Self Guided Bike Tour:
Beautiful Landscape in Terre di Siena
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.
Day One – Pienza
We'll meet you at Pienza, the purest Renaissance town in the world. Please note that the closest station to Pienza is Chiusi, 35 km from Pienza, on the Rome-Florence train line. After checking-in at your pre-arranged location in a former 15th century convent, itself is a rare masterpiece: entirely rebuilt between 1459 and 1462, it was the brainstorm of Pope Pius II.Bike fitting and meticulously go over the itinerary. Pienza is one of the four UNESCO World Heritage Sites you’ll encounter during your week-long history-laden cycling trip.
Lodging at hotel Relais Il Chiostro di Pienza
Day Two – Montepulciano & nobile wine
Level: Moderate to easy Distance: 55 km/34 miles
You’ll follow a route that winds through a scenic landscape checkered with vineyards, cypresses, and medieval village. Stop Monastery where part of “English Patient” was filmed. Among the sites you’ll ride through is the hilltop hamlet of Castelmuzio and Montepulciano, another hilltop village that will make a perfect lunch/wine stop. Montepulciano is home to the famous Vino Nobile and full of renaissance palaces. After your relax head back to Pienza through Monticchiello, the quintessential Tuscan hill town.
Lodging at hotel Relais Il Chiostro di Pienza.
Day Three – Montalcino brunello land
Level: Moderate to challenging Distance: 46 km/28,5 miles
Ride from Pienza to Montalcino, with a pause in fairy-tale Bagno Vignoni, a miniature spa that is among the most unique towns in Europe. You can have lunch in Castiglione d'Orcia, then push on to the monastery of Sant'Antimo, where you might catch one of several vesper services performed each day by the monks. The famed wine town of Montalcino is your destination. Visit the fortress to see a breathtaking view of the entire valley you've just biked, then reward yourself with dinner at our favourite wine cellar.
Lodging at hotel hotel Vecchia Oliviera in Montalcino
Day Four – Siena & Monte Oliveto abbey
Level: Moderate to strenuous Distance: 58 km/36 miles
Ride from Montalcino to Siena, your detailed directions will take you through typical postcard Tuscan scenery, Italy’s most photographed region—for good reason. Following a picturesque crest road, you’ll ride by the Monte Oliveto Maggiore Abbey. Stop here to visit the beautiful buildings and frescos in the cloister. Afterwards, you'll travel through the fascinating area called Le Crete, Tuscany's answer to the Badlands.bike ride end in Siena, beest preserved medieval town and visit the famous Piazza del Campo where twice a year the disputed “Palio” horse race is held opposing the 17 “contrade” of this fascinating city.
Lodging at hotel Palazzo Ravizza in Siena
Day Five – San Gimignano
Level: Moderate Distance: 60 km/37,5 miles
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. 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. 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. Continue to Castel San Gimignano pedaling a a very minor scenery road. Also seen in the distance are the seventeen towers of San Gimignano, just after San donato village. 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!
Lodging at at Antico Pozzo in San Gimignano.
Day Six – Chianti hills
Level: Moderate Distance: 50 km/31 miles
The previous days have prepped our legs for the famed hills of Chianti, which await us today! The first stretch crosses an almost impossibly scenic clutch of hills blanketed with vineyards and thick forests. It's breathtaking, and so is the ride! Hill climbing with many recovery sites on your way including medieval Barberino and Tavernelle the gateway town to the Chianti Classico wine-producing region! Back in the saddle, we continue along the same winding panoramic road to Castellina in Chianti. The town occupies a kind of panoramic balcony over Chianti, positioned on a high hill at the centre of three valleys. It is one of the most important centres of inhabitation in the Chianti. Worth the visit and stop for lunch and one of the best artisanal gelateria. Now only 12 km up and own to Radda in Chianti, the vineyard village: from the high ground on which it was built in the middle ages you gaze over a very dense interweave of vineyards
Lodging hotel palazzo san Niccolo
Day seven: optional bike ride to Gaiole in Chianti
Level moderate to challenging distance 35 km
Departure: train and bus available to reach Firenze where extension of vacation is suggested or where you can take fast train to other town
medium difficult: up and down on rolling hills and some climbs..rarely flat
person based on double accomodation
Same itinerary is available at less expensive hotel:
classic 3 Star Hotel Euro 1,180 Inclusions:
Six nights in excellent three-star superior hotels
Route notes and itineraries & sightseeing, restaurant and shopping suggestions
All Baggage transfers
Pick-up of bikes and gear in San Gimignano
Keepsake Cicloposse water bottle
All tax and service charges
Rent of bike
touring/hybrid bike euro 140
high-end race bike euro 170
:7 days / 6 nights Dates:
Tour Departures any date between 15th March to end of October - not suggested in july and august.
: This is a self-guided touring and offers total freedom of dates - you can choose whatever dates you wish. We can accommodate small parties of 2 persons up to large groups.