Traverse the hills and valleys of central Italy

Embark on an unforgettable cycling adventure through the enchanting landscapes of Umbria and Tuscany, where history, art, and nature blend seamlessly into a perfect ride. This road cycling tour takes you deep into the heart of Italy, exploring historic cities such as Assisi, Montefalco, Cortona, Chiusi, and Gubbio—each brimming with centuries-old architecture, artistic masterpieces, and cultural heritage.

In the rolling hills of Umbria, golden fields, olive groves, and vineyards stretch as far as the eye can see. Follow scenic roads alongside winding rivers, past tranquil lakes, and beneath towering cliffs, taking in the region’s breathtaking natural beauty. Along the way, marvel at medieval castles, including the imposing Long Bards Castle, a testament to Umbria’s storied past.

Whether you’re drawn by the flourishing landscapes, the allure of Renaissance art and Romanesque cathedrals, or the charm of historic hilltop towns, this journey promises a perfect blend of cycling, culture, and discovery.

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Highlights

• Historic cities such as Assisi, Montefalco, Cortona, and Chiusi Gubbio
• Art and architecture throughout Umbria and Tuscany
• Magnificent countryside with rolling hills, rivers, lakes, and cliffs
• Long Bards Castle

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Learn more about our self-guided tours or see more bike tours in Italy.

Daily program

Day 1: Arrival to Assisi
The start of this cycle tour is Assisi, a UNESCO World Heritage Site. In this enchanting city, 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 a delight to explore.

Overnight in Assisi.

Day 2: Assisi – Torgiano (42 miles/68 km or 67 miles/108 km)
Today's longer route crosses the valley of Spoleto. You will pass stunning little towns like Montefalco, built on a hilltop and famous for its excellent wines, and Bevagna with its medieval square.

Today's shorter route passes the small medieval towns of Spello-Montefalco-Bevagna-Torgiano. You start your journey through the valley of Spoleto, passing Foligno, before your route heads up to Montefalco, known as ‘the balcony of Umbria’ because of its fantastic panorama. Here's a spot for capturing phenomenal photographs! The Franciscan church, now a museum, is decorated with magnificent frescoes from the 15th and 16th century by artists like Benozzo Gozzoli and Perugino. The next town you will visit is Bevagna, whose characteristic medieval square still hosts two Romanesque churches.

Your overnight stay is in Torgiano, once a fortified medieval village that 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 in Torgiano.

Day 3: Torgiano – Passignano (50 miles/80 km)
Today you cycle through spellbinding Umbrian scenery. You will bike through an undulating landscape with a few steep climbs to conquer, 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 still boasts a preserved 13th-century Palazzo del Podestà.

Overnight in Passignano.

Day 4: Rest Day or Ride around Lake Trasimeno (58 miles/94 km)
Today you can enjoy a rest day or choose to cycle around the lake. Lake Trasimeno is the fourth largest lake in Italy. It is 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 an Etruscan origin. After your visit, you return to your hotel at the lake.

Overnight in Passignano.

Day 5: Passignano – Umbertide (55 miles/88 km or 28 miles/47 km)
Today's longer route passes Cortona in Tuscany and is a very nice ride through the valley of the Tesse, which 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.

Today's shorter route also goes from the lake to Umbertide. It leads you through unspoiled scenery to the quiet little town of Umbertide, whose town center is dominated by a majestic tower - the remains of a castle dating back to 1385. A steep climb brings you to Castel Rigone from where you will have a magnificent view over the lake. Then, your route follows undulating landscapes to Umbertide.

Overnight in Umbertide.

Day 6: Umbertide – Gubbio (52 miles/84 km)
Today you will reach the fortified hill town of Gubbio. You will cycle through the mountains and the green hills of the lower Apennines. You'll visit Montone, a quiet little town built (1,582 feet/482 m) on a hilly ridge, situated between the Lana and Carpina streams, which are both tributaries of the Tiber. Then, the route takes you slowly uphill to Pietralunga with its old partially, walled-in centre and the Long Bards Castle (8th century). You will enter Le Marche and cycle along a quiet country road to arrive in Gubbio, where you will stay in a hotel in the center of town.

Overnight in Gubbio.

Day 7: Gubbio – Assisi (44 miles/70 km)
On this last day of the tour, you will cycle through a beautiful 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, finally, you will see Assisi from afar, built on a spur of Mount Subasio.

Overnight in Assisi.

Day 8: Departure from Assisi

Photos

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Dates & Prices

Questions about pricing or options? Call +1-215-613-0874 to talk to a Tour Advisor now.

Included services

• 7 nights accommodation
• Breakfasts
• Road bike
• Luggage transportation from hotel to hotel
• Tourist information and brochures
• 7 days emergency support hotline
• Route briefing on arrival day
• Ride with GPS App 1 access code per room: GPS tracks/cue sheets/tour info*

Local hotel taxes are not included and are to be paid directly to each hotel (approximately €1-5 per person/night).

*Paper route descriptions and maps on request with supplement of €10.

Tour Company

Map

Maps are for information purposes only and reflect typical routes between overnight locations. They may not reflect your actual route.

Surface and terrain

The route is hilly and mountainous, with several steep climbs. Most of the tour takes place on paved, quiet country roads.

Some of the days of this tour give cyclists two distance options. Should a cyclist choose the shorter option, the routes are between 28-40 miles (45-65 km). The longer routes are 56-71 miles (90-115 km).

How to get there

Tour start and end
Nearest airport: Sant' Egidio Airport (PEG), Italy
Nearest train station: Assisi, Italy

Tips on getting to and from your tour