italy/chianti/00113e/View-of-San-Gimignan-g.jpg

Secrets of San Gimignano Cycling

from $2,249.00

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!

  • Reviews 46 Reviews
    5/5
  • Vacation Style Holiday Type
    Self-guided
  • Activity Level Moderate plus
    6/8
All about the Secrets of San Gimignano Cycling.

This eight night holiday is, quite simply, outstanding in every way – think rich scenery, fantastically contrasting hotels, superb local cuisine and exceptional wines.
You’ll start off in Volterra, a beautifully preserved hilltop gem whose eclectic mix of Etruscan, Roman and Renaissance art and architecture has inspired artists and writers for centuries. From here, you pedal north east along quiet, rolling country lanes as you coast towards honey-coloured Pancole, nestled in the Tuscan hills. The cycling is truly glorious as you continue, via fortified towns and hill villages, to medieval Colle, from where you can also head to Florence and Siena for day trips. Then it’s on to Pescille, which is perfectly positioned overlooking San Gimignano. Your final stretch takes you through a timeless and kaleidoscopic landscape of ochre-coloured hills and verdant vineyards, giving you a real sense of achievement as you loop back to Volterra for your final night.
Superb 3-star and 4-star contrasting hotels, all with sparkling swimming pools, are an added highlight of this holiday. In Colle di Val d’Elsa, you stay in a fabulously restored 12th century Benedictine abbey, complete with original frescoes, whilst in Volterra, your 4-star hotel has a panoramic infinity pool, with stunning, sweeping views over the Tuscan countryside. Of course, you’re in the heart of some of Europe’s finest wine country too, so you’ll never be short of tasting opportunities.

The tour package inclusions and exclusions at a glance
What is included in this tour?Items that are included in the cost of tour price.
  • 8 nights hotel-to-hotel accommodation in a mix of *** and **** hotels
  • All continental breakfasts and 6 evening meals included
  • Services of your Headwater Representative
  • GPS route directions and maps
  • RideWithGPS navigation app
  • RidePlus route options (more challenging routes)
  • High quality hybrid bikes provided
  • Luggage transfers between hotels
What is not included in this tour?
  • Flights
  • Arrival & departure transfers (available on request, inquire for supplement)
  • Room upgrades and extra nights at selected hotels (inquire for prices and details)
  • Single Accommodation (available on request, inquire for supplement)
  • E-Bike (available on request, inquire for supplement)
  • Tandems available (inquire for supplement)
  • RidePlus road bike (inquire for supplement)

Highlights

  • Exhilarating cycling through open and totally unspoilt countryside
  • San Gimignano’s soaring towers; Volterra’s Etruscan treasures; great art cities of Florence, Pisa and Siena
  • Fabulous hotels all with stunning pools; superb cuisine and fine wines
  • Cypress-studded hills, sun-drenched olives, row upon row of sunflowers and world-famous vineyards
  • Pretty hamlets, hidden chapels, timeless vermilion villas
  1. Day 1 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.

  2. Day 2 Day 2: Volterra to Certaldo 35km/22mi

    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 where you stay for the next two nights.

  3. Day 3 Day 3: At Certaldo

    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 medieval centre for spectacular views across the Val d’Elsa.

  4. Day 4 Day 4: Certaldo to Colle di Val d'Elsa 33km/ 20.5mi

    Today’s route explores the panoramic wine country between Certaldo 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 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.

  5. Day 5 Day 5: At Colle di Val d'Elsa

    There’s masses of choice today: explore the medieval old town which dates back to Etruscan times; take the bus to Siena (30 mins) or to Florence (60 mins); take in the medieval 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.

  6. Day 6 Day 6: Colle di Val d'Elsa to Pescille 43km/ 26.5mi

    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 12th century 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 medieval towers of San Gimignano as you pedal on to Pescille.

  7. Day 7 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.

  8. Day 8 Day 8: Pescille to Volterra 39km/ 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.

  9. Day 9 Day 9: Leave Volterra
c08ty_map
Where you stay
Park Hotel Le Fonti
The 4 star Park Hotel Le Fonti is located just below the Porta dell’Arco entrance to Volterra’s beautifully preserved medieval 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 Certaldo
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.
Relais della Rovere
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 12th century 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
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, 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.
Eating and Drinking

All continental breakfasts and 6 evening meals included

Italy’s most famous export is probably its cuisine and the traditional dishes of Tuscany are the most influential and revered. The region’s food is based on cucina povera, ‘poor/peasant cookery’, a rural cuisine based on available natural ingredients: olive oil, unsalted bread, pulses and vegetables, wild mushroom or porcini, and salt-cured meats such as salame and prosciutto. In particular, Tuscan olive oil is renowned for its quality and is the most important ingredient in the region’s cookery. You will find it in almost every dish – as a salad dressing, poured over vegetables and into soups and even as a replacement for butter on bread (very nice with a sprinkling of salt!).

Of course the Chianti region is best known for its regional wine (the very best ones are Chianti Classico and have a black cockerel stamped on the label). Chianti is produced in the vineyards dotted around the Tuscan hills; we actually visit the hills to the north of Siena, where the Chianti Colli Senesi wine is produced. Made from the Sangiovese grape, this is an excellent light, fruity red. Although best known for its red wine, a good white wine is also produced in the Chianti region. Made from the Vernaccia grape, the Vernaccia di San Gimignano is a crisp dry white which has greatly improved over recent years. It is best drunk young.

You’ll start off in Volterra, a beautifully preserved hilltop gem whose eclectic mix of Etruscan, Roman and Renaissance art and architecture has inspired artists and writers for centuries. From here, you pedal north east along quiet, rolling country lanes as you coast towards honey-coloured Pancole, nestled in the Tuscan hills. The cycling is truly glorious as you continue, via fortified towns and hill villages, to mediaeval Colle, from where you can also head to Florence and Siena for day trips. Then it’s on to Pescille, which is perfectly positioned overlooking San Gimignano. Your final stretch takes you through a timeless and kaleidoscopic landscape of ochre-coloured hills and verdant vineyards, giving you a real sense of achievement as you loop back to Volterra for your final night.

This is a self-guided cycling trip for those who like to cycle independently, but with back up to take out the hard work and planning. We arrange your accommodations, provide you with a map and route notes so that you can cycle at your own pace, while your bags are transported from one hotel to the next.
Activity Level: 2 (Leisurely/Moderate)
Please see the introductory pages of the cycling holidays brochure or our website for more important information on classification and grading.
Av. daily ride: 38km (24miles).
No. of days cycling: 4
Terrain & route: The suggested cycling is along quiet, tarmac roads (mainly traffic-free). There are a few ascents and descents along the way.
Vehicle Support: A representative will be there to meet you, make sure the bikes are all set up and will be on call throughout the trip should you need.

It is important that you are happy reading maps and following route notes, we make these as accurate as possible and they are regularly checked. Where possible we stick to cycle tracks and quiet roads to make the journeys as pleasant as possible, however, on occasion we have to use busier routes.

As this is a self-guided holiday there is no group and no leader. There maybe others on the same departure date as you, but you will not be organised together. The route notes contain an emergency assistance telephone number should you need it and in emergencies, the local representative is normally able to dispatch a taxi or pick you up themselves. They may wish to charge for this service.

Overall Rating
5/5
Reviewed On 14/10/2019
5/5

Mr Jenkinson

We have travelled with Headwater many times and holidays obviously vary. Frankie the rep was excellent and had good practical knowledge of e-bikes. We found the roads were rather busy and not suitable for families. We realised the choice of routes was limited. Our first night coincided with two coach loads of visitors, the food was poor and we were not happy to be asked to vacate our table immediately at the end of our meal. The places we visited were all fascinating and the bus trip to Sienna was brilliant.

Reviewed On 02/10/2019
4/5

Mr Metcalf

Tuscany is indeed hilly, be prepared for some pretty hard cycling. You will be rewarded with some fantastic views though and some great food along the way. Our rep Frankie was incredibly helpful and offered some great advice. All of the places we visited along the way were very friendly and our stop off at the end in Pisa was a great addition.

Reviewed On 23/09/2019
5/5

Mr Oliver

Fabulous scenery, food and wine. Some of the gradients were challenging for those less used to cycling, but the views were worth the effort.

Reviewed On 31/07/2019
5/5

Ms Harris

Our holiday experience was everything we had hoped it would be.

Reviewed On 16/05/2019
5/5

Mrs Walden

Fantastic rep who couldn't have been more helpful. Helpful office staff in the UK. Mixed bag of accommodation. Most was very good. One definitely let everything down. Same with food - some truly excellent some distinctly average. Route information very good but could have done with slightly longer routes. If you happen to have bad weather as we did for a couple of days you can end up quite stranded with very little to do - especially in Pancole. Taxis are very expensive but often no alternative form of transport. This was very nearly a truly excellent holiday. Just needs a couple of tweaks with some of the accommodation and meal options to have given it full marks.

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