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Chianti Classic Walk

Chianti Classic Walk

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
  • Holiday typeSelf-guided walking
  • Duration10 nights, hotel-to-hotel
  • Activity level
  • Excellent for
  • From $2075
  • Holiday details
  • Departs Every two days from 11 May '17 to 14 Oct '17
  • Continental breakfast and 6 evening meals
  • Managed locally by Headwater employed representative
  • Sustainability rating: 76%
  • Headwater wine service
  • Route notes and maps provided
  • Luggage transfers between hotels
  • Walking transfers
  • Option to shorten to 8 nights

We're here to help

If you've any questions about this holiday call to our sales team on 1-800-567-6286 , or email sales@headwater.com

On this self-guided ten-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 mediaeval Colle di Val d'Elsa, enjoying balcony views across the Elsa Valley. As you move towards stunning San Gimignano, the mediaeval '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 mediaeval 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 C12 abbey where you spend 4 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!

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.

Day 1 - Arrive in Volterra

We meet you at Pisa airport, and take you to your 4-star hotel (75 mins) just outside Volterra's mediaeval gates, where you have time to relax in the pool before dinner.

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.

Day 3 - At Casole d'Elsa

Casole d'Elsa is a picture perfect etruscan village atop a panoramic ridge. From the vermillion hued C14 castle, views stretch as far as Monte Amiata in the south of Tuscany. A leisurely lunch maybe in the mediaeval piazza, before visiting the small but intact amphitheatre and Etruscan tombs.

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 4-star hotel, a beautifully converted C12 Benedictine Abbey with garden and pool.

Days 5 - 7 At Colle di Val d'Elsa

Regular buses to Siena (30mins) 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.

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.

Day 9 - At San Gimignano

Visit San Gimignano's mystical towers this morning built by warring neighbours in the C12 to outdo one another! Or for a longer day out, hop on a local bus to Siena (30 mins), a perfectly preserved mediaeval gem with a stunning striped C14 Gothic Cathedral and beautiful square.

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 sensano and Ulignano, historic hamlets with C16 villas. Perhaps picnic by the Era Valley before ascending an ancient mule track back to Volterra.

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. You can call our sales team on 1-800-567-6286 to discuss accommodation options.

Park Hotel Le Fonti, Volterra (4 Star)

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The 4 star Park Hotel Le Fonti is located just below the Porta dell'Arco entrance to Volterra's beautifully preserved mediaeval 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.

Find out more on the hotel website and read customer reviews on Tripadvisor.

Dates Deluxe Room with Terrace Junior Suite Suite
11/05/2017 - 31/10/2017 £12 £22 £36

All prices shown above are valid from 21/04/2017. Supplements are per person per night based on 2 sharing. 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.

Dates Double Room Single Room
11/05/2017 - 31/10/2017 £86 £116

All prices shown above are valid from 21/04/2017. Prices are per person per night including evening meal. Bike hire is not included in the above tariffs. If only B&B is required you can reduce the price by £22 per person per night.

Hotel Terre di Casole, Casole d'Elsa (3 Star)

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Just a 10 minute walk from the centre of the village, the 3* Hotel Terre di Casole has recently reopened after being completely refurbished - and the end result is stunning! The hotel boasts 40 ensuite 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 pattissier, so you will be really spoilt for desserts!

Find out more on the hotel website and read customer reviews on Tripadvisor.

Dates Superior
11/05/2017 - 31/10/2017 £14

All prices shown above are valid from 03/04/2017. Supplements are per person per night based on 2 sharing. Superior rooms are larger with private balcony and tea and coffee making facilities.

Please contact us for extra night prices.

Relais della Rovere, Colle di Val d’Elsa (4 Star)

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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 C12 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.

Find out more on the hotel website and read customer reviews on Tripadvisor.

Dates Luxury Double Junior Suite Suite
11/05/2017 - 31/10/2017 £24 £34 £50

All prices shown above are valid from 01/12/2016. Supplements are per person per night based on 2 sharing. 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.

Dates Double Single
11/05/2017 - 31/10/2017 £114 £164

All prices shown above are valid from 01/12/2016. Prices are per person per night including evening meal. Bike hire is not included in the above tariffs. Please note that extra nights at the Relais della Rovere are also possible on a bed and breakfast basis. Please call for prices.

Relais Santa Chiara, San Gimignano (4 Star)

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Situatued just 400m from the mediaeval 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-confitioning, satellite TV, minibar and hairdryer. You can also upgrade to a room with balcony and views of the surrounding vineyards and stunning countryside.

Find out more on the hotel website and read customer reviews on Tripadvisor.

Dates Superior room Classic room with countryside view and balcony Superior room with balcony and view
11/05/2017 - 31/10/2017 £12 £16 £28

All prices shown above are valid from 24/04/2017. Prices are per person, per night. 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.

Please contact us for extra night prices.

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.

Hotel Alessandro della Spina, Pisa (3 Star)

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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.

Find out more on the hotel website and read customer reviews on Tripadvisor.

Room upgrades are not available at this hotel.

Dates Double Room Single Room
11/05/2017 - 14/10/2017 £60 £106

All prices shown above are valid from 03/04/2017. Prices are per person per night including breakfast.

Hotel Cosimo De‘ Medici, Florence (3 Star)

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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.

Find out more on the hotel website and read customer reviews on Tripadvisor.

Room upgrades are not available at this hotel.

Dates Single room Double room
01/05/2017 - 30/06/2017 £100 £80
01/09/2017 - 31/10/2017 £100 £80

All prices shown above are valid from 01/12/2016. Prices are per person per night including breakfast.

Hotel Chiusarelli, Siena (3 Star)

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Hotel Chiusarelli is located just beyond Siena's mediaeval 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 AC 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.

Find out more on the hotel website and read customer reviews on Tripadvisor.

Room upgrades are not available at this hotel.

Please contact us for extra night prices.

Hotel La Luna, Lucca (3 Star)

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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.

Find out more on the hotel website and read customer reviews on Tripadvisor.

Room upgrades are not available at this hotel.

Dates Single Double Double for single use
01/05/2017 - 31/10/2017 £96 £72 £106

All prices shown above are valid from 01/12/2016. Prices are per person per night including breakfast.


Transfers included from Pisa airport at 12:00, and back to Pisa airport at 10:00.

Please call our sales team on 1-800-567-6286 or email info@breakaway-adventures.com to arrange connecting flights.


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, of course, an overall rating and comments about their holiday.

Any feedback collected is posted straight to our website - totally unedited. So, for the real tales, twists and turns of our holidays, look no further than the reviews from our previous travellers.

Mrs McKenzie

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

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

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 ... read moreVolterra 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

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

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

Mr Clarke

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

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

Beautiful area but let down by inattention to detail.

Disappointing largely for small but cumulative reasons.

Mr Lawrence

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

Mrs Price

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

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

Mr Larcombe

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

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

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

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

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

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

Mrs Allen

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 las... read moret 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

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

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 ... read moreupgraded 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

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

Mrs Graham

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

Mr Harrison

A wonderful holiday - very well thought through and organised with a perfect mix of great walking in beautiful countryside and opportunities for sightseeing in nearby cities.

Dates and prices

The prices quoted below for each individual departure supercede those published in our current brochures. Air prices are subject to change and are shown for guide purposes only. Please see our Planning your holiday and What's included in the price? pages for additional information.

Alternatively, you can call our sales team on 1-800-567-6286 to discuss your requirements in more detail.

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.

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Holiday details

Please contact us for child prices.

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

Every two days from 11th May 2017 to 14th Oct 2017, for 10 nights.

Continental breakfast and 6 evening meals

Tailor-made travel

Tour only
Transfers included from Pisa airport at 12:00, and back to Pisa airport at 10:00.


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 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 1-800-567-6286 to discuss your requirements in more detail.

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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.

Let us know any queries you might have about departure dates, similar holidays or other questions. If you’d like to travel by an alternative method, i.e. Ferry / Eurotunnel etc. please give details here so we can advise you on appropriate options.

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