From the wonderful Siena to the blue Elba island, a cycling experience through the beautiful Tuscan countryside and Elba coastal roads.Five days up and down, between the hills and the sea, along the scenic Elba island roads. A road bike is a preferred viewpoint to appreciate the rare variety of panoramas: on the mainland, we can discover unspoiled small towns full of history and surrounded by a lush nature.


For this road bike tour in Tuscany, we have chosen charming accommodation and excellent dinners in Tuscan restaurants, where you can taste typical local food and the famous Tuscan wine .

You could join this road bike tour in spring or autumn when you can appreciate the beautiful local landscapes at their magic colours , meanwhile in summer you can take advantage of the long days to cycle in the morning and have long moments of relaxation in the rest of the time . The tour is divided into stages, which are appropriate for cyclists with an intermediate level of training. Besides, we ensure you the constant presence of our car support and a local expert guide.



This is an intermediate tour and requires a good level of training !


Group Bookings

Groups of 4 or more riders: can opt to make a tour private and choose their own dates.
Groups of 8 or more riders: can benefit from a 5% discount.

6 Nights 5 Days 24 Oct Siena, Toscana
What we'll give. What we won't

What is included in the tour

  • Accommodation in double rooms in a charming  farmhouses or superior bike hotel on double occupancy  . 
  • Full Cyclist Breakfast
  • Dinner providing all the evening meals along with beer and soft drinks either at the house or hotel or out at carefully selected restaurants . Our tours aren’t just about great cycling they’re also about great food.
  • High Quality Cycle ( Alloy , Carbon or E-Bike )
  • Expert Local Cyclist will drive you during all your cycling experience
  • First Aid / Medical kit
  • Cost for 1 or 2 guides (for the group of maximum 16 cyclists so 1 guide for 8 group members)
  • First mechanical aid kit (our cyclist and support vehicle are certified in handling first mechanical aid situations)
  • Car Support with Cycle porter ( if you wish to stop your ride , a car will pick you and bring you at home )
  • Luggage Transfer
  • Arrival/departure transfers from Florence/Pisa Airports   . We will pick you up and drop you off at the required airport. If it’s a shared tour we will ask all the clients to arrive around a certain time to enable us to collect everyone and avoid people waiting for too long at airports. 
  • Taxes and VAT

What is NOT included in the tour

  • Any meals/services not mentioned in the inclusions
  • Mandatory Travel Insurance for Cyclists and Travel Insurance Bike / EUR 50 per person
  • Any charges for video cameras, still cameras, etc.
  • Wine, alcoholic beverages , long drinks, etc.
  • Personal expenses like tips, telephone calls, laundry, etc.
  • Any costs arising out of unforeseen circumstances like landslides, road blocks, bad weather, etc.
What makes this tour special
  • Take in stunning views of Chianti hills
  • Reach the wonderful towns like Siena , San Gimignano and Volterra
  • Enjoy the hard Elba Island Climbs
  • Discover the Elba Island wild and lush nature 
  • Experience the Tuscan famous food and wine 
Pickup point
53100 Siena, SI, Italia View on Map
Route Map
Route Map

Tours 5 Distance 361 km Elevation 6,250 m

Itinerary Route Map
Itinerary Route Map
Day 1 Day 2 Day 3 Day 4 Day 5
Road Bike, Road E-Bike
5 Days

Day 1 

Arrival in Siena, welcome from the organization.
Road BIke Tour introduction , preparation of bicycles , Tuscan dinner at Monteriggioni Castle.
Overnight at Sangallo Park Hotel

Day 2

There is no better way to get in touch with this extraordinary area than to take a unique day trip through the famous and breathtaking Chianti hills by bike. These rolling hills are world-famous for their delicious wines.
We will begin our cycling day in Radda in Chianti, a charming ancient Tuscan village. Our route will be an easy and continuous climbing and descending roads, surrounded by many vineyards and pristine natural scenery. After leaving Radda in Chianti, we will head to Castellina in Chianti. When we arrive in the village, we will bring a delicious cappuccino to restore energy, which is our last effort, and then return to Siena. A famous typical restaurant is waiting for us to close this unforgettable first day.
Overnight at Sangallo Park Hotel

Day 3

Starting from Siena, passing through small villages on the hillside and enjoying the view of Monteriggioni Castle on the way, we reach Isola (Abbadia), This is an important stop along Via Francigena, an ancient route that connected Canterbury and Rome in the Middle Ages. Then, we continue to Castel Pietraio and Colle Val d'Elsa, an ancient Etruscan town whose development in the 15th century is attributed to glass production. Step on the pedals and we'll reach San Gimignano a medieval town, many of its towers are still intact, occupying the entire landscape. Finally, we arrived at the ancient town of Volterra with a history of more than 3000 years. Volterra, located in the province of Pisa, has the Acropolis, surrounding walls and gates to the historical center, and one of Italy’s oldest municipalities is the city. The cathedral, the imposing Medici fortress and the Priority Palace date back to the Middle Ages.
Overnight at Hotel Le Fonti

Day 4

We had a hearty breakfast and set off from Volterra with our bicycles and passed through a small village called Saline di Volterra, famous for its salt water springs and salt production. Passing through Pomarance and Montecerboli, which are important areas for the development and utilization of geothermal energy, and passing through historical villages such as Sarezzano, Monteverdi Maritime and Donoratico, we arrived at our destination: San Vincenzo.

On the famous Tyrrhenian coast of the Ligurian Sea, San Vincenzo developed into a small town in ancient times, so it has extremely important historical and cultural significance. In 1971, Giro d’Italia started and ended in San Vincenzo, which has now become an important tourist attraction. After entering your room, you will have time to relax and prepare to enjoy typical local specialties with other teams.
Overnight at Villa Le Luci

Day 5

After breakfast, take a ferry from Piombino to Portoferraio on Elba Island. We set out to explore the island by bike. The green oasis of the Tuscan archipelago, Elba Island is the habitat of beaches and cliffs, terraces overlooking the sea, and villages on the hillsides. The colors, flavors and aromas of these villages are magnificent, leaving people with a long stay. impression. Elba is the third largest island in Italy, thanks to its iron deposits, the heart of Etruscan civilization and the remains of outposts and necropolises, which can still be seen today. After the transfer of Roman rule to the Ostrogoths and Lombards, the island is full of thousands of years of testimony. And, when you look at the horizon, please keep your eyes open, because if you see a ship with a "skeleton and crossbones" flag, it probably means that the inhabitants of the island had been against the Ottomans in the 15th and 16th centuries. The pirates of the Empire were terrified. Back...

Overnight at Hotel del golfo-Procchio

Day 6

The day starts with breakfast to provide energy for our day's cycling, and then head to Procchio and the smallest municipality on the island: Marciana Marina. As we climbed the hills, we passed through the small village of Poggio, located in a century-old chestnut forest, until we reached Marciana, one of the oldest inhabited areas on the island, with a height of 375 meters.Descending in the direction of the most famous beach, we pass through Chiessi, a small village on the coast of "Costa del sole", at the westernmost point of the island. Ride your bike to the next stop and arrive at Marina di Campo (Marina di Campo), a village at the foot of two hills on a plain called Maremma dell’Elba. The famous Italian writer Dante Alighieri mentioned in his works that "Maremma" is also located in the continental region between Tuscany and Lazio. Thanks to its prehistoric, Roman and Etruscan settlements, the Maremma region on the mainland and islands has provided visitors with stunning scenes for centuries. Return to Procchio and then to Portoferraio. At a grand dinner of the group company, we ended our beautiful journey on the island. The island has a variety of scenery and we can enjoy the fun of cycling.
Overnight at Hotel del Golfo-Procchio

Day 7

Breakfast and transfer by boat and minibus back to Siena.





Guided Tours