings of the beautiful and fascinating town of Assisi, the pilgrims’ town built against the slopes of Mount Subasio. However, Assisi is not the only highlight of this tour. You’ll pass many other interesting small towns such as Spello, which has Roman origins, as several features including the Porta Venere and Porta Consolare town gates remind us. Montefalco is famous for its delicious wines, and Bevagna, which has a lovely medieval square with two Romanesque churches. The lovely towns, the biker-friendly roads, and the green hills with cypresses, vineyards, and olive trees make this tour unforgettable.

Cycle this beautiful Tour of Umbria, Tuscany, and Marche in Italy!

  • Challenging routes with hilly landscapes and average distances of 70-100km a day!
  • The start of this cycle tour is in the UNESCO World Heritage City of Assisi
  • The route goes up to Montefalco; also called ‘the balcony of Umbria’ with incredible panoramas
  • Cycle around Lake Trasimeno: the fourth-largest lake in Italy, surrounded by green rolling hills covered with olive trees
  • Discover Umbria and peddle through peaceful, friendly, and historic medieval villages
  • Boutique 3* star hotels

Difficulty level 3

Hilly terrain with average daily distances of 35 – 65km, for bikers with cycling experience and a good degree of fitness, because of the significant differences in level. Mostly cycling along quiet asphalted and now and then dirt roads.

Day 1
Individual arrival at your hotel in Assisi
The start of this cycle tour in Assisi belongs to the UNESCO World Heritage. In Assisi, many places and monuments have a strong unbreakable bond with the saints Francis and Clare, who lived here in the 13th century. The medieval character of Assisi is well-preserved and there is a lot to see. At the end of the afternoon, drop off bicycles, if rented, bike fitting, and route briefing. Overnight in 3*- or 4*-hotel near Assisi old town center
Day 2
Assisi, Spoleto, Montefalco, Bevagna to Torgiano - 68km / 108km
Today, you can choose between two routes: a longer route and a shorter route. Today's bike is dedicated to the valley of Spoleto, also named the Valle Umbra. Both routes end in Torgiano, which in medieval times was a fortified village and is situated on a hilltop above the confluence of the rivers Chiascio and Tiber. Interesting to visit are the wine museum and the "osteria" of the Lungarotti family, where you can taste their excellent wines. The longer route passes through the entire valley. The terrain is varied from flat to hill. You pass many small characteristic towns, like Montefalco, built on a hilltop and famous for its excellent wines, and Bevagna with its medieval square. The shorter route also passes the small medieval towns. Leaving your hotel, you start your journey through the valley of Spoleto, passing Spello and Foligno, then your route goes up to Montefalco; also called "The Balcony of Umbria", because of its fantastic panorama. Artists like Benozzo Gozzoli and Perugino decorate the Franciscan church, now a museum, with magnificent frescoes from the 15th- and 16th-century. The next town you will visit is Bevagna, whose characteristic medieval square still hosts two Romanesque churches. Overnight in 3*-hotel.
Day 3
Torgiano to Passignano on Lake Trasimeno - 80km
Today, you cycle through fantastic Umbrian scenery. You will bike through an undulating landscape with now and then a steep climb to conquer, but in the end, be rewarded with a magnificent view of Lake Trasimeno. You will pass small, typical Umbrian "Borghi", built on a hilltop such as Castiglion del Fosco, Pietrafitta, and Panicale, which has still a well-preserved 13th-century Palazzo del Podestá. Overnight in 3*- or 4*-hotel
Day 4
Tour around Lake Trasimeno - 94km
Today you can have a rest day or cycle around Lake Trasimeno. It is the fourth largest lake in Italy, surrounded on three sides by a backdrop of gently rolling hills covered with olive trees. On the side facing Tuscany, a wide open plain stretches out. You will cross this plain to the Tuscan town of Chiusi, which has an Etruscan origin. After your visit, you return to your hotel in Passignano for another overnight.
Day 5
Passignano to Umbertibe - 45km / 88km
Also today you can choose between two routes to Umbertide The longer route passes Cortona in Tuscany A very nice ride through the valley of the Tesse brings you to Cortona. This lovely Tuscan town is built on a hilltop. Leaving it you will cycle over a ridge through mountainous terrain with magnificent views over the surrounding mountains. The shorter route is through unspoiled scenery to the quiet little town of Umbertide. A steep climb brings you to Castel Rigone from where you will have a magnificent view over the lake. Then a final lovely descent into the Valley of the Tiber will lead you to Umbertide, whose town center is dominated by a majestic tower, the remains of a castle dating back to 1385. Your overnight stay will be just outside Umbertide in a country house with a swimming pool.
Day 6
Umbertide to Gubbio - 84km
Today, cycling through mountainous scenery, you will reach the fortified hill town of Gubbio. It is a beautiful tour through the green hills of the lower Apennines. You visit Montone, a quiet little town built (+482m) on a hilly ridge, situated between the Lana and Carpina streams, which are both tributaries of the Tiber. Then it is going slowly uphill to Pietralunga with its old partially, walled-in center and the Long Bards’ Castle (8th century). You will enter in the region Le Marche and from there you arrive at Gubbio, where you will stay in a 3*- or 4* hotel in the center of town.
Day 7
Gubbio to Assisi - 68km
On this last cycle day of the tour, you will cycle through (again) a green hilly landscape passing quiet mountain villages. The first stretch begins with a steep climb, but after that, the road undulates gently until it brings you to the bottom of a valley. The last stretch brings you through characteristic little villages and cycling over Mount Subasio finally, you will see Assisi from afar, built on a spur of this mountain. Overnight in a 3*- or 4*-hotel.
Day 8
Departure day
Departure day... Time to say goodbye, a good flight back home, or a pleasant stay in Italy. Transfers upon request.



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Booking Information

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  • All prices are based on double rooms - for bookings & inquiries: send an email to info@cycleclassictours.com

Extra Information

  1. Fill out and submit the online booking request or send an email to info@cycleclassictours.com
  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.
  • Overnight stays in good 3*-hotels based on B&B (Half Board and upgrades are possible)
  • Luggage transportation
  • Route notes in English, Italian, German, or Dutch and maps
  • Local backup service
  • Route briefing in starting hotel
  • Tour information
  • Lunches
  • Dinners
  • Price Single supplement 3* Hotel €875
  • Price Single supplement 4* Hotel €1299
  • Bike rental carbon RB (Inc. pick-up at Lake Trasimeno) €195
  • Bike rental gravel bike €205
  • Helmet €5
  • Half Board 3* Hotel €185
  • Half Board 4* Hotel €233
  • Airport transfers
  • Insurance & Airfares
  • Wine tasting
  • Tracks for Gps
  • Tourist tax to be paid directly in the hotel (1,50-3,50 / Price depends on hotel category)
  • Everything not mentioned under “Included in the tour”

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