Italy : Tuscany

Volterra to San Gimignano Walk

Trip code: W08TY 4.8 (64 reviews)

Self-guided walking

8 nights,

Level: 2

14.0Kg CO2e


  • Quintessential Italian landscapes: rolling hills, sunflowers, endless vines and hilltop hamlets
  • Scenic walking on Etruscan trails and pilgrims' paths; wildlife in abundance
  • Mouth-watering local cuisine; world-famous wines
  • Optional day trips to Florence, Siena and Pisa


  • 8 nights accommodation
  • All continental breakfasts and 2 evening meals
  • Briefing at the start of your holiday
  • Comprehensive route directions
  • Luggage transfers between hotels
  • Walking transfers


On this self-guided, 8-night walking holiday, you explore the timeless countryside between picturesque Volterra and the soaring towers of San Gimignano. You'll feel as though you're strolling through history as you discover sleepy hilltop hamlets crowning sun-dappled hills, verdant vineyards and panoramic picnic spots in fields ablaze with sunflowers. You also have the option to visit the eternal cities of Siena and Florence - Tuscan favourites right on your doorstep!

You start in Volterra, a real Etruscan gem with its tangle of alleys home to alabaster workshops and secret chapels, from where you walk through the verdant Berignone Nature Reserve and up to a fantastic panoramic ridge before a final climb to Casole d'Elsa. Your journey then takes you east to medieval Colle di Val d'Elsa, enjoying balcony views across the Elsa Valley. As you move towards stunning San Gimignano, the medieval 'Manhattan of Tuscany', the landscape is dominated by vines so there are plenty of wine-tasting opportunities here!

Our carefully picked hotels are full of contrasts, from a 4 star hotel in Volterra to the classic elegance of Palazzo San Lorenzo in Colle Val d'Elsa, a renovated 17th century building that used to be a hospital. Chianti is synonymous with excellent food and wine and evening meals are a celebration of the local cuisine. Perhaps try pappardelle alla lepre (fresh ribbons of pasta with a hare sauce) or bruschetta (toasted bread rubbed with garlic and olive oil, topped with sun-ripened tomatoes), all washed down by a glass or two of full-bodied Chianti!


The walking mainly follows flat strade bianche (white roads) with some asphalt lanes and partly shaded forest and valley trails. Walking boots and poles are recommended. Strade bianche are mainly exposed, affording excellent views - a sunhat is essential.

Read more about this holiday in The Headwater Blog.




Day 1: Arrive in Volterra

Arrive at your 4 star hotel just within Volterra's medieval gates, where you have time to relax in the pool before dinner.

You stay at Hotel San Lino.

hotel details


Hotel San Lino, Volterra



Hotel San Lino is set within the medieval walls of Volterra, a 5-minute walk from Piazza dei Priori. Originally built as a convent in 1480, Hotel San Lino has been attentively renovated to preserve the original architectural features that celebrate its historical charm.

Rooms here are spacious and bright, exquisitely decorated in Tuscan style, with traditional terracotta floors and wooden furniture. All rooms are equipped with ensuite bathroom, TV, air conditioning and Wifi.

A buffet breakfast is served in the main dining room, and includes homemade cakes, cured meats, yogurt and cereals.

The property also benefits from a garden with outdoor swimming pool and panoramic terrace.

Day 2: Volterra to Casole d'Elsa (15km/9.3mi)

There's a short transfer (30 mins) this morning to the start of your walk. Forest trails lead east through the Berignone Nature Reserve where you may be lucky enough to see wild boar, deer and fox. As you leave the forest, the ridge opens up giving wonderful valley views out towards Casole d'Elsa where you'll spend the next two nights.

You stay at Torre dei Serviti.

hotel details

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Hotel Torre dei Serviti, Casole d'Elsa


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Set in the heart of the medieval village of Casole d'Elsa, the Hotel Torre dei Serviti is a beautifully converted monastery with an impressive 14th century tower, which gives the hotel its name. The bedrooms are in keeping with the building's ancient history, with wooden beams, tiled floors and exposed stone and brickwork, as well as some rooms retaining remnents of the frescoes that adorned the walls in days gone by. The hotel also boasts a panoramic terrace - where you'll find the jacuzzi - as well as a bar and restaurant.

Room upgrades: Superior suite
The superior suites have a sitting area on a separate level to the sleeping area

Day 3: At Casole d'Elsa

Casole d'Elsa is a picture perfect Etruscan village atop a panoramic ridge. From the vermillion hued 14th century castle, views stretch as far as Monte Amiata in the south of Tuscany. A leisurely lunch maybe in the medieval piazza, before visiting the small but intact amphitheatre and Etruscan tombs.

Day 4: Casole d'Elsa to Colle di Val d'Elsa (19km/11.8mi)

Today's walk takes you down to the valley floor passing fields of sunflowers and orchid-sprinkled paths, before coming to the small hamlet of Quartaia, a good lunch stop. Continue through the woods along the famous pilgrims' path, the Via Francigena, where the fossils in the stones beneath your feet bear witness to the time when this area was covered by the sea. A final easy stroll takes you along the milky-blue, limestone-rich River Elsa and to your stunning 4 star hotel.

You stay at Palazzo San Lorenzo.

hotel details


Palazzo San Lorenzo & Spa, Colle di Val d'Elsa



The Palazzo San Lorenzo and Spa is located in the upper part of the medieval town of Colle di Val d'Elsa, better known as the old village of the “town of lead crystal-glass”. The building dates back to the 17th century when it started life as a hospital, whilst today, the public spaces are decorated with statues and crystal chandeliers.

The spacious rooms come with free Wi-Fi, Flat screen TV, free mineral water in the minibar and air conditioning. They have parquet floors and marble bathrooms. Headwater customers get the Superior rooms as standard.

A buffet breakfast is served in the breakfast room, a wonderful 'winter garden' completely lit by natural light, where you can find a large range of sweet and savoury delicacies. Your evening meals (when included), will be taken in the hotel’s restaurant which serves traditional Tuscan dishes.

Day 5: At Colle di Val d'Elsa

Take the local bus to Siena (30 mins) or Florence (1 hour). Or stroll into impressive Colle di Val d'Elsa, a fascinating town of two halves with a lift linking the lower New Town with the upper medieval Old Town.

Day 6: Colle di Val d'Elsa to San Gimignano (16km/9.9mi)

Today you follow in pilgrims' footsteps along the Via Francigena. Bright with sunflowers and fragrant apple orchards, this historic path skirts tiny hamlets and lonely chapels towards the lazy Foci river. You may like to make a short detour to take in a wine tasting at Montauto, before retracing your steps to rejoin the Via Francigena up to San Gimignano.

You stay at Hotel La Cisterna or Hotel Pescille.

hotel details


Hotel La Cisterna, San Gimignano



Enjoy your stay at this picturesque 14th century building hotel nestled in the heart of San Gimignano.

La Cisterna offers beautifully decorated rooms in both Florentine and modern style all of which are equipped with air conditioning, free Wifi and a flat-screen satellite TV.

A continental buffet breakfast is served at the on site restaurant Le Terrazze, where you can enjoy panoramic views over the historical square whilst your sip on your morning caffé.

The advantageous position of this property will allow you to easily reach shops, points of interest and a vast choice of restaurants in the town centre.


Hotel Pescille, Pescille



The Hotel Pescille is located just 4km outside San Gimignano, in the heart of the Tuscan countryside, surrounded by olive groves and vineyards. It started life as an old farmhouse before being converted into the 3 star hotel it is today. Evidence of its origins still remains however, with its ancient tower housing the hotel's small agricultural museum. There are pleasant gardens surrounding the hotel - with lovely views of the surrounding landscape - and it also benefits from an outdoor swimming pool.

All rooms at the Hotel Pescille are ensuite and are simple yet spacious with tiled floors, whitewashed walls and pristine white linen; air conditioning. satellite TV, minibar and hair dryer also all come as standard. Rooms have views onto either the timeless Tuscan countryside, or the roofs and mediaeval towers of San Gimignano itself.

The hotel does not have a restaurant open for dinner, a short walk will be leading you to a local restaurant.

Room upgrades: Superior room
Superior rooms are much larger than standard rooms

Day 7: At San Gimignano

Visit San Gimignano's mystical towers built by warring neighbours in the 12th century to outdo one another! Or for a longer day out, hop on a local bus to Siena (30 mins), a perfectly preserved medieval gem with a stunning striped 14th century Gothic cathedral and beautiful square.

Day 8: San Gimignano to Volterra (22km/13.7mi)

A short taxi ride (10 mins) from your hotel takes you to the start of the walk in Caggio, at the Castelvecchio Nature Reserve. From here you follow a woodland trail dotted with rock roses and wild strawberry plants to reach a panoramic strada bianca, where hawks soar overhead. With open views across cypress-studded ochre fields to Monte Voltraio, you pass through Sensano and Ulignano, historic hamlets with 16th century villas. Perhaps picnic by the era Valley before ascending an ancient mule track back to Volterra.

Day 9: Leave Volterra

See our Classic Chianti Walk for a 10-night version of this holiday.

Extending your holiday

If you'd like to extend your trip with extra hotel nights we recommend: Hotel Cosimo De Medici, Florence; Hotel La Luna, Lucca; Hotel Alessandro della Spina, Pisa; Hotel Chiusarelli, Siena.

hotel details


Hotel Cosimo De Medici, Florence


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This 3-star hotel is beautifully decorated, with rooms in individual styles - some are traditionally Tuscan whilst others are funky and modern. Parts of the the building actually date back to the 18th century, and the reception and public rooms are designed with this in mind, with Persian rugs, stained glass windows and wrought iron doors in evidence.

Although just off the main Via Nazionale, only 2 minutes' walk from the central station and 5 minutes from the Duomo, the hotel faces an internal courtyard for peace and quiet. All the rooms are double glazed, and all have air-conditioning so there is absolutely no reason not to have a good night's sleep!

There is no restaurant at the hotel, but there is plenty of choice nearby.

Extra nights: Please contact us for details.


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.

Extra nights: Please contact us for details.


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.

Extra nights: Please contact us for details.


Hotel Chiusarelli, Siena


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Hotel Chiusarelli is located just beyond Siena's medieval 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 Robur 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.

Extra nights: Please contact us for details.


Show prices including flights?  


These tour only prices are based on two people sharing. Single supplement from £380.

These flight inclusive prices are based on two people sharing. Single supplement from £380.

  • Flights from Heathrow to Pisa with British Airways
  • Other flights, including regional departures
  • Alternative flights, including regional departures
  • Business/club/first class fares
  • Room upgrades and extra nights at selected hotels
  • Option to extend to 10 nights

Our aim is to provide holidays that are unbeatable for choice and flexibility. We've listed our most popular travel options below, however you aren't limited to these - we can tailor-make virtually any holiday to suit.

Air prices include our standard flights/transfers
British Airways Heathrow to Pisa, then transfer to hotel 75 minutes. Return: Transfer to airport 75 minutes, British Airways Pisa to Heathrow

Business/club/first class seats are available on request.

Alternative Air Travel
Alternative flights, onward rail to your holiday area, and connecting private transfers can be arranged from most UK airports. If you would like to use one of the many 'low cost' airlines, we can book these on your behalf. We can also book UK shuttles to connect with your onward flight, please call for details and prices.

Self drive
We can arrange various channel crossings for you. Please call for details and prices.

Alternative transfers
If you require alternative transfers (because you will be arriving at a different time to our standard flights), then we can usually arrange these for you (there may be an additional charge).

To find out more about the travel options available call our sales team on 01606 720199, use our live webchat (we open again 9am Monday) or email

Should you require overnight airport accommodation, airport parking or even a uniformed chauffeur to take your car from your departure terminal and park it for you, we can arrange this for you through Holiday Extras. You can book airport parking, airport hotels and executive lounges through their website or contact us for further details. Early booking is recommended to obtain the best availability and prices.


Very straightforward and enjoyable. Upgrade the hotel choice in Volterra. The local guide was excellent- helpful & professional. I would have liked the option to go to the airport a bit earlier but apart from that excellent. Some of the walking notes need tweaked a bit and the map proved very valuable but overall they were accurate enough. The Headwater app would have made the walking more relaxing. It was EXCELLENT in Provence holiday.

Jacqueline Parkes, 2 Jun 2024


Overall a good experience…had a few accommodation hiccups that were quickly resolved by the local agent and the team at headwater. The routes were clear and mostly easy to follow, but I did have to use my OS Map app on a couple of occasions for peace of mind. The amount of road/strada bianca walking was a little disappointing but the countryside, hamlets, hilltop towns, vineyards and olive groves in Tuscany are beautiful. It is definitely worth visiting/walking there, the views are outstanding and hearing a cuckoo sing made my day!!

Susan Fuller, 9 May 2024


Fantastic few days walking. Walks were well documented, hotels good and the day rest in between meant we could enjoy the location we walked to. May was a fabulous time of year to do this walk with the abundance of wildflowers and warm temperatures.

FITZPATRICK, 21 May 2023


Fabulous walks and incredible scenery

Ms Dawson, 4 Sep 2022


Circumstances forced us to choose mid-July, which predictably was a bit too hot for walking after c.11am. We nevertheless enjoyed the beautiful scenery, and the outdoor pools at three of the hotels were very welcome. The old town centres visited are also beautiful, with local museums/galleries of interest on the "non-walking" days. The restaurant of the Volterra hotel is closed on Tuesdays, necessitating a 20 minute uphill walk for dinner (food included).

The Walking notes seemed a bit "tired" and sometimes ambiguous: we lost the route on two of the walks, but (thanks to a kind local lady with a car, and Google map on our phone) these mistakes were soon rectified. The local agent Alessandro was also very helpful.

Recommended, but avoid July/August if possible.

Mr Cross, 12 Jul 2022


A wonderful selection of places to visit, staying in quality accommodation and a good balance of walking and relaxing. Comprehensive walks directions and well researched routes.

Mrs Edmondson, 16 Jun 2022


A lovely holiday - beautiful scenery, butterflies and birdsong. Our photographs (of which there are many) will never do it justice.

Some challenging walking as it was particularly hot, hotter than usual for early June. The last walk from San Gimignano back to Volterra was particularly challenging in the heat . We had taken plenty of water with us but the restaurant Prato d'Era suggested in the walking notes was closed, and looked as if it had been for some time, and there was nowhere else to buy water. We had JUST enough.........

THe walking notes were generally good but may need updating in places. The Volterra to Casole d'Elsa walk mentions areas of woodland clearance (Dispensa di Tatti ) but the trees and shrubs have regrown and the two barrier posts are no longer there.

Hotel Park le Fonti rooms are rather tired but food and service were excellent and the swimming pool was superb. Relais Santa Chiara 'classic' room faced a wall, but Headwater sorted this out very quickly.

Mr Milsom, 8 Jun 2022


Overall a most enjoyable holiday. The walks are fine until the last 1-2kms steep uphill which is quite arduous in the heat. We were pleased to have a rest day in between to enjoy the local sites. Scenery was great and the tracks easy to navigate.

As vegetarians the food options were rather restricted.

The guy who collected us from Pisa was rather cavalier with road safety. The agent was very welcoming and helpful.

Mr Newmarch, 19 May 2022


I would recommend at least one holiday a year like this - it's different - feels good and is very satisfying. The team were very helpful and everything went smoothly.

Mr Powell, 11 May 2022


A very enjoyable holiday. The scenery and places on route were very interesting. The walks are a good length but it's worth remembering, particularly when the weather is hot, that apart from to Colle they all end with chunky climbs. The hotels were generally very good but we suffered some poor service at times at Terre di Casole and Relais de Rovere. Hotel Pescille - not the standard hotel Headwater use for San Gimignano - was great; a lovely location and the staff were excellent, and benefitting from a top-notch restaurant Zafferano 400 yards down the track from the hotel. We added on a day in Siena which worked really well. Special mention for Headwater's rep Frankie; a super guy, extremely helpful, flexible and informative and he clearly works very hard for the company.

Mr Foster, 24 Sep 2019


We really enjoyed our 8-day walking holiday in Tuscany - we have been with Headwater many times before and this trip didn't disappoint! We enjoyed the beautiful scenery, the hotels (all very welcoming), trying the Tuscan food and wine and of course the walking. We found the notes particularly good this year - no extra mileage! - which was good because it is a hilly area and the last day is a long one - but we finished it with a smile and a beer and gelato in Volterra! Lastly I'd like to say how helpful and informative our rep Frankie was (and we fell in love with his puppy Drago!)

Miss Robbinshallam, 20 Sep 2019


We really enjoyed our stay in Tuscany. The walks were all in beautiful places with the right amount of challenge for my level of fitness and stamina. I really like the balance of having a day's rest between walks, which makes it a more restful holiday. It was lovely to explore the towns and villages we stayed in. Most of the routes were strade bianche, and we also enjoyed the sections which were on the Via Francigena. We hardly saw a soul on the walks, which was nice. It's worth mentioning that there were very few cafes or places to stop en route, which wasn't a problem, but you need to be prepared. Day 1 walk - we wished we'd taken our swimming things to swim in the Elsa river on the last section - the water was fabulous. San Giminano was a fantastic place to visit, despite the volume of tourists - it was August, after all! Park Hotel Le Fonti was our favourite hotel with a gorgeous pool and restaurant on the terrace, serving delicious meals. Our Rep was very helpful indeed - much appreciated. This was a great tour, with an added day in Pisa, which we loved, and a morning in Lucca by train from Pisa, also beautiful, where we easily squeezed in a parkrun around the old city walls. A great trip which we would recommend!

Ms Lanchbury, 1 Aug 2019


The entire trip was a pleasure, Frankie was punctual efficient and friendly. All the hotels were good. The only exception were some of the staff at Relais Rovere. Details with Frankie

An excellent holiday thoroughly enjoyed.

Mr Fowler, 26 Jun 2019


The holiday was extremely well organised and the walking exactly what we expected. All of the hotels were of a very high standard, and food, where provided, was also of a high standard, except for Relais della Rovere, where the menu was very limited. The grading of the walks was right, and even the 22km on the final day didn't prove as daunting as I had expected! This is definitely a holiday I would recommend to others looking for a week of beautifully scenic walking in his area.

Ms Ullmann, 16 Jun 2019


Overall an excellent holiday, with a great balance between walking and stopovers on alternate days. A great way to see hidden Tuscany. While the daily distances did not seem very challenging, the heat made a massive difference - we tended to start well first thing in the morning but struggled as the day got hotter. The food, and wine, was excellent throughout, and each hotel had its own unique character. Our rep, Mark "Frankie" Franklin was outstanding. He gave an excellent welcome / introduction at the start of the holiday, and was always available to offer advice and support throughout the week - please pass on our thanks.

Mr Wright, 12 Jun 2019


Beautiful hill towns in Tuscany, but rather defeated by the heat!

Ms Dempster, 4 Jun 2019


Clear information

Clulow, 2 Jun 2019


Wonderful accommodation, very helpful and friendly reps in Phaedra and Paul.

Mr Armstrong, 10 Sep 2018


Having a challenge, along with rest days at lovely comfortable hotels was just the ticket. A super holiday which we hope to do again in a new location.

Mrs Mousley, 12 Jul 2018


A hugely enjoyable waking holiday in Tuscany staying at excellent hotels in beautiful hilltop town locations. Reps were excellent and the walks enjoyable.

Mr Macdonald, 24 Jun 2018


Very well organised holiday in a beautiful part of Italy. Paul and Pheodra were very helpful and nothing was too much trouble.

Mrs Freeman, 8 Jun 2018


Our walking holiday was at the end of May, and there had been an unusual amount of wet weather before we arrived. We walked through the rain on our first day, which wasn't too bad as it wasn't cold. From then on, the weather improved considerably.

Due to the heavy rain, some parts of our route, which involved crossing rivers on stepping stones, were not safe. Paul and Phaedra did an excellent job of keeping an eye on our route and letting us know whether each section was safe or not, due to the extraordinary weather conditions. They really were looking out for us and our safety and were able to provide us with an alternative route.

The scenery was stunning and the routes very enjoyable. We were amazed at how few people we passed along the way; we felt like we had the place to ourselves! There was an abundance of poppies and other interesting wild flowers. Every day we could hear nightingales singing, and we also heard golden oriels, hoopoes and cuckoos. We were delighted to sit on a shady bank and watch a flock of bee-eaters (stunningly colourful birds) displaying for us.

On the whole, the hotels were very good with comfortable beds and welcoming staff. The Tuscan food was delicious, and most of the locals were very welcoming and friendly. We also enjoyed a day in Siena, which is quite do-able in a day, and only a short bus journey from Colle Val d'Elsa.

We appreciated the fact that, on this holiday, the distances walked were built up over the week, so that the longest and probably the toughest day was the last day, with the longest climb. We felt comfortably challenged; there is plenty of time to cover the distances, and we enjoyed taking our time and stopping to admire the views or have a closer look at the wild flowers...or pick and eat some wild cherries!

We were very well looked after by Paul and Phaedra, our reps, and we are very grateful to them for their care and attention, which definitely added to our overall enjoyment of the holiday.

Mrs Allen, 21 May 2018


A good mix of walking, sight seeing and relaxing. We went first 10 days of October and had lovely warm sunshine everyday too.

Ms Honeyball, 2 Oct 2017


Very enjoyable holiday with a good range of locations in good hotels with easy access to the local town. Excellent and really helpful reps added to our enjoyment of a lovely holiday.

Mr Todman, 12 Sep 2017


first class reps in Paul and Phaedra who made our holiday with their care and attention which we felt was beyond the call of duty,they were amazing.Great experience,with wonderful walks ,superb views and brilliant locations.Would recommend the holiday to anyone.

Mrs Mcdonagh, 6 Sep 2017


An excellent varied holiday and a wonderful way to explore the unspoilt Tuscan countryside.

Mr Reeves, 4 Sep 2017


With Inntravel walking holidays you do not normally have contact with an agent / or rep .

This holiday was different and to be honest we enjoyed the contact which we had we your 2 reps . We realised we had met them in a previous life.. They were absolutely professional in every way made us most welcome and we both felt they added something to the holiday for us.

I would say if you can retain them please do and if they take up another location we would even consider choosing that holiday.

Some adverse comment criticising route over the stepping stones was mentioned by the other couple walking same days as us however we where comfortable with our experience on that day and in fact all other walking was great . I am sure the following days after our holiday will have presented plenty of problems with the weather. .

Please give them the official feed back as excellent and thankyou

From Ros and Allan

Mr Hargreaves, 2 Sep 2017


Tuscany was absolutely stunning although very hot in Aug

Mrs Georghiou, 5 Aug 2017


Great holiday with a good mix of activity and comfort. The walks take you through some beautiful countryside and the notes are accurate and useful. The length and difficulty of walks build up over the week so that the long final day feels reasonable. Our holiday was in July, consequently we started walking early to avoid the worst of the afternoon heat. This meant that we were arriving at our hotels in the early afternoon. We found places to eat a late lunch close to the end of the walks, which meant we didn't need packed lunches and made the glass of beer in the café feel well deserved and taste fantastic. All of the hotels were good and all had different areas of merit. We found the food in Le Fonti very good despite the surly head waiter; the rooms in Terre di Casole were great with a patio just a few steps across the lawn from the pool; the Relais della Rovere is a beautiful building with great poolside service, and the Relais Santa Chiara is very well located to explore beautiful San Gimignano.

Overall an enjoyable holiday if you like walking in the countryside, relaxing in decent hotels with good food, and meandering around Tuscan hill towns and villages.

Mr Holland, 10 Jul 2017


It was a magnificent experience again. We have used Headwater before, and were extremely satisfied with their product.

Our Reps in Italy were stunning. They couldn't do enough for us, and were so helpful. The hotel accommodation was outstanding, and the food excellent. We will certainly use Headwater again as the whole trip was brilliantly lubricated. We were more than satisfied. Thank you for everything!

Mrs Dunnill, 2 Jul 2017


Headwater's service takes the hassle out of a walking holiday so you can relax and enjoy at your own pace. Accommodation, while not 5 star luxury, is a reliably good standard, better than most walking holidays, and the meals are usually excellent. Local reps are knowledgable and helpful, walking notes thorough, and transfers smooth. We loved the walks in Tuscany, which are well thought out to get to the picturesque town and hotel with time to relax.

Mr Catton, 2 Jun 2017


The walking was great but might be challenging when the summer temperatures occur. Good combination of walking and sight seeing.

Mr Owen-Jones, 25 May 2017


A holiday that we enjoyed so much in 2013 that we went again this year!

Walks are not too challenging and provide beautiful views of Tuscany. Be aware that generally the hardest walking is the final ascent to your destination so reserve some energy and water.

A trip to Florence or Siena is really easy from Colle Val D'Elsa by bus and the location of the hotel in San Gimignano is perfect for dipping in and out of the crowds during the day

Mrs Sillett, 28 Sep 2016


Varied walking with except for the first morning no need for a lift to the start of the walk although limited opportunities to find drinks or nibbles en route.The final day was longer than we anticipated and we did flag down a passing taxi to take us up the huge hill to Volterra.The hotels varied but with good accommodation, views and the food was generally good. The best meal by far was in the agrotourismo down the road from Hotel Pescille (3 * with no restaurant) which was a real gem as the hotel was a fair walk from San Gimignano and avoided taxis at night.

Mr Stevenson, 14 Sep 2016


We had an amazing trip walking around Tuscany. San Gimignano was probably the highlight but everything was excellent. Walking in mid-August was very hot, but we found the if we left early the walking temperature until about 11am was just right. On our off days we visited Sienna, took a vineyard tour near San Gimignano (the excellent Cappellasantandrea is a 30 min walk away) and explored around Casole. The meals outside at the Relais della Rovere were also fantastic. Overall a great trip we would highly recommend.

Mr Cumber, 21 Aug 2016


Headwater take all the uncertainty out of your holiday: you know the hotels are going to be excellent in every respect, you know you are going to get picked up at the right time, you know the walks are going to be through beautiful countryside. Everything runs smoothly and efficiently. We find the balance between a walking day and a rest day just perfect. This was our eighth holiday with Headwater and we are already talking about next year's.

Mrs Walker, 2 Jul 2016


Beautiful countryside and villages with fantastic unspoilt views, fabulous hotels and food. Plus being very well looked after by excellent Headwater staff.

Mr Mackrill, 22 Jun 2016


A wonderful holiday with excellent walks in beautiful countryside; staying in comfortable, well appointed hotels, which for us were marred by the fact that very few concessions were made to guests who did not eat meat, and therefore we did not eat very well throughout the week except on the evenings when we had to eat out at restaurants of our own choice (when we were very well catered for). However, one of the most attractive aspects of a Headwater holiday is to be accommodated in a comfortable hotel offering good cuisine at the end of a day's walking, and not having to go out again searching around for somewhere attractive to eat.

Mr Loaring, 2 Jun 2016


The walking was varied and interesting. The stretch along the river d'Elsa on the way to Colle di Val d'Elsa was the most interesting. Some of the hotels are quite busy with tour groups. The hotels also vary markedly. Hotel Terre di Casole was easily the best, particularly for service. One minot point however was that the room we were allocated the room (204), despite plenty of empty rooms alongside it that were a bit bigger. The reception staff and the main waitress in the restaurant were fantastic and we particularly appreciated that there were plenty of special options offered to us in the restaurant that were not on the menu but were suitable for vegetarians. The poorest hotel was Relais della Rovere. Reception staff were uninterested and the restaurant (not run by the hotel) was poor for vegetarians. The pool at Relais Santa Chiara was hopeless for swimming. San Gimignano was very touristic and not very pleasant. On the other hand, Volterra was very interesting and worth more time that it was allocated as a start/finish point.

Dr Scally, 31 May 2016


Very good well balanced trip

Mr King, 18 Sep 2015


Very well organised from start to finish

Mrs Houghton, 16 Sep 2015


Perfect holiday. Beautiful countryside, great walks and the pools at the end of every walk were a real treat. Also there was the perfect mix of culture and countryside.

All the hotels were very good, the walks varied. Headwater holidays take the stress out of the holiday, once you have booked, all you need to do is turn up,

relax and enjoy.

We wanted to attend our son's wedding at the beginning of our holiday, in the area, and Headwater made it possible to combine the wedding, the walking and some extra nights in Pisa!

The staff at the office give you an excellent service!

Mr Howell, 27 Aug 2015


This holiday was a perfect mix of walking and relaxation. It was reassuring to have reps on the ground, although everything went perfectly and so we didn't need to call on them. The route notes were first rate and the accommodation excellent and in just the right locations for our rest days.

Lad Blackwell, 17 Aug 2015


A very enjoyable mix of interesting walks and good hotels. Probably best-suited for adults whose idea of a good holiday is not sitting around on a beach.

Mr Gray, 24 Jul 2015


This holiday was one of the best we have had.Tuscany was beautiful and the chance to see it on foot made all the difference. The hotels were terrific and the food amazing.We will be back next year.

Mrs Clark, 20 Jun 2015


Wonderful holiday in beautiful surroundings. Good hotels each of which had their own character. Excellent walking notes. Our local reps Audrey and Chris were a very pleasant and helpful couple and they did a sterling job in a quiet but very efficient manner, we couldn't have asked for better!

Mrs McGaw, 4 Jun 2015


Choice of venue for walking very good. Notes extremely helpful, reps very good with local information. They were also very helpful when needed to help with a blistered foot on a bank holiday.

Mrs Napier, 31 May 2015


It was a lovely holiday and we saw lots of things that visitors to the region wouldn't normally see. However, we feel that you need to be fit to undertake it. We are used to walking in the Peak District but still found some of the days quite challenging. We travelled in May when the weather was reasonably warm for most of the week. We feel that later in the summer when the weather was hot the walking would have been very hard in places where there wasn't shade.

Mrs Sheardown, 17 May 2015


Holiday was very enjoyable. Good but not intrusive support from local representatives who gave some very useful hints and were always contactable. Hotels were very excellent with one notable exception.:

- one notable exception - Hotel Terre di Casol, see below for more details,

- the welcoming receptionist at Casolare LeTerre Ros who had no interest in helping us locate our forwarded luggage (which had arrived).

Mrs Gorman, 4 Oct 2014


The walking was relatively easy although there was more need to carry your own picnic lunch than on other holidays as there were few opportunities to pass cafes/restaurants. Walking was scheduled for every other day so we needed to arrange things to do on days off. In addition, there was probably less 'sights' to see than on previous holidays unless by independent travel on the non-walking days. However, as usual, the arrangements were superb and everything went smoothly including the lovely warm weather in October.

Mrs Grant, 30 Sep 2014


A superb holiday. The scenery was spectacular and moving from hotel to hotel makes the holiday interesting and varied.

Mrs Wakefield, 22 Sep 2014


I enjoyed looking through the website which was very informative. The whole holiday was very well organised; being met at the airport and being given chilled water bottles when we got in the mini bus was great. Our reps couldn't have been more helpful; they stopped at a shop on the way to our hotel so we could buy food and water for the following day's walking, they offered us equipment and leant us waterproofs. We felt very well looked after and listened too. For us this was the ultimate, stress free holiday! The walks were quite long and it was hot, but the terrain was pretty easy and we never found ourselves struggling - there was always the knowledge that there was a lovely hotel with pool and meal waiting for us at the other end. As a family we are fairly active, but not very fit - my husband plays racquetball once a week and I go for a daily 50 minute dog walk which proved to be enough to allow me to enjoy the walks. Our children all do sport at school and our eleven year old found the walking easy!

Mrs O'Carroll, 30 Jul 2014


Well organised walk through beautiful countryside. Perfect opportunity to see the rural Tuscany and taste local food. Wonderful mix of walking sightseeing and relaxing.

Mrs Spalding, 4 Jul 2014


Katie and Jim put every possible effort into making our stay problem free. On the first afternoon they sat with us for an hour giving us very helpful information about the route and terrain that we would be walking, places en-route where we could get food and drink, landscape features and sights to look out for. Although we no cause to call upon their assistance during our holiday it was clear that nothing would have been too much trouble for them.

With regards to the holiday itself, the route had been carefully planned and all the hotels were in wonderful locations (Medieval Tuscan hilltop towns).

We would recommend the region and this holiday to anyone.

Mr Gallagher, 24 Jun 2014


The care and attention that the Reps provided in the area was outstanding, and having been on 2 previous Headwater holidays they both worked very hard trying to please everyone.. I felt that the holiday was accurately graded as a 2 boot holiday and all the walks were well within our capabilities but sufficiently challenging. The area was fantastic and May appears to be a great time to visit with all the spring flowers in bloom and pleasant temperatures. I am usually happy to return home but I could have stayed another week so am looking to repeat the experience in a similar region next year as is my walking companion.

Ms Pilgrim, 21 May 2014


Tuscany was a beautiful region with a great mix of walks in wonderful countryside and stunning cities/towns full of history and lovely architecture. The reps, Jim and Kate, were so helpful, thoughtful and genuinely caring - the best we've come across.

Mrs Lai, 17 May 2014


Probably not for 'casual' walkers as the walks seemed appropriate for experienced ones.

Mrs Cushion, 17 May 2014


We had a wonderful week with a perfect combination of walking, sightseeing, swimming and sunbathing plus delicious food and glorious landscapes. The local reps couldn't have been more friendly and helpful; it was very reassuring to know that they were there in case anything went awry - but it didn't.

Ms Gibson, 15 May 2014


This is our second HeadWater holiday and both times we have not been disappointed. We have been pleased wit the standard of hotels in Italy, better than the ones we had in Switzerland - clearly you get more for the money in Italy. Breaking the holiday into 2 and spending 2 nights in Florence was a highlight for us.

Mrs Brown, 8 Sep 2013


Generally well organised, as above hotel selection varied and some of instruction on walks info could've better. Walks much harder than appear to as advertised.

Mr Galbraith, 7 Sep 2013


We did enjoy our walk. The scenery is good. To ans the 'no' above - we would seek out a different type of holiday as we are getting on in years. It is a fairly steep walk for parts of the day, particularly the final ascent to the villages and hotel and can be hot in the sun. Suggest picking a time of year when temp is 24-28 degrees max. If you are over 60 you may wish to consider an easier walk as this one will test your fitness. You will have to train up for the event, as we did, if you are only of average fitness for your age. The other 4 members were younger than us (in their early and middle 50's) and handled it fairly well without any real training. Choice of footwear was not critical as one member did it only in runners. The rest had slightly more hike specific gear.

Mr Prestage, 27 Aug 2013


Headwater always come up with the perfect balance between walking, time for relaxation and interesting, well-appointed hotels.

Mrs Slater, 5 Aug 2013


We had a fantastic time and will certainly recommend this type of holiday to our friends. Even our 15 year old son got into the swing of it. We went in early July which was hot but it had the benefit of the walks being reasonably dry underfoot.. Our guides had changed one of the routes as a result of previous bad weather which was good as I would imagine that some of the walks could be quite difficult after rain. The route descriptions were generally very good and we didn't get lost but there were a few times where this was more by luck. The hotels were all good, some of the rooms were a little tired but the welcome, service and food made up for it. We completed our walks between 2-3pm each afternoon and our luggage had always arrived before us. Thank you Roger and Monika for your support and for taking us back to Pisa airport so early on Sunday morning.

Mrs Turner, 6 Jul 2013


What a fantastic experience ! Not a tourist in sight and walking in the middle of nowhere with just the sound of the birds and wildlife to break the silence.

The beauty of this holiday was the fact that we were walking most of the day but HeadWater have appreciated that just because you are walkers you don't need to 'rough it' in down market accommodation it was such a joy to have he freedom to enjoy the beautiful countryside and arrive to find your luggage already in your room and a luxurious hotel with fabulous food and absolutely breath taking views !!!

We had some great moments and despite eating and drinking copious amounts of wonderful food and local wine because of all the exercise, amazingly we didn't put on any weight

We cannot praise the reps highly enough. Monika and Roger made us so welcome and at ease from the moment they greeted us at the airport with chilled bottles of water for the journey to our hotel NOTHING was too much trouble for them ! A HUGE THANK YOU TO YOU BOTH

For anyone considering this holiday , you do need quite a high level of fitness. Both of us are EXTREMELY ACTIVE and fit people and were pleased to find that we were suitably challenged by the walks in the heat. The hotels all had stunning views as they were all at the top of mountains ( so bare in mind the end of your walks when the sun is at its hottest are all uphill!!)

A fab holiday!! Something so different. I would not hesitate to recommend!

Mr Goldstone, 6 Jun 2013


Self-guided walking

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