Three Regions road bike tour

a 5 or 8 day tour
Cycling tour
Cycling Tour
Difficulty level 4
Individual tour
Self guided tour
code: C004UMB
Italy
Tuscany, Umbria

Prices

from 403€

A tour for racing bike enthusiasts

Assisi-Montefalco-Bevagna-Passignano-Chiusi-Cortona-Umbertide-Gubbio

This is the right tour for racing bike lovers. It is for those who would like to discover Umbria in all its aspects, thanks to this perfect combination of nature, history, hospitality and local traditions. The Umbrian landscape consists of rolling hills covered with woodland, vineyards and silver-green olive groves alternated with colourful fertile valleys.

View on Mount Subasio and Assisi
Balcony of Montefalco

The nature in the North of Umbria becomes more rough and unspoilt. Here friendly hills change into a mountain landscape with scenic views of the Apennines. However, everywhere after the tranquillity of nature you will find friendly, lively little towns with atmospheric town squares surrounded by monumental palazzos, little alleys and many impressive churches and castles that will take you back to a time long-gone.

Tuscan landscape
Tuscan landscape

Except Umbria the tour passes also through Tuscany. Cycling in the typical wavy landscape of Tuscany you pass the Tuscan towns of Chiusi and Cortona. On your day to the medieval town of Gubbio, you will have a short impression of the MARCHE region and its picturesque town of Cagli.

The tour has also a short version of 5 days, which doesn’t pass through the Marche.  

The daily program of the 5-day tour

The start of this cycle tour is in the medieval town of Assisi, part of the Unesco World Heritage. 

At the end of the afternoon drop off bicycles, if rented, bike fitting and route briefing. Overnight with breakfast in *** or **** star hotel near the old town centre.

Today you can choose between two routes: a longer route or 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. Overnight stay in *** or ***** hotel in the centre of town.

 

The longer route passes through the entire valley. The terrain is varied from flat to hilly. You pass many small characteristic towns, like Montefalco, built on a hilltop and famous for its excellent wines, and Bevagna with its medieval square.

Distance 108 km / 67 miles; Ascent & Descent + 774m – 946m

 

Shorter route also passes also the small medieval towns. Leaving your hotel you start your journey through the valley of Spoleto, passing Spello and Foligno, than your route goes up to Montefalco; also called ‘the balcony of Umbria’. The next town you will visit is Bevagna, whose characteristic medieval square still hosts two Romanesque churches.

Distance 68 km /42 miles; Ascent & Descent + 552m – 718m

Today you cycle through a fantastic Umbrian scenery. You will bike through an undulating landscape with now and then a steep climb to conquer, but in the end to 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 good preserved 13th century Palazzo del Podestà. Your overnight is Passignano that lies on Lake Trasimeno. It has a nice beach with swimming pool and lively bars. Hotel *** or Hotel ****

 

Overnight with breakfast in Passignano sul Trasimeno

Distance 80 km / 50 miles; Ascent & Descent + 986m – 934m

Today cycle around Lake Trasimeno. It is the fourth largest lake in Italy, surrounded on three sides by a backdrop of gentle rolling hills covered with olive trees. On the side facing Tuscany, a wide open plain stretches out. You will cross this plain going to the Tuscan town of Chiusi, which has Etruscan origins. After your visit, you return to your hotel at Passignano for another overnight.

 

Overnight with breakfast in Passignano sul Trasimeno

Distance 94 km / 58 miles;  Ascent & Descent + 835m – 826m

 

After breakfast ends your racing bike tour through a part of Umbria & Tuscany

view of Isola Polvese
Polvese Island

The daily program of the 8-day tour

The start of this cycle tour is in the medieval town of Assisi, part of the Unesco World Heritage. If you arrive early you can already explore the old town centre.

At the end of the afternoon drop off bicycles, if rented, bike fitting and route briefing. Overnight with breakfast in *** or **** star hotel near the old town centre.

Today you can choose between two routes: a longer route or 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. Overnight stay in *** or ***** hotel in the centre of town.

 

The longer route passes through the entire valley. The terrain is varied from flat to hilly. You pass many small characteristic towns, like Montefalco, built on a hilltop and famous for its excellent wines, and Bevagna with its medieval square.

Distance 108 km / 67 miles; Ascent & Descent + 774m – 946m

 

Shorter route also passes also the small medieval towns. Leaving your hotel you start your journey through the valley of Spoleto, passing Spello and Foligno, than your route goes up to Montefalco; also called ‘the balcony of Umbria’. The next town you will visit is Bevagna, whose characteristic medieval square still hosts two Romanesque churches.

Distance 68 km /42 miles; Ascent & Descent + 552m – 718m

Today you cycle through a fantastic Umbrian scenery. You will bike through an undulating landscape with now and then a steep climb to conquer, but in the end to 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 good preserved 13th century Palazzo del Podestà. Your overnight is Passignano that lies on Lake Trasimeno. It has a nice beach with swimming pool and lively bars. Hotel *** or Hotel ****

 

Overnight with breakfast in Passignano sul Trasimeno

Distance 80 km / 50 miles; Ascent & Descent + 986m – 934m

Today cycle around Lake Trasimeno. It is the fourth largest lake in Italy, surrounded on three sides by a backdrop of gentle rolling hills covered with olive trees. On the side facing Tuscany, a wide open plain stretches out. You will cross this plain going to the Tuscan town of Chiusi, which has Etruscan origins. After your visit, you return to your hotel at Passignano for another overnight.

 

Overnight with breakfast in Passignano sul Trasimeno

Distance 94 km / 58 miles;  Ascent & Descent + 835m – 826m

 

Also today you can choose of two routes to Umbertide

The longer route passes Cortona in Tuscany. It is 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 a mountainous terrain with magnificent views over the surrounding mountains.

Overnight with breakfast in Umbertide

Distance 88 km /54 miles;  Ascent & Descent + 1405m – 1430m

 

The shorter ride 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 descend into the Valley of the Tiber, will lead you to Umbertide, whose town centre 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 swimming pool.

Overnight with breakfast in Umbertide

Distance 45 km /28 miles;  Ascent & Descent + 837m – 855m

Today, cycling through a 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 centre and the Long bards Castle (8th century). You will  enter in the region Le Marche and from there you arrive to Gubbio, where you will stay in a *** or **** hotel in the centre of town.

Overnight with breakfast in Gubbio

Distance 84km / 52,2 miles;  Ascent & Descent + 1699m – 1408m

On this last 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 *** or **** star hotel

 

Overnight with breakfast in Assisi

Distance 68 km/ 42 miles;  Ascent & Descent + 1158m – 1254m

After breakfast ends this tour through Umbria with a pinch of Umbria and Toscana

Road bike tour in Umbria, Tuscany & Marche

Three Regions road bike tour
Self guided tour
Difficulty level 4
a 5 or 8 day tour

Assisi-Montefalco-Bevagna-Passignano-Chiusi-Cortona-Umbertide-Gubbio

Code | C004UMB
LEVEL 4

For those who like challenging rides in rolling hilly terrain. It is a tour for bikers with experience and good physical condition. Hilly and mountain terrain with steep climbs and daily significant km/mi to cycle. Cycling on asphalted roads, for the bigger part quiet country roads. This tour is not suitable for children under 16 years old, because the terrain is too hilly and the tour too strenuous

Average daily distances:
Longer routes vary between 68 – 108 km

Shorter routes vary between 47 – 94 km.

Total km:

Total km 8-day tour minimum 448 km / 278 mi – maximum 529 km / 328 mi

Total km 5-day tour minimum 242 km / 150 mi – maximum 282 km / 175 mi

DEPARTURES:

Daily from April to the end of October (except 10/08-24/08/2025)

PARTICIPANTS:

1 or more people.

START / FINISH:

Assisi / Assisi

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Three Regions road bike tour

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