Secrets of San Gimignano Cycling

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Cycling in Tuscany was a great way to see the superb scenery and enjoy local food and wine. Headwater organised everything exceedingly efficiently and everyone involved was reliable and friendly.

Valerie Harris, 27 Apr 2024

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An excellent holiday. Proved to be tougher than envisaged. The final road into Certaldo was concerning at times, sharing with very large cement transporters. Hotels were truly excellent.

Diane Hall, 26 Sep 2023

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

Stephen Power, 26 Jun 2023

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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.

TWIGG, 31 May 2023

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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.

Mr Jones, 6 Jul 2022

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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

Mr Yellen, 29 May 2022

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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.



Mr Jenkinson, 30 Sep 2019

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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.

Mr Metcalf, 16 Sep 2019

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

Mr Oliver, 6 Sep 2019

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

Ms Harris, 16 Jul 2019

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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.

Mrs Hardy, 18 Jun 2019

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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.

Mrs Walden, 3 May 2019

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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.

Mrs Driver, 24 Sep 2018

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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!

Mrs O'Donnell, 16 Jun 2018

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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.

Mr O'Keeffe, 27 May 2018

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

Mrs Bennett, 2 Oct 2017

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

Mr Moody, 22 Sep 2017

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Lovely way to see the country and get fitter

Miss Perry, 6 Sep 2017

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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!

Ms Bates, 27 Aug 2017

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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 Anderson, 25 Aug 2017

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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

Mr Hughes, 10 Jun 2017

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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

Mr Haxton, 8 Jun 2017

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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.

Mr Campbell, 31 May 2017

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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...

Mr Bill, 27 May 2017

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

Mr Mcgeoch, 21 May 2017

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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.

Mrs Pincott, 2 Oct 2016

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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.

Mr Dick, 9 Sep 2016

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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!

Mrs Craig, 6 Sep 2016

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

Mr Davies, 20 Jul 2016

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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.

Mis Aplin, 21 Jun 2016

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

Mrs Ryan, 16 Jun 2016

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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.

Mr Precious, 8 Jun 2016

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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 Payne, 4 Jun 2016

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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.

Mrs Prentis, 29 May 2016

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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.

Ms Woodall, 25 May 2016

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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.

Mrs Thomas, 25 May 2016

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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 !

Mr Wightman, 21 May 2016

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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.

Mr Flett, 17 May 2016

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Beautiful cycling! Great route and some excellent hotels.

Ms Vipond, 8 Oct 2015

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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.

Ms Morris, 4 Sep 2015

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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 Elliott-Jones, 2 Sep 2015

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

Mr Quick, 21 Aug 2015

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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 Firth, 30 Jul 2015

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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.

Mrs Stockton, 29 Jul 2015

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A fun way to exercise in a beautiful location

Mis Barrie, 29 May 2015

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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

Mr Hill, 2 Oct 2014

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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 Holman, 22 Jul 2014

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

Mrs Marks, 4 Jun 2014

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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!

Mis Wilson, 2 Jun 2014

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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.



Ms McLellan, 14 Sep 2013

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

Mr Fletcher, 14 Sep 2013

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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.

Mrs Lee, 6 Sep 2013

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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 Thomas, 20 Jul 2013

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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.

Mr Alexander, 24 Jun 2013

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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 Gillison, 21 May 2013