The Tuscany Road Biking Tour will take you through some of the most picturesque landscapes in the world as you expore the Italian countryside. Ride through immersed in history and through unique scenery. This is a tour that allows you to discover the real Italy.
In a region that has made hospitality an art, you will enjoy a combination of excellent accommodation and acclaimed restaurants, carefully and personally selected from those specialized in local cuisine. The objective of this cycling adventure is to ensure that you discover new, captivating places, enjoy the best the area offers, and take advantage of the adventurous nature of road biking. You will ride through two regions of Italy, both with scenery to die for that you’ll appreciate from the saddle.
Tuscany Road Biking Tour
The Tuscany Road Biking Tour will take you through some of the most picturesque landscapes in the world as you expore the Italian countryside. Ride through immersed in history and through unique scenery. This is a tour that allows you to discover the real Italy.
In a region that has made hospitality an art, you will enjoy a combination of excellent accommodation and acclaimed restaurants, carefully and personally selected from those specialized in local cuisine. The objective of this cycling adventure is to ensure that you discover new, captivating places, enjoy the best the area offers, and take advantage of the adventurous nature of road biking. You will ride through two regions of Italy, both with scenery to die for that you’ll appreciate from the saddle.
Ride for a week in gorgeous Tuscany, one of the gems of Italy’s world-class travel scene.
Challenge yourself on some rides and sit back to enjoy the view on others.
Explore villages with gorgeous churches and monasteries that date back centuries.
Between rides, revel in the first-class cuisine and hospitality of Tuscany at restaurants and hotels.
Trip map for Tuscany Road Biking Tour
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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.
After breakfast, you’ll ride towards Monteroni D’Arbia on quieter secondary roads through the magnificent Val d’Arbia. You will then continue towards Asciano, with its splendid Monte Oliveto Maggiore abbey. Riding up and down between hills and cypress trees, you will arrive at Buonconvento in the Ombrone Valley.
The final stretch of the day’s ride takes you to your destination, Montalcino. This town is well-known for its production of the famous Brunello wine, which is never sold less than five years after the grape harvest.
Today is all about the unique Val D’Orcia as you ride on peaceful backroads. You’ll start your day with the descent from Montalcino to Torrenieri, then you will ride through ancient villages, where you’ll have breaks for cappuccino and espresso.
Stop to visit the splendid San Quirico d’Orcia, where you can have a lunch in a typical “trattoria” to recovery energy for taking on the demanding Montalcino ascent. An exclusive dinner in this fairytale village will end your day.
San Quirico d’Orcia is the first village you’ll encounter today, and the spa in its hamlet of Bagno Vignoni is famous. Radicofani, a wonderful village dominated by a castle, is waiting for you further along the way.
Finally, you’ll ride into the Lazio region at Acquapendente, where you will be justly rewarded for your efforts with a visit to the historical centre and an excellent dinner.
Ride back, briefly, into the Tuscany region and arrive in Pitigliano, with its characteristic historical center called “Little Jerusalem” because of the presence of an ancient Jewish community. After leaving Pitigliano, head for Lake Bolsena, where Civita di Bagnoregio is waiting for you. Here, a very different landscape will provide the ideal setting for an evening in good company with a delicious dinner.
After a wonderful week, you’ll head back to Siena to depart. Safe travels!
These reviews reflect all trips offered by this local tour partner on 10Adventures, not just the tour you’re viewing.
This guided tour is always run as a group tour where you’d be joining a group, however, custom private tours can be organized for groups of 4 and more. 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 | ||
|---|---|---|---|---|---|---|
2025-09-07 Siena, Italy 7 days / 5+ Spaces Left | 2025-09-13 Bolsena, Italy | 7 | 5+ | $3,850USD | ||
2025-09-21 Siena, Italy 7 days / 5+ Spaces Left | 2025-09-28 Bolsena, Italy | 7 | 5+ | $3,850USD | ||
2025-10-05 Siena, Italy 7 days / 5+ Spaces Left | 2025-10-11 Bolsena, Italy | 7 | 5+ | $3,850USD |
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
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 Road Biking Tour
This tour is based in hotels. Hotels on this trip are 3 and 4-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. Solo travellers may be required to pay a supplement.
How hard is the Tuscany Road Biking Tour?
We rate this tour as a 3/5. Each day you’ll be riding between 60 and 80km, 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 Road Biking 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 Road Biking Tour in English?
Yes, the tour guides are English-speaking.
Where does the Tuscany Road Biking Tour end?
It will end in Alba.
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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