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Umbria is one of the less famous neighbors of Tuscany, but though it is less know it doesn't lack for beautiful sights and countryside! Many important cities and sites such as Assisi, Castiglione, Perugia, and Orvieto are among them on this tour. Climate and lifestyle is similar however, and this makes it very charming and somewhat off the beaten trail of Tuscany. You start in Castiglione and finish in Orivieto where upon completion you can easily go north to Florence and beyond or south to Rome. You can enjoy very charming 3/4 star accommodations and devour your choice of divine mediterranean cuisine. This is also hilly terrain and makes this tour somewhat challenging!
Duration: 7 days / 6 nights; Enjoy deluxe 3/4 star lodging while discovering all the charms of Umbria.
Note that we cannot offer either a 4 night option in this region, nor can we take solo travelers. Note that we can accommodate custom requests for Tuscany and Umbria including villa stays. Villa rentals are Saturday to Saturday only.
Dates :
March 15-November 15. This is self-guided touring and offers total freedom of dates - you can choose whatever dates you wish. We can accomodate small parties of 2 persons up to large groups. Custom guided groups are possible for groups of 6 or more; please inquire.
Level 3 - Consistently hilly countryside with mostly hilltop finishes; challenging terrain can be moderated or made more challenging by daily mileage.
Minimum 2 persons.
Options:
Ride options - longer/shorter
Florence/Rome addons
Custom itineraries for groups of 4 or more
Marco and Giuliana are our local experts; they live in Tuscany and will meet you for orientation on arrival day as well as provide emergency support throughout your trip.
"We had a great time on our trip in Umbria. The biking portion was fantastic. Bikes were great, overall great … Thanks for the effort in getting it set up !"
- David S./USA
Click on a day to see that days itinerary.
DAY 1 DAY 2 DAY 3 DAY 4 DAY 5 DAY 6 DAY 7
Day 1 | Arrival Day - Castiglione/Lake Trasimeno
We'll meet you at hotel miralago (you will arrive by the train to Chiusi-Chianciano station, a major stop on all the Rome-Florence lines). After the orientation and delivery of bikes you're free to explore this delightful hill town, which gazes down on tranquil Lake Trasimeno's fishing boats and beaches. Castiglione boasts a 16th-century Town Hall and a ruined medieval castle. Dinner on your own. Foods to try in Italy.
Castiglione del lago
Recently restored, the Hotel Miralago is situated in the historical centre of Castiglione del Lago. ...
Day 2 | Ride Day - to Perugia
Your first tour skirts this very large lake, winding past cornflower fields and isolated farmhouses, then into a series of gently rolling hills studded with minuscule towns that you'll want to stop and visit. Your destination is Perugia, one of Italy's most fascinating medieval cities. Take the strangely out-of-place escalator up to the ruined castle, pay a visit to the National Gallery to see many of local hero Perugino's works, stroll the quiet lanes and back alleys, pop into a few silent churches. After sundown, this university city livens up considerably, first with the traditional passeggiata (evening stroll) and then with music and fun at many local night clubs and bars. Level: Moderate with steep climb at the end. Distance: 45 km with steep climb up to Perugia. (Breakfast included - B)
Via Bonazzi 19
The hotel is uniquely designed with an open central area extending up all five floors, with interior...
Day 3 | Ride Day - to Assisi and Spello
Today is an easy day, expressly designed to give you plenty of time to visit Assisi. You begin with a nice downhill ride into Torgiano, followed by a short climb up to the hometown of Saint Francis, perched on an outcrop overlooking the valley, gleaming soft pink against the dark-green backdrop of wild Mount Subasio. You'll want to explore the city's revered and very beautiful churches, its romantic castle and impossibly narrow streets. visit Saint Mary of the Angels, one of the largest Christian basilicas in Umbria. Last stop is Spello and arrive in Bevagna a picturesque hamlet with one of the most authentic Romanesque town squares in Italy. It is also home to some of Pinturicchio's most glorious frescoes. Lodging in Bevagna and dinner on your own. Level: Moderate. Distance: 60 km with short option 30km. (B)
Corso G. Matteotti, 79 - Bevagna (PG)
Once the home of the noble Pietro Brunamonti and of his wife, the poetess Alinda Bonacci, this Palac...
Day 4 | Ride Day - to Montefalco and Trevi
Today is dedicated to the quintessential Umbrian delicacy: the medieval hill town. After bidding farewell to Assisi, you're off to visit "The Balcony of Umbria," Montefalco. Extremely tiny, it sits on a hilltop placed so strategically that splendid views are available at the end of every street. Along the way, you breeze past a few isolated rural churches and through a couple of towns too small to even make it onto the map Level: Moderate to challenging! Return to lodging in Bevagna. Distance: 50 km. (B)
Corso G. Matteotti, 79 - Bevagna (PG)
Once the home of the noble Pietro Brunamonti and of his wife, the poetess Alinda Bonacci, this Palac...
Day 5 | Ride Day - to Todi
Back roads are the main roads today, as you wend your way over hill and dale, past the tail end of mountain streams, silent forests and wild mushroom stands. You'll see fewer people today, hear fewer 20th-century sounds and see fewer modern sights than any other day. At the end of this unique excursion you'll take the customary uphill incline leading into Todi, whose proximity is heralded by the wonderful Santa Maria della Consolazione, a magnificent Renaissance church set amidst shrubs and treetops on the outskirts of town. Todi still has almost all of its medieval walls, and its pristine charm has made it a favorite country home of wealthy Romans and artists, as well as a host of artisans who have enlivened its streets with their shops. Dinner on your own. Level: Moderate to strenuous. Distance: 45 km. (B)
Todi
To stay at the Hotel Bramante means treating yourself to an unrepeatable mixture of art, culture and...
Day 6 | Ride Day - to Orvieto
Yet another - perhaps the most glorious - church awaits you at the end of this day, your reward for mastering some pretty steep inclines. Along the way you'll pass several ruined castles which provide a perfect backdrop for a picnic, perhaps based on local salamis, cheeses and breads purchased in the morning. By late afternoon you'll see Orvieto, looming ahead on its strange plateau, crowned by the cathedral of Santa Maria, considered by one and all to be among the very finest churches in all of Europe. Dinner on your own. Level: Strenuous Distance: 46 km. (B)
Orvieto
The hotel is located in the heart of the small town of Orvieto, in the historic center, in front of ...
Day 7 | Departure Day
Departure after breakfast, at your leisure. If you want to go on to Florence or Rome, we can arrange transportation and hotels. Trains, car rentals can be arranged as well additional stays throughout Italy. Orvieto is on the Rome-Milan train line and offers easy return to Rome or Florence. (B)
Deluxe lodging 3 and 4 stars - double room with private bath, buffet breakfast daily, all luggage transfers from hotel to hotel, local emergency support throughout your tour during daylight riding hours, arrival orientation and bike set up, route maps, route cue sheets with suggestions for visitation and site information, all pre and post travel planning services and a package of pre-travel documents sent electronically to help you prepare for your trip.
There is an upgrade option available for this tour as well with upgraded hotels or upgraded rooms; please see the price section. All hotels in either the 3 and 4 star version or upgraded 4 star are superior hotels with excellent locations and amenities. See the information shown for each day in the Itinerary tab.
Lodging on this tour is the same as that found in guided group tours costing $4000 and more!
Cycling in Umbria is one of the best ways to experience this famously romantic countryside. Traveling from one famous village to another along small country roads, this bicycle tour can be adapted to your needs.
Accommodation: [Virtual Hotel Tour] 6 nights in deluxe hotels: Castiglione - Miralago Hotel, Perugia - Hotel Fortuna or Dei Pirori, Palazzo Brunamonti in Bevagna, Todi - Bramanti , Orvieto - Duomo or Palazzo. These properties are all excellent hotels offering views, and charming typical ambiance. They are also in demand, so last minute requests can be difficult. In case of no availability; we will check equivalent alternative hotels that may require a change in price.
We can upgrade to very deluxe hotels including: Relais Alla Corte del Sole, Locanda Della Posta, Orto Degli Angeli, Fonte Cesia, Palazzo Piccolomini.
Hybrid Bike Rentals are available for a supplement of 95 euros, please see the Bike Rental tab for all details about the bikes we offer. Road bikes are also available for 150 euros.
Private transfer Chiusi to Castiglione: 85 euros up to 4 persons.

Bike rentals are available for every tour. We offer top quality custom built hybrid and road bikes.
Note: pedals are flat or with clips; if you bring your own clipless pedals and shoes we can install them.
Bike: [Click for image and more details ] Custom hybrid; aluminum frame with carbon fork, Shimano Ultegra or Deore; 3x9. Bikes come equipped with handlebar bag, lock, water bottle, gel saddle, tire repair kit, cycle computer. Hybrids are fitted with thin tires for better road performance. 95 euros rental rate for this tour.
Racing models also available see details . 150 euros rental rate for this tour.
Hilly terrain, rated as intermediate to advanced. All towns where lodging is located are perched hilltop villages.
A Cannondale tandem is also available for experienced tandem riders. Persons from 5 ft to 6-5 can be accommodated. Bike quality is top; averaging $1500 each retail.