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Secrets of San Gimignano Cycling

Secrets of San Gimignano Cycling

      from 39 reviews

Secrets of San Gimignano Cycling

  • 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
  • Holiday typeSelf-guided cycling
  • Duration8 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From $2015 per person, tour only
  • Holiday details
  • Departs Every two days from 11 May '18 to 14 Oct '18
  • All continental breakfasts and evening meals included
  • Managed locally by Headwater employed representative
  • Headwater wine service
  • Route notes and maps provided
  • High quality bikes provided
  • Luggage transfers between hotels

We're here to help

If you've any questions about this holiday call our sales team on 1-800-567-6286 , or email info@breakaway-adventures.com

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 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.

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 C12 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.

Read more about this holiday in The Sunday Times.

Day-by-day itinerary

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

Where you stay

During your holiday you stay at the following hotels. If you'd like to extend your time at any of these or, if you'd like to enhance your stay with an upgraded room, just let us know at the time of booking. You can call our sales team on 1-800-567-6286 to discuss accommodation options.

If you'd like to keep your bikes with you for any extra nights we can arrange this for you for just £25 per adult per day. Please contact us on 1-800-567-6286 for further details.

Park Hotel Le Fonti, Volterra

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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.

Find out more on the hotel website and read customer reviews on Tripadvisor.

Dates Deluxe Room with Terrace Junior Suite Suite
11/05/2018 - 31/10/2018 £10 £16 £34

All prices shown above are valid from 17/11/2017. Supplements are per person per night based on 2 sharing. Deluxe rooms with terrace have their own terrace overlooking the pool. Junior suites are much larger than a standard room, with a sitting area. The suite is situated in the tower, and is larger than a junior suite. It has a balcony and a jacuzzi.

Dates Double Room Single Room
11/05/2018 - 31/10/2018 £82 £114

All prices shown above are valid from 17/11/2017. Prices are per person per night including evening meal. Bike hire is not included in the above tariffs. Bike hire is not included in the above prices.

Hotel Le Renaie, Pancole

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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.

Find out more on the hotel website and read customer reviews on Tripadvisor.

Dates Double Room with a Balcony
11/05/2018 - 31/10/2018 £7

All prices shown above are valid from 18/11/2017. Prices are per person, per night based on 2 adults sharing. Deluxe rooms have a private balcony.

Please contact us for extra night prices.

Relais della Rovere, Colle di Val d'Elsa

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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.

Find out more on the hotel website and read customer reviews on Tripadvisor.

Dates Luxury (Double Only) Junior Suite Suite
11/05/2018 - 31/10/2018 £22 £33 £49

All prices shown above are valid from 18/11/2017. Supplements are per person per night based on 2 sharing. Luxury rooms are located in the Renaissance Villa and feature antique furniture and prints, and precious tapestries and ceilings with encased beams and parquet flooring. Large windows with a view over the historical centre of Colle Val D'Elsa. Bathroom with whirlpool bath, courtesy kit, bathrobe and slippers. Junior Suites are located in the Benedictine Convent and in the farmhouse. They comprise an entrance hall with living room and one double bedroom, and feature modern, solid oak furniture. They have beamed ceilings and parquet flooring. One/two bathrooms, one with shower, the other with whirlpool bath, courtesy kit, bathrobe and slippers. Suites are in the Benedictine Convent and in the Villa. They are larger with an entrance hall, living room and sofa bed and a double bedroom, with two bathrooms. Some have modern decor with solid oak furniture, beamed ceilings and parquet flooring. Others feature antique furniture and prints, and precious tapestries, ceilings with encased beams and parquet flooring.

Please contact us for extra night prices.

Hotel Pescille, Pescille

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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.

Find out more on the hotel website and read customer reviews on Tripadvisor.

Dates Double with view of San Gimignano
11/05/2018 - 31/10/2018 £12

All prices shown above are valid from 18/11/2017. Prices are per person, per night. Rooms with balcony offer wonderful views of San Gimignano.

Please contact us for extra night prices.

Extending your stay

If you'd like to extend your trip with extra nights at the start or end, or if you'd like to arrange a stop off point en-route, then we recommend the following hotels.

Relais Santa Chiara, San Gimignano

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Situatued just 400m from the mediaeval walls of UNESCO listed San Gimignano lies the charming, four star Relais Santa Chiara Hotel. This elegant property is surrounded by some of Tuscany's most beautiful scenery and enjoys countryside views over hills covered with vineyards and olive groves, not to mention its own private garden featuring a swimming pool and hydro massage pool. There is also a terrace on which you can enjoy breakfast in the morning and a selection of drinks from the hotel's cocktail bar in the evening.

All the ensuite rooms come with air-conditioning, satellite TV, minibar and hairdryer. You can also upgrade to a room with balcony and views of the surrounding vineyards and stunning countryside.

Find out more on the hotel website and read customer reviews on Tripadvisor.

Dates Classic room with countryside view & balcony Superior Double Superior double with separate lounge Superior double with countryside view
11/05/2018 - 31/10/2018 £13 £13 £25 £26

All prices shown above are valid from 18/11/2017. Prices are per person, per night. Classic rooms with balcony and view offer stunning views of the Tuscan countryside. Superior rooms are more spacious with a lounge area and a sofa bed (120cm) and a jacuzzi bath. Superior rooms with balcony and views come with all the amenities of the Superior room with the addition of a balcony offering stunning views of the Tuscan countryside.

Please contact us for extra night prices.

Hotel Alessandro della Spina, Pisa

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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.

Find out more on the hotel website and read customer reviews on Tripadvisor.

Room upgrades are not available at this hotel.

Please contact us for extra night prices.

Hotel Chiusarelli, Siena

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Hotel Chiusarelli is located just beyond Siena's mediaeval 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 AC 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.

Find out more on the hotel website and read customer reviews on Tripadvisor.

Room upgrades are not available at this hotel.

Please contact us for extra night prices.

Hotel La Luna, Lucca

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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.

Find out more on the hotel website and read customer reviews on Tripadvisor.

Room upgrades are not available at this hotel.

Please contact us for extra night prices.


Transfers included from Pisa airport at 11:35, and back to Pisa airport at 09:00.

Please call our sales team on 1-800-567-6286 or email info@breakaway-adventures.com to arrange connecting flights.


Everyone who goes on a Headwater holiday will be emailed a link to our post-holiday questionnaire where they can give us an honest assessment of all aspects of their holiday - everything from how quickly we answer the phone to how clean the hotels were - plus, of course, an overall rating and comments about their holiday.

Any feedback collected is posted straight to our website - totally unedited. So, for the real tales, twists and turns of our holidays, look no further than the reviews from our previous travellers.

Mr Moody

Overall an excellent holiday in a region new to us .... Headwater Reps excellent ...

Mrs Bennett

Wonderful way to see Tuscany. The fitter you are though, the more you will enjoy it.

Miss Perry

Lovely way to see the country and get fitter

Mrs Anderson

This is the second holiday we have taken with Headwater and both have been excellent. Two years ago we did the Gastronomic Barollo cycling holiday. Both were really enjoyable. Tuscany was stunning, the hotels excellent and our reps really friendly and helpful. On balance we preferred the Barollo holiday, but only because the cycling is on less busy roads and it is slightly less touristy, but I don't think we could find fault with either holiday.

Mrs Pincott

The Secrets of San Gimignano holiday was fantastic. Eleanor and Luke, the reps, simply could not have been more helpful, the cycling was excellent (but hard work - Tuscany is hilly) and the hotels and food amazing.

Mr Dick

The cycling routes and notes were excellent, the food was gorgeous and the scenery beguiling. Luke & Eleanor were more than welcoming and helpful. When I reported a small technical issue with one of our bikes, it was changed within an hour. The restaurant suggestions were lovely for the nights not on half board.

The opportunity to take a day in Sienna or Florence should not be missed.

Mrs Craig

I was initially somewhat trepidatious about attempting a' two and a half cycle' difficulty holiday with my younger, fitter, regular cyclist husband and so ,probably, was he. I am dog walking fit and that's about it. Some of the hills were fairly challenging but the bikes supplied have plenty of gears and the views from the top and the downhills are well worth the effort involved getting up and I was never that far behind him in the end! We went in September during the grape harvest, a lovely tim... read moree of year. I'm not sure I would have coped with the cycling quite so well in July or August! The reps were very helpful but not intrusive and the hotels were all good. My husband is a map man and thought the quality of maps supplied was poor so we used the written instructions which were accurate and detailed. You don't need to be an olympic athlete to get the most out of this holiday, you have all day to complete the 40k between hotels, just take your time and enjoy those views!

Mr Davies

This was my fourth holiday with Headwaters and have enjoyed them all

Mis Aplin

This is a lovely cycling holiday but quite challenging with regard to the hills especially when its 34C! An early start is recommended to avoid the hottest part of the day. The hotels are all good and food at the Della Rovere is excellent. Nice pools at all the hotels. Plenty to do on the off days. The walled town of Monteriggioni is a relatively easy cycle from the Della Rovere. Worth booking an extra night at the end of the holiday in Volterra. Beautiful town with lots of little shops, cafes and alleyways. Thanks to Luke and Eleanor who were excellent reps.

Mr Precious

This was our first Headwater Cycling Holiday and our first visit to Tuscany, we felt that we were able to get up close and personal with the beautiful countryside. We would recommend this type of activity to anyone, we had a wonderful time and we look forward to booking another trip soon.

Mrs Payne

We were surprised at how strenuous the cycling actually was! The distances were not long, and so we really expected to complete the routes much quicker than we did.Very big hills, but the bikes have good gears and we managed to cycle to the top of them all. The downs were brilliant. Roads were mainly very quiet.

The hotels were all lovely and we enjoyed having non cycling days to explore the interesting hill top towns.

Lots of great food and wine was had.

Mrs Ryan

This holiday delivered on great food, amazing scenery, friendly staff along the route and comfortable hotels. We thoroughly enjoyed the whole experience

Mr Wightman

We really enjoyed this first cycling holiday, we loved the Tuscan countryside and the rustic food, delicious wine! We regularly enjoy our bicycles at home but are not 'cyclists'. So the 'undulating hills' and ' steady climbs' mentioned in the brochure were a lot more challenging than we expected. Having said this, we completed the route with a great sense of achievement and looked forward each day to a new adventure !

Mrs Prentis

I was a little sniffy with the 40km every other day distance. However the hills more than make up for it. We are both very fit and did manage the hills but it was warm and quite a few are long and on the stranda bianca which are unmade up and with the wrong size of stones which makes cycling quite difficult at times. The area is lovely and the reps were delightful and extremely helpful.

Ms Woodall

Great holiday. Good challenging cycling days and a region with great food and wine for lunch and dinner. Headwater looked after us well again in Italy.

Mrs Thomas

Don't be put off by the two and a half star rating of this holiday. We are two averagely fit 50+ couple that managed all the hills and they were well worth it for the fantastic views. Each hotel was unique and individual and the welcome you received at the end of a days cycling was lovely. The standard of food for most was good. We thoroughly enjoyed our holiday and have come back invigorated and amazingly pounds lighter! The reps Luke and Eleanor were very helpful and couldn't do enough for you - even texting us to see if we were alright on the only rainy day we had.

Mr Flett

A fabulous way to explore the beauty of rural Italy. The exercise during the day is balanced by delightful food and wine in the evenings. Self-guided cycling with Headwater offers independence, but with the comfort and reassurance of excellent local Reps. This was our second holiday with Headwater and is unlikely to be our last.

Ms Vipond

Beautiful cycling! Great route and some excellent hotels.

Ms Morris

Everybody was so professional, friendly and helpful from our first phone call to the office to our final goodbye to the reps. The routes were great - enough cycling to feel we'd earned our lovely hotel, pool and dinner but not too much to feel disheartened. There was plenty of time built in to sight see with excellent suggestions for rest days. We visited some great places that we'd never have found on our own as well as some more main stream destinations. A lovely combination and so well organised.

Mr Elliott-Jones

A fantastic package, great value for money in superb, friendly & family-run hotels. Great cycling routes through some challenging terrain, very good, sensibly built bikes. Reps & Headwater office staff were very helpful, couldn't do enough to make sure we were sorted.

Mr Quick

Our most scenic Headwater cycling holiday to date and well worth the physical effort!

Mrs Firth

We found the holiday provided a good mix of cycling and relaxation. The cycling in July was very hot and the hills quite challenging while the hotels were very comfortable and quiet. Enough choice of things to do from the hotels or simply relax by the pool.

Cycle routes were very well mapped, cycles were properly geared for the climbs and well maintained.

Transfers from the airport to the hotel were well organised and on cycling days our luggage was promptly transferred between hotels.

Mrs Stockton

An excellent first holiday with Headwater. We chose a 2+ cycle standard which was tougher than we expected, however the heart had a large effect on our ability. All the hotels were beautiful my only complaint was the air conditioning could of been a lot more powerful. The scenery was just breathtaking on the rides and over all i would highly recommend this trip.

Mis Barrie

A fun way to exercise in a beautiful location

Mr Hill

The scenery is spectacular - typical Tuscany -but beware the cycling is not for the inexperienced. The region is hilly and you do cycle on some busy roads. Good location for visits to Sienna and other famous hill top villages We very much enjoyed the holiday

Mrs Holman

Excellent service from Kate and Jim starting with a postcard before hand saying that they were looking forward to meeting us. Excellent combination of sight seeing and cycling

Mrs Marks

This was our third holiday with Headwater and as always everything was great, the guides, accommodation, trip routes, bikes, excellent and memorable holiday

Mis Wilson

A solitary bat swinging from the arched roof of an underground Marmini Etruscan tomb. Lizards posing on sun bleached steps or rustling through the undergrowth as you cycle past. The call of frogs, the flash of jays. An abundance of flowers, butterflies, insects and birds and stunning panoramic views. Loads of local colour and culture. Pasta, gnocchi, pecorino cheese with a honey and pine nut dip, ricotta cheesecake, pizza al taglio, gelato. Buongiornos and waves from Italian cyclists. Enj... read moreoy those downhill whizzes because there are also some climbs - but you will survive to tell the tale!

Mr Fletcher

A very good holiday. All the hotels were good and the local reps were fantastic.

Ms McLellan

Helpful reps and decent kit with good route notes but accommodation and food variable; slightly disappointing overall. 50 euro 'cash back' for dinner in San G when hotel restaurant closed was a bit tight based on what the hotel charged for a 3 course meal (but did mean that we had a good night out in San G and the best meal of the holiday by far!). Cycling tough at times, more road work than expected and would have struggled if it had been in the height of the summer heat but rewarding and some memorable views.

Mrs Lee

Overall, very enjoyable with delicious local food and beautiful scenery. The thrilling downhill sections made up for the uphill challenges. Volterra is a gem and a wonderful place to celebrate your cycling achievements on the final night.

Mr Thomas

Our Tuscany Holiday (Secrets of San Gimignano) was totally brilliant and was enjoyed by the whole family ( 6 of us) - age range 24 to fit 70!.Our reps made life very easy for us and were incredibly helpful. The hotels were varied and all really lovely and well chosen by Headwater. The food was excellent - and being Italy, there were plenty of options for my vegetarian daughter ( no meat or fish). There was plenty to do on our non-cycling days which is always important.

Mr Alexander

Beautiful countryside, gorgeous hilltop towns, good accommodation, superb reps; cuisine (in and out of hotels) generally somewhat disappointing - ordinary and predictable (except Relais della Rovere) - this is more a comment on the region than on the Headwater aspects.

Mrs Gillison

A well organised holiday with very helpful reps onsite. We haven't needed them in past holidays but had saddle trouble this time which was fixed in a trice (with a lift up one of the VERY steep hills as well!). Although we discussed this holiday on the phone before booking we didn't get a clear picture of difficulty from the brochure, so be very clear about how good a cyclist your are!!!

Mrs Wright

All arranged at very last minute and your staff were up to the challenge. Thanks especially to Karen Ross in the office,particularly as we added an extra day in the middle to our itinerary. Also appreciated being able to discuss this 'upper 2 bikes' holiday with Catherine Crone as she and her husband had done it previously - helped us decide we would be able to manage it!

Routes very varied with lots of scenic and historic interest.

Hotel Le Renaie at Pancole was the best one for... read more us - delightful staff, gorgeous evening meals and lovely setting.

We wouldn't have managed this in the heat of the summer but late Sept/early Oct the weather was pleasant especially as we managed not to get caught in any of the thunderstorms.

Great to have all swimming pools still open as we used them all.

We ended our holiday with a great sense of achievement and we can't wait to go back to Italy.

Charles and Ruth aged 50 something and only moderately fit.

Ms Meadows

We could write pages about a lovely combination of cycling and walking but the best recommendation that we can give is that at the end of the holiday we were thinking about how we could just stay in Tuscany and do the holiday all over again

Mrs Melhuish

we thoroughly enjoyed all aspects of our holiday.

Mis Lording

The Secrets of San Gimignano is definitely an upper two bike holiday! There were plenty of hills going up but the rewards were the breath taking scenery, excellent hotels and lovely places that could be visited. Thank you Headwater for another great holiday. I can't wait until 2013 to book the next one!

Mr Park

Great hotels, lovely scenery

Dates and prices

You can be confident that our pricing includes all the standard requirements of your holiday and many additional extras. Always ensure that you are comparing like for like when booking your holiday. Find out about The Headwater Price Promise to ensure you're getting the very best value for money.

For further details, or to check availability, speak to our sales team on 1-800-567-6286 or complete our holiday enquiry form (we'll contact you at a time that's most convenient for you).

To enquire about this holiday, or for further information, call our sales team on 1-800-567-6286 or complete our holiday enquiry form.

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Sep 2018 Tour only Availability
2nd Sep US$2275 Check availability
4th Sep US$2275 Check availability
6th Sep US$2275 Check availability
8th Sep US$2275 Check availability
10th Sep US$2275 Check availability
12th Sep US$2275 Check availability
14th Sep US$2275 Check availability
16th Sep US$2275 Check availability
18th Sep US$2275 Check availability
20th Sep US$2275 Check availability
22nd Sep US$2245 Check availability
24th Sep US$2245 Check availability
26th Sep US$2245 Check availability
28th Sep US$2245 Check availability
30th Sep US$2245 Check availability
Oct 2018 Tour only Availability
2nd Oct US$2015 Check availability
4th Oct US$2015 Check availability
6th Oct US$2015 Check availability
8th Oct US$2015 Check availability
10th Oct US$2015 Check availability
12th Oct US$2015 Check availability
14th Oct US$2015 Check availability

The prices quoted for each individual departure supercede those published in our current brochures. Air prices are subject to change and we advise early booking to obtain the best prices. Please see our Planning your holiday and What's included in the price? pages for additional information.

Holiday details

Please contact us for child prices.

Holiday type
Self-guided cycling Managed locally by Headwater appointed rep.

Every two days from 11th May 2018 to 14th Oct 2018, for 8 nights.

All continental breakfasts and evening meals included

Tailor-made travel

Tour only
Transfers included from Pisa airport at 11:35, and back to Pisa airport at 09:00.

How to book

For further details, or to check availability, speak to our sales team on 1-800-567-6286 or complete our holiday enquiry form (we'll contact you at a time that's most convenient for you).

To enquire about this holiday, or for further information, call our sales team on 1-800-567-6286 or complete our holiday enquiry form.

We are ATOL registered We are an ABTA member
Independent customer reviews and ratings

Due to the tailor-made nature of our holidays, we need a little more information in order for us to check availability for Secrets of San Gimignano Cycling. Simply complete the form below and a member of our sales team will contact you (when it's most convenient for you) to provide availability information, travel options and an accurate price. Of course there's no obligation, but if you do wish to proceed with a booking they will be on-hand to assist you throughout the process.

Alternatively, you can call our sales team on 1-800-567-6286 to discuss your requirements in more detail.

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We can often obtain preferential rates with our travel partners.

We can call you when it's most convenient for you, or contact you by email if you'd prefer. During busy periods we cannot always guarantee a specific call time but we promise to try our very best.

Let us know any queries you might have about departure dates, similar holidays or other questions. If you’d like to travel by an alternative method, i.e. Ferry / Eurotunnel etc. please give details here so we can advise you on appropriate options.

Headwater may use the information you provide for marketing and promotional purposes. By clicking the 'Enquire now' button, you confirm that you have read and understood our Privacy Policy and consent to our use of your information.

We've been creating high-quality relaxed activity holidays since 1985 and our wealth of experience means we're able to build the perfect tailor-made tour for you. Our 'Gold Trusted' rating on Feefo, the independent review site, underlines our exceptional levels of customer service, and our ATOL bonding and ABTA membership guarantees your holiday is safe with us.

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