This Tuscany’s combination of natural beauty, medieval and renaissance art, architecture and friendly people will enchant you. Pedal to lofty hill towns, spin through broad valleys and follow sinuous country roads past cypress-lined lanes and quiet woodland.
Cycling through unparalleled countryside by day complements incredible Tuscan cucina by night. This gastronomic paradise beckons to lovers of sublime provincial cooking and superb wine; fresh pastas, porcini mushrooms, and locally produced pecorino cheese from Pienza mark the region’s celebrated dishes, which just happen to be the perfect match for its world-class wines. Every day will bring new experiences enriching you.
Off your bike, discover unforgettable Renaissance art and architecture, visit winery and cellars: you will be in the heart of Chianti Classico, savour meals created from the finest local ingredients and relax in charming Tuscan retreats.
Highlights riding Terre di Siena
- Explore some of the region’s most celebrated towns, including Siena, San Gimignano, Gaiole in Chianti
- Sample fine wines before dining on local specialties
- Castelli road: the Chianti castles route: the surprising number of castles, fortified farm houses, towers and fortified Abbeys in the area
- a visit to the famous Castello di Brolio before Gaiole is a must!
Welcome to Siena
Piazza del Campo is famous because here it is held twice a year the disputed “Palio” horse race, which opposes the 17 “contrade” of this fascinating city. Here you'll have time to shop while exploring the many hidden medieval walkways. Meet and Greet, we'll fit your bikes and introduce you to each day ride.
Chianti hills: castello di Brolio & Eroica
Ride from Siena to Castellina in Chianti, following the “chiantigiana” road. Along the way you can stop at Castelnuovo Berardenga, a medieval town that marks the gateway to Chianti country. From here you will ride inside the vineyard of famous chianti classico wine passing through many little hamlet. Not-to-be-missed is Castello di Brolio, a castle and winery. Gaiole the Eroica town worth to stop.
Arrive in time in Radda for a light lunch and enjoy the last 10 km of gentle rolling hills to get in Castellina.
Montefioralle & Panzano
Circular bike ride to Florentine chianti: bike along quiet roads to the three villages that formed the Chianti Alliance centuries ago. Visit Tuscany's forgotten abbeys and hamlets then enjoy a winery tour and taste their supple reds, fresh honeys and rich olive oil . Have a stop at Greve's main piazza, characterized by an original formation of irregular triangular shape, defined by beautiful long porticos. Back via Panzano with preserved the old walls, gate and the keep of the medieval castle. relax by the vanishing edge pool spilling into the countryside of endless vineyards
San Gimignano citta delle torri
Ride to San Gimignano: more vineyards await us today, but you'll be amazed at how different they look once we get into the district of San Gimignano. Hill climbing with many recovery sites on your way including medieval Barberino and Tavernelle the gateway
Soft, colorful, rolling hills of vineyards and sunflowers provide the backdrop to pre-Roman Etruscan remnants on your route to San Gimignano’s "medieval skyscrapers” in the distance you will see the seventeen towers. You'll have plenty of time to wander through the cobblestoned streets, window shop and buy a few last-minute Tuscan mementos for our friends and...why not, for ourselves too!
Ride back to Siena via casole d’elsa Stop in Casole d’elsa: originally inhabited by the Etruscans that means before roman empire. The fortress and the defensive walls are still visible today, although the town gates have unfortunately been destroyed during the Second World War.You will be soon in quiet road through Santa Colomba and Celsa pass the medieval hamlet “Fungaia” known to the sienese chronicle since 1247, it is on the old medieval pilgrim trail Via Francigena.
end of tour - arrivederci!
Distance: 60 km/37.5 miles
The bike ride is an exploration of Montagnola Senese, pass through charming little villages and borgo: Sovicille, Ancaiano, Simignano, Pieve Scola all medieval village with picturesque houses. You will be in the Via Francigena, the ancient road and pilgrim route running from France to Rome, very important in medieval times. The subsoil, mainly limestone, is full of marble, including the famous yellow marble, being used also for the Duomo of Florence
Villa STR - Siena
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.
Cost: Euro 1280 per person in double occupancy
Single room supplement Euro 350
Solo Traveller Supplement Euro 450
Five nights in excellent three-star superior hotels
One Goumet dinner
Route notes and itineraries & sightseeing, restaurant and shopping suggestions
All Baggage transfers
Pick-up of bikes and gear in Castellina
Keepsake Cicloposse water bottle
All tax and service charges
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
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!