Chianti Classic Walk

Mr Mcintyre, 28/09/2019

We had a great time on the ‘Chianti Classic’ walking holiday. The only glitch was when Ryanair lost our luggage, but Headwood staff and local rep came to the rescue and couldn’t have been more helpful. The walking trips were excellent, the directions provided faultless and our destinations interesting. The choice of hotels was very good and our luggage (once received) was transported effortlessly and always waiting for us at the end of each walk. Would definitely recommend.

Mrs Provan, 18/09/2019

Well planned route, excellent travel rep and lovely area

Mrs Shannon, 12/09/2019

Really enjoyable walking holiday mixed with days for other cultural activities which for us worked really well. Food and wine opportunities on the trip were fantastic. September proved to be great weather but bad time for mosquitoes so be prepared!

Mr Morgan, 06/07/2019

As described in the brochure/online. Good combination of walking/sightseeing/leisure. Great locations and hotels.

Representative (Frankie) particularly helpful and provided reassurance by always being available, contactable by phone and ready to assist. We could not have asked for more.

Mrs Skinner, 04/11/2018

It was an excellent introduction to walking holidays abroad, we will be returning to Italy with Headwater next year. There was a good variety in the countryside experience during the walks. On the whole the hotels and food were good. The only negative issue was at Relais della Rovere where the restaurant was taken over by a large bus tour party of Koreans.

Mr Hill, 16/10/2018

An excellent experience in terrific countryside. The walking was good and in some cases quite exhausting but we had all day to complete the journey with a refreshing drink at the end. The hotel accommodation was very good with three of the hotels being excellent and the fourth being good. Great walking, good weather and good reps. We had an extra two nights in Coll di Vald'Elsa which enabled us to travel by bus to Sienna and Florence.

Mr Housden, 18/07/2018

One of the easiest holiday operators ever used. Great responses from all staff contacted both at home and on holiday.

Mr Firth, 08/07/2018

Our holiday was a good balance of walking days and free sightseeing days, giving us the opportunity to visit Sienna and Florence as well as completing over 70km of self-guided walking. We were pleased to have the very agreeable company of 5 others who were on similar holidays. The weather was as hot as expected but the first walk ended in a thunderstorm which none of us were properly prepared for as we arrived at our hotel completely soaked. The remaining days were dry and sunny except for the last which was mainly cloudy - which we were grateful for as it was the longest and most tiring. The routes passed through very varied countryside and villages, and the stopovers were all in small towns which were very enjoyable to explore. The self-guiding notes were very detailed and easy to follow, except for a very few places where they were ambiguous or misleading but none of us got seriously lost or delayed more than a few minutes. Accommodation, hospitality and food were all of high standard.

Mr Mckenzie, 25/06/2017

A great holiday. A great combination of walking and relaxing at comfortable hotels. Lovely walks with clear instructions. Our reps were really friendly and helpful: when we got into difficulty with blistered feet (our responsibility entirely, we ignored advice given on suitable footwear!) they bailed us out and arranged for us to do a shortened version of the walk, picking us up at an agreed point.

, 07/11/2016

thoroughly enjoyed the walking-especially when following the river. Accomodation comfortable and staff in the hotels welcoming and friendly. We had really personable and informative couriers able to supply us with local information on the areas-they went the extra mile!

, 26/09/2016

Really attractive area,great hotels.We interspersed some extra days for additional relaxation and chance to visit additional restaurants for dinner.Fonti was weakest for dinner but other 3 were all excellent. Terrific wine tasting and dining at San Gimiagno

, 25/09/2016

We enjoyed this holiday but with the following proviso in comparison with the Footsteps of St Francis Umbria which we did last year there was much more hard surface and road walking particularly on the last day.

Our first and last Hotel San Limo was without doubt the poorest hotel that we have experienced on a Headwater holiday. there was no atmosphere in the restaurant the staff both at dinner and breakfast did not give a friendly or welcoming approach. We actually decided to eat out in Volterra on the final night rather than eat at the hotel. The room we were given 403 was supposed to be a superior room it was the smallest of all the rooms we had and the only thing that could have made superior was that it had a small balcony.

Hotel Relias della Rovere whilst the food was excellent and the room good, the pool and the pool area was very poor, grass uncut and pool a little dated

, 18/09/2016

Challenging, enjoyable walking in a scenic setting.Easy access to visit Sienna, Florence and the small historical towns along the way a real bonus.

, 20/07/2016

Stunning countryside and food. Best reps we've ever had.

, 10/07/2016

Wonderful hilltop towns and beautiful, diverse scenery. Good hotels and excellent food. Luke and Eleanor were lovely reps. Nothing was too much trouble. We found we needed to shorten the walks and they helped us work out a way to do this, yet ensuring we did the best parts of each one. They ensured we had a stress free holiday and overall we had a very relaxing and memorable time. Ten days was ideal. A holiday we would recommend.

, 15/06/2016

Luke & Eleanor the reps couldn't have been more helpful and made the holiday a special experience. Taking the extra days to allow for visits to Sienna and Florence added an extra dimension to the holiday and would thoroughly recommend doing this as an addition to visiting the hilltop towns.

, 30/09/2015

Wonderful scenery, good friendly hotels, tough walks but worth it! Mosquitoes, especially the new 'tiger mosquitoes' are a real problem it would seem even in September so take lots of insect repellent and a spray to do your room before bedtime. I covered my legs and sprayed my arms for walking when I realised this and that did the trick!

, 19/09/2015

Beautiful area but let down by inattention to detail.

Disappointing largely for small but cumulative reasons.

, 18/09/2015

Relaxing yet active walking holiday - lovely locations and good back up if needed

, 17/09/2015

This was one of our very best Headwater holidays. We liked the mix of walks and sight-seeing. We felt very well looked after.

, 25/09/2014

Well organised and supported walking holiday assisted by friendly and knowledgeable staff. Fine food and accommodation.

, 21/09/2014

We really enjoyed the holiday. Katie and Jim were very good representatives. There has been a problem with an outbreak of horse flies and so they went out of their way to suggest an alternative walk that avoided walking through woods. This was really appreciated. My only issue was the last walk between Casolare Le Terre Rosse and Park Hotel Le Fonti. I found this walk to be too long especially as the last couple of miles was up hill. Luckily it was a relatively cool day, if the sun had been out I don't think I would have been able to complete the walk.

, 08/08/2014

Thank you for a wonderful holiday! We enjoyed the walking, the days off by the pool, the scenery, the swimming pools, the food and the wine immensely. All five of us, including the kids, had a fantastic time.

, 02/08/2014

The holiday was very enjoyable, very well organised, and the reps went out of their way to be helpful.



As Headwater guests, we felt that we were being given particularly good treatment at each hotel.

, 12/10/2013

This was a well organised holiday with 4 excellent hotels with swimming pools, good food, 4 quite long days walking through interesting and varied terrain, and opportunities to explore Siena and Florence on the rest days. The reception staff at all the hotels were very helpful, providing local information including booking tickets for the Accademia/Uffizi in Florence. Excellent and knowledgeable support from Roger and Monika, the holiday reps - who were always there when needed.

, 30/09/2013

Lovely walks particular second and third ones. Wouldn't recommend extension to 10 nights as food at Rovere was very limited in choice.

, 25/09/2013

An excellant Holiday company for all the local knowledge it incorporates. The reps were great.

, 21/08/2013

Roger and Monika had changed the routing of the first day's walk as a result of storm damage. We really enjoyed this walk as we felt it added more variety and more open views than the original route which would have meant more walking in less open woodland. The walk was shorter than the original but we felt this was a good idea as it broke us in more gently and meant we had more time to savour the landscape. We recommend you amend your notes to keep this new route and ditch the original. The last day's walk was lovely until we reached the agriturismo San Antonio junction; from then on until Restaurant Prato d'Era we were on quite a busy strada bianca with quite a lot of traffic (not just tractors) for a long time, followed by and another long walk on a tarmaced lane. We would have preferred more 'off-road' walking if it had been possible at this point without losing the views. All the other days were simply lovely, the views wonderful and the walking very much enjoyed.This is our fifth holiday with you and we have had some excellent reps but we must say Roger and Minika were outstanding and provided a personal, friendly and humerous service above and beyond what we could have expected.

, 15/08/2013

1. Make sure you get the details you need before you travel.

2. If travelling with friends, insist on separate invoicing if that is what you want. Keep insisting

3. Self guided holidays offer great flexibility and also require more effort. Guided holidays have the potential to give local knowledge.

, 13/08/2013

Four very varied walks, challenging in places given my fitness level (poor!) but all definitely do-able - and very, very rewarding - in fact, unforgettable. It was unseasonably hot (35-38 degrees) but we were able to stop for leisurely lunches on two of the walks. The weather meant we made full use of the pools a each hotel - just wonderful. Our room at the Terre Casole will go down as one of my favourite ever - wonderful terrace with a walk across the lawn to the pool. At the relais we were upgraded to a superior room at no extra charge - just a most lovely room with a jacuzzi bath. As for the rest days ... with easily arranged trips into Florence, Sienna and San Gimignano - just wonderful, giving great lunch opportunities too.



This was a complete break from our daily lives. Whilst undoubtedly costly ( we had three extra nights) it was the main holiday we will take this year, the only holiday abroad and was just superb. I'm usually very attached to 'seaside' holidays but the landscape, countryside, towns and hotels all combine on this holiday to make iot a real experience to treasure

, 09/08/2013

A really lovely mix of hotels with excellent walking and sight seeing opportunities

, 03/07/2013

we really enjoyed the holiday-great way to visit these lovely hiiltop towns and cities of Tuscany