Our challenging bike trip from Pienza to San Gimignano; a combination of a lot – to enjoy a blast! The unique val d’Orcia and ideal renaissance town of Pienza, Montalcino the top wine brunello town, the medieval castello di Gargonza where you will be guest, cross Chianti Classico vineyards, “citta delle torri” or Tuscan Manhattan those are the nicknames of San Gimignano, Etruscan town Volterra.
All together in this self guided for experienced bikers – anyway the average is 60/70 km and allow time to visit all the sight along the way.
Available Carbon frame race bike, hybrid and high-end E-bike and Gravel
- Breathe the history: Magical stay in Gargonza medieval castle, XV century convent in Pienza, renaissance palace in San Gimignano.
- Oldest town in Tuscany Volterra founded before roman times!
- Pecorino cheese, brunello wine & bruschetta -please spell brusketta.
- Artisanal gelato tour
Do you prefer the guided version? Essence of Tuscany is the right bike tour
Pienza & Montepulciano
Montalcino & Orcia valley
Bagno Vignoni: The ancient village is located in the heart of Tuscany, in the Val d'Orcia Natural Park. Thanks to the Via Francigena (which was the main route followed by pilgrims in antiquity who went to Rome), these thermal waters were found and have been used since Roman times. The heart of the village is the "Square of sources", namely a rectangular tank of 16th-century origin, which contains the original source of water that comes from the underground aquifer of volcanic origins
Along the way face the hearty uphill to Castiglione d'Orcia, with the imposing Rocca A Tentennano. After a rest, enjoy a long downhill to Sant'Antimo Abbey , 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. It is a fortified town which was used as a shelter by Siena nobles during the 16th Century. Today it is even more famous thanks to the production of one of Italy's premier fine red wines, Brunello di Montalcino. Back to Pienza via San Quirico d’orcia: stop in the village at Horti Leonini Garden, the top attraction of town.
Total Distance 68 km/42 miles available longer ride via San Filippo and Abbadia 100km
Le Crete - Castelmuzio, Trequanda, Lucignano
Total Distance: 57 km/35 miles. Available extension via Asciano
Chianti Wine & Abbeys: Castello di Brolio & Gaiole
Total Distance 64 km/40 miles - available extension to Monte Luco
San Gimignano & Monteriggioni
Total Distance: 60 km/37 miles
Volterra & Etruscans
Total Distance 60 km / 37 miles
See you soon at next bike trip
Hotel Il Chiostro di PienzaIl 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.
Luxury upgrade in Pienza: Bandita TownhouseLa 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.
Castello di GargonzaCastello di Gargonza is a thirteenth- century fortified village. Enclosed inside the medieval walls, the careful restored houses have retained the simplicity of rural life. Forest trails, relax in the Limonaia garden, sit at our bar with view of medieval tower and the woods surrounding the village
Palazzo Squarcialupi - CastellinaPalazzo Squarcialupi is part of the history of Castellina in Chianti. It is situated in the historical town center, on a road running along the XV century City Wall. Set in the spacious garden, in a most suggestive position, is the swimming-pool. The palazzo has medieval origins and it has been renewed becoming a luxury palace
Antico Pozzo - San GimignanoAntico Pozzo the building, now completely restored,preserves the original style of the 15th century, although the earliest part dates back to the middle ages and the founding of the town itself:traces remain of the well and the area around it.
Luxury upgrade in San Gimignano: La CollegiataOriginally a Franciscan convent built in 1587, Hotel La Collegiata is located just 1 km from San Gimignano. Rooms are furnished in a style that reflects the Sienese Renaissance palaces and located in the former cloister. The top-floor rooms overlook the 13 towers of San Gimignano. Ample pool and beautiful, Italian-style garden opposite the ancient building.
Cost: Euro 1590 per person in double occupancy
Single room supplement Euro 550
Solo traveller supplement Euro 650
Six nights in excellent four & three-star superior hotels
One gourmet dinner
Route notes, maps, elevation gain and city map
Sightseeing, restaurant and shopping suggestions
All Baggage transfers
Pick-up of bikes and gear in San Gimignano
Keepsake Cicloposse water bottle
Bike Rental per entire tour
Hybrid bike euro 180
Race bike euro 210
E-Bike euro 210
City Tax each village charges a tax per day between euro 0,70 to euro 4,00
Cooking lesson & Wine tasting