Tuscany the best of
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.
wow moment
- 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: old monastery, medieval castle and palace!
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.
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 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.
At a glance
Day 1 Welcome To Pienza! Benvenuti in Toscana | Arrival Pienza on your own. Meet you: fitting of bikes and introducing the tour. | Pienza |
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 | Pienza |
| 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. | Gaiole |
| Day 5 Distance: 54 km/33,5 miles | Loop bike ride to Badia a Coltibuono, Castellina & Radda | Gaiole |
| Day 6 Arrivederci | Optional bike ride |
DAY 1
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.
DAY 2
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 Elevation +1,391 m / -1,396 m
Shorter option Moderate Distance: 46 km/28,7 miles
DAY 3
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
Elevation +961 m / -1,110 m
DAY 4
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 !
Total Distance: 45 km/ 28 miles
Elevation +831 m / -773 m
DAY 5
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: 57 km/35 miles
Elevation 1066 m / -1063 m
DAY 6
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
INFO TOUR
best period from March to End of October
DIFFICULTY Moderate to Challenge
TOTAL DISTANCE 231 km / 144 miles in 4 stages
TOUR REVIEWS
Price & Inclusions
Price
Cost: € 2450 per person in double occupancy
Single room supplement€ 750
Inclusions
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
Not Included
Bike Rental per entire tour
Hybrid bike % 190 | Road bike, E-Bike, gravel euro 260
City Tax Each village charges a tax per each day between euro 0,70 to euro 3,00
Optional
Cooking lesson & Wine tasting
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.
Relax, savor Tuscan flavors, and embrace the rhythms of daily life in this enchanting setting
Experience timeless charm at La 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.
A tranquil haven blending heritage, serenity, and contemporary elegance for an unforgettable Tuscan escape.
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.
Guests can relax by the stunning pool, indulge in exceptional dining at two renowned restaurants, and enjoy the tranquil charm of the Tuscan countryside from the serene terraces
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Tour Reviews
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.
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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