Self-guided cycling
10 nights,
hotel-to-hotel
Level: 2+
Moderate plus
15.0Kg CO2e
Headwater
Navigation App
Optional
e-bike hire
This ten night holiday has been carefully crafted to cleverly balance cultural highlights and historic treasures with natural beauty and stunningly scenic cycling. It's a perfect choice too if you like the idea of combining timeless countryside cycling with the use of local transport to explore the eternal cities of Siena and Florence on foot.
Your holiday starts in Volterra, a real Etruscan gem with its tangle of alleys home to alabaster workshops and secret chapels, in the heart of the Era Valley. You'll pedal through the archetypal Tuscan countryside, cypress dotted rolling hills, olives, vines, sunflowers, and on, via postcard-pretty Certaldo, to Colle di Val d'Elsa where you'll spend four nights. From here, you can enjoy day trips to the great art cities of Florence and Siena before pedaling on through panoramic wine country to the tiny hamlet of Pescille, a short cycle from medieval San Gimignano. Your route then takes you through the Castelvecchio Nature Reserve (great for bird spotting) giving you a real sense of achievement as you loop back to Volterra for your final night.
The hotels we've selected for this holiday are among our best, and include a magnificently restored 17th century palazzo, a wonderfully renovated, stylish watermill which dates back to the 16th century and belonged to the famous Medici family, and a family-run, traditional hotel overlooking the soaring towers of San Gimignano. As Chianti is synonymous with great food and wine, we've made sure evening meals are a celebration of local flavours throughout.
Distances vary and parts of the countryside are fairly hilly, so take your time on the steeper climbs and admire the wonderful long distance views.
Read more about this holiday in The Headwater Blog and The Headwater Blog.
Arrive in Volterra where you've time for a dip in the hotel pool and a wander round the town's tangle of cobbled alleys and hidden squares before dinner.
Today it's a downhill whizz out of hilltop Volterra and into the pretty Era Valley where spectacular views of the surrounding timeless Tuscan countryside open up as you pedal. After climbing out of the valley, you'll soon pass through the pretty hamlet of Castagno where we suggest a well-deserved coffee stop in the local bar. Your route continues on to Gambassi Terme, a well-preserved spa town with cobbled streets, 12th century church and lovely shaded gardens. Lunch here perhaps in one of the many trattorie then, soon after leaving the town, you'll pick up the famous Via Francigena for the gentle, mainly downhill stretch to medieval Certaldo.
You stay at Hotel San Lino.
Mastercard
AmEx
Pool
Hairdryer
WiFi
TV
Minibar
Aircon
Safe
Hotel San Lino is set within the medieval walls of Volterra, a 5-minute walk from Piazza dei Priori. Originally built as a convent in 1480, Hotel San Lino has been attentively renovated to preserve the original architectural features that celebrate its historical charm.
Rooms here are spacious and bright, exquisitely decorated in Tuscan style, with traditional terracotta floors and wooden furniture. All rooms are equipped with ensuite bathroom, TV, air conditioning and Wifi. You will stay in a superior room with a view of the swimming pool.
A buffet breakfast is served in the main dining room, and includes homemade cakes, cured meats, yogurt and cereals.
The property also benefits from a garden with outdoor swimming pool and panoramic terrace.
Explore stunning Certaldo, Boccaccio's birthplace. Split into two distinct halves, the medieval centre of Certaldo Alto with its fabulous ancient buildings, is accessed by funicular and offers spectacular views across the Val d'Elsa. On the other hand, Certaldo Basso is the more modern part of the town with shops, bars and restaurants. You could also spend time today, relaxing by the hotel pool.
Today's route explores the panoramic wine country between Certaldo and Colle di Val d'Elsa. You'll follow the official, mainly off-road, Chianti Wine Route where you'll find lots of tasting opportunities! It's then on to the old town of Poggibonsi, a perfect stop for lunch and to visit the ruins of its unfinished 15th century fortress. The day ends with gentle pedalling through tree-lined meadows and a valley of poppy and sunflower fields to Colle di Val d'Elsa.
You stay at Hotel Certaldo.
Shops
Market
Bank
Cash machineMastercardAmExPoolHairdryerWiFiTVAirconSafe
Located on the fringe of Certaldo Basso, on the River Elsa, the stunning 4 star Hotel Certaldo dates back to the 1500s when it belonged to the infamous and all powerful Medici family. It started life as a water mill and signs of its original use are still in evidence, including its mighty water wheel. Over the 20th century, the mill was used as a power turbine and produced enough electricity to service the entire town of Certaldo up to the 1950s!
The mill was lovingly restored and converted into a hotel in 2007 and now boasts 30 modern and stylish rooms with all the amenities you would expect of a comfortable 4 star hotel. There is also a pleasant garden (with pool) and terrace area overlooking the river, and a lounge area with tv and books where you can relax after a day's exploring.
Room upgrades: Superior Room, Deluxe Room or Junior Suite.
Superior rooms are larger than standard rooms and have a minibar and free wifi. Deluxe rooms are larger than the superior rooms, they also have a minibar and free wifi. The Junior Suites are larger than all the other room types, they have a minibar and free wifi.
Extra nights: Please contact us for details.
There is so much to see and do in and around Colle di Val d'Elsa that you really will be spoiled for choice. However, today we recommend hopping on the local bus (from just outside the hotel) for the 30min ride to the great medieval city of Siena. Visit the Palazzo Pubblico with its impressive pre-Renaissance frescoes and climb the Torre del Mangia for the best views of the town and surrounding Sienese countryside. For lunch, or simply a drink, there is no better place than Siena's beautiful shell-shaped Piazza del Campo.
After a fairly long day yesterday, we propose that you spend a relaxed morning in Colle di Val d'Elsa. The historic town dates back to Etruscan times with a cathedral, museums and fine Renaissance buildings. After lunch in the old square, maybe spend relax in the hotel's spa before a pre-dinner stroll along the lovely River Elsa where limestone-rich rapids come crashing dramatically downstream.
No trip to Tuscany would be complete without a visit to the charming city of Florence, arguably the most beautiful city in the world! It's just an hour on the local bus (which leaves from just outside the hotel) giving you plenty of time to explore the Uffizi (closed Mon), Duomo and Baptistery. If you want to escape the crowds, we suggest you cross the Ponte Vecchio to the quieter side of the Arno to visit the Boboli Gardens.
Get back on your bike this morning and enjoy superb rolling views before the ride up to Casole d'Elsa, a beautiful village characterised by ancient vermilion-hued buildings and blessed with stunning views from its hilltop position. Take time to explore its 12th century church (frescoes by Gano da Siena) and impressive fortress before an early lunch perhaps in the lovely piazza. You then wind north through wonderfully scenic countryside, the fabulous medieval towers of San Gimignano providing a formidable backdrop as you pedal on to Pescille.
You stay at Palazzo San Lorenzo & Spa.
Mastercard
VisaAmExPoolHairdryerWiFiTVMinibarAirconSafe
The Palazzo San Lorenzo and Spa is located in the upper part of the medieval town of Colle di Val d'Elsa, better known as the old village of the “town of lead crystal-glass”. The building dates back to the 17th century when it started life as a hospital, whilst today, the public spaces are decorated with statues and crystal chandeliers.
The spacious rooms come with free Wi-Fi, Flat screen TV, free mineral water in the minibar and air conditioning. They have parquet floors and marble bathrooms. Headwater customers get the Superior rooms as standard.
A buffet breakfast is served in the breakfast room, a wonderful 'winter garden' completely lit by natural light, where you can find a large range of sweet and savoury delicacies. Your evening meals (when included), will be taken in the hotel’s restaurant which serves traditional Tuscan dishes.
San Gimignano is just a short cycle away, its towers giving this hilltop town a distinctive Manhattan-style skyline. Explore its myriad of narrow streets and many hidden cobbled squares before popping back to your tranquil hotel for a refreshing dip in the sparkling swimming pool.
It's a short downhill ride to San Gimignano before a gentle climb up through classic Tuscan landscapes of vines, olive groves and fields ablaze with sunflowers. It's then an almost entirely downhill cycle into the pretty Era Valley. There's a real sense of achievement on your final pedal through open countryside, enjoying spectacular views, before your last climb back to the ancient cobbled streets of Volterra.
You stay at Hotel Pescille.
MastercardAmExPoolHairdryerWiFiTVMinibarAircon
The Hotel Pescille is located just 4km outside San Gimignano, in the heart of the Tuscan countryside, surrounded by olive groves and vineyards. It started life as an old farmhouse before being converted into the 3 star hotel it is today. Evidence of its origins still remains however, with its ancient tower housing the hotel's small agricultural museum. There are pleasant gardens surrounding the hotel - with lovely views of the surrounding landscape - and it also benefits from an outdoor swimming pool.
All rooms at the Hotel Pescille are ensuite and are simple yet spacious with tiled floors, whitewashed walls and pristine white linen; air conditioning. satellite TV, minibar and hair dryer also all come as standard. Rooms have views onto either the timeless Tuscan countryside, or the roofs and mediaeval towers of San Gimignano itself.
The hotel does not have a restaurant open for dinner, a short walk will be leading you to a local restaurant.
Room upgrades: Superior room
Superior rooms are much larger than standard rooms
You stay at Hotel La Cisterna.
ShopsHairdryerWiFiTVAirconSafe
Tea/coffee
Enjoy your stay at this picturesque 14th century building hotel nestled in the heart of San Gimignano. With your room either overlooking the main piazza or the classic Tuscan countryside be prepared to lose time as you soak in the timeless charm of San Gimignano.
La Cisterna offers beautifully decorated rooms in both Florentine and modern style all of which are equipped with air conditioning, free Wifi and a flat-screen satellite TV.
A continental buffet breakfast is served at the on site restaurant Le Terrazze, where you can enjoy panoramic views over the historical square whilst your sip on your morning caffé.
The advantageous position of this property will allow you to easily reach shops, points of interest and a vast choice of restaurants in the town centre.
Room upgrades: Double room with view and balcony
Upgrade to a room with a private balcony and immerse yourself in the stunning vistas of San Gimignano.
If you'd like to extend your trip with extra hotel nights we recommend: Hotel Cosimo De Medici, Florence; Hotel La Luna, Lucca; Hotel Alessandro della Spina, Pisa; Hotel Chiusarelli, Siena.
ShopsMarketBankCash machineMastercardAmExHairdryerWiFiTVAirconSafe
This 3-star hotel is beautifully decorated, with rooms in individual styles - some are traditionally Tuscan whilst others are funky and modern. Parts of the the building actually date back to the 18th century, and the reception and public rooms are designed with this in mind, with Persian rugs, stained glass windows and wrought iron doors in evidence.
Although just off the main Via Nazionale, only 2 minutes' walk from the central station and 5 minutes from the Duomo, the hotel faces an internal courtyard for peace and quiet. All the rooms are double glazed, and all have air-conditioning so there is absolutely no reason not to have a good night's sleep!
There is no restaurant at the hotel, but there is plenty of choice nearby.
Extra nights: Please contact us for details.
ShopsMarketBankCash machineMastercardAmExHairdryerWiFiTVMinibarAirconSafe
The Hotel La Luna is a friendly hotel, tucked away in a quiet side street, just off the atmospheric Via Fillungo, the most sophisticated and exclusive street in Lucca's historic centre.
The original part of the hotel dates back to the 1200s when it was built elsewhere and then 'moved' about a century later to its present location. It now comprises of 2 buildings, with the 29 en suite rooms divided between the two. Breakfast is taken in the buffet breakfast room in the reception building, where there is also a small bar.
Extra nights: Please contact us for details.
ShopsBankCash machineMastercardAmExHairdryerWiFiTVMinibarAirconSafe
The Hotel Alessandro della Spina is located just 500m from Pisa central train station and just a 10 minute walk from most of the city's main monuments. This modern and cosy property welcomes its guests with an elegant, warm atmosphere, enhanced by its charming garden, and friendly staff that are always on hand to ensure you a relaxed stay.
Hotel facilities include internet and wi-fi access in the lobby and a bar and comfortable seating area. Guest rooms are spacious, furnished with wood and marble and have air conditioning, a safe and satellite TV. Buffet breakfast includes homemade bread and croissants.
Extra nights: Please contact us for details.
ShopsMarketBankCash machineMastercardAmExHairdryerWiFiTVAirconSafe
Hotel Chiusarelli is located just beyond Siena's medieval walls and a ten-minute walk away from town's main square, Il Campo. Its position on the edge of the historical centre is perfect as the hotel is spacious and quiet but still within walking distance of all the sights and restaurants. There is even a small garden to the front with palm trees and a quiet (except on Sunday afternoons when you will have a grandstand view of Robur Siena's matches!) veranda to the rear of the hotel.
The en-suite rooms have recently been renovated and are quite simple but comfortable.
In order to give the best available rate, prices are on request. Please contact us for a quote.
Extra nights: Please contact us for details.
We do not currently have departure dates and prices available on-line. The season may have ended for this tour, or we are still in the process of adding these details to our website.
Please contact our sales team on 0044 1606 720199 to for further details or to discuss alternavie trip options.
Self-guided cycling
10 nights,
hotel-to-hotel
Level: 2+
Moderate plus
15.0Kg CO2e
Headwater
Navigation App
Optional
e-bike hire
