Road Bike Tours Italy
Just Like You... We Ride
Just Like You... We Ride
Imagine cycling through one of the most beautiful regions in the world, where endless rolling hills, ancient vineyards, elegant cypress-lined roads, and magnificent medieval villages create landscapes that seem almost too beautiful to be real.
Our Tuscany Cycling Tour is much more than a road cycling holiday. It is an unforgettable journey through the history, culture, traditions, and extraordinary beauty of Italy, designed for those who believe that the greatest cycling adventures are about far more than kilometres and elevation gain.
Every day brings new discoveries as we ride along peaceful country roads, through picturesque villages, magnificent vineyards, and breathtaking countryside. Here, every climb reveals another spectacular panorama, and every descent leads us deeper into the authentic heart of Italy.
But the magic of Tuscany doesn’t end when we get off our bikes.
We believe that an exceptional cycling holiday deserves an equally exceptional experience beyond the saddle. That’s why we personally select outstanding accommodations, charming historic properties, and excellent local restaurants, where traditional cuisine, celebrated regional wines, and genuine Italian hospitality become an essential part of the adventure.
Over six unforgettable days, our journey explores two beautiful Italian regions, with daily rides of approximately 60–80 kilometres, making this tour ideal for cyclists with an intermediate level of fitness.
Our experienced local cycling guides ride alongside the group, while a dedicated support vehicle provides luggage transport, technical assistance, and support whenever needed. With our carefully designed routes and small-group approach, you can simply enjoy every moment, knowing that every detail has been thoughtfully arranged.
This is our philosophy: not simply to show you Italy, but to let you experience its beauty, flavours, traditions, and emotions in a truly unforgettable way.
Because cycling through Tuscany is not just about discovering extraordinary places. It’s about experiencing extraordinary moments that will stay with you long after the journey ends.
7 days
7 people
335 km
65/75 km
medium difficulty
bike & e-roadbike rent
.
Your extraordinary Tuscany Cycling Tour begins in the heart of one of Italy’s most beautiful and historic regions: Siena.
Upon arrival, our Road Bike Tour Italy team will warmly welcome you, introduce your local cycling guides, and present the exciting journey ahead. We’ll also take care of assembling and preparing your bicycles, ensuring everything is ready for the adventure.
In the evening, a truly special experience awaits: a welcome dinner in the enchanting medieval setting of Monteriggioni Castle, one of Tuscany’s most remarkable fortified villages. Surrounded by ancient stone walls and centuries of history, we’ll enjoy authentic Tuscan cuisine and excellent local wines, the perfect introduction to the flavours and traditions of this extraordinary region.
After dinner, we return to Siena for our overnight stay.
An ancient castle, the finest Tuscan flavours, and the promise of unforgettable roads ahead. Your Italian cycling adventure begins here!
Our Tuscany Cycling Tour begins with an unforgettable ride through one of the most celebrated landscapes in Italy: the magnificent Chianti Hills.
Leaving directly from our hotel in Siena, we head towards Gaiole in Chianti, following peaceful country roads that wind through endless vineyards, ancient olive groves, and breathtaking rolling hills. This is the heart of Chianti, a region famous around the world for its exceptional wines, timeless beauty, and centuries-old traditions.
Every turn reveals another extraordinary panorama, with charming stone farmhouses, elegant cypress trees, and historic villages nestled among the hills.
Our journey continues to Radda in Chianti, one of the most enchanting medieval towns in the region. Here, we’ll stop in the beautiful historic centre for a traditional Italian cappuccino and cornetto, enjoying a moment of authentic local life.
Back in the saddle, we continue along a wonderful succession of rolling climbs and exhilarating descents, surrounded by spectacular vineyards, peaceful countryside, and the unmistakable charm of rural Tuscany.
Returning to our hotel in Siena, there will be time to relax by the swimming pool before gathering for another memorable evening of delicious Tuscan cuisine and excellent local wines.
Overnight in Siena.
Legendary vineyards, quiet roads, medieval villages, and the pure pleasure of cycling. This is Tuscany at its most beautiful, and our adventure has only just begun.
Today, our Tuscany Cycling Tour takes us deeper into the heart of one of Italy’s most extraordinary landscapes, where rolling hills, ancient abbeys, and endless cypress-lined roads create a world of timeless beauty.
After a delicious breakfast, we leave Siena behind and follow peaceful country roads towards Monteroni d’Arbia, cycling through the magnificent Val d’Arbia and the breathtaking scenery of the Crete Senesi.
Here, the Tuscan countryside reveals its most authentic character: golden hills, isolated farmhouses, elegant rows of cypress trees, and winding roads that seem to disappear into the horizon.
Our journey continues towards Asciano and the remarkable Abbey of Monte Oliveto Maggiore, a magnificent Benedictine monastery surrounded by one of Tuscany’s most enchanting natural landscapes.
Riding through a wonderful succession of rolling climbs and rewarding descents, we reach Buonconvento, a beautifully preserved medieval village nestled in the Ombrone Valley.
But one final destination awaits.
Rising proudly above the surrounding vineyards, Montalcino welcomes us to the legendary homeland of Brunello di Montalcino, one of Italy’s most prestigious and celebrated wines. Produced under strict traditions, Brunello must mature for at least five years before release, or six years for the prestigious Riserva.
After an unforgettable day in the saddle, our carefully selected accommodations offer the perfect place to relax before enjoying a delicious dinner featuring authentic local specialities and exceptional Tuscan wines.
Overnight in Montalcino.
From the timeless hills of the Crete Senesi to the legendary vineyards of Brunello, today is a journey through the very essence of Tuscany: extraordinary landscapes, centuries of history, and unforgettable flavours.
Another unforgettable day awaits as our Tuscany Cycling Tour takes us into the magnificent Val d’Orcia, a UNESCO World Heritage landscape and one of the most breathtaking regions in Italy.
Leaving Montalcino behind, we begin with a beautiful descent towards Torrenieri, before following peaceful country roads through a spectacular succession of rolling hills, ancient villages, vineyards, and iconic cypress-lined landscapes.
This is Tuscany at its most enchanting, where every turn reveals another picture-perfect panorama and every village invites us to slow down and enjoy the authentic Italian way of life. Naturally, there will be time for a traditional cappuccino or espresso along the way!
Our journey continues towards the magnificent Pienza, a Renaissance jewel overlooking the extraordinary Val d’Orcia. Here, we’ll enjoy a leisurely lunch in a traditional trattoria, discovering delicious local specialities and the warm hospitality of this remarkable region.
But our cycling adventure is not over yet.
The final challenge awaits: the ascent back to Montalcino, a rewarding 10-kilometre climb with approximately 500 metres of elevation gain. As we make our way towards this beautiful hilltop town, the surrounding countryside offers one last magnificent panorama.
In the evening, a wonderful dinner featuring authentic Tuscan cuisine and excellent local wines provides the perfect ending to another extraordinary day.
Overnight in Montalcino.
From the Renaissance beauty of Pienza to the legendary vineyards of Montalcino, today is a celebration of everything that makes cycling through Tuscany an experience of a lifetime.
Our Tuscany Cycling Tour continues through another extraordinary landscape, where ancient villages, peaceful country roads, and breathtaking panoramas reveal the timeless beauty of southern Tuscany.
Our first destination is San Quirico d’Orcia, a charming medieval town surrounded by the magnificent hills of the Val d’Orcia. Nearby lies the enchanting hamlet of Bagno Vignoni, famous for its ancient thermal waters and remarkable central square, where a large historic thermal pool creates one of the most unusual and beautiful settings in Tuscany.
Continuing through rolling countryside and spectacular natural scenery, we reach Radicofani, a magnificent hilltop village dominated by its imposing medieval fortress. Rising high above the surrounding valleys, this historic stronghold offers unforgettable views across the landscapes of southern Tuscany.
Our journey then takes us across the regional border into Lazio, where we discover Acquapendente, a historic town along the ancient Via Francigena pilgrimage route. Here, we’ll have the opportunity to explore its charming historic centre and experience another authentic corner of Italy.
After a rewarding day in the saddle, we head to Piancastagnaio, a picturesque Tuscan village on the slopes of Monte Amiata, where a delicious dinner featuring traditional local cuisine and excellent regional wines awaits.
Overnight in Piancastagnaio.
Ancient thermal springs, medieval fortresses, timeless villages, and magnificent countryside. Another unforgettable journey through the authentic heart of Italy.
Today, our Tuscany Cycling Tour reveals an entirely different side of Italy, where dramatic volcanic landscapes, ancient hilltop towns, and breathtaking scenery create another unforgettable cycling adventure.
Our journey takes us briefly back into southern Tuscany, where we discover the extraordinary Pitigliano, one of Italy’s most fascinating medieval towns.
Perched dramatically on a massive volcanic tuff cliff, Pitigliano appears almost to rise directly from the rock itself. Known as “Little Jerusalem” for its historic Jewish community and remarkable cultural heritage, this enchanting village offers a unique glimpse into centuries of Italian history.
Leaving Pitigliano behind, we continue along peaceful country roads towards Lake Bolsena, crossing once again into the beautiful region of Lazio.
Surrounded by gentle hills and picturesque villages, this magnificent volcanic lake, the largest of its kind in Europe, introduces us to another extraordinary landscape.
But one more unforgettable destination awaits: Civita di Bagnoregio, one of the most spectacular and extraordinary villages in Italy.
Often called “The Dying City”, Civita rises dramatically above a landscape of deep valleys and eroded volcanic cliffs, connected to the outside world by a long pedestrian bridge. Its timeless beauty and almost surreal setting make it one of the most remarkable places to discover in Central Italy.
After a day filled with history, spectacular scenery, and unforgettable discoveries, we reach Bolsena, where a relaxing evening and a delicious dinner featuring authentic regional specialities await.
Overnight in Bolsena.
From the dramatic cliffs of Pitigliano to the peaceful waters of Lake Bolsena and the extraordinary beauty of Civita di Bagnoregio, today is a journey through landscapes that seem to belong to another world.
After breakfast, our team will arrange your transfer to the airport or train station, bringing our extraordinary Tuscany Cycling Tour to an end.
We leave with unforgettable memories of breathtaking landscapes, peaceful country roads, enchanting medieval villages, and the authentic flavours of Italy.
More than a cycling holiday, this has been a journey through history, culture, friendship, and the timeless beauty of Tuscany.
The roads may be behind us, but the memories will stay with us forever. Arrivederci, Italy. Until we ride together again!
Yes, we provide your transfer from the airport/station on the arrival day and to the airport/station on the departure day.
You don’t need to be an athlete to take part in one of our tours. We offer different levels of difficulty, from the easy/medium tours in Tuscany, the Northern lakes Area, and Piedmont to the more demanding on the mountains. In any case, our van is constantly with the group to provide any kind of assistance.
In order to provide the best service and guarantee the best cycling vacation to our guests, we have chosen to organize tours only for small groups, a maximum of 7 people. So, in case of tiredness, bad weather, or others reason, a spot in the van is always guaranteed. Our team is made up of a bike guide and a driver, these guides are focused on the group, taking pictures, and providing assistance during the stage.
Our van is constantly with the group, providing any kind of assistance. Two guides will take care of the group and being in a small group, everyone will be assisted.
Yes, being a boutique Tour Operator, we are specialized in private and tailor-made tours. If you are a group of friends, a family, or a cycling club, write us your preferences and we’ll come up with the perfect tour for you.
We can provide different types of bikes, speaking about road bike tours we can rent:
For tailor-made and private tours, we can rent the bike most suitable for you.
“Medical Assistance Insurance” is included in all of our tours. We can’t provide Cancellation Insurance to extra Schengen clients, so we strongly suggest to our guests purchase Cancellation coverage.
Night accommodation in the best hotels
Photo book & welcome kit
Bike guide & technical assistance
Fill out the form with your details, pick the date you prefer and send us your request! We will reply you as soon as possible!
