Tuscany  the best of Senza titolo 2 Hills&Wheels Luxury Retreats



Tuscany’s best scenery roads to cycling! Whether crowned by timeless villages, covered by vineyards and olive groves or strewn with wildflowers, the hills of Tuscany have one thing in common: they’re perfect for exploring on two wheels. Pedal to lofty hill towns, spin through broad valleys and follow sinuous country roads past cypress-lined lanes and quiet woodland.

Off your bike, discover unforgettable Renaissance art and architecture, visit wineries and cellars: you will be in the heart of Chianti Classico and the Brunello wine town, savour meals created from the finest local ingredients and relax in charming luxury Tuscan retreats.
First of all you start the tour staying at beautiful La Bandita Townhouse, stylish new hotel in downtown Pienza, let you discover Montalcino & Val d’Orcia. In Siena’s historic centre overnight at Relais Campo regio, a boutique hotel and finally in Gaiole in Chianti stay at sophisticated estate, Castello di Spaltenna, exclusive atmosphere and unique landscape.

Hills & Wheels bike tour’s Highlights

  • shadow the hilly course of L’Eroica, Tuscany’s international recognized vintage bike race
  • Relax at day’s end in cozy luxury hotels where you’re welcomed like family

At A Glances:

Day one- Welcome To Pienza!

Benvenuti in Toscana

Arrival Pienza on your own. Meet you: fitting of bikes and introducing the tour. Pienza

La bandita townhouse  


Day two Distance: 68 km/42 miles

Shorter option:  Distance: 46 km/28,7 miles.

Loop bike ride from Pienza to Montalcino brunello land Bagni Vingoni , Castiglione d’Orcia, Sant’antimo Pienza

La bandita townhouse  

Day three Distance: 56 km/35 miles Bike ride to Siena via San Quirico and Le crete Siena

B&B Campo Regio


Day four Distance: 44 km/ 27,5 miles Bike ride from Siena to Gaiole  in Chianti via Castelnuovo and Castello di Brolio. Gaiole

Castello di spaltenna


Day five Distance: 54 km/33,5  miles


Loop bike ride to Badia a Coltibuono, Castellina & Radda Gaiole

Castello di spaltenna


Day six Arrivederci Optional bike ride

Welcome in Val d'Orcia - Pienza

We'll meet you at Pienza, the purest Renaissance town in the world (you will arrive by the train to Chiusi-Chianciano station, a major stop on all the Rome-Florence lines).
Meet Cicloposse team during a bike-fitting session
OPTIONAL short ride to 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. Welcome dinner at la bandita, where you will taste the special homemade pasta.

Montalcino brunello land

Today we'll start out on a long descent into the rolling green pastures of the Val d'Orcia: You are now at Parco Naturale e Artistico della Val d’Orcia, an Unesco site with this main justification: “The Val d’Orcia is an exceptional reflection of the way the landscape was re-written in Renaissance times to reflect the ideals of good governance and to create an aesthetically pleasing pictures”. Imagine cycling up and down in a scene from painting.
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. On your way to the Etruscan village and wine town of Montalcino you’ll pedal through magnificent vineyards 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, top attraction of town.
Total Distance: 68 km/42 miles
Shorter option Moderate Distance: 46 km/28,7 miles


Le Crete & Siena

Your detailed directions will take you through typical postcard scenery of Tuscany, Italy’s most photographed region—for good reasons. 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.
Continue always on a breathtaking scenery up to Siena arch gate Porta San Marco. Often described as Italy's best preserved medieval city, Siena rivaled Florence for dominance in Tuscany during the 1300s. You'll have time to take a leisurely stroll about this medieval art city in the afternoon and to visit Piazza del Campo, Torre del Mangia and the famous Duomo. 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.
Total Distance: 56 km/35 miles

Gaiole in Chianti - Eroica town

Ride from Siena to Gaiole Along the way you can visit Castelnuovo Berardenga, a medieval town that marks the gateway to Chianti county. You'll be surprised to see vistas are almost alpine, encompassing deep green hillsides with very few houses scattered here and there. Many of the "houses" we'll see on this route are the venerable castles that are the source of the road's unofficial nickname. This is the best route for the serious wine lovers and cyclist travellers. It wends through the vineyards, past abandoned and renovated farmhouses on the way to one of Tuscany's most renowned castles, Brolio. This is the heart of the Ricasoli empire, family headquarters since 1067 and center of countless battles between Florence and Siena during the Middle Ages. Destination is Gaiole in Chianti a lively town located along the river Massellone and home to the annual l'Eroica vintage (pre-1987 steel frame) bicycle race-
Total Distance: 44 km/ 27,5 miles

Castellina & Radda

Circular bike ride to Castellina and Radda
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 group of hills blanketed with vineyards and thick forests. It's breathtaking, and so is the ride! First stop at Badia a Coltibuono, Abbey of the Good Harvest, dates from the middle 11C . Continue along the same winding panoramic road to Lucarelli and get to Castellina. The medieval fort dominates the country, but what bears witness more than anything else to Castellina's medieval past is surely the Via delle Volte, a walkway set into the walls of the town which offers a limited but exceptional panorama seen through the arrow-slits. On the way back stop in Radda.
Total Distance: 63 km/39 miles
Shorter option 32 km to Radda and Badia a Coltibuono

Arrivederci a presto!

Enjoy your farewell breakfast at the beautiful castle - optional short bike ride to san Sano and the enchanting Ama. Or wander in Gaiole village home of the annual Eroica vintage bicycle race

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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 www.la-bandita.com
Relais Campo Regio - Siena
More of a boutique guest house than traditional hotel, Campo Regio Relais’ 6 rooms are centrally positioned in the heart of Siena’s historic centre, allowing guests to easily reach the most important monuments of the city; the main square, Piazza del Campo, the Duomo, and the museums that house the masterpieces of Sienese art.
Castello di Spaltenna - Gaiole
A sophisticated manor, Castello di Spaltenna offers an exclusive atmosphere amidst a unique landscape. Located in the heart of the Chianti Classico wine region, the manor’s luxurious guestrooms offer any possible comfort along with wonderful views over the valley. From the grassy terraces, guests can enjoy the calm of the countryside and beauty of the surrounding landscape

Price & Inclusions 

Cost: Euro 1950 per person in double occupancy
Single room supplement euro 650
Solo Traveller Supplement Euro 850

Five nights in excellent four & three-star superior hotels
Five breakfasts
Route notes, maps, elevation gain and city map
Garmin Gps Touring Edge
Sightseeing, restaurant and shopping suggestions
All Baggage transfers
Pick-up of bikes and gear in Gaiole
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 each day between euro 0,70 to euro 4,00

Cooking lesson & Wine tasting


Tour Reviews

17 Ottobre 2016

Hey Guy’s .. I just wanted to drop you guy’s a note to tell you how much fun you made my bike trip through Italy. I really believe that without all of you being involved, the trip would not have been half as fun as it was. Marco, the way you handled all of us was great. You treated us tremendously and everything went as smoothly as anyone could ask for. And I am well aware that without Giuliana’s work behind the scenes, things would have been a disaster!!! Give my best to John-Luca and I hope our paths cross again soon.

17 Ottobre 2016

Everything was absolutely great, the rides, the bikes, the people everywhere, the hotels and kindness of people, the itinerary, the climbs, the downhills, everything so beautiful!! We enjoyed a lot, starting with the first loop ride from Pienza with a lot of rain the whole time, we were brave and resisted rsrs, and kept going!! very nice!

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