8 Days/ 7 Nights

1574 € per person

The package includes:

  • Transfers included. Transportation included from and to the airport: – by car for 1-3 people – by shuttle bus 4-8 people
  • 7 nights’ accommodation
  • Three nights stay in a 3 star hotel in Chianti half board
  • Four nights stay in a 4 star hotel in Val d’Orcia half board
  • Experienced bike guide for four days
  • Bike rental for six days
  • All the afternoon activity: Tour Montefioralle, Tour San Pietro in Bossolo, Nobile wine tasting, tasting Cinta Senese and Chianti, Brunello tasting and farewell dinner
  • Trip to Siena and lunch in a selected restaurant
  • Accompanist for all the activities by car or by shuttle bus
  • Welcome cycle pack: drink bottle, energy bar



Single room, en-suite bathroom – from €1574 per person

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

  • Room typeSingle room
  • BathroomEn-suite
  • Sleeps up to 1
  • Total number of rooms 6

Double room, en-suite bathroom – from €1574 per person

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

  • Room typeDouble room
  • BathroomEn-suite
  • Sleeps up to 2
  • Total number of rooms 10


Non-participating guests – prices from €1374 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.


A week cycling in the beautiful settings of Chianti and Val d’Orcia; an opportunity to cycle roads in the heart of Tuscany incorporating the two different areas with famous wines and gastronomy. During this holiday you’ll have the opportunity to immerse yourself in the Italian culture and way of life, whether shopping at local outdoor markets, frequenting local bars for a real cappuccino or dining at a typical authentic restaurant. The first part of your holiday will be spent in the glorious wine region of Chianti amongst hills of vines and castles. Following this you’ll spend a day in the city of Siena, famous for the Palio – the bareback horserace around the main square, before your transfer to another special area, the Val d’Orcia filled with its vineyards and rolling countryside. The routes have been carefully chosen so that you cycle on quiet roads with a low volume of traffic thanks to the knowledge of the guide accompanying the group. Along the way you will admire our outstanding countryside, vineyards, and medieval hamlets. At the end of the daily bike tour, you will be able to enjoy the wine, gastronomy, spas, art and culture. With stunning views, vintage wines and glorious Italian food, this journey encompasses all the best aspects of Tuscany and Italy.


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 and enjoy some of the most beautiful landscapes and local points of interest. You’ll be able to immerse yourself in the Tuscan culture and enjoy the spectacular terrain around you. Each and every afternoon following the cycle rides, there are interesting wine and food tastings from long established and high quality producers. There is also day set aside for you to visit Siena and enjoy lunch at a charming local restaurant serving regional specialties.

An example of a usual weeks itinerary

Day 1

Collection from the airport or station and check into your hotel in Chianti where you’ll receive a warm welcome and a relaxing evening.

Day 2

Your first morning ride in the beautiful area surrounding Badia a Passignano, an interestingly shaped fortified abbey with corner towers founded on an isolated site reachable by a road known in medieval times as the ‘Strada Senese del Sambuca’.  This is a special area where plant and animal species are protected by regional laws and where the surrounding area is covered by wooded hills, cultivated areas of vineyards and olive groves. There is a low level volume of traffic, ideal for cycling which is considered to be one of the best ways to view the countryside. Our route will return us in the direction back to your hotel. In the afternoon, you’ll be taken to visit Montefioralle “uno dei borghi più belli d’Italia” which means, one of the most beautiful hamlets in Italy.

Day 3

After a quick briefing, we’ll head out on today’s route which is in the area of Montefiridolfi where you’ll enjoy a ride through the typical Chianti rolling countryside of wine estates and forested areas dotted with olive groves. Along our route we’ll stop at a natural coffee bar where you can purchase a locally produced delicacy while resting and enjoying the spectacular scenery. After our break we’ll head back towards your hotel where as always, we’ll take the most scenic route with the most low level of traffic as possible, passing along our way the occasional white road, which this area is famous for.

Afternoon activity: You’ll be taken to San Pietro in Bossolo where you’ll visit the Romanesque Pieve, a stunning Parish church once property of Florentine bishops before the Cathedral Chapter until 1340. Afterwards you’ll be able to taste the local products.

Day 4

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. Then we’ll take you to your next hotel ready for your Val d’Orcia experience.

Day 5

Today’s cycle route will find us travelling down the Nobile wine road around the area of Montepulciano with rolling vineyards and wine estates providing a glorious route and the grapes for the famous wine you’ll sample this evening. 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. In the afternoon, you will be able to taste the world renowned Nobile wine of Montepulciano at a chosen historic cellar.

Day 6

We’ll meet as usual in a local coffee bar before heading out on a ride that takes us to Monticchiello di Pienza, a very small and quaint medieval village close to Pienza, founded in Roman times, before it was expanded during the middle ages. It has a Roman Gothic style church which overlooks the castle and the village 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’ll be a good occasion to take a stroll or rest and soak up the ambience of this historical location. Later in the afternoon, you will be able to enjoy Chianti wine, olive oil and Cinta Senese (cured meat) tastings at a superb local producer.

Day 7

Once we’ve had our cappuccino briefing, we’ll head on to the Brunello Wine Road in the direction 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 have the opportunity to wander around this unspoilt renaissance town, birthplace of Pope Pius II, also well-known for the wonderful Pecorino cheese and specialist shops. In the afternoon you’ll visit the old abbey of Sant’Antimo and later you’ll enjoy a guided Brunello wine tasting in a historic cellar followed by a farewell dinner.

Day 8

Departure day and transfer to the airport or station.