Total tour distance: 278 miles
Daily tour distance: 35 miles
Difficulty: 70 / 100
Tuscany and Umbria in 1 trip! This custom request we organized so many times over recent years is now a tour ready to book! A great combination of these two famous regions, the cycling offers a challenging ride to visit some of the most beautiful villages of both regions while soaking up the enchanting local lifestyle. A vacation to enjoy all that is good: food, sun, lifestyle, wine, amusement, and relaxation. Some of the highlights include Montalcino, Pienza, Orvieto, Todi, and Assisi; among many more! Brunello wines, cheeses, historical sites, medieval villages...prepare for a complete immersion in another time and way of living! You can enjoy very charming 3/4 star accommodations and devour your choice of divine mediterranean cuisine. The hilly terrain makes this tour somewhat challenging!
Arrival Day - Pienza (optional loop if you arrive early 22km)
From Chiusi train station (Rome-Florence high speed line) you can easily reach Pienza by taxi. Arrival at hotel and meeting for the bike fitting and orientation. 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. 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.
Day 2 | Montalcino Brunello Wine Country; Ride Distance 70 km
Today’s ride will take you to Bagno Vignoni, a thermal spa town that dates back to Roman times right before reaching the beautiful Castiglione d'Orcia, with the imposing Rocca A tentennano. Enjoy a long downhill to the monastery of Sant'Antimo, your next stop: if you have luck, you will hear the monks chanting. On your way to the Etruscan village and wine town of Montalcino you’ll pedal through magnificent vineyards. Arrive to the fortified town today famous thanks to the production of one of Italy's premier fine red wines, Brunello di Montalcino. After your visit back in the saddle and ride back to Pienza via ex-cassia road still inside the Sangiovese grapes vineyards., dinner on your own with suggestions.
Day 3 | Vino Nobile di Montepulciano; Distance 55 km
Start your day with a pleasant downhill, You’ll follow a route that winds through a scenic landscape checkered with vineyards, cypresses, and medieval villages…This is where “the English Patient” was filmed. Among the sites you’ll ride through there are the hilltop villages of Castelmuzio and Petroio. Today’s ride will take you to Montepulciano, which is famous for the production of Vino Nobile di Montepulciano. After a stroll about the medieval streets of this village, you can stop to visit one of the typical wine cellars in town, the oldest one which is situated under the Ricci Palace. Back to Pienza through Monticchiello… another hilltop village!
Day 4 | San Casciano Bagni; Distance: 53 km
Today is completely out in the country on a quiet Tuscan ride: for the first 15 km you will ride downhill and after you have gentle rolling hills. Then you will see Radicofani medieval and enchanting village with a 1200 population. After lunch (on your own) at this hill town, continue to small outlying district of Celle sul Rigo with its majestic 13th century tower and an unforgettable view. A few kilometers more and you arrive to San Casciano Bagni hot spring. The spa is very old and in town there is an impressive town hall of renaissance era. The historic centre worth a visit with its characteristic hill town-plan of alleys and small piazzas. Away from the center, 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 favorite 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. You move on to lodging at an Agriturismo, la crocetta in San Casciano Bagni. Dinner on your own.
Day 5 | Orvieto; Distance via Allerona and Castel Viscardo Distance 48km
Today you will pass into Umbria after a short downhill- just after the village of Trevinano- you will be in Umbria. Across a park and forest you then arrive at Allerona, immersed in the wood-covered hills of beech, ilex, and juniper trees. Visible here are the ruins of the Castle of Meana, a small fortress, known as rudere dell Armata and the Bisenzio Tower. Back on the back again, you can next enjoy the long downhill of the day. But of course, there is 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. Lodging at hotel Piccolomini or Il Virgilio; dinner on your own again, but suggestions always provided.
Day 6 | Todi via Prodo and Colonetta Distance 44km
After breakfast, you will ride from Orvieto to Todi via Prodo and Colonnetta. 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. Lodging at the Hotel Fonte Cesia. Dinner on your own.
Day 7 | Montefalco; Todi to Montefalco via Trevi, distance 69 km (shorter option: 30km)
Today is dedicated to the quintessential Umbrian delicacy: the medieval hilltown. After bidding farewell to Todi, you're off to visit Trevi, it rises up on a hill dominating the plain where the river Clitunno flows, between Foligno and Spoleto. Your destination is the Balcony of Umbria: Montefalco. Extremely tiny, it occupies a hilltop placed so strategically that majestic 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. Among the most important typical products in the city we should absolutely mention the Sagrantino of Montefalco wine. The cultivation of vineyards in this territory, in particular Sangiovese, dates back to the pre-Roman era. Lodging at country estate Villa Pambuffetti on the outskirts of Montefalco.
Day 8 | Assisi, Spello & Torgiano bike ride , Distance 56 km
Today is expressly designed to allow you plenty of time in Assisi. You begin with a nice downhill ride into Bevagna and you will surely want to stop in this picturesque hamlet at whose nucleus is one of the most authentic Romanesque town squares in Italy. 13 km later you get in Spello, not-to-be missed: among the neighboring cities, this is the one which preserves the major number of monuments testifying to the Roman era; for example, the town walls, which later became the foundations for the medieval walls, the ruins of the theater and the amphitheater, the thermal baths and the splendid town portals A short climb up to the famous town of Assisi, hometown of Saint Francis, which is perched on an outcrop overlooking the valley and gleaming soft pink against the dark-green backdrop of wild Mount Subasio. You will want to explore the cities revered and very beautiful churches, its romantic castle and impossibly narrow streets. Visit Saint Mary of the Angels built in the 16th century, it houses the very ancient Porziuncola, a tiny rustic chapel where the saint founded the first Franciscan friary. Enjoy the downhill form Assisi to the valley for 10 miles, taking you to the beautiful tiny village of Torgiano. Lodging at 3 star hotel Grappolo d’Oro.
Day 9 l Departure day, optional loop ride Distance 30km
Optional short bike ride to Deruta, Castelleone, Bettona. Distance 30 km The little excursion allow you to visit the pottery and artistic majolica town of Deruta ceramics are a milestone in the history of Italian pottery. They gained worldwide fame during the Renaissance thanks to their creative and qualitative excellence. Back to hotel where you leave bikes and continue your trip. Trains from Chiusi are possible. We can arrange extra nights in Rome or Florence and advise you on train travel, please inquire in advance.
- 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
- A package of pre-travel documents sent electronically to help you prepare for your trip.
Stay in deluxe 3 & 4-star hotels in convenient locations. All lodging includes private bathroom and a variety of other amenities. Hotels included:
- Relais Chiostro di Pienza (3 nights)
- Agriturismo La Crocetta
- Palazzo Piccolomini
- Villa Pambuffetti
- Hotel le Tre VaselleAl Grappolo d'Oro
Road bikes and upgraded hotels available. Please inquire.