8 Days/ 7 Nights

1358 € per person

The package includes:

  • Transfers included. By car for 1-3 people, by shuttle bus for 4-8 people from and to the airport.
  • 7 nights’ accommodation
  • 5x cycle tours with experienced cycle guide
  • Rental bike for duration of stay, with repair kit, pump etc
  • Daily breakfast
  • Evening meal
  • Afternoon activities including cured meat and Chianti wine Tasting, Brunello wine tasting and dinner, Cheese Tasting, Beer Tasting, and Nobile Wine Tasting
  • 1x Trip to Siena and lunch in a selected restaurant
  • Guide for all activities by car or by shuttle bus
  • Welcome cycle pack, water bottle, energy bar
  • Farewell dinner in selected typical restaurant



Single room, en-suite bathroom – from €1358 per person

Comfortable single room with a single bed and en-suit bathroom

  • Room type Single room
  • Bathroom En-suite
  • Sleeps up to 1

Double room, en-suite bathroom – from €1358 per person

Double room with single beds that can be made up as a double with en-suite bathroom

  • Room type Double room
  • Bathroom En-suite
  • Sleeps up to 2


Non-participating guests – prices from €1208 per person

It’s possible for a partner or friend to join this holiday even if they don’t want to participate in the activity, but they must share a room with a participating guest.

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.


  • Cycle kit (seasonal)
  • Cycle crash hat
  • Cycle shoes and pedals (unless using normal pedals supplied with bike)
  • Money for lunches, beverages and visits
  • At time of booking:-
  • Request for crash hat,
  • and if possible the following measurements -taken from the centre of cranks to top of your seat, from the front of your seat (nose) to the middle of your handle bars where the bars are clamped into the stem.


Bring your helmet and your appetite for this fantastic 7 night cycling, food and wine holiday in the Val d’Orcia, located in the heart of Tuscany. You’ll admire breathtaking views, medieval hamlets and rolling vineyards, enabling you to be totally immersed in this truly spectacular countryside as you cycle through some outstanding scenery with your experienced local guide. All our routes have been carefully chosen so that you cycle on quiet roads with a low volume of traffic with the best places of interest for you to enjoy, all thanks to the expert knowledge of the guide accompanying you. Enjoy delicious dinners each evening as well as world renown wine, olive oil and cured meat tastings. You’ll have the opportunity to stroll around Chianciano Terme in the evenings relaxing to the sound of local night life in the coffee bars, restaurant and squares, hassle free. There’s a day trip to the beautiful city of Siena the home of the Palio a bare-back horse race, a chance to shop in the city ‘Italian style’, and to spend some time soaking up the atmosphere.  There is an afternoon visit to an interesting craft beer company. The scenery, wine and gastronomy are just three of the many things that define Tuscany, and with this unique break, you’ll have the chance to experience a lot more!


The routes you’ll be cycling have been handpicked for the quiet roads and their low levels of traffic. Depending on the ability of the participants, the routes can be adjusted accordingly. During each ride you’ll have a well-deserved coffee stop along the way at an authentic coffee bar, where you can treat yourself to a freshly prepared coffee, tortina or panino. All of the rides will be guided by an English speaking cyclist who has an excellent knowledge of the area.

Every morning you will meet at a local coffee bar to discuss your cycle route before setting off. These routes are designed for you so that you have the chance to cycle through some of the most beautiful landscapes and cultural places of interest in this area of Tuscany. You’ll be able to immerse yourself in the Italian lifestyle and enjoy the spectacular countryside around you. Each and every afternoon following the cycle rides, there are interesting wine and food tastings from long established and high quality producers, these include the sensational local Pecorino (sheep) cheese, world famous wines and the cured meats of the Cinta Senese(ancient breed of pig) There is also a day set aside for you to visit Siena, famous for it’s Palio ( a bare-back horse race) which is held in Piazza del Campo the centre of the historical old town, also you will be able to enjoy lunch at a charming local restaurant serving regional specialties.

An example of a usual weeks itinerary

Day 1: Transfer from the airport or station to check in at your hotel in Tuscany, where you’ll receive a warm welcome.

Day 2: After breakfast, we’ll meet at a local coffee car and go over the day’s route. 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 ride to Chianciano Terme. Later in the afternoon, you will be able to enjoy Chianti wine, olive oil and Cinta Senese (an ancient breed of pig) cured meat tasting at a local producer in the historic old town.

Day 3: Once we’ve had our cappuccino briefing, 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. Later, we’ll visit Montalcino, a charming hill top town and also the old abbey of Sant’Antimo. In the evening, we’ll enjoy a guided Brunello wine tasting along with a delicious dinner in a selected historic cellar.

Day 4:  We’ll meet over a coffee before heading out on a ride that takes us to the hamlet of Montefollonico located on a wooded ridge looking down onto Val di Chiana and the Val d’Orcia and just a stone’s throw from Montepulciano. It is locally appreciated for the Vin Santo, a delicioius dessert win having been enjoyed as far back as the middle ages. This hamlet was founded around the year 1000 but digs nearby testify that the area was settled during prehistoric times. The name derives from the wool-dyeing carried out by the villagers which the Romans named Fullonico, which developed over time into Monte a Fullonico then as it’s known today as Montefollonico. It is a place off the usual tourist map accessible by a road which runs up the side of the wooded ridge. A great place to stop for a light snack and a chance to stroll around to explore this extraordinary place where life continues with or without the influence of outsiders, changing only by the seasons.
In the afternoon you’ll enjoy a guided wine tasting at a well- known historic wine cellar.

Day 5: Today we take a break from the saddle to visit the city of Siena (famous for the Palio which is a bare-back horse race around the centre) where we will enjoy some sightseeing and a delicious lunch in a handpicked typical restaurant. Here in Siena you’ll have the opportunity of experiencing this calm, small city with many sights including the beautiful Cathedral as well as the unusual fan-shaped main square, Piazza del Campo. It is a bustling university city with many interesting shops and coffee bars.

Day 6: After our morning coffee, our cycling route takes us to Monticchiello di Pienza, a very small and quaint medieval village close to Pienza, founded in Roman times, then it was expanded during the middle ages. It has a Roman Gothic style church which overlooks the castle and is locally well known for its theatre productions. The village is set amongst beautiful rolling countryside with heavily forested hillocks. After you’ve treated yourself to a snack it’s an occasion to take a stroll or rest and soak up the ambience of this historical location.
The afternoon we will take a trip to a local craft beer company, where you can enjoy sampling some fantastic products.

Day 7: Today’s splendid route will find us travelling along the Nobile wine road with Montepulciano in the distance. You’ll pass the rolling vineyards and wine estates which grow the grapes of the Nobile wine you will sample later. We’ll ride 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.   During the afternoon you’ll enjoy tasting the Nobile wine ( which grapes you have seen growing during the morning cycle ride) in a renowned historic cellar. In the evening there will be a farewell dinner at a selected typical restaurant.

Day 8: Breakfast and Departure day with transfer to station or airport.

A stay in Chianciano Terme lets you enjoy the exceptional local culture, wine, gastronomy and gelato as you take part in your cycling activities. A small lively town, with shops, restaurants, Etruscan museum, historic thermal spas, swimming complex and walks with wonderful views. 

cycling cortona