Cycling with Tuscany around 
Yes, there are hills to climb, but your efforts will be well rewarded with a sunny Mediterranean ambiance and a spirited flair for hospitality, Tuscany nourishes the soul and leads you to rejoice in the earthly pleasures of daily life.
Route we selected takes you along tranquil country lanes tracing the expanses between farmland crowned with walled villages, ancient monasteries in secluded valleys, and medieval forts. Staying in Pienza, Montalcino, Siena and heart of Chianti, you are sure to experience the true essence of Tuscany, where history and beauty fill the heart as water fills a well. Strongly suggested, after spinning through rolling vineyards, golden wheat fields and chalky white hills by day, savor pecorino cheese, homemade pasta pici, fruity olive oils and sip Tuscan wines Brunello and Nobile.
This is our best seller bike tour !
Available Carbon frame race bike, hybrid and high-end E-bike
Classic Tuscany Bike tour’s Highlights
- Journey into the heart of Chianti—and back in time—to sensational Siena and Castelllina
- Shadow the hilly course of L’Eroica, Tuscany’s internationally recognized vintage bike race
- In ancient cellars, taste superb Tuscan wines, from Vino Nobile di Montepulciano to Brunello di Montalcino
on request Cooking lesson in Castellina in Chianti with dinner
1
Pienza - the perfect town
Meet & Greet in Pienza, the purest renaissance town in the world, for welcome and bike fitting. Pienza the “perfect town” 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 around its cobblestone streets. Optional test ride to San Quirico d'Orcia 20km /12,5 miles
2
Montepulciano & Vino Nobile
Your tour starts with a circular ride from Pienza. Be sure to stop along the way to visit the remote convent where parts of The English Patient were filmed, and in the enchanting little hamlet of Castelmuzio. By lunchtime you'll come to Montepulciano, the jewel of southern Tuscany, full of Renaissance palaces. After relaxing a while, return to Pienza with a stop in the village of Monticchiello, the quintessential Tuscan hill town.
Total Distance: 55 km/34 miles
Total Distance: 55 km/34 miles
3
Montalcino Brunello Land
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.
Total Distance: 46 km/28,5 miles
Total Distance: 46 km/28,5 miles
4
Siena & Monte Oliveto Maggiore Abbey
Your detailed directions will take you through typical postcard scenery of Tuscany, Italy’s most photographed region—for good reasons. Following a picturesque crest road, you’ll ride by Monte Oliveto Maggiore Abbey , a Benedictine abbey built in the 13th century and famous for its frescoed cloister and stunning setting. Afterwards, you'll travel through the fascinating area called Le Crete, Tuscany's answer to the Badlands. Here the verdant hills give way to little domes of clay and Tuscany reveals another face of its identity, an unusual, almost lunar landscape of chalk cliffs and gullies soaked in a primeval atmosphere.
Total Distance: 58 km/36 miles
Total Distance: 58 km/36 miles
5
Chianti Hills
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. There's also the chance to shop at a first-class ceramics workshop just before Radda in Chianti. Arrive in time in Radda for a light lunch and enjoy the last 10 km of gentle rolling hills to get in Castellina Castellina's medieval street, the Via delle Volte, was originally open to the sky, but over the years houses and shops have encroached on the ancient city walls, covering the street and providing an intriguing underground home for shops and restaurants.
Total Distance: 50 km/31 miles
Total Distance: 50 km/31 miles
6
Greve in Chianti & 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
Total Distance: 56 km/35 miles
Total Distance: 56 km/35 miles
7
Monteriggioni loop
Optional short ride to Monteriggioni 32 km/20 miles
The short bike ride allow you to visit Monteriggioni, literally a town-in-a-castle. Barely two hundred yards across, its eighty residents all reside within the picture-perfect round turreted walls that crown the hilltop visible for miles around. Back to Castellina where you will leave bikes.
Departure: train and bus available to reach Firenze where extension of vacation is suggested or where you can take fast train to other town
The short bike ride allow you to visit Monteriggioni, literally a town-in-a-castle. Barely two hundred yards across, its eighty residents all reside within the picture-perfect round turreted walls that crown the hilltop visible for miles around. Back to Castellina where you will leave bikes.
Departure: train and bus available to reach Firenze where extension of vacation is suggested or where you can take fast train to other town
8
Extra stage on request: Castellina to San Gimignano
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. Pretty soon you pass Monteriggioni, literally a town-in-a-castle. Barely two hundred yards across, its eighty residents all reside within the picture-perfect round turreted walls that crown the hilltop visible for miles around. Also seen in the distance are the seventeen towers of San Gimignano. 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! Distance: 58 km.
il Chiostro - 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.
La Bandita Townhouse - Pienza
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
Hotel Giglio - Montalcino
A charming retreat in the heart of town, hotel Giglio, family-run, in a warm and quiet building, facing a gorgeous landscape, the best part is the view of the cliff-clinging houses of Montalcino to your left and the rumpled patchwork of green valleys stretching out below. Plus a great restaurant where enjoy gourmet tuscan dinner
Si Montalcino - Montalcino
Hotel SI Montalcino is small charming hotel completely renovated, located on the panoramic road to S.Angelo in Colle, one km away from the walls of Montalcino. It is on a natural terrace that dominates the valley overlooking Monte Amiata and from here you can admire the vineyards of Brunello. Pool Belvedere
Chiostro Del Carmine - Siena
Il Chiostro del Carmine has been meticulously restored from a XIV century Carmelite Monastry, place of history and holiness, remained intact in the centuries, with its delightful and quiet courtyard. It is situated a few hundred metres from the Siena Cathedral and from Piazza del Campo
Palazzo Squarcialupi - Castellina in Chianti
Palazzo 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
Hotel Salivolpi- Castellina in Chianti
Salivolpi is an old country house recently converted into a hotel whilst keeping its original architectural features. It is located on the hills on the site of the former Etruscan Castellina, surrounded by vineyards, olive groves and cypress trees, it has a wonderful panorama stretching over the Elsa valley
Price & Inclusions
Price
Cost: Euro 1290 per person in double occupancy
Single room supplement Euro 350
Solo Traveller supplement Euro 450
Inclusions
Six nights in excellent four & three-star superior hotels
Six breakfasts
Route notes, maps, elevation gain and city map
Sightseeing, restaurant and shopping suggestions
All Baggage transfers
Pick-up of bikes and gear in Castellina
Keepsake Cicloposse water bottle
Sales taxes
Not Included
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
Optional
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
Tour Reviews
Thanks very much guys for a great trip. We really appreciated the extra touches you add to the Tour and tried most of your recommended Restaurants which were excellent. The countryside was beautiful and the wine….well …say no more
We had an absolutely great time! Castellena de Chianti and Pienza were our two favorite areas to bike in and I am so glad we chose Cicloposse
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