Road Bike Tours Italy
Just Like You... We Ride
Just Like You... We Ride
From the magnificent medieval city of Siena to the breathtaking beauty of Elba Island, this unforgettable road cycling adventure through Tuscany takes you on a journey through some of Italy’s most spectacular landscapes.
Seven incredible days of cycling, where rolling hills, charming medieval villages, unspoiled countryside, and the sparkling Mediterranean Sea create an extraordinary variety of scenery. From the peaceful roads of mainland Tuscany to the spectacular coastal routes of Elba Island, every ride reveals a new perspective on this remarkable region.
But this journey is about much more than cycling. Carefully selected accommodations, authentic Tuscan cuisine, outstanding local wines, and memorable dinners are all part of an experience designed to immerse you in the true spirit of Italy.
Offered in spring and autumn, when Tuscany reveals some of its most beautiful colors, this tour is ideal for cyclists with an intermediate level of fitness.
As always, our experienced local guides and fully equipped support van will accompany you throughout the journey, ensuring comfort, safety, and complete assistance.
Discover Tuscany and Elba Island the way they deserve to be experienced: on two wheels, surrounded by beauty, history, and unforgettable emotions.
7 days
7 people
352 km
65/75 km
medium difficulty
bike & e-roadbike rent
There is no better place to discover the timeless charm of Tuscany than Siena, a city where centuries of history come alive along its narrow streets and magnificent medieval architecture.
After meeting our team and preparing the bikes for the days ahead, we’ll head to the extraordinary walled village of Monteriggioni for a special welcome dinner. Surrounded by ancient stone walls and the atmosphere of another era, we’ll enjoy our first taste of authentic Tuscan cuisine and local wines.
A wonderful introduction to the landscapes, flavors, and traditions that make this region so extraordinary.
Overnight in Siena.
Our first day on the bike takes us into the heart of Chianti, one of Tuscany’s most iconic landscapes, where endless vineyards, ancient stone villages, and rolling hills create scenery that seems almost too beautiful to be real.
Leaving Siena behind, we follow peaceful country roads through the vineyards and unspoiled countryside, climbing steadily towards Radda in Chianti, a charming medieval village surrounded by some of Italy’s most celebrated wine country.
The journey continues to Castellina in Chianti, another jewel of this extraordinary region. Here, a well-deserved Italian cappuccino offers the perfect excuse to slow down, soak up the atmosphere, and recharge before our final ride back to Siena.
We’ll end the day around the table of a traditional Tuscan restaurant, celebrating our first cycling adventure with authentic local flavors and excellent wines.
Overnight in Siena.
Today, our Tuscany cycling tour takes us on a fascinating journey through centuries of history, where spectacular countryside, ancient villages, and legendary medieval towns reveal the timeless soul of this extraordinary region.
Leaving Siena behind, we ride through peaceful rolling hills, enjoying beautiful views of Monteriggioni Castle before reaching Abbadia a Isola, an ancient stop along the historic Via Francigena pilgrimage route connecting Canterbury to Rome.
Our journey continues past Castel Pietraio and through Colle Val d’Elsa, a charming town with Etruscan origins and a centuries-old tradition of glassmaking. Ahead lies one of Tuscany’s most iconic destinations: San Gimignano, the magnificent medieval town famous for its impressive towers rising above the surrounding vineyards and countryside.
But the adventure doesn’t end here. Following scenic Tuscan roads, we make our way to Volterra, an extraordinary hilltop town with over 3,000 years of history. Its ancient Etruscan walls, medieval palaces, and breathtaking views make it one of Tuscany’s most fascinating treasures.
After an unforgettable day of road cycling through the Tuscan countryside, we’ll have time to explore Volterra’s atmospheric streets before enjoying a delicious dinner featuring authentic local cuisine.
Overnight in Volterra.
Today, the landscape begins to change as we leave the ancient hilltop town of Volterra and set off on a spectacular road cycling journey towards Tuscany’s Mediterranean coast.
Our route takes us through Saline di Volterra, historically known for its salt production, before continuing towards Pomarance and Montecerboli, a fascinating region where geothermal energy has shaped the landscape and local history.
A beautiful succession of climbs and descents leads us through quiet country roads, unspoiled nature, and charming villages such as Monteverdi Marittimo. As we approach Donoratico, the rolling Tuscan hills gradually give way to the refreshing sea breeze and the stunning scenery of the Etruscan Coast.
Our destination is the coastal area of San Vincenzo, a beautiful stretch of the Tyrrhenian Sea where cycling history also has its place: the town hosted both the start and finish of a stage of the 1971 Giro d’Italia.
After a rewarding day in the saddle, we’ll settle into our accommodation in Marina di Castagneto Carducci, with time to relax and enjoy the coastal atmosphere before gathering for another wonderful dinner celebrating the flavors and wines of Tuscany.
Overnight in Marina di Castagneto Carducci.
Today, our Tuscany cycling adventure takes us across the sea to one of the Mediterranean’s most captivating destinations: Elba Island, a paradise for road cyclists seeking breathtaking scenery, challenging climbs, and unforgettable coastal roads.
After breakfast, we transfer to Piombino and board the ferry to Portoferraio, where a completely different world awaits. Crystal-clear waters, dramatic cliffs, hidden coves, and colorful villages perched above the sea create an extraordinary setting for a day of cycling.
Elba is not only a natural paradise but also an island steeped in history, from ancient Etruscan settlements and iron mines to medieval fortresses and tales of pirates who once sailed these waters.
Our ride follows the spectacular Volterraio road, winding through Bagnaia, Nisporto, and Nisportino, with magnificent views of the coastline. We continue towards Rio nell’Elba, a charming medieval village, before tackling more scenic climbs and descents on our way to Capoliveri, one of the island’s most beautiful hilltop towns.
Every turn reveals another stunning panorama, making road cycling on Elba Island an experience unlike anywhere else in Tuscany.
We eventually return to Portoferraio, the island’s historic capital, renowned for its impressive Medici fortifications and its connection to Napoleon Bonaparte.
Our day ends in the lovely seaside village of Procchio, where we’ll relax and enjoy a delicious dinner inspired by the flavors of the island.
Overnight in Procchio, Elba Island.
Today, we discover another extraordinary side of Elba Island, following some of its most spectacular cycling roads, where rugged mountains plunge into the turquoise Mediterranean Sea and every climb rewards us with unforgettable views.
Leaving Procchio, we ride towards the charming seaside village of Marciana Marina before climbing into the island’s lush green hills. Our route takes us through Poggio, surrounded by ancient chestnut forests, and up to Marciana, one of Elba’s oldest villages, perched 375 meters above the sea.
From here, the scenery becomes truly spectacular. We descend towards the legendary Costa del Sole, the island’s wild western coastline, passing through Chiessi, a tiny village where dramatic cliffs, crystal-clear waters, and winding coastal roads create a paradise for road cycling enthusiasts.
Continuing along this magnificent stretch of coastline, we reach Marina di Campo, a lively seaside town overlooking one of Elba’s most beautiful bays. The contrast between the island’s mountainous interior and its stunning Mediterranean beaches makes every kilometer of this ride a memorable experience.
Our route eventually leads us back towards Procchio, completing another exceptional day of road cycling on Elba Island.
In the evening, we’ll gather for a special dinner, sharing stories and memories of two incredible days exploring this Mediterranean jewel on two wheels.
Overnight in Procchio, Elba Island.
After breakfast, we say goodbye to the beautiful island of Elba and head to Portoferraio, where we’ll board the ferry to Piombino. From there, our private minibus will take us back to Siena, through the wonderful Tuscan countryside.
Our journey may be coming to an end, but the memories of spectacular rides, breathtaking landscapes, and wonderful moments shared together will stay with us long after we return home.
This is not goodbye, but simply arrivederci. Until we meet again on the roads of another unforgettable cycling adventure!
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
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