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7 Days Hills and Sea Cycling Holiday in Tuscany, Italy
This listing has no upcoming availability. Check out these similar experiences

This listing has no upcoming availability. Check out these similar experiences

(No availability) 7 Days Hills and Sea Cycling Holiday in Tuscany, Italy

Siena, Province of Siena, Tuscany, Italy

Guided Cycling Holiday in Italy

From splendid Siena to the unique Elba Island, you will have an exciting journey in road bike through the beautiful Tuscan countryside. Between the hills and the sea, along with the scenic island roads, through hidden villages full of history and unspoiled nature, a road bike is a privileged viewpoint to appreciate the inimitable variety of landscapes. This trip is offered in spring and autumn when you can appreciate the beauty of the local landscapes at their best. Divided into stages, this holiday is appropriate for cyclists with a medium level of training, but the constant presence of the minibus and the guides are a safeguard in case of unexpected problems and ensure complete assistance. You can also have a private tour if you would like to. Come and cycle through the beautiful Tuscan countryside!

Key information

  • Trip type: Guided
  • Lodging: Point to Point
  • Terrain: Paved road
  • Difficulty level: Challenging (Cyclist needs to have high level of fitness, must be an active rider, the terrain includes really challenging climbs/or 46-80 or more miles per day)
  • Total Distance : 226.8 Miles / 365 Kilometers
  • Vacation type: Road cycling holiday
  • Type of bike: Road bike
  • E-bike: Available to rent


  • 5 days of cycling
  • Technical guide and assistance
  • Luggage transfers through the tour
  • Technical bike shirt for your cycling holiday
  • Return ferry and transfer to hotel
  • 6 breakfasts and 6 dinners
  • 6 nights’ lodging


5 days with instruction
Group size: Maximum of 7 participants
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You will be staying in various accommodations through the holiday. On the first and the second night, you will overnight in Siena. You will move to Volterra on the third night and San Vincenzo on the fourth night. Finally, on the fifth and the sixth night, you will stay in Portoferraio.


Day 1

Upon your arrival in Siena with your own transport, the staff will welcome you. There will be presentation of the bike tour, preparation of bikes, welcome drink, and then dinner at Monteriggioni Castle.

Day 2: Siena - Chianti Hills (loop)

There is no better way to get in touch with this extraordinary region than starting your unique tour with a cycling day through the famous and breathtaking Chianti Hills. These rolling hills are famous all over the world for their delicious wine. You will start your day pedaling towards Radda in Chianti, an enchanting old Tuscan village. Your road will be an easy and constant ascent, surrounded by a lot of vineyards and pristine nature. After leaving Radda in Chianti, you head to Castellina in Chianti. When you arrive in the village, you will take a delicious cappuccino to recover energy for your last effort, coming back to Siena. A typical acclaimed restaurant is waiting for you to close this unforgettable first day.

  • Distance: 65 kilometers

Day 3: Siena - Volterra

Starting from Siena, crossing small hillside villages with a view of the castle of Monteriggioni on the way, you reach Abbadia a Isola, which was an important stop along the Via Francigena, the ancient route that in medieval times connected Canterbury to Rome. You then continue to Castel Pietraio and Colle Val d’Elsa, an ancient Etruscan town that owes its development in the 15th century to glass production. Pedaling, you reach San Gimignano at 324 meters a.s.l.

In the Val d’Elsa, a small medieval town whose many towers still intact dominate the landscape. Finally, you arrive in Volterra, an ancient town with over 3,000 years of history. Situated in the province of Pisa, Volterra is considered, with its Acropolis, its surrounding walls and its “gates” to the historic center, one of the Italian municipalities that has best conserved its Etruscan origins. The cathedral, the imposing Medici Fortress, and Palazzo dei Priori instead date back to the medieval period. Moreover, for fans of the Twilight saga, it was here that the fascinating vampire Edward Cullen gives himself up to the dreaded Volturi. At night, it is dinner time and you can visit the town.

  • Distance: 78 kilometers

Day 4: Volterra - San Vincenzo

You leave from Volterra with your bikes after an excellent breakfast to ride through a small hamlet, Saline di Volterra, which famous for its saltwater springs and salt production. Through Pomarance and Montecerboli, important areas for the development and utilization of geothermal energy, up and down through historical villages such Sarezzano, Monteverdi Maritime, and Doronatico, you arrive at your destination: San Vincenzo.

On the Ligurian Sea, the famous Etruscan Coast, San Vincenzo developed as a town in ancient times and is therefore of extreme historical and cultural importance. In 1971, the Giro d’Italia started and finished in San Vincenzo which is now an important tourist resort. After settling into your room, you will have time to relax and get ready for an excellent dinner with the rest of the group based on typical local produce.

  • Distance: 80 kilometers

Day 5: Portoferraio (eastern part of Elba Island)

After breakfast and transfer by ferry from Piombino to Portoferraio on Elba Island, you leave to explore the island by road bike. Green oasis of the Tuscan archipelago, Elba island is a mixture of beaches and cliffs, terraces overlooking the sea, villages perched on the hillsides with magnificent colors, and flavors and fragrances that give the impression of visiting places where time has stood still. The third largest island in Italy, Elba was, thanks to its iron deposits, the heart of the Etruscan civilization and the remains of outposts and the Necropolis can still be seen today.

After passing from Roman rule to the Ostrogoths and the Lombards, the Island is full of testimonies covering thousands of years of history. Keep your eyes well open when you look at the horizon, because if you see a ship flying the “skull-and-crossbones” flag, it could well mean that the Ottoman corsairs, dreaded by the island’s inhabitants in the fifteenth and sixteenth centuries, have returned. From the Volterraio road (Bagnaia, Nisporto, Nisportino), you will arrive in Rio dell’Elba, a typical medieval hamlet where a rushing stream worked the many mills.

Soon after, continuing up the road which offers breathtaking views at every turn, you will reach Capoliveri, a beautiful medieval village perched on a hill at 167 meters a.s.l. You then return to Portoferraio, a Medici town with museums, mansions, and fortresses. Capital of the island, it was founded in the sixteenth century thanks to the Grand Duke of Tuscany Cosimo I. After arriving at your hotel, there will be time to check your bikes, relax, and enjoy the local food for dinner.

  • Distance: 60.6 kilometers

Day 6: Portoferraio (western part of Elba Island)

The day starts with breakfast to give you energy for the day’s cycling before heading off in the direction of Procchio and the smallest municipality on the island: Marciana Marina. As you climb up through the hills, you go through the hamlet of Poggio, nestled among century-old chestnut woods, until you reach Marciana, one of the most ancient inhabited areas of the island at a height of 375 meters a.s.l. Descending in the direction of the most famous beaches, you go through Chiessi, a small hamlet situated on the “Costa del sole”, to the far west of the island.

Cycling towards your next stop, you reach Marina di Campo, a village situated at the foot of two hills, in the plain called Maremma dell’Elba. “Maremma” is also an area on the mainland, between Tuscany and Lazio, mentioned by the famous Italian writer Dante Alighieri in his works. Thanks to its prehistoric, Roman and Etruscan settlements, over the centuries the Maremma areas, both on the mainland and on the island, offer visitors stunning scenarios. Returning to Procchio, you then arrive back in Portoferraio. An excellent dinner in the company of the group concludes your superb stay on the Island. It is a land of diverse landscapes which you have been able to appreciate better by riding your bikes.

  • Distance: 81.4 kilometers

Day 7

You will have breakfast and transfer by minibus back to Siena.


This cycling holiday takes place in Tuscany, Itay, covering towns of Siena, Volterra, San Vincenzo, and Portoferraio.


You will have breakfasts and dinners served for you during the holiday. Your delicious dinners take place in the specially chosen restaurants where you can taste typical local dishes and wines of the best vineyards.

The following meals are included:

  • Breakfast
  • Dinner

The following dietary requirement(s) are served and/or catered for:

  • Regular (typically includes meat and fish)
If you have special dietary requirements it's a good idea to communicate it to the organiser when making a reservation

What's included

  • 5 days of road cycling
  • Technical bike guide
  • Technical assistance
  • Technical bike shirt
  • Luggage transfer
  • Return ferry to Elba Island
  • Transfer from station to the hotel
  • Taxes
  • 6 nights’ accommodation
  • 6 breakfasts and 6 dinners

What's not included

  • Road bike hire (Giant TCR Advanced)
  • Lunches
  • Drinks at dinner
  • Laundry service
  • Tips
  • Medical insurance

Cancellation Policy

  • A reservation requires a deposit of 30% of the total price.
  • The deposit is non-refundable, if the booking is cancelled.
  • The rest of the payment should be paid on arrival.
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