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From splendid Siena to the unique Elba Island, the Tuscany Hills and Sea Road Bike Tour is a perfect way to soak up the world-class scenery of Tuscany, one of Italy’s most desirable regions. With rides taking you up and down, between the hills and the sea, you’ll experience the views while also adventuring. A road bike is a privileged viewpoint to appreciate the inimitable variety of landscapes from, and with your wheels to take you everywhere, you can discover hidden villages full of history and acres of unspoiled nature.
Each night, you’ll enjoy carefully chosen characteristic accommodation and delicious dinners in restaurants serving local dishes and the wines of the best vineyards. With a guide and a minibus always at hand, the intermediate cyclist and better can take the adventure of a lifetime from the hills to the sea of Tuscany.
Tuscany Hills and Sea Road Bike Tour
From splendid Siena to the unique Elba Island, the Tuscany Hills and Sea Road Bike Tour is a perfect way to soak up the world-class scenery of Tuscany, one of Italy’s most desirable regions. With rides taking you up and down, between the hills and the sea, you’ll experience the views while also adventuring. A road bike is a privileged viewpoint to appreciate the inimitable variety of landscapes from, and with your wheels to take you everywhere, you can discover hidden villages full of history and acres of unspoiled nature.
Each night, you’ll enjoy carefully chosen characteristic accommodation and delicious dinners in restaurants serving local dishes and the wines of the best vineyards. With a guide and a minibus always at hand, the intermediate cyclist and better can take the adventure of a lifetime from the hills to the sea of Tuscany.
Ride through the rolling hills that make the Tuscan countryside so beautiful and recognizable.
Adventure along islands in the sea, the perfect complement to your countryside adventure.
Experience the fine-tuned hospitality of one of Italy’s most sought-out regions.
Dine on delicious local foods and sleep in carefully chosen hotels each evening.
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When you arrive in Siena, you’ll enjoy a welcome drink, get your bike fitted, and then have dinner with the group.
You first ride takes place in the Chianti Hills area. This area, famous all over the world, is the birthplace of Chianti wine. You’ll start your cycling day riding through rolling hills surrounded by vineyards.
Once you arrive in Radda in Chianti, you’ll stop for a cappuccino and cornetto in the magnificent old square. After your stop, keep on riding with views of vineyards and historic villages. At the hotel, wind down in the swimming pool and get ready for a delicious dinner.
Starting from Siena, cross through small hillside villages and enjoy a view of the castle of Monteriggion. Reach Abbadia a Isola, which was an important stop along the Via Francigena, the ancient route that in medieval times connected Canterbury to Rome. 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. Finally, arrive in Volterra, an ancient town with over 3,000 years of history. Situated in the province of Pisa, Volterra is considered one of the Italian municipalities that has best conserved its Etruscan origins.
Begin today with a ride through a small hamlet, Saline di Volterra, famous for its saltwater springs and for salt production. Continue through historical villages including Sarezzano, Monteverdi Maritime and Doronatico en route to your destination, San Vincenzo.
On the Ligurian Sea on 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.
After breakfast and a ferry from Piombino to Portoferraio on Elba Island, you ride out to explore the island. The green oasis of the Tuscan archipelago, Elba Island is a mixture of beaches and cliffs, terraces overlooking the sea, and villages perched on the hillsides with magnificent colour. 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.
Arrive in Rio dell’Elba, a typical medieval hamlet where a rushing stream worked the many mills. Soon after, continue up the road, which offers breathtaking views at every turn. Reach Capoliveri, a beautiful medieval village perched on a hill, for a break before returning to Portoferraio, a Medici town with museums, mansions, and fortresses.
The day starts with breakfast 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 will pass through the hamlet of Poggio, nestled among century-old chestnut woods. Reach Marciana, one of the most ancient inhabited areas of the island, then descend in the direction of the island’s most famous beaches. Reach Marina di Campo, a village situated at the foot of two hills.
Arrive back in Portoferraio. An excellent dinner in the company of the group concludes your superb stay on the island.
After breakfast, you will transfer by minibus back to Siena. Safe travels!
The reviews below are from all the tours organized by the local team in Italy.
This guided road biking tour in Tuscany is run as a fixed-departure tour where you’d be joining a group, however, custom private tours can be organized for those willing to travel with their group only (please contact us with your preferred date and the number of people in your group and we will create the itinerary just for you).
Prices below are per person:
| Start | Finish | Duration | Places Left | Price | ||
|---|---|---|---|---|---|---|
2025-09-14 Siena, Italy 7 days / 5+ Spaces Left | 2025-09-20 Siena, Italy | 7 | 5+ | $3,950USD | ||
2025-09-21 Siena, Italy 7 days / 5+ Spaces Left | 2025-09-27 Siena, Italy | 7 | 5+ | $3,950USD |
Meals
6 breakfasts and 6 dinners are included.
Accommodations
Accommodations for 6 nights are included.
Transportation during the Tour
Transportation for this tour will include a minibus, both for the transport of your luggage and for any type of assistance that may be required, and the presence of a technical guide cycling alongside you. Airport transfers are not included, however, you will be transferred to/from Alba Train Station.
Also Included
- Minibus assistance
- Taxes
- Technical bike guide and assistance
- Technical bike shirt
- Station and hotel transfers
- Return ferry to Elba Island
Not Included
- Tips
- Laundry
- Drinks at dinner
- Medical insurance
- Lunches
- Anything not mentioned as included
Optional Extras
- Additional nights before or after the tour
- Single occupancy upgrades
- Optional activities or excursions
- Bike rental:
- Road bike
- E-road bike
Accommodation for Tuscany Hills and Sea Road Bike Tour
This tour is based in hotels. Hotels on this trip are 4 and 5-star and offer modern conveniences that can make this trip more pleasant. Rooms may have fireplaces or access to amenities such as hot tubs, steam rooms, or private decks to lounge on.
In some cases, the accommodation listed below may need to be substituted for other comparable accommodations.
Single Rooms and Solo Travelers
Rooms are double occupancy. You can pay a supplement of $425 to have a private room in a hotel where possible (please enquire about the pricing). Solo travellers may be required to pay a supplement.
How hard is the Tuscany Hills and Sea Road Bike Tour?
We rate this tour as a 3/5. Each day you’ll be riding between 65 and 70km, so the tour is suitable for intermediate cyclists.
Do I need a visa to travel to Italy?
Check with your local country about visa requirements. You could also try this website, though you should verify with your government.
Are meals included on the Tuscany Hills and Sea Road Bike Tour?
6 breakfasts and 6 dinners are included.
Do I need insurance?
Yes, it is mandatory to have health and medical insurance to join this trip, and your insurance should cover cycling. Get your Travel Insurance.
How do I get to Siena to start this tour?
The closes airport to Siena is Florence (FLR), from where you can take the train to Siena.
Is the Tuscany Hills and Sea Road Bike Tour in English?
Yes, the tour guides are English-speaking.
Where does the Tuscany Hills and Sea Road Bike Tour end?
The tour ends in Siena.
Can I rent a bike?
Yes, you can rent a bike during the booking process. Bikes available are the Giant TCR Advanced 2 model in all sizes. In addition, you can choose between road bikes, trek bikes, and E-road bikes.
Can I bring my own bike?
Yes. If you bring your own bike, it should be a road bike suitable for the demands of the tour
Can I change the departure date?
Yes, if you are a group of at least 4 people we can adapt our departures to your needs.
Can you accommodate dietary restrictions?
Yes, we can. All of the included restaurants can provide a personalized menu.
Do I need special vaccines to travel to Italy?
Check with your family doctor.
Are there any travel restrictions for Italy?
Please check with your local government about travel restrictions before you book your tour. This map from the US Department of State provides an overview of the current status in countries around the globe. The UK‘s Foreign Office and Government of Canada also provide advice on foreign travel. Note that the travel advice may change depending on your nationality.
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