Road Bike Tours Italy
Just Like You... We Ride

Tuscany (Italy)


Available dates:

  • April 14th 2024
  • May 19th 2024 Sold Out
  • June 2nd 2024
  • July 7th 2024
  • September 8th 2024 Confirmed
  • October 6th 2024

Bike Tour

Tuscany – A Fantastic Journey

Tuscany Bike Tours

The best of Tuscany: Chianti, Siena, Montalcino, San Quirico D'orcia, Pitigliano, Lago di Bolsena, Civita di Bagnoregio.

This road bike tour in Tuscany will take you through some of the most picturesque landscapes in the World, immersed in history with unique scenery full of surprises, where you can 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 among those specialized in local cuisine.

The objective of this cycling holiday, as indeed that of the other tours we organize, is in fact not just to ensure that you discover new and captivating places while riding your road bike, but also to make sure that you enjoy the very best that the area can offer. This Tuscany road bike tour will take you through two regions of Italy in 6 days. Each day you’ll be riding between 60 and 80 km, so the tour is suitable for medium-trained cyclists, always accompanied by our guide riding alongside the group as well as our minibus providing support as required.

Tuscany (Italy)
Start point:
Finish point:


  • 6 nights accommodation
  • 6 dinners
  • 6 breakfasts
  • Luggage transfer
  • Taxes
  • Minibus assistance
  • Technical bike guide
  • Technical assistance
  • Technical Bike Shirt
  • Transfer station/hotel
  • Medical Assistance Insurance
Not included:
  • tips
  • laundry service
  • drinks at dinners
  • lunches
  • everything is not explicitly written on this page!


Available dates:

  • April 14th 2024
  • May 19th 2024 Sold Out
  • June 2nd 2024
  • July 7th 2024
  • September 8th 2024 Confirmed
  • October 6th 2024

Why tour with us?

Got a Question?

Feel free to reach out! We’re happy to answer any questions you may have.


Customer testimonials




7 days


7 people

Total KM

335 km

Daily KM

65/75 km


medium difficulty


bike & e-roadbike rent

Contact us

Do you want to customize your tour?


Day by day

Day 1: Arrival

Arrival in Siena, welcome from the staff. Presentation of the trip, assembly and preparation of bikes. Welcome drink.

Dinner Monteriggioni Castle. Overnight at Sangallo Park Hotel.

Day 2: Siena and Chianti Loop

  • Distance: 73 km45 mi
  • Elevation: 1150 m3773 ft

Our first contact with this extraordinary region takes place in the Chianti Hills area. This area, famous all over the world, gives the name to the excellent Chianti wine. We’ll start our cycling day directly from our Hotel in Siena and heading to Gaiole in Chianti, we’ll ride through these rolling hills, surrounded by vineyards deep in an enchanting landscape.

Once we arrive in Radda in Chianti we’ll stop for a cappuccino and cornetto in its magnificent old square.
After our stop, we’ll keep on riding up and down, enjoying breathtaking views: vineyards and wild areas. going through historic villages. Getting to the Hotel, we can wind down in his swimming pool and get ready for our delicious dinner in Siena.

Overnight at Sangallo Park Hotel.

Day 3: Siena – Montalcino

  • Distance: 72 km45 mi
  • Elevation: 1200 m3937 ft

After an excellent breakfast, departure towards Monteroni D’Arbia on quieter secondary roads, through the magnificent Val d’Arbia. We 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 us to our destination today: Montalcino. This town is well-known for the production of the famous Brunello wine, which you may be interested to know is never sold less than five years after the grape harvest, and becomes “Reserve” after at least six years . Welcoming accommodation and an excellent dinner of local food and fine wine bring this first day by bike to an end.

Overnight at Hotel dei Capitani.

Day 4: Montalcino Loop

  • Distance: 68 km42 mi
  • Elevation: 1000 m3281 ft

A new unforgettable day is waiting for us. Today we’ll get in touch with the unique Val D’Orcia,riding on peaceful back roads. We’ll start our day dealing with the descent from Montlcino to Torrenieri, then we ride with continuous up and down through ancient villages, where we’ll have our inevitable cappuccino and espresso.

Then, we must absolutely visit the splendid San Quirico d’Orcia, where we can have a lunch in a typical “trattoria” to recovery energy for taking on the demanding Montalcino ascent. This ascent is 10 km long with a difference in altitude of 500m. An exclusive dinner in this fairy-tale village will close our fourth day.

Overnight at Hotel dei Capitani.

Day 5: Montalcino – Acquapendente

  • Distance: 76 km47 mi
  • Elevation: 1200 m3937 ft

Another superb day through villages surrounded by breathtaking nature. San Quirico d’Orcia is the first village we encounter, the spa in its hamlet Bagno Vignoni is famous. Radicofani, a wonderful village dominated by a castle, is waiting for us along the way. Finally, we ride into the Lazio region at Acquapendente, where we will be justly rewarded for our efforts with a visit of the historical centre and an excellent dinner.

Overnight at Sant Apollinare Farmhouse.

Day 6: Acquapendente – Lake Bolsena

  • Distance: 61 km38 mi
  • Elevation: 700 m2296 ft

A change of scenery is the main feature of today’s ride: we 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 we head for Lake Bolsena, a destination that coincides with our return to the Lazio region, Civita di Bagnoregio is waiting for us. Here, a very different landscape will provide the ideal setting for an evening in good company and a delicious dinner.

Overnight at Hotel Royal.

Day 7: Departure

Breakfast and transfer to Siena.

Does this look like fun? Book your tour now!


Customer testimonials


Frequently Asked Questions

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:

  • entry-level carbon frame road bike;
  • high-end road bike;
  • E-road bike.

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.

Feel like Home

Night accommodation in the best hotels

Holidays with friends

Photo book & welcome kit

We take care of you!

Bike guide & technical assistance

contact us

Request information about this tour

Fill out the form with your details, pick the date you prefer and send us your request! We will reply you as soon as possible!

Would you like a more direct contact with our team? Feel free to reach out!

More tours

Discover more bike tours

Open chat
Scan the code
Hello! Can we help you?