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. The tour starts staying at beautiful La Bandita Townhouse, stylish new hotel in downtown Pienza, let you discover Montalcino & Val d’Orcia. In Siena we selected Certosa di Maggiano, a former monastery located 1.2 mi from Siena's famous Piazza del Campo, built in 1314. Rooms are monastic cells with all contemporary comfort. Finally in Gaiole in Chianti stay at sophisticated estate, Castello di Spaltenna, exclusive atmosphere and unique landscape. Day 1 Welcome To Pienza! Benvenuti in Toscana. Arrival Pienza on your own. Meet you: fitting of bikes and introducing the tour. Day 2 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 Day 3 Distance: 56 km/35 miles. Bike ride to Siena via San Quirico and Le crete. Day 4 Distance: 44 km/ 27,5 miles. Bike ride from Siena to Gaiole in Chianti via Castelnuovo and Castello di Brolio. Day 5 Distance: 54 km/33,5 miles. Loop bike ride to Badia a Coltibuono, Castellina & Radda Day 6 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. 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. 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. 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. 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 bicycle race - pre-1987 steel frame ! 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. 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. Tour start Pienza. Tour end Gaiole. best period from March to End of October DIFFICULTY Moderate to Challenge TOTAL DISTANCE 231 km / 144 miles in 4 stages Five nights in luxury four & five star hotels. Five breakfasts. All Baggage transfers. RideWithGPS App: tracks, route notes, off-line navigation. Trip notes: Sightseeing & meals suggestions. Maps with elevation gain. Delivery bike at Pienza hotel & bike fitting. Pick-up of bikes and gear in Gaiole. Keepsake Cicloposse water bottle. Sales taxes. La Bandita Townhouse, nestled in the heart of Pienza’s historic center, is a Renaissance-era palazzo with over 500 years of history, once home to nuns. Blending seamlessly into the village, it feels like a local’s home, offering stylish comfort, warm hospitality, and vibrant charm. Certosa di Maggiano, a 14th-century monastery just a mile from the ancient gates of walled medieval Siena. Immerse yourself in history, where monastic cells have been transformed into luxurious rooms with unique design and modern comfort. Castello di Spaltenna is a refined manor at the edge of Gaiole, in the heart of the Chianti Classico region. Luxurious guestrooms offer every comfort and captivating views over the valley.
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