Feefo - Independent reviews
  Contact Us

Request a Brochure | Newsletter

Chianti Classic Walk

Chianti Classic Walk


Email us
  • Holiday type
    Self-guided walking
  • Duration
    10 nights
  • Accommodation
  • Activity level
  • From $2849per person, tour only
  • Departures
    Every two days from 1 May '20 to 8 Oct '20
  • What your holiday price includes
  • 10 nights hotel-to-hotel accommodation in a mix of hotels
  • All continental breakfast and 4 evening meals
  • Services of your local Headwater Representative
  • Headwater Wine Collection Service
  • Route directions and maps
  • Standard transfers at the start/end of the trip (if booking inclusive flights)
  • Luggage transfers between hotels
  • Walking transfers
  • Optional Upgrades
  • Room upgrades and extra nights at selected hotels
  • City break add-ons in Florence, Lucca, Pisa and Siena
  • Option to shorten to 8 nights
  • Excellent choice for
  • Food lovers, wine lovers, flora & fauna, art & history, swimming opportunities, solo travellers, couples

For 2020 departures our trip inclusions are changing - please contact us for full details

      from 32 reviews

Mr Mcintyre says...
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 ...
Read reviews »

Italy: Tuscany

Chianti Classic Walk

  • Quintessential Italian landscapes: rolling hills, sunflowers, endless vines and hilltop hamlets
  • Scenic walking on Etruscan trails and pilgrims' paths; wildlife in abundance
  • Exceptionally friendly hotels, family-run, with gorgeous swimming pools
  • Mouth-watering local cuisine; world famous wines
  • Possible trips to the 'Super Tuscans': Florence, Siena and Pisa

On this self-guided 10-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. There's the option too 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 Forest 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, all with pools, are full of contrasts. From a recently renovated, elegant boutique hotel just outside the medieval town of Casole d'Elsa to the refined elegance of the 4 star Relais della Rovere in Colle di Val d'Elsa, a magnificently restored 12th century abbey where you spend four nights, and which is an excellent base for day trips to the eternal cities of Siena and Florence. 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!

Read more about this holiday in The Headwater Blog.

We're here to help

If you have any questions about this holiday call our sales team on 1-800-267-3347, use our live webchat or email usa@exodustravels.com

Day-by-day itinerary

Walking information

The walking mainly follows reasonably 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.

We're here to help

If you've any questions about this holiday call our sales team on 1-800-267-3347 , or email usa@exodustravels.com

Day 1: Arrive in Volterra

We meet you at Pisa airport, and take you to your hotel (75 mins) just outside Volterra's medieval gates, where you have time to relax in the pool before dinner.
You stay at the Park Hotel Le Fonti (breakfast and evening meal)

Day 2: Volterra to Casole d'Elsa 14km/9mi/4hr

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 the Hotel Terre di Casole (breakfast included)

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.
You stay at the Hotel Terre di Casole (breakfast included)

Day 4: Casole d'Elsa to Colle di Val d'Elsa 19km/12mi/5hr

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 pilgrim's 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 d'Elsa and to your stunning hotel, a beautifully converted 12th century Benedictine Abbey with garden and pool.
You stay at the Relais Della Rovere (breakfast and evening meal)

Days 5-7: At Colle di Val d'Elsa

Regular buses to Siena (30 mins) and Florence (1hr) leave from just outside the hotel grounds so you can easily explore Il Campo, the Duomo, and the treasures of the world-famous Uffizi. The historic town of Colle di Val d'Elsa dates back to Etruscan times with cathedral, museums and fine Renaissance buildings. Back at the hotel, you can relax in the pleasant gardens surrounding the sparkling outdoor pool.
You stay at the Relais Della Rovere (breakfast and evening meal)

Day 8: Colle di Val d'Elsa to San Gimignano 16km/10mi/4.5hr

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. Time for a swim in the pool before dinner.
You stay at the Relais Santa Chiara (breakfast included)

Day 9: At San Gimignano

Visit San Gimignano's mystical towers this morning built by warring neighbours in the 12th century to out-do 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.
You stay at the Relais Santa Chiara (breakfast included)

Day 10: San Gimignano to Volterra 22km/14mi/6.5hr

A short taxi ride (10 mins) from your hotel takes you to the start of the walk 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 the villages of Sensano and Ulignano, historic hamlets with 16th century villas. Perhaps picnic by the Era Valley before ascending an ancient mule track back to Volterra.
You stay at the Park Hotel Le Fonti (breakfast and evening meal)

Day 11: Leave Volterra

Return home after breakfast.

See our Volterra to San Gimignano Walk for an 8-night version of this holiday.

Where you stay

During your holiday you stay at the following hotels. If you'd like to extend your time at any of these or, if you'd like to enhance your stay with an upgraded room, just let us know at the time of booking.

To find out more call our sales team on 1-800-267-3347, use our live webchat or email usa@exodustravels.com

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Park Hotel Le Fonti, Volterra

Swimming Pool IconHair dryer iconNEARBY:

The 4 star Park Hotel Le Fonti is located just below the Porta dell'Arco entrance to Volterra's beautifully preserved medieval centre. It's an easy 10 minute stroll into arguably one of Italy's oldest towns.

The hotel has over 50 comfortable rooms, all of which are furnished in a simple style with terracotta floors and elegant fabrics. All rooms have ensuite facilities.

The real highlight of the hotel is the breathtaking view from the terrace and fabulous infinity pool - the sweeping panorama over the rolling Pisan hills is truly outstanding.

Room upgrades: Deluxe Room with Terrace, Junior Suite or Suite.
Deluxe rooms with terrace have their own terrace overlooking the pool. Junior suites are much larger than a standard room, with a sitting area. The suite is situated in the tower, and is larger than a junior suite. It has a balcony and a jacuzzi.

Extra nights: Please contact us for details.

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Terre di Casole, Casole d

Swimming Pool IconHair dryer icon

Just a 10-minute walk from the centre of the village, the 4 star Hotel Terre di Casole has recently reopened after being completely refurbished - and the end result is stunning! The hotel boasts 40 en-suite modern yet stylish rooms which come with either a garden terrace or a balcony - both have views over the pool and the lovely gardens to the rear of the hotel.

The public rooms at the Terre di Casole reflect the attractive, modern decor in the bedrooms. Both the lounge/bar area and the restaurant are large, airy rooms with a white colour scheme, which lends them a stylish yet minimalist feel. Ideal for relaxing in!

Your evening meal will be taken in the hotel's restaurant. The menu features a number of classic Italian/Tuscan dishes with a modern twist, all made with herbs from the hotel's garden! The hotel also has a resident patissier, so you'll be really spoilt with the quality of the desserts!

Room upgrades: Superior Room.
Superior rooms are larger with private balcony and tea and coffee making facilities.

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Relais della Rovere, Colle di Val d

Swimming Pool IconHair dryer iconNEARBY:

The Relais della Rovere is a stunning 4-star hotel located at the edge of Colle di Val d'Elsa. The Cellerai family have sympathetically converted this 12th century Benedictine Abbey into a 31 room luxurious hotel, retaining many of the abbey's original features.

The bedrooms are split between two buildings and decorated in a contemporary style with wooden floors and beech furniture. The rooms are quite large with ensuite facilities.

The hotel has a lovely outdoor pool which is surrounded by pleasant gardens.

Room upgrades: Luxury (Double Only), Junior Suite or Suite.
Luxury rooms are located in the Renaissance Villa and feature antique furniture and prints, and precious tapestries and ceilings with encased beams and parquet flooring. Large windows with a view over the historical centre of Colle Val D'Elsa. Bathroom with whirlpool bath, courtesy kit, bathrobe and slippers. Junior Suites are located in the Benedictine Convent and in the farmhouse. They comprise an entrance hall with living room and one double bedroom, and feature modern, solid oak furniture. They have beamed ceilings and parquet flooring. One/two bathrooms, one with shower, the other with whirlpool bath, courtesy kit, bathrobe and slippers. Suites are in the Benedictine Convent and in the Villa. They are larger with an entrance hall, living room and sofa bed and a double bedroom, with two bathrooms. Some have modern decor with solid oak furniture, beamed ceilings and parquet flooring. Others feature antique furniture and prints, and precious tapestries, ceilings with encased beams and parquet flooring.

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Relais Santa Chiara, San Gimignano

Swimming Pool IconHair dryer iconNEARBY:

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

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

Room upgrades: Classic room with countryside view & balcony, Superior Double, Superior double with separate lounge or Superior double with countryside view.
Classic rooms with balcony and view offer stunning views of the Tuscan countryside. Superior rooms are more spacious with a lounge area and a sofa bed (120cm) and a jacuzzi bath. Superior rooms with balcony and views come with all the amenities of the Superior room with the addition of a balcony offering stunning views of the Tuscan countryside.

Extending your stay

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

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Chiusarelli, Siena

Hair dryer icon

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.

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Alessandro della Spina, Pisa

Hair dryer iconNEARBY:

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.

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel La Luna, Lucca

Hair dryer icon

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.

Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Cosimo De Medici, Florence

Hair dryer icon

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.


Transfers can be arranged at a supplement from Pisa airport at 11:45 (10:30 Saturdays), and back to Pisa airport at 109:00 (07:45 Saturdays).

Call now to speak to our specialist team at 1-800-267-3347 or email us at usa@exodustravels.com for enquiries or to book your trip.


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

Any feedback collected is posted to our website, so that people can make an informed decision based on past experiences before heading off on holiday. We don’t edit the reviews, the only thing we do is proofread them and alter any typos, where necessary, to ensure they are easy to read for everyone. All reviews will be published (except in certain extreme circumstances), and a member of the Headwater team will respond to any constructive criticisms/comments under the reviews, at their discretion. So, for the real tales, twists and turns of our holidays, look no further than the reviews from our previous travellers.

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.

Mrs McKenzie, 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!

Mr Dent, 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

Mr Ford, 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

Mrs Handley, 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.

Mr Smith, 20/07/2016

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

Mrs Cox, 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.

Mr Clarke, 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.

Mr Creswell, 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!

Mr McGregor, 19/09/2015

Beautiful area but let down by inattention to detail.

Disappointing largely for small but cumulative reasons.

Mr Lawrence, 18/09/2015

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

Mrs Price, 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.

Mr Kell, 25/09/2014

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

Mr Larcombe, 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.

Mrs Buckle, 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.

Mrs Osborne, 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.

Mr Beresford, 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.

Mr Gunn, 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.

Mrs Rouse, 25/09/2013

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

Mrs Allen, 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.

Ms Merrick, 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.

Mrs McIntosh, 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

Mr Sillett, 09/08/2013

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

Mrs Graham, 03/07/2013

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

Dates and prices

You can be confident that our pricing includes all the standard requirements of your holiday and many additional extras. Always ensure that you are comparing like for like when booking your holiday.

Find out about The Headwater Price Promise to ensure you're getting the very best value for money.

For 2020 departures our trip inclusions are changing - please contact us for full details.

This 10 night self-guided walking holiday includes:

Hotel-to-hotel accommodation in a mix of hotels

All continental breakfast and 4 evening meals

Services of your local Headwater Representative

Headwater Wine Collection Service

Route directions and maps

Standard transfers at the start/end of the trip (if booking inclusive flights)

Luggage transfers between hotels

Walking transfers

How to book:

For further details, or to check availability, speak to our sales team on 1-800-267-3347 or complete our holiday enquiry form (we'll contact you at a time that's most convenient for you).

To enquire about this holiday, or for further information, call our sales team on 1-800-267-3347 or complete our holiday enquiry form.

  • May 2020
  • Jun 2020
  • Jul 2020
  • Aug 2020
  • Sep 2020
  • Oct 2020
DepartingTour only Availability
1st May US$2849 Check availability
3rd May US$2849 Check availability
5th May US$2849 Check availability
7th May US$2849 Check availability
9th May US$2849 Check availability
11th May US$2849 Check availability
13th May US$2849 Check availability
15th May US$2849 Check availability
17th May US$2849 Check availability
19th May US$2849 Check availability
21st May US$2849 Check availability
23rd May US$2849 Check availability
25th May US$2849 Check availability
27th May US$2849 Check availability
29th May US$2849 Check availability
31st May US$2849 Check availability
DepartingTour only Availability
2nd Jun US$2849 Check availability
4th Jun US$2849 Check availability
6th Jun US$2849 Check availability
8th Jun US$2849 Check availability
10th Jun US$2849 Check availability
12th Jun US$2849 Check availability
14th Jun US$2849 Check availability
16th Jun US$2849 Check availability
18th Jun US$2849 Check availability
20th Jun US$2849 Check availability
22nd Jun US$2849 Check availability
24th Jun US$2849 Check availability
26th Jun US$2849 Check availability
28th Jun US$2849 Check availability
30th Jun US$2849 Check availability
DepartingTour only Availability
2nd Jul US$2879 Check availability
4th Jul US$2879 Check availability
6th Jul US$2879 Check availability
8th Jul US$2879 Check availability
10th Jul US$2879 Check availability
12th Jul US$2879 Check availability
14th Jul US$2879 Check availability
16th Jul US$2879 Check availability
18th Jul US$2879 Check availability
20th Jul US$2879 Check availability
22nd Jul US$2879 Check availability
24th Jul US$2879 Check availability
26th Jul US$2879 Check availability
28th Jul US$2879 Check availability
30th Jul US$2879 Check availability
DepartingTour only Availability
1st Aug US$2879 Check availability
3rd Aug US$2879 Check availability
5th Aug US$2879 Check availability
7th Aug US$2879 Check availability
9th Aug US$2879 Check availability
11th Aug US$2879 Check availability
13th Aug US$2879 Check availability
15th Aug US$2879 Check availability
17th Aug US$2879 Check availability
19th Aug US$2879 Check availability
21st Aug US$2879 Check availability
23rd Aug US$2879 Check availability
25th Aug US$2879 Check availability
27th Aug US$2879 Check availability
29th Aug US$2879 Check availability
31st Aug US$2879 Check availability
DepartingTour only Availability
2nd Sep US$2879 Check availability
4th Sep US$2879 Check availability
6th Sep US$2879 Check availability
8th Sep US$2879 Check availability
10th Sep US$2879 Check availability
12th Sep US$2879 Check availability
14th Sep US$2879 Check availability
16th Sep US$2879 Check availability
18th Sep US$2879 Check availability
20th Sep US$2879 Check availability
22nd Sep US$2879 Check availability
24th Sep US$2879 Check availability
26th Sep US$2879 Check availability
28th Sep US$2879 Check availability
30th Sep US$2879 Check availability
DepartingTour only Availability
2nd Oct US$2849 Check availability
4th Oct US$2849 Check availability
6th Oct US$2849 Check availability
8th Oct US$2849 Check availability

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

Holiday details

Please contact us for child prices.

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

Every two days from 1st May 2020 to 8th Oct 2020, for 10 nights. All dates are subject to availability, please contact us to check.

All continental breakfast and 4 evening meals

Tailor-made travel

Tour only

Transfers can be arranged at a supplement from Pisa airport at 11:45 (10:30 Saturdays), and back to Pisa airport at 109:00 (07:45 Saturdays).

How to book

For further details, or to check availability, speak to our sales team on 1-800-267-3347 or complete our holiday enquiry form (we'll contact you at a time that's most convenient for you).

Call now to speak to our specialist team at 1-800-267-3347 or email us at usa@exodustravels.com for enquiries or to book your trip.

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

Alternatively, you can call our sales team on 1-800-267-3347 to discuss your requirements in more detail.

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

If you would like to subscribe to our emails in accordance with our Privacy Policy, please tick this box.

+ Add More Passengers

We can often obtain preferential rates with our travel partners. We can often obtain preferential rates with our travel partners.

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

By clicking the 'Enquire now' button, you confirm that you have read and understood our Privacy Policy and consent to our use of your information.

You may also like