Secrets of San Gimignano Cycling

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Stephen Power, 26/06/2023

Travel and adventure made easy. A great experience end to end seeing an area of Italy at our pace and mostly alone. Hassle free

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TWIGG, 31/05/2023

The itinerary has clearly been well thought out to showcase some of the loveliest places in Tuscany, both the historic towns and routes through beautiful countryside. We had had misgivings about the bikes before the trip as we had looked them up and found that they were very heavy. However they had great gears and tyres which negotiated the hills and Strada Bianca's very well. Overall well suited to the task. Only one hotel was really disappointing, although the staff were great. Room was tiny with no air conditioning, even though we had upgraded. Food at the linked restaurant wasn't good and we paid ourselves for somewhere else on our return night there. The other three hotels were really exceptional. Highlights were the restaurant in the Certaldo hotel and Zaferano ( restaurant by Il Pescille). Great experience.

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Mr Jones, 06/07/2022

The beautiful views of the Tuscan landscape never failed to draw a smile whether it was a daytime view across fields of sunflowers or an evening sunset over the vineyards. The wine tasting experiences were first class and we have many beautiful memories thanks to the passion of the wine makers and their families. The cycling was fun and not difficult for anyone in moderate physical condition.

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Mr Yellen, 29/05/2022

Fantastic scenery and lovely villages to visit

Can be very hot and is constantly uphill or downhill for cycling with some very steep sections and some busy roads

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Mr Jenkinson, 30/09/2019

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.

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Mr Metcalf, 16/09/2019

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.

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Mr Oliver, 06/09/2019

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

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Ms Harris, 16/07/2019

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

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Mrs Hardy, 18/06/2019

What a great way to see part of Tuscany - electric bikes such a help up the many hills. Hotels chosen for us were great - varied but consistently good service and most of the meals were excellent. GPS app so helpful - made navigating so easy. Had a few technical hitches on two days, but Frankie our Rep was at the other end of the phone and found us promptly to sort us out. All in all a great holiday. Not a cheap holiday but worth it for the great organisation by Headwater which allowed us to really relax and focus on enjoying the experience. Would thoroughly recommend.

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Mrs Walden, 03/05/2019

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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Mrs Driver, 24/09/2018

Great cycling - some challenging- in a beautiful area. Fabulous reps - Paul and Phaedra who were helpful, informative and assisted in every way they could. Siena and San Gimignano were good places to explore on the rest days.

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Mrs O'Donnell, 16/06/2018

Phaedra and Paul made us so welcome, and were very helpful (returning our key one day when we rode off with it). They gave us some very useful tips about the routes and hotels, and they set the tone for a lovely week right from the start. The bikes are easy to ride, good quality and very smooth. We were provided with water bottles and a cage each, so we could drink on the go. That helped a lot - do not underestimate the heat and the hills - those rest days are needed! We're reasonably fit, regular road cyclists and we found the hills quite challenging in the heat.



We saw some beautiful countryside in Tuscany, met some very friendly people and ate some good food. We will go back - but maybe not in June!

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Mr O'Keeffe, 27/05/2018

We had a fantastic trip, a great mix of cycling in spectacular surroundings and relaxation, sightseeing and indulging in the local food and wine. For people of average fitness, the cycling is challenging in parts, not because of the distances involved, but because of the hills in some sections. The lovely reps, Phaedra and Paul, were friendly, helpful, professional, available and unobtrusive. The bikes were sparkling clean/new and well equipped with water cage, phone holder and panniers. Remember to bring a helmet as these are not supplied. GPS worked well. The accommodation was varied and generally good and we really appreciated having a pool at every stop. We did not meet any other Headwater holiday makers on the trip, so it very much felt like an intimate private holiday.

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Mrs Bennett, 02/10/2017

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

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Mr Moody, 22/09/2017

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

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Miss Perry, 06/09/2017

Lovely way to see the country and get fitter

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Ms Bates, 27/08/2017

Stunning scenery, stunning locations - a holiday to remember! We weren't really sure what to expect with the 2+ rating for cycling - I would say on average the cycling ranged between enjoyable undulating roads & exhilarating descents which were interspersed with some really (really!) tough climbs - beware of the Strava Biancas & just enjoy the scenery on route - the pain is quickly forgotten & the achievement of arriving at each destination makes it all worthwhile! I truly memorable holiday - thank you Headwater!

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Mrs Anderson, 25/08/2017

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.

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Mr Hughes, 10/06/2017

We left Manchester in pouring rain to spend a week climbing Tuscan hills at 34c. The theme of the accommodation is Tuscan hill towns so every morning was an easy start but you soon realise every days ride finishes with a picturesque uphill! The hotels were always a good standard and a couple of the swimming pools were simply amazing. Eating outside in the courtyard at the 'Relais della Rovere' was particularly special. We had researched eating out in San Gimignano beforehand which proved well worthwhile and it is definitely wiser to book ahead from UK if you can.

The first day is quite a challenge so carry plenty of water. We hadn't realised that Headwater don't supply the water bottles anymore but luckily our local reps found us a couple of spares from last year. Phaedra and Paul were kind and attentive keeping in touch by text if we needed them. The bikes were reliable and comfortable to ride. The routes do get easier after the first day and it is worth carrying a small picnic most days as the cafes tend to be towards the end of the ride. There are some good sights to see on the rest days or else there are the lovely pools just to lounge by instead.

It was a great holiday and the hills made sure you felt fitter coming home.

Thanks again Headwater

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Mr Haxton, 08/06/2017

The holiday provided a wonderful experience of cycling in this most scenic of Tuscan landscapes. Some of the cycling was tough in the hot weather but the excellent hotels were perfect for relaxing after the cycle rides

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Mr Campbell, 31/05/2017

The route was generally disappointing, lots of detours through small hamlets where there was nothing, very few places to stop for a coffee. May just be that the topography dictates the route but I would have hoped Chianti could have yielded more places of interest. This was our 3rd Headwater holiday and I'd place this route 3rd by some margin. The hotels were generally excellent, Le Fonti in Volterra was very professional with good views, La Renaie in Pancole was the highlight, excellent family run hotel with nice feel and really good food. Relais della Rovere was Ok but needs to employ some gardeners, the grass everywhere hadn't been cut for weeks, bushes badly trimmed etc all contributing to an unkempt appearance. The catering being separate from the hotel was unusal and contributed to the disjointed feel. This should be a fantastic hotel but needs a lot of work to get there. Pescille was really good with great views of San Gimignano.

The bikes were new so in perfect condition, should have had a bottle cage on each bike rather than 2 on one bike and none on the other. We would have brought our own water bottles if we'd known these were no longer provided, contrary to what your literature said.

Headwater response:
Dear Mr Campbell,
Thank you for taking the time to provide your post-holiday feedback. We were pleased to read you had an enjoyable holiday. We were however sorry to read there were areas of your holiday that you felt required improvement. Please be assured all of the feedback we receive, whether positive or constructive is valued and used to help improve our holidays for the future. With this in mind, we were sorry to read you felt the gardens at Relais della Rovere required maintenance. This is the first time we have received constructive feedback for this hotel. We have discussed your comments with the hotelier; we expect to see an immediate improvement. We are sorry for any disappointment this may have caused.
We were pleased to read you found the bikes in perfect condition; our Reps receive extensive training in this area and do pride themselves on providing well-serviced bikes. They do not provide water bottle cages to our low framed bikes; this is due to past customer feedback, where customers advised us they were banging their legs on the cages, our Reps will provide water bottle cages if requested. Again, due to customer feedback we discontinued providing our water bottles, customers advised they preferred to use their own. Our Reps may have a surplus if required. This information is included in our pre travel information booklets; we are sorry you were unaware and hope this did not cause you an inconvenience.
In closing, we would like to thank you for your continued loyalty and look forward to welcoming you on another of our holidays in the future.
Kind regards,
Headwater Customer Service team

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Mr Bill, 27/05/2017

Great time, hills in Tuscany are not hills....So get in shape, but scenery worth the ride...amazing! We were able to meet the locals and enjoy ourselves without any pressure when and when not to ride...

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Mr Mcgeoch, 21/05/2017

Great combination of challenging cycling, breathtaking views, a range of different hotels with excellent food and wine

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Mrs Pincott, 02/10/2016

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.

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Mr Dick, 09/09/2016

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.

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Mrs Craig, 06/09/2016

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 time 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!

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Mr Davies, 20/07/2016

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

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Mis Aplin, 21/06/2016

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.

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Mrs Ryan, 16/06/2016

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

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Mr Precious, 08/06/2016

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.

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Mrs Payne, 04/06/2016

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.

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Mrs Prentis, 29/05/2016

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.

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Ms Woodall, 25/05/2016

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.

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Mrs Thomas, 25/05/2016

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.

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Mr Wightman, 21/05/2016

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 !

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Mr Flett, 17/05/2016

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.

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Ms Vipond, 08/10/2015

Beautiful cycling! Great route and some excellent hotels.

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Ms Morris, 04/09/2015

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.

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Mr Elliott-Jones, 02/09/2015

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.

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Mr Quick, 21/08/2015

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

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Mrs Firth, 30/07/2015

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.

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Mrs Stockton, 29/07/2015

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.

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Mis Barrie, 29/05/2015

A fun way to exercise in a beautiful location

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Mr Hill, 02/10/2014

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

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Mrs Holman, 22/07/2014

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

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Mrs Marks, 04/06/2014

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

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Mis Wilson, 02/06/2014

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. Enjoy those downhill whizzes because there are also some climbs - but you will survive to tell the tale!

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Ms McLellan, 14/09/2013

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.

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Mr Fletcher, 14/09/2013

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

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Mrs Lee, 06/09/2013

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.

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Mr Thomas, 20/07/2013

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.

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Mr Alexander, 24/06/2013

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.

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Mrs Gillison, 21/05/2013

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!!!