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
Pienza - the perfect town
Montepulciano & Vino Nobile
Total Distance: 55 km/34 miles
Montalcino Brunello Land
Total Distance: 46 km/28,5 miles
Siena & Monte Oliveto Maggiore Abbey
Total Distance: 58 km/36 miles
Chianti Hills
Total Distance: 50 km/31 miles
Greve in Chianti & Panzano
Total Distance: 56 km/35 miles
Monteriggioni loop
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
Extra stage on request: Castellina to San Gimignano

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 valleyPrice & Inclusions
Price
Cost: Euro 1290 per person in double occupancy
Single room supplement euro 350
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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