This is a not-too-strenuous, albeit hilly tour. All will enjoy the classic Tuscany landscape of small hills, olive groves and vineyards. Some days have more difficult, more off road options for more experienced cyclists. The tour starts in San Gimignano, world famous for its beautiful towers. Our route takes you to a series of historic towns and villages: Radda-in-Chianti, with its all-round views over the rolling hills of the Chianti Classico country, Castellina-in-Chianti also on a hill-top site, the exquisite walled village of Monteriggioni, surrounded by well-tended vineyards, Volterra, with its Etruscan walls and museum. The tour ends at the wonderfully well-preserved medieval city of Siena, whose centrepiece is the shell-shaped tiled square called the Campo where the famous Palio (traditional horse race) is held twice a year. Both Radda and Castellina are in the Chianti Classico region, world famous for its red wines, while San Gimignano is known for its 'Vernaccia' (a dry white wine, particularly refreshing after a hot afternoon's ride). The vineyards are interspersed with olive groves and there is a range of gourmet olive oils in the shops. The higher hills and steeper slopes are often covered with oak forest. Among the culinary specialities of the region are the sausages and salamis made from wild boar. Before or after your cycling tour there is an opportunity to visit Pisa or Florence but you may want to spend a minimum of two nights in Florence if you want to see much of the city.

Season

April to November

Level of Difficulty

Moderate. A high standard of fitness is not necessary but clients should be able to cycle for up to 45 km/28miles per day across undulating hilly terrain in rain or sun. Most days can readily be shortened.

The Bikes

We provide 24 speed, front suspended Mountain Bike but on request there are also 24 speed hybrid bikes. We usually provide mountain bikes with wider tyres, which are more suitable for off-road or rough tracks. Included is a rear baggage rack with panniers, puncture repair kit, tyre pump,  a water bottle is not included for hygiene reasons but the holder is on the bike,  chain lock with key and a bar bag for carrying maps, snacks etc.. Tool kits are not provided, so you should bring a simple lightweight metric multi-tool and two tyre levers. Helmets we advise for hygiene reasons that you bring your own or buy a new one on arrival in Siena for between 31 and 62 Euros. Cycle hire fee is 80 Euros per bike per week, payable at the start of the tour in cash only.  We need to know customers' height and inside leg measurements. The bikes are delivered to the first hotel in San Gimignano at the start of the tour and collected from the hotel in Siena at the end of the tour. We also need your approximate arrival time in San Gimignano so that we can arrange for your bikes to be handed over to you on arrival, please make sure that we are informed.

Baggage Transfers

Each day that you move on to new accommodation during the tour, your baggage (normally up to 20kg/44 pounds per person) will be transferred to await your arrival at the next night's stop. Please note that for cycling tours this service does not include bikes or riders.

Maps & Route Notes

We provide specially written route descriptions for each day's cycling, together with a road map of Siena province with the non-urban sections of the route highlighted.

General Information

Hotels: The hotels described are our usual choice of accommodation, however if these are not available then alternatives are used and if these are of a different standard you will be informed at the time of booking.

Baths/showers: Many rooms with ensuite/private facilities have a shower rather than a bath, usually because of limited space. Some hotels/guesthouses may however have a separate room in the house where a bath is available to guests.

Breakfast: in countries such as Italy are usually coffee and toast/croissant, if you want more for breakfast then we would suggest you purchase some food the night before. 

Special Dietary Requirements: It is important for you to tell us if you have any dietary requirements when you book your holiday so that we can inform everyone that you are staying with.

Single Supplements: are payable on most of our tours.  The single supplement guarantees the privacy of your own room, however, rooms can at times be small and in some places may not enjoy the same facilities as double/twin rooms. 

Solo Traveller Supplements: are payable when the cost per bag of moving luggage increases.

Language: When travelling in less frequented areas you will not necessarily come across people speaking English. Remember you are experiencing a different culture, buy a phrase book and try to learn a little of the local language!

Luggage: When staying in hotels, sometimes your luggage will have been taken to you room awaiting your arrival. However don’t be surprised if your luggage is waiting for you to take it up to your room. Please politely ask someone if you need assistance.

Route Notes: Please note that one set of route notes per room booked is included in the cost of the holiday. If you require more sets of notes then there is a charge of £25 per set ordered.
Route notes are not issued to clients booking escorted departures.

Insurance: All clients must have appropriate cover for the activities included for the duration of our trip.

Accommodation & Meals

Accommodation is in a variety of 3 star hotels with two nights spent in a comfortable guesthouse and one night in a guesthouse. One evening meal is included. Picnic lunches are not included, but materials for picnics can be purchased in each of the towns and villages where you stay. On some days there are also conveniently located restaurants en route. Please note that this is a popular route and we sometimes have to use alternative hotels.

q       Nights 1 and 2: San Gimignano. Our first choice of hotel in the ‘Town of Towers’ is a comfortable and very popular 3-star hotel set in the central square of the town which has changed little since mediaeval times. Dinner is normally taken in the hotel’s own restaurant, which has a commanding view over rooftops and the surrounding countryside.

q       Night 3: In Volterra, in origin one of the oldest cities in Italy, our first choice is a welcoming and comfortable 3 star hotel, in a restored late 17th century villa, situated in a peaceful area between the mediaeval and Etruscan town-walls. All rooms are ensuite. The hotel even has an outdoor swimming pool with a magnificent view south-westwards towards the sea. 

q       Night 4: A very pleasant guesthouse within the the medieval walled village of Monteriggioni; once the day-visitors have gone it is a haven of peace; the rooms (limited in number) are simply furnished, but all have private facilities.

q       Nights 5 & 6: We stay in a clean and comfortable guesthouse.

q       Night 7: The tour ends at the wonderfully well-preserved medieval city of Siena, whose centrepiece is the shell-shaped tiled square called the Campo where the famous Palio (traditional horse race) is held twice a year.

Note: In Italian law, all hotels must close their restaurants one night a week, so alternative evening meal arrangements at restaurants in the near vicinity of your hotel are a possible occurrence on this and other tours in Italy.

 
Arrival

The tour starts in San Gimignano. From Florence there is a regular bus service by “TRA-in” (the Sienese bus company), the bus leaves from Florence close to the train station, travel time 1 hour 15 mins (sometimes a change is necessary at Poggibonsi). From Pisa, take the train to Poggibonsi via Empoli and pick up the bus from here. Approx journey time is 2 hours 15 mins. Alternatively if booked in advance we can arrange a taxi transfer from Pisa to San Gimignano for Euro’s 85 (approx) and from Florence Euro’s 85 (approx). This is to be paid in cash to the driver.

Itinerary

q       Day 1: Arrive in San Gimignano. If you haven't organized the private transfer then please let us know at approx what time you will be arriving so that we can organize for your bikes to be delivered to the hotel. Alternatively your bikes will be delivered on the morning of Day 2.

q       Day 2:  Your are free to relax around San Gimignano or alternatively  you can do a circular ride to Certaldo riding through Vernaccia’s, San Gimignano’s white wine vineyards. Distance: 38km

q       Day 3:  San Gimignano – Volterra. A spectacular ride westwards over the hills to the Etruscan fortress town of Volterra. Distance: 37km. For those clients that are fitter and who want a more challenging day today then a visit to the Monastery of San Vivaldo is also an option. Distance: 48km

q       Day 4: Volterra – Monteriggioni. Two options are available to you again today. Option 1 which passes through the  small town of Colle di Val d’Elsa. Distance: 41km. Option 2 which crosses the natural reserve of Tatti, the medieval town of Casole. Distance: 59km. Both rides visit the monastic settlement of Abbadia Isola.

q       Day 5: Monteriggioni – Radda in Chianti. Today you will be cycling into the Chianti hills and you will have the opportunity to sample several Chianti wines. The high point of today ride is Fonterutoli and the incredible open views. Distance: 45km

q       Day 6: A circular ride today throughout the Chianti hills visiting some of the most beautiful villas, castles and land church. Distance: 39km

q       Day 7: Radda in Chianti – Siena. Your last day is an easy short ride which will lead you to the interesting “Palio” town of Siena. En route why not visit the cantines and test the wines of Dievole. The proprietor is always ready to lead you on a memorable tour. Distance: 28km

q       Day 8: End of Tour in Siena.

The hotel in Siena is a short taxi ride from the train station.  There is an approximately hourly train service to Florence.  For Pisa and Pisa airport change trains at Empoli. If you are travelling from Siena to Rome airport: buy tickets for the complete journey to Rome airport before starting your journey from Siena. It is often difficult to buy train tickets in Rome Termini station and there are heavy fines for travelling to the airport without a ticket. Change trains in Chiusi. You may need to pay an inter-city supplement for the leg between Chiusi and Rome.

Extend your stay

We can book extra nights in Pisa, Siena, Florence or in the “Cinque Terre”, a rugged and picturesque coastal region,  centred at Monterosso near La Spezia. Details and prices on request. Extra nights added in during the cycling tour can also be booked, this will normally entail a small supplementary cycle hire charge.