8 Days/ 7 Nights

1208 € per person

The package includes:

  • 7 nights’ accommodation in double room (4 star hotel)
  • Transfers from and to airport or train station (Florence, Rome, Perugia, Pisa)
  • 4 x Days of guided cycling through handpicked routes
  • English speaking local cycle guide for 4 days
  • Bike rental (high level) for duration of stay, including repair kit, pump and lock (Crash hat on request)
  • Transfer from and to Siena or Orvieto (day 4) (lunch not included)
  • Transfer from and to Firenze or Assisi (day 7) (lunch not included)
  • 1 x Trip to Italian Shopping Style
  • Transfer for all visits and activities in the programme by car or by shuttle bus



Double room, en-suite bathroom

A spacious double room with two comfortable single beds, which can be made into a double-bed. It is equipped with amenities and has it’s own private bathroom.

  • Room type Double room
  • Bathroom En-suite
  • Sleeps up to 2
  • Total number of rooms 10

Single room, en-suite bathroom – supplement € 210 per person

A lovely room with a comfortable single bed, which is fully equipped with amenities. It also has it’s own private bathroom.

  • Room type Single room
  • Bathroom En-suite
  • Sleeps up to 1
  • Total number of rooms 4

This very nice 4 star hotel hotel is located in the lively little town of Chianciano Terme, well positioned, with easy connections to Italy’s major central cities. The hotel is within walking distance to all of the bars, restaurants and shops, which you can easily explore on foot. With its modern and spacious rooms complete with en-suite bathrooms and extremely comfortable beds, you’ll find it easy to unwind and relax during your free time! You can enjoy a refreshing drink on the sun-drenched terrace and dine in the restaurant, which features delicious traditional Tuscan delicacies and regional specialties


Non-participating guests – prices from €741 per person

It’s possible for a partner or friend to join this holiday even if they don’t want to participate in the cycling tours.

Non participants guests must share a room with a participating guest and they are included in the excursions: day 4 (Siena o Orvieto) and 7 (Firenze o Assisi).

Prices for non-participating guests vary depending on when you travel and the room you stay in, check availability and prices when you proceed to the booking page.


Brunello Wine Tasting

You will be taken to a very good Brunello wine cellar where you’ll have the opportunity to taste the world famous wine together with cured meats and cheese. € 40 pp

Nobile Wine Tasting

Another superb wine produced in this area. You’ll be taken to a very good wine cella and you’ll be able to sample the world famous wine together with cured meats and cheese. € 25 pp

Pecorino Sheeps Cheese Tasting

You’ll be able to visit a sheeps cheese producer in the heart of the Val d’Orcia and you’ll be able to taste the different varieties of this truely wonderful cheese accompanied with cured meats, bread, salad and wine. € 16 pp

Cinta Senese – ancient breed of pig

An opportunity to visit this particular breed of pig, once almost extinct, and learn how they are bred and well cared for. Then you’ll be able to appreciate the taste and quality of the meat. € 25 pp


  • Cycle kit (seasonal)
  • Cycle shoes and pedals (unless using normal pedals supplied with bike)
  • Money for lunches, beverages and visits
  • Your own crash hat (or you can request)


Bronze package

This week-long recreational cycling holiday in the south-eastern corner of Tuscany is a unique opportunity to cycle around this stunning area of Val di Chiana and the UNESCO national heritage park of the Val d’Orcia. On booking, you’ll be able to choose either a hybrid or an ebike (electric motor assisted) cycle. You’ll join an experienced cycle guide who knows this area very well and you’ll be able to cycle on quiet picturesque routes through this stunning countryside which includes rolling woodlands, vineyards, medieval hamlets and hilltop towns. Perfect Cycling conditions for leisure cyclists who wish to calmly ride through this beautiful region at a leisurely pace enabling you to experience the culture and many places of interest on two wheels instead of inside a car. During the ride there will be opportunities to stop and take photographs as you please, we’ll pause for a coffee break at a local coffee bar chosen for its natural ambience. Our routes are carefully selected and designed for low level of traffic and the point of destination will also have a historical and architectural appeal, giving you a close-up experience of this part of Tuscany around the areas of Montepulciano, Montalcino, Pienza and Cortona.


Every morning we’ll meet at a local coffee bar to talk about your mornings cycle ride before setting off. The less taxing routes have been created so that you’ll be able to ride at a comfortable and leisurely pace arriving at the destination where you’ll be able to treat yourself to a panino, cappuccino or a refreshing beer! You’ll be able to immerse yourself in the Tuscan culture and enjoy the spectacular terrain around you. Once you’ve enjoyed exploring the destination stop you’ll be able to decide if you wish to return to Chianciano Terme by bike with the cycle guide, or take the option of returning by minibus with Luca. Once you’ve returned, you’ll be free to relax and explore the town of Chianciano Terme with its spas, shops, museum, swimming pools or you can explore further afield. There is a very good bus service connecting the towns which is economical and reliable. There are many ways in which you can spend your free time. If you would like suggestions, feel free to ask your friendly hosts or guides. This is a good opportunity to really experience this part of Italy!

  • Day 1:Transfer from the airport or station to check in at your hotel in Chianciano Terme where you will receive a warm welcome and an evening meal.
  • Day 2: Today we’ll take the scenic road with views of Lago di Trasimeno in the distance, to the pretty medieval town of Cortona (also known for the novel Tuscany Under the Sun)set on the side of a large forested hill which was founded by the Etruscans over 2000 years ago. We’ll take a well deserved break at a local coffee bar where you’ll be able to treat yourself to a panino or tortina or a light lunch. Then you’ll have the opportunity to look around this beautiful town before the return to Chianciano Terme by minibus. In the afternoon you’re free to explore the town or surrounding area. You’ll have lunch or evening meal at your hotel.
  • Day 3:We’ll head on to the Brunello Wine Road around the area of Montalcino where we’ll cycle through rolling vineyards and wine estates heading for Pienza and a well-deserved break at a local bar where you can treat yourself to a snack. You’ll love Pienza a classic renaissance town also well-known for the wonderful Pecorino cheese shops which you can explore at your leisure before returning to Chianciano Terme by bike with the cycle guide or by minibus with Luca. The afternoon can be spent relaxing or taking advantage of the local bus service to explore interesting nearby towns and villages. We can assist with information on tickets etc. Or suggest particular things to do. You’ll have lunch or evening meal at your hotel.
  • Day 4: You have a cycle-free day today and Cycling Tuscany will take you to either Siena or Orvieto where you can wander, browse and explore one of these outstanding cultural places. You’ll return for evening meal at your hotel.
  • Day 5: Today we’ll cycle along the Nobile wine road to Montepulciano which is said to be one of the highest hilltop towns in Tuscany situated on a ridge with Val d’Orcia on one side and Val di Chiana on the other providing spectacular views. Then you’ll have the opportunity to reward yourself with a snack and after, walk the steep historic narrow roads lined with specialist shops of leather and local products including cheese and wine and situated at the top of the town is Piazza Grande with its wonderful ancient buildings. The return journey to Chianciano Terme can either be by bike with your guide or in the minibus with Luca. In the afternoon you are free to relax, but don’t forget that your town of Chianciano Terme has a public swimming pool complex, Etruscan museum and thermal spas and delicious icecream parlours. You’ll have lunch or evening meal at your hotel.
  • Day 6: We’ll be heading out on a ride that takes us to the hamlet of Montefollonico located on a wooded ridge looking down onto Val d’Chiana and the Vall d’Orcia and just a stone’s throw from Montepulciano. It is locally appreciated for the Vin Santo, a delicious dessert wine having been enjoyed as far back as the middle ages. A great place to stop for a light snack and a chance to stroll around to explore this extraordinary place where in the historical centre, life seems to continue at a gentle pace. After, you can decide if you’d like to return by bike to Chianciano Terme with your cycle guide or in the minibus with Luca. You’ll have lunch or evening meal at your hotel.
  • Day 7:Enjoy another cycle-free day, where Cycling Tuscany will take you to either Florence or Assisi where you can wander, browse and explore one of these outstanding and historical places. You’ll return for evening meal at your hotel.
  • Day 8:Departure Day and transfer to airport or station, we wish you a pleasant return journey.
cycling cortona