Secrets of San Gimignano Cycling

  • Overview
  • Itinerary
  • Dates
  • Headwater

This 8-night cycling holiday combines fabulously unspoilt Chianti countryside with the chance to visit the world-famous cities of Florence and Siena. You'll stay in high quality hotels, enjoy superb meals and relax by panoramic pools - views extend as far as Corsica on a clear day!

Travel
British Airways Heathrow to Pisa 08:25/11:35 transfer to hotel 75 minutes. Return: Transfer to airport 75 minutes British Airways Pisa to Heathrow 12:35/14:00
Single Supplement
Add 36 per person per night for sole occupancy of a double room.
Accommodation
Park Hotel Le Fonti (4 star)
The 4 star Park Hotel Le Fonti is located just below the Porta dell'Arco entrance to Volterra's beautifully preserved mediaeval centre. It's an easy 10 minute stroll into arguably one of Italy's oldest towns. The hotel has over 50 comfortable rooms, all of which are furnished in a simple style with terracotta floors and elegant fabrics. All rooms have ensuite facilities. The real highlight of the hotel is the breathtaking view from the terrace and fabulous infinity pool - the sweeping panorama over the rolling Pisan hills is truly outstanding.

Hotel Le Renaie (3 star)
Hotel Le Renaie is a lovely family run 3 star hotel run by the Sabatini family in the pretty hamlet of Pancole, midway between San Gimignano and Certaldo. The hotel started life as a restaurant but over time, it has grown into the charming 25 room hotel it is today. The bedrooms are spacious and decorated in a traditional style. All have ensuite bathroom facilities. Surrounding the hotel is a pretty terrace with bright flowers and scented gardens. There is an outdoor pool, a tennis court and a shop which sells wine as well as the family's own home grown and produced olive oil.

Relais della Rovere (4 star)
The Relais della Rovere is a stunning 4-star hotel located at the edge of Colle di Val d'Elsa. The Cellerai family have sympathetically converted this C12 Benedictine Abbey into a 31 room luxurious hotel, retaining many of the abbey's original features. The bedrooms are split between two buildings and decorated in a contemporary style with wooden floors and beech furniture. The rooms are quite large with ensuite facilities. The hotel has a lovely outdoor pool which is surrounded by pleasant gardens.

Hotel Pescille (3 star)
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* 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, we have therefore arranged for you to have return taxi transfers to the centre of San Gimignano, where there is a wealth of restaurants to suit all budgets and tastes.

Meals
All continental breakfasts and evening meals
Destinations
  • Italy
  • Tuscany
  • Europe
  • Siena
  • Florence
  • San Gimignano
  • Nice
Tour Types
  • Cycling
  • History
  • Self Guided
Departure Points
  • London Airport
Day 1 Arrive at Volterra
Arrive in Volterra where you've time for a dip in the pool and a wander round its myriad of cobbled alleys and hidden squares before dinner. (Staying at Park Hotel Le Fonti, Half Board)

Day 2 Volterra to Pancole 41km/ 26mi
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, C12 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 mediaeval Certaldo where you can stop for a gelato before your final climb through olive groves and vineyards to the hamlet of Pancole. (Staying at Hotel Le Renaie, Half Board

Day 3 At Pancole
If you fancy a day off from cycling, the pool here is simply gorgeous and nice lunches are served on the geranium-scented terrace. There's also a small shop where you can buy olive oils, produced by the owners, and Tuscan wines. The more energetic might want to cycle past orchards and vines to visit Boccaccio's birthplace, stunning Certaldo. Take the funicular to its mediaeval centre for spectacular views across the Val d'Elsa. (Staying at Hotel Le Renaie, Half Board

Day 4 Pancole to Colle di Val d'Elsa 32km/ 20mi
Today's route explores the panoramic wine country between Pancole and Colle di Val d'Elsa. You'll first retrace your route to Certaldo and then follow the official, mainly off-road, Chianti Wine Route where you'll find lots of tasting opportunities - don't forget, we can collect any purchases for you! It's then on to the old town of Poggibonsi, a perfect stop for lunch and to visit the ruins of its unfinished C15 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. (Staying at Relais Della Rovere, Half Board)

Day 5 At Colle di Val d'Elsa
There's masses of choice today: explore the mediaeval old town which dates back to Etruscan times; take the bus to Siena (30 mins) or to Florence (60 mins); take in the mediaeval town of Monteriggioni, an easy cycle or short bus ride away; or simply laze by your hotel's sparkling swimming pool, surrounded by lovely gardens. (Staying at Relais Della Rovere, Half Board)

Day 6 Colle di Val d'Elsa to Pescille 40km/ 25mi
It's easy pedalling this morning as you head south past the old town of Colle di Val d'Elsa, gradually climbing 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 C12 church (frescoes by Gano da Siena) and impressive fortress before an early lunch perhaps, in the lovely piazza. You then wind north, gently uphill, through wonderfully scenic countryside against the backdrop of the impressive mediaeval towers of San Gimignano as you pedal on to Pescille. (Staying at Hotel Pescille, Breakfast at the hotel, evening meal taken at a local restaurant)

Day 7 At Pescille
San Gimignano is just a short cycle away; explore its myriad of narrow streets and many hidden cobbled squares before returning to your tranquil hotel for a refreshing dip in the sparkling swimming pool. (Staying at Hotel Pescille, Breakfast at the hotel, evening meal taken at a local restaurant)

Day 8 Pescille to Volterra 38km/ 24mi
It's a short ride to San Gimignano today before a climb up through classic Tuscan landscapes of vines, olive groves and fields ablaze with sunflowers. Enjoy the 16km, mainly downhill run into the Era Valley. There's a real sense of achievement on your final climb through open countryside and you'll enjoy spectacular views before heading back to the ancient cobbled streets of Volterra. (Staying at Park Hotel Le Fonti, Half Board)

Day 9 Leave Volterra


You will have the option to book your own flights independently with the operator.

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Touring with Headwater

In 1985, Richard and Christine Bass made the life-changing decision to turn a passion into a business and thus Headwater was born at their kitchen table.

The first Headwater tours were launched in summer 1986 and modestly comprised three holidays in the Upper Loire Valley in France: a canoeing holiday and two self-guided walking holidays.

Their vision for Headwater was clear, right from the start. Richard and Christine wanted to offer their customers exactly what they loved in a holiday – family-run, friendly hotels, an authentic experience of a region, including culture, cuisine and fine wines, and above all a fantastic level of personal service, with staff on hand in resort to help and guide as required.

After a successful 10 years specialising in France, Headwater launched a new Great Walks in Europe brochure in 1995, offering a selection of hand-picked guided walking holidays in eight countries. As a result of the phenomenal success of this, a year later the first self-guided walking and cycling holidays in Italy were launched.

In 1999, Richard and Christine decided to retire and enjoy the fruits of their labour, and sold Headwater – but not before ensuring it was in the safest of hands to continue their legacy.

Today, they enjoy taking customers (new and loyal) on journeys on foot or by bike throughout 18 countries worldwide. Whilst they have embraced modern technology and changing times since 1985, Richard and Christine’s ethos remains key to all of their holidays and they consider it their mission to ensure that the same detail, knowledge and passion goes into delivering each and every trip.

With more than 32 years’ experience, their collection now includes 59 self-guided and 12 guided walking holidays and 62 cycling holidays. Their canoeing holiday in the Dordogne remains as popular as ever, as well as their choice of winter snow holidays (cross-country skiing and winter walking) that run between December and April in Austria and Norway.

They are particularly proud of their Headwater-employed representatives (reps) who are on-hand in 15 regions in France, Italy, Spain, Portugal, Austria and Bavaria. Burgundy is their longest-standing “repped region” – Richard and Christine researched the holidays and they have been running them since 1992. Their reps provide 24-hour support in resort including: briefing you on arrival, transporting your luggage from hotel to hotel, offering a ‘Wine Service’ where they collect any bottles you’ve purchased en route and transport them to your final hotel for you, and giving you tips and advice and sharing their knowledge of the local area, the routes, the best views and generally helping you to make the most of your trip. Each year, before the season starts, the reps have an in-depth training session at Headwater HQ to make sure they’re ready for the summer ahead.

Their newest addition to the Headwater portfolio is a selection of single-centre activity holidays in Brittany and the Dordogne, France and Catalunya, Spain. These are ideal for multi-generational families and groups – take a look below for some Headwater inspiration.

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