With its thirteen outstanding medieval towers, it is clear why the town is on the UNESCO world heritage list. You will ride over clouds of sunflower fields under the Tuscan sun and along cypress lined country roads through olive groves and vineyards, which produce some of the world’s finest olive oil and wine.
You shall savour the flavour of these ingredients in the outstanding local cuisine.
Travel to Etruscan and Roman times, from one picturesque hilltop to the next, each with its own history and charisma. Get pinched, this is the real thing.
TRIP HIGHLIGHTS
• Stay in a quintessential Tuscan Estate with swimming pool and excellent traditional Tuscan restaurant
• Visit the natural, artistic and cultural treasures of San Gimignano and the surrounding area, on the UNESCO heritage list
• Wonderful landscapes, wide open fields, cypress lined avenues, vineyards and olive groves
• Incredibly well preserved medieval and renaissance villages and hilltop towns
• Peaceful country roads, friendly Tuscans and delicious regional culinary specialties

8 DAY PROGRAMME

Day 1 - Arrive in San GimignanoSan Gimignano on HB basis
Arrive at the farmhouse near San Gimignano and unwind, as this shall be your comfortable Tuscan home for the next week. Breathe in the wonderful country air and take a stroll along the classic green rolling hills, marvelling at the breath-taking views of the surrounding countryside. Immerse yourself in the tranquillity! And If you arrive early, you can visit San Gimignano, one the pearls of this wonderful Region. A delicious Tuscan dinner is included tonight at the accommodation.
Day 2 - Vineyards of Ulignano and Certaldo Alto & BarberinoSan Gimignano on BB basis.
Today you will cycle through prestigious vineyards towards Ulignano and the charming hilltop village of Certaldo, hometown of the renowned Italian writer Boccaccio. The ascent to Certaldo is either by funicular or by a very steep climb. After visiting its ceramic-decorated main square and stunning churches, you can choose an extended ride to Barberino and Tavernelle in the Chianti Classico area, offering magnificent views.
Short or long look ride to Uglignano and Certaldo - km 47,3 or km 66,7

Day 3 - San Gimignano and Poggio del Comune San Gimignano on BB basis
This day offers a lovely circle tour around the highest hill in the immediate area, Poggio del Comune. Pedal along country lanes to Castel San Gimignano where we recommend a stop at the local bar for a delicious sandwich (panino). Continue through a nature reserve of woods and cow pastures as you return to San Gimignano for a glimmering ride and a refreshing drink.
Loop ride via Poggio del Comune - km 36,5

Day 4 - Colle Val d’Elsa, Monteriggioni, Lilliano & Castellina in Chianti San Gimignano on BB basis
Today you choose the ride that suits you best. A morning transfer takes you to Colle Val d’Elsa. Cycle along the undulating hills of the Val d’Elsa to the perfectly preserved medieval hamlet of Monteriggioni. Continue uphill, past abundant vineyards and stimulating woods, either towards Lilliano or directly up to Castellina in Chianti, where the views are spellbinding.
Afternoon transfer from Colle Val d’Elsa back to the accommodation.
Transfer to Colle Val d’Elsa and ride to Monteriggioni, Lilliano and back to Colle Val d’Elsa for return transfer to San Gimignano (Castellina in Chianti extension) - km 40 or km 66.

Day 5 - Rest Day in Siena or FlorenceSan Gimignano on BB basis
Today, you can choose to visit the nearby cities of Siena or Florence, both easy to reach with public transportation. Famous for its “Palio” horse race, promenade the narrow streets of Siena marvelling at the magnificent palaces, churches and squares. Alternatively, visit the Duomo, the “Ponte Vecchio” and experience the unforgettable Renaissance splendour of Florence.

Day 6 - Volterra to San Gimignano San Gimignano on BB basis
A morning transfer takes you to the magic and mysterious Ancient Etruscan city of Volterra, where you can explore its Alabaster artisan shops, the interesting Etruscan Museum and the Roman Theatre, superb palaces and alluring city walls. Then hop on your bike for an exhilarating downhill ride into the valley, through a patchwork of wheat fields and impressive villas, followed by a delightful ascent to return to San Gimignano.
Transfer to Volterra and ride back to San Gimignano. km 43,5

Day 7 - Casole d’Elsa and the Montagnola to San Gimignano San Gimignano on BB basis
Transfer to Casole d’Elsa. The romantic landscape between Castel San Gimignano and Casole d’Elsa is mostly open pasture used for sheep grazing and wheat cultivating. The essence of the Montagnola area shall captivate you with its quiet, peaceful countryside. Cross-beautiful rolling green hills and marvel the small local churches and quintessential Tuscan farmhouses.
Transfer to Casole d’Elsa and ride back to San Gimignano km 28

Day 8 - Arrivederci San Gimignano!
The trip and our services end after breakfast, unless you have booked a transfer to the airport or other supplementary services.


5 DAY PROGRAMME


Day 1 - Arrive in San Gimignano San Gimignano on HB basis
Arrive at the farmhouse near San Gimignano and unwind, as this shall be your comfortable Tuscan home for the next week. Breathe in the wonderful country air and take a stroll along the classic green rolling hills, marvelling at the breath-taking views of the surrounding countryside. Immerse yourself in the tranquillity! And If you arrive early, you can visit San Gimignano, one the pearls of this wonderful Region. A delicious Tuscan dinner is included tonight at the accommodation.
Day 2 - Colle Val d’Elsa, Monteriggioni, Lilliano & Castellina in Chianti
San Gimignano on BB basis Today you choose the ride that suits you best. A morning transfer takes you to Colle Val d’Elsa. Cycle along the undulating hills of the Val d’Elsa to the perfectly preserved medieval hamlet of Monteriggioni. Continue uphill, past abundant vineyards and stimulating woods, either towards Lilliano or directly up to Castellina in Chianti, where the views are spellbinding. Afternoon transfer from Colle Val d’Elsa back to the accommodation.
Transfer to Colle Val d’Elsa and ride to Monteriggioni, Lilliano and back to Colle Val d’Elsa for return transfer to San Gimignano (Castellina in Chianti extension) - km 40 or km 66.
Day 3 - Vineyards of Ulignano and Certaldo Alto & Barberino San Gimignano on BB basis.
Today you will cycle through prestigious vineyards towards Ulignano and the charming hilltop village of Certaldo, hometown of the renowned Italian writer Boccaccio. The ascent to Certaldo is either by funicular or by a very steep climb. After visiting its ceramic-decorated main square and stunning churches, you can choose an extended ride to Barberino and Tavernelle in the Chianti Classico area, offering magnificent views. Short or long look ride to Uglignano and Certaldo - km 47,3 or km 66,7


Day 4 - Volterra to San Gimignano San Gimignano on BB basis
A morning transfer takes you to the magic and mysterious Ancient Etruscan city of Volterra, where you can explore its Alabaster artisan shops, the interesting Etruscan Museum and the Roman Theatre, superb palaces and alluring city walls. Then hop on your bike for an exhilarating downhill ride into the valley, through a patchwork of wheat fields and impressive villas, followed by a delightful ascent to return to San Gimignano.
Transfer to Volterra and ride back to San Gimignano. km 43,5
Day 5 - Arrivederci San Gimignano!
The trip and our services end after breakfast, unless you have booked a transfer to the airport or other supplementary services.
Getting there and away
Florence and Pisa Airports, are served by major and low cost international flight carriers. Rome Airport is a bit farther away. There is a regular bus and train service from Florence to Poggibonsi and San Gimignano, as well as connections possible from Pisa, Bologna and Rome. For more and detailed information visit the website www.trenitalia.it
We can also arrange private transfer to and from the airport.

Accommodation and Meals
You stay in a family run accommodation located 5km from San Gimignano, is a wine-and oil-producing Tuscan farmhouse. It covers an overall area of 40.00 hectares, much of which used to grow fodder and cereals. The accommodation is simple in style but very characteristic, with great views on the hills and the valley surrounding, a good Tuscan style home-cooking restaurant and a nice swimming pool open from May to September. All rooms have private en-suite bathroom. A good continental breakfast is served each morning.

Alternative accommodation
During high season, you might be booked into alternative accommodation which may not be listed in your route notes. The start or end of the cycling routes may be slightly altered, if so pay attention at the start and end of the routes. In some cases, we provide extra descriptions to be used when starting from / returning to an alternative accommodation. In choosing alternate accommodation we have tried to maintain the same standards and quality and, whenever possible, location (in the same town or village), in order to modify the routes as little as possible.

Activity characteristics
In this part of Italy there are no bike lanes so the routes follow mostly small secondary asphalt roads and the so-called strade bianche (sing. strada bianca), i.e. ‘white roads’. These roads, which are paved with compacted gravel, are peculiar to Tuscany. You will occasionally meet a car on them. Certain “strade bianche” can be probably asphalted in the near future: if you come across a newly asphalted stretch, please inform us so that we can change the route description at that point. We have done our best to keep to a minimum sections of road with traffic, but unavoidable there are a few short sections of primary roads where there is traffic, specially near larger towns or important intersections. Some of the routes are marked with red/white markings and you will be cycling through vineyards, fields and some forest.

Luggage transfer
There is no luggage transfer included in this trip. When you travel with public transport you always take your luggage with you.

A note on our self guided adventures
Self guided walking or cycling requires individuals to use problem solving skills, be adaptable and have a keen eye. It is recommended that you are comfortable map reading, referring to route notes and that you have a good sense of direction (or are willing to work on improving this!) Sometimes route finding, losing your way, finding it again and asking the locals for help is all part of the adventure. If you’ve never been on a self guided trip, after the first couple of days you will get the hang of if as the vast majority of our first time travellers attest. Please be assured that our written material issued to you for route finding is updated regularly and we provide a 7day service hotline in the event of any problems. There is a certain level of the unknown that comes with self guided trips; however with a methodical approach potential problems will be averted. The freedom of a self guided trip is something that, once experienced, is sought time and time again.

Fitness preparation
The concept behind most of our trips is active holidays and the fitter you are the more easily you will adjust and enjoy yourself. We expect participants to take responsibility for their fitness and preparations on a consistent basis prior to departure, and INCREASE the regular weekly training schedule in the two months leading up to departure. That way, when you start walking, you will feel relaxed and comfortable and strong, having done more than sufficient preparation for the trip. You will also have more energy to enjoy the views, take photos and explore the sights in your spare time, rather than just make it to the next hotel. During the day is when the most interesting features of interest will be found, and being fit allows you to optimize every situation you encounter. As a minimum, we recommend 40 minutes of aerobic type exercise; running, swimming, biking, hill walking, or gym work two to three times a week for two to six months leading up to your walk. Note the best training is the activity that you are actually going to be doing; walking up and down hill, and cross-country. Practice this as much as possible. Training should be stepped up as you get closer to departure, to an amount you feel appropriate (you don’t want to cause yourself an injury!). Using your gear before departure (boots, daypack, clothing, etc.) gives familiarity and comfort whilst on the walk. It makes sense to know that all your gear ‘works for you’ BEFORE departure, rather than discovering how things work or fit (or don’t!) on the trip you have invested so much in. Use the philosophy of ‘getting fit to go walking’, rather than ‘going on a walk to get fit’, to avoid problems.

CYCLING TIPS & INFORMATION
Cycling responsibility Bicycle touring has its inherent risks. It is a sport whose safety is dependent upon the judgment and alertness of the cyclists. As a cyclist you are responsible for the way you ride and the condition of your bicycle. We, nor the local agent, are responsible for possible damages (physical or not) to the participants due to: physical activity during the tour, not following road regulations, alcohol consumption, breaking of means or materials, lack of medical assistance in far-off places or other not predictable circumstances.
Rental Bikes
If you have rented a bike with us, you can pick it up the next day of your arrival at the bike shop in town, near the accommodation. Our adult hybrid-bikes are provided with comfortable seats, reliable components, 21 gears and Shimano Alivio components. All bikes, before being handed out are cleaned and overhauled. All bikes are equipped with: a padlock and key that must be used at all times when not riding the bike; luggage pannier attachments at the rear and 1 rear side bag per bike; 1 front bag and map compartment; front and back lights; puncture repair kit; pump and spare inner tube all of which you should know how to use. One every 2 bikes there is a KM distance counter. You are expected to know the vary basics of bike mechanics and how to mend a puncture or change a tire. If something more serious happens to the bike that you cannot repair on the spot, call the shop and they will help you fix it or suggest the best and fastest solution