Cycling with Tuscany Around
Experience the Essence of Tuscany’s Wine Culture
Yes, there are hills to conquer, but these ascents lead to unforgettable rewards amid Tuscany’s sunny Mediterranean aura and its vibrant hospitality. In this journey, Tuscany nourishes the soul and elevates your spirits with life’s earthly pleasures.
Wow Moments
#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
#Delight in Tuscan wines within ancient cellars, savoring Vino Nobile di Montepulciano and Brunello di Montalcino
New for 2026 — Brunello wine experience along the route
On the ride from Pienza to Montalcino, it is now possible to stop at a beautiful estate just before reaching town, for a 🍷 dedicated wine experience.
Enjoy a guided cellar visit, followed by a tasting of Brunello di Montalcino and Rosso, paired with local olive oils and a relaxed lunch overlooking the Abbey of Sant’Antimo.
This experience is not included in the standard tour price, but can be easily arranged upon request as a special addition to your journey.
Discover a Journey through Tuscany’s Iconic Wine Regions
Venture into the heart of three renowned wine areas that have propelled Tuscany to oenological fame.
Pedal through the rolling hills adorned with Sangiovese vines, each turn revealing a breathtaking landscape. Here, vineyards seamlessly blend with olive groves, vegetable gardens, and verdant woodlands. Amidst this tapestry of biodiversity, Tuscany’s commitment to organic and biodynamic principles shines brightly.
Explore Beyond the Vineyards
Embrace the authentic essence of the region, where history whispers from ancient monasteries nestled in secluded valleys and medieval forts dotting the horizon.
The carefully selected route weaves through tranquil country lanes, linking farmland adorned with walled villages, and offering stays in quintessential Tuscan towns like Pienza, Montalcino, Siena, and the heart of Chianti.
Savor the Flavors of Tuscany
After days spent amidst rolling vineyards, golden wheat fields, and chalky white hills, indulge in the culinary delights that Tuscany is renowned for. Relish the tangy pecorino cheese, handmade pasta pici, fruity olive oils, and sip the Tuscan wines Brunello and Nobile.
It’s not just a bike tour: it’s an immersion into Tuscany’s culture, history, and tantalizing flavors — with the option to enrich your experience with a 👨🍳 hands-on cooking class with our Chef Paolo.
DAY 1
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
DAY 2
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.
Distance: 53,5 km / 33 miles
+ 1068 m / – 1070 m
DAY 3
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.
New for 2026: along this route, it is now possible to stop at a beautiful estate just before reaching Montalcino for a dedicated Brunello wine experience, including a guided cellar visit, tasting of Brunello and Rosso di Montalcino, local olive oils, and a relaxed lunch with a view of Sant’Antimo. (This experience is optional )
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 a wine tasting at local Enoteca. Have a dinner following our suggestions.
Distance: 44,4 km / 28 miles
+ 920 m / -876 m
DAY 4
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.
Distance: 56,7 km / 35,5 miles
+1035 m / -1217 m
DAY 5
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.
Distance: 55,6 km / 34,5 miles
+ 1019 m / -787 m
DAY 6
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
Distance: 55 km / 34 miles
+1019 m / -1019 m
DAY 7
YOUR TOUR ENDS AFTER BREAKFAST
Departure: train and bus available to reach Firenze where extension of vacation is suggested or where you can take fast train to other town
DAY 8
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
difficulty: challenging
INFO TOUR
best period : from March to end October
DIFFICULTY : medium to challenge
TOTAL DISTANCE : 280 km / 177 miles in 5 stages
TOUR REVIEWS
Price
Cost: € 1580 per person in double occupancy
Single room supplement € 590
What’s included
- Six nights in excellent four & three-star superior hotels
- Six 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 Castellina
- Keepsake Cicloposse water bottle
- Sales taxes
Not Included
Bike Rental per entire tour
Hybrid bike € 190 | Road bike, E-Bike, Gravel Bike € 260 | E-gravel € 350
City Tax each village charges a tax per day between € 0,70 to 3,00
Optional
Cooking lesson & Wine tasting
Cloister is one of those places where you really feel the history of Pienza. Set in a former 15th-century convent directly on Corso Rossellino, the town’s main street, it still retains the atmosphere and character of the original building, with its beautiful cloister at the heart of the property. What we particularly love is the garden at the back, with its swimming pool and wonderful views stretching across Val d’Orcia. You are right in the center of Pienza, with cafés, restaurants and little shops just outside the door, yet once inside, the hotel feels remarkably peaceful.
For those looking for a more refined and intimate stay in Pienza, La Bandita Townhouse is our luxury upgrade. This small boutique hotel occupies a beautifully restored historic building right in the heart of town, combining the character of old Pienza with contemporary Italian design and a wonderfully relaxed atmosphere. We like it for its stylish interiors, spacious and comfortable rooms, and the personal feel that comes with a small boutique property. Step outside and you are immediately in the historic center, with Pienza’s restaurants, cafés and charming streets all within a few minutes’ walk.
Vecchia Oliviera is one of our favorite choices for a self-guided stay in Montalcino. Located just inside the historic center, next to one of the ancient town gates, it is very convenient to reach by bike while restaurants, wine bars and the lively streets of Montalcino are all within easy walking distance. We particularly like its panoramic terrace, where breakfast is served overlooking the surrounding countryside, and the lovely small outdoor pool – a very welcome treat after a day on the bike. Comfortable, friendly and perfectly located for cyclists.
For those looking for a little extra comfort, Palazzo Saloni is a wonderful upgrade in Montalcino. Set right in the historic center yet quiet and peaceful, it offers spacious suites, beautiful views over the Val d’Orcia and the convenience of having restaurants, wine bars and shops just steps away. We particularly like it for our cycling tours: you can arrive and leave directly by bike, and the hotel has a dedicated bike room. A perfect combination of comfort, location and cycling practicality.
Villa STR is a great choice for a cycling stay in Siena. Set in a 19th-century villa just outside the busiest part of the historic center, it combines a quiet setting with the convenience of being only about a 10-minute walk from Piazza del Campo.
For us, its location works particularly well: once you arrive, the bikes can be safely stored in the hotel garage and you are free to explore Siena entirely on foot. After the lively streets and squares of the city, the peaceful garden is a lovely place to come back to and relax.
For those looking for a more luxurious and peaceful stay in Siena, Certosa di Maggiano is a very special upgrade. Set in a beautifully restored 14th-century monastery just outside the ancient city walls, it combines centuries of history with contemporary design, spacious surroundings and exceptional comfort.
What we particularly love is the sense of space and tranquility – you feel immersed in the Tuscan countryside while still being just minutes from the historic center of Siena. The beautiful grounds and swimming pool make it an especially welcome place to relax after a day on the bike.
Palazzo Squarcialupi is a charming 4-star hotel set right on the main street of Castellina in Chianti, in a historic building that forms part of the old town walls. Its location is ideal: step outside and you are immediately among the little shops, wine bars and restaurants of the village.
What makes it particularly special is what you find on the other side of the palazzo: a beautiful garden and panoramic swimming pool overlooking the Chianti countryside. After a day of cycling, it is a wonderful place to relax while still enjoying all the convenience and atmosphere of staying right in the heart of the village.
Salivolpi offers a different way to experience Castellina in Chianti. Set in a traditional Tuscan country house just outside the historic center, it is surrounded by vineyards, olive groves and cypress trees, with lovely views across the Elsa Valley.
We like its relaxed countryside atmosphere and swimming pool – always welcome after a day on the bike – while the shops, wine bars and restaurants of Castellina are still within easy reach. It is a peaceful and comfortable base from which to enjoy the heart of Chianti.
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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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