Short escape cycling from Tuscany to Umbria

Senza titolo 2 Umbria Getaway: 4 Nights


A bike tour that combines the charmed land of Southern Tuscany + the Umbrian corner around Orvieto.
Above all you will start with immersion in Val d’Orcia  a Renaissance jewel and the first example of an urban planning project, realized by Rossellino. Wander the evocatively-named streets, like Via dell’Amore and Via del Bacio, filled with characteristic shops offering the typical products of the Val d’Orcia; the standout is the famous pecorino cheese.
Furthermore  your days and rides will be off the beaten path: San Casciano hot springs and lovely town around.
Finally enter in Umbria thorough lush chestnut groves and elm forests. This landlocked region’s overwhelmingly medieval character harkens one back to the mysticism and mysteries of the Dark Ages, a land whose rolling hills are dotted with castles, fortresses and watchtowers, whose well-preserved hill towns produce world-renowned handmade ceramics

Pienza to Orvieto cycle vacation Highlights

  • Magnificent Orvieto Cycle from an ancient spa to the “Golden Lilly of Cathedrals”
  • Off the beaten path crossin Tuscany Umbria borders: San Casciano dei bagni and Cetona
  • Be awed by the recently renovated “dying city” of Civita
    hot spring thermal bath


Arrival at Chiusi Chianciano train station transfer on your own to the first hotel Il Chiostro in Pienza. The “perfect town” almost entirely built between 1459 and 1462, Pienza is a remarkable example of Renaissance-era town planning. If you have even the least appreciation for beautiful architecture, it is a treat to stroll about its cobblestone streets. Gift hunters will also be enthralled, and Pienza is a veritable gastronomic paradise.
Meet and Greet, we'll fit your bikes and introduce you to each day ride. First loop to San Quirico to test the bicycle and the equipment! Stop in the village at Horti e leonini Garden, the top attraction of town.
total Distance 22 km

San Casciano dei Bagni

Bike ride from Pienza to San Casciano dei Bagni
Today is a completely country ride: for the first 15 km you will ride downhill and after easy gentle rolling hills. You will see Radicofani medieval and enchanting village with a 1200 dating Rocca After lunch at the hill town continue to small outlying district of Celle sul Rigo with its majestic 13th century tower and an unforgettable view
Few km more and arrive to San Casciano Bagni hot spring. The spa is very old and in town there is impressive town hall of renaissance time. The historic centre worth a visit with its characteristic hill town-plan of alleys and small piazzas. Away from the centre, near the Spa, the Chiesa Basilicale which dates to the year 1000 is of great interest. But though San Casciano, immersed in a lush and uncontaminated nature, is a favourite with farm holiday visitors, it should not be forgotten that a great many tourists come for spa cures such as inhalations, baths and mud treatments.
Total Distance: 53 km/33,1 miles

Cetona & Sarteano

Loop ride to Sarteano & Cetona
Cetona is situated on the slopes of the mountain of the same name, the mount you will climb to get there! So, prepare for some hills today. Cetona retains the characteristic medieval design that consists of small alley ways and little roads that spiral and wind their way to the fortress. This is a must see town and worth the effort! Later you will also visit Sarteano and can take in the unique castle found there! Return to your same hotel in San Casciano Bagni - and maybe a visit to one of the baths?!
Total Distance 45 km/28,1 miles


Bike ride from San Cascino to Orvieto via Allerona and Castel Viscardo
Today you will pass the border after short downhill- just after the village of Trevinano you will be in Umbria. Across a park and forest and get to Allerona immersed in the wood-covered hills of beech, ilex, and juniper. visible are the ruins of the Castle of Meana, home of the homonymous barony, of a small fortress, known as "rudere dell'Armata" and the Bisenzio Tower. back in the saddle and enjoy the long downhill of the day. Another climb to Castel Viscardo. 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.
Total Distance 48 km/30 miles.

Optional loop to Civita - End of Tour

Loop ride Civita di Bagnoregio Today the bike ride highlight is visit Civita di Bagnoregio The town is noted for its striking position atop a plateau of friable volcanic tuff overlooking the Tiber river valley, in constant danger of destruction as its edges fall off, leaving the buildings built on the plateau to crumble. As of 2004, there are plans to reinforce the plateau with steel rods to prevent further geological damage. The city is also much admired for its architecture, some spanning several hundred years. Civita di Bagnoregio owes much of its unaltered condition to its relative isolation: the town was able to withstand most intrusions of modernity as well as the destruction brought by two world wars. The population today varies from about 12 people in winter to over 100 in the summer.
Total Distance 44 km/27,5 miles
Back to Hotel where you leave bikes. Orvieto station is on fast line Rome Florence and can reach your next destination.
Orcia valley bike tour Cicloposse
bike trip Umbria
cellar in tuscany tour
cicloposse bike jersey
cycling in umbria italy
cypress road cycling trip
Pienza bike tour Tuscany
wineyards in tuscany by bike
bike tour umbria by cicloposse
Hotel Il Chiostro di Pienza
Il Chiostro di Pienza is housed in a 15th C convent and sits protected and quiet right in the center of this tiny town. It has been renovated but all the beamed ceilings frescoed walls and ancient tile floors have been preserved, nice garden overlooking val d’Orcia with pool.
Sette Querce - San Casciano
The hotel Sette Querce is a recently renovated thirty year old inn constructed of traditional building materials: brick, wood and internal walls painted with different colors. The decor, curated by owner with the invaluable support of the English designer, is a happy union of traditional Tuscan furniture and the bright colors of the designer.
Palazzo Piccolomini - Orvieto
The Hotel Palazzo Piccolomini is remarkable for its beautiful palace created for the pontifical family Piccolomini. The accurate restoration has given new splendour to the different age-long structures; from the refined facade overlooking Piazza Ranieri down to the underground rooms cut into the tuff mass, on which the Etruscan Orvieto rises.
Luxury upgrade in Pienza: Bandita Townhouse
La Bandita Townhouse is a luxury boutique hotel tucked inside the historic center of Pienza. The building is a rambling Renaissance-era palazzo where nuns have lived for over 500 years. the property itself blends in completely with the Renaissance character, is a comfortable, and stylish place
Luxury upgrade in San Casciano: Fonte verde
The exclusive resort Fonteverde was built in the 17th century by the Duke Ferdinando I de' Medici amid precious hot springs whose therapeutic properties were known since ancient times. Extensive spa centre with various treatments and natural thermal hot waters, 7 swimming pools, a holistic centre and beauty centr
Umbria bike trip map
Map tour in Umbria from Pienza to Orvieto


Price & Inclusions 

Cost: Euro 1020 per person in double occupancy
Single room supplement Euro 250
Solo Traveller Supplement Euro 350

Four nights in four-star superior hotels
Four breakfasts
Route notes, maps, elevation gain and city map
Sightseeing, restaurant and shopping suggestions
All Baggage transfers
Pick-up of bikes and gear in Orvieto
Keepsake Cicloposse water bottle
Sales taxes

not included: 

bike rental per entire tour 

Hybrid bike        euro 105
Race bike            euro 120
E-bike                  euro 120

City Tax   each village charges a tax per day between euro 0,70 to euro 4,00

Renting GPS for 6 days – 50 euro
We can rent you a Garmin Edge Touring. It works like the GPS navigator you use in your car, only with maps and features specifically designed to help you find your way by bike. We will upload all the route notes and you will have really no problems in finding your way to the next town!

Tour Reviews

17 Ottobre 2016

We wanted to take the opportunity to tell you how much we enjoyed the ride and the itinerary couldn’t have put is more beautiful places. My husband and I travel at different paces and while he likes to get from point A to point B as fast as he can, I like to meander, stop and linger at will. This is a personal issue with us. I wish I had more time to wander the beautiful places… time. The hotels we stayed at were all very nice too and everybody so helpful. We will definitely recommend Cicloposse to our cycling friends and community back home. Ciao and Grazie!

17 Ottobre 2016

Dear Giuliana, I have been telling so many of my friends about the wonderful holiday we had with you. Did you get the photos I sent you ? Also what did you do with all the photos you took? We would love to see them. Our friends who live in Tuscany are wanting to get a group and do a tour so I have given them your web site.

Leave a Review