Contrasts of Andalucia Cycling

From $1394 per person

****. Based on 13 customer reviews
  • Classical Spain - flamenco dancers, Sherry and great regional food
  • Stay in atmospheric Pueblos Blancos - the old frontier hilltop towns
  • Historical cities: Jerez and Cadiz
  • Delightful mix of coast, rolling hills, Roman roads and greenways
  • Excellent hotels full of character
  • Bird-spotter's paradise - storks, kingfishers, waders

What's included?

  • 7 nights, hotel-to-hotel
  • Departs Daily from 25 Oct '16 to 31 Dec '17
  • All continental breakfasts included
  • Managed by Headwater appointed agent
  • Sustainability rating: 91%
  • Route notes and maps provided
  • High quality bikes provided
  • Luggage transfers between hotels
  • Distance computer provided

Excellent for...

Contrasts of Andalucia Cycling

Our 7 night holiday is based in the Andalucian province of Cadiz, a region full of history and natural beauty, penned in by atmospheric mountain ranges and the crashing Atlantic Ocean. This is Spain at its most simplistic and yet at its most beautiful; whitewashed hilltop villages make way for lush undulating meadows, interspersed with ancient forests, olive groves and vineyards. Spain's early modern history started here, with Cadiz the capital of 'Al-Andalus' and Spain's first parliament. Along the way you get the sense of the real Spain - flamenco dancers, bulls and horsemen, mixed with wonderful scenery full of rich flora. The birdlife is outstanding too, with storks nesting on chimneys whilst Bonelli's eagles soar above.

Starting in the home of flamenco, Jerez, with its wide boulevards, impressive bodegas and stunning C17 cathedral, you then head along eco-friendly greenways, tracks and quiet roads, passing small picturesque villages on a route around the Pueblos Blancos, the original Moorish outposts. Next is the Atlantic coast with its rolling waves and perfect sandy beaches, before you arrive in Cadiz, the oldest continuously inhabited city in Europe; its New World feel can leave you thinking of faraway climes in Latin America, and the city's charm is added to by its wonderfully pristine beaches.

You stay in an eclectic mix of hotels, a boutique hotel in a nouveau-style family mansion in historic Jerez, a renovated 3-star Andalusian-style house in Arcos de la Frontera, a palace with a view and pool in Median Sidonia, a 3-star C17 convent in Vejer de la Frontera and a unique townhouse in Cadiz, where each room tells a different historical story of the city.

For evening meals, choose from an abundance of restaurants offering a range of regional cuisine such as Gazpacho and Sopa de Ajo. Sherry is king in this region and the local sherry bars are a story in themselves, with glassfuls served from barrels and a unique way of giving you the bill!

Day-by-day itinerary

Day 1 - Arrive in Jerez

Arrive at your 4-star hotel in Jerez in time for a walk around the historic centre before dinner (not included).

Day 2 - Jerez to Arcos de la Frontera 48.8km/30.5mi

Leaving Jerez you follow a lovely route passing vineyards, ancient settlements and riverside towns. Quiet country roads and gravel tracks alongside the River Guadalete take you past villages full of pretty, pastel-coloured houses and on towards Arcos de la Frontera. Why not stop to try the local Tierra Blanca white wines en route?

Day 3 - At Arcos de la Frontera

Enjoy a day in this beautiful Pueblo Blanco, one of the frontier villages of the new Spain. Follow the old Arabic walls, passing the impressive Castillo de los Duques, as you make your way to the Iglesia de San Agustin with its fantastic viewpoint over the river and rich fertile valley of orange, almond and olive trees. Spend some time in the unique miniature art museum and lunch at one of the array of restaurants, or follow our recommended circular cycle route (notes provided).

Day 4 - Arcos de la Frontera to Medina Sidonia 48km/32mi

Follow a winding road, passing orange and almond orchards through the town of Junta de los Rios where two rivers converge. Passing through San Jose del Valle, which dates back to Roman times, and the impressive El Tempul, you then follow a tree-lined trail past the Moorish Gigonza castle and head onto Paterna de Rivera, famous for its healing waters. Arriving in Medina Sidonia with its grand plaza, mediaeval Moorish architecture, narrow streets and views of the bay of Cadiz, take time to explore this little gem before dinner.

Day 5 - Medina Sidonia to Vejer de la Frontera 46.6km/29mi

A countryside trail takes you from Medina Sidonia down into La Janda, once the biggest lake in Spain, following the 'route of the bulls' and passing Roman bridges and grand old Haciendas. A lovely greenway then criss-crosses this stunning landscape for irresistible views of dark green meadows as they melt into the Sierra de Cadiz (look out for Egyptian vultures and Bonelli's eagles).

Day 6 - At Vejer de la Frontera

The most picturesque of our three Pueblos Blancos, Vejer de la Frontera has been decreed an historic site. It is enough to simply wander through its maze of streets discovering its Roman walls, Visigoth hermitage and its castle at the highest part of the old town combining both Moorish and Christian architecture. Lunch in one of the many cafes and restaurants, or walk up to the highest point with panoramic vistas and picnic next to the lovingly restored windmills of San Miguel.

Day 7 - Vejer de la Frontera to Cadiz 21.35km/13mi or 38.5km/24mi

You head to the coast today, with a choice of shorter or longer routes; both end in the charming seaside frontier town of Conil de la Frontera. The longer route heads east, passing the town of Barbate, and the pretty surf village of El Palmar. Taking the shorter route affords you more time to wander around the whitewashed houses of Conil de la Frontera, before being transferred (30 mins) to magical Cadiz.

Day 8 - Leave Cadiz

Please note that cycling helmets are compulsory in Spain for all customers. As we are unable to provide these, we strongly recommend that you bring your own.

Please see our Planning you holiday page for full details.

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.

If you'd like to keep your bikes with you for any extra nights we can arrange this for you for just £25 per adult per day. Please contact us on 1-800-567-6286 for further details.

Casa Grande, Jerez   (3*)

Room at the hotel Casa Grande, Jerez

The charming hotel Casa Grande, is located in the historical centre of Jerez, on a palm lined square. This boutique hotel is based a nouveau style family mansion which dates back to the 1920's built by the famous Basque architect Teodoro Anasagasti. It was restored, renovated and turned into a hotel in 2004.

The hotel has a lovely roof top terrace to watch over the busy square, and has a cosy lounge bar and well-stocked library, They serve a healthy breakfast of local products.

The hotel opens up to a lovely courtyard with original cast iron pillars, the 15 charming rooms are tastefully decorated with a discrete elegant feel, all have air conditioning, flat screen tv, free wifi and safes.

With the hotels location in the centre of historical Jerez this is an ideal place to have extra nights at the start of your holiday.

Further details on the hotel website, and independent reviews on Trip Advisor.

Local facilities:

  • Mastercard accepted
  • American Express accepted
  • Hairdryer
  • Wifi hotspot
  • Internet access
  • Television
  • Air conditioning
  • Safe

Nearby facilities:

  • Shops
  • Market
  • Banking / cheques cashed
  • ATM / Cash machine

Hotel los Olivos, Arcos de la Frontera   (3 Star)

Hotel los Olivos

Hotel Los Olivos is situated just a short walk from the historic centre of the beautiful town of Arcos de la Frontera and close to the many bars and restaurants the town has to offer.

The hotel has been created from a typical Andalusian house, with a typical 'patio Andaluz' central courtyard around which the 19 rooms are housed. The rooms are of a good size and offer all modern amenities.

Further details on the hotel website, and independent reviews on Trip Advisor.

Local facilities:

  • Shops
  • Market
  • Banking / cheques cashed
  • ATM / Cash machine
  • Mastercard accepted
  • American Express accepted
  • Hairdryer
  • Wifi hotspot
  • Internet access
  • Television
  • Minibar
  • Air conditioning

La Vista de Medina, Medina Sidonia   (2*)

Pool and view from La Vista de Medina

This charming oasis in the 'balcon de Cadiz' Medina Sidonia; comprises of 6 apartments and 2 outdoor swimming pools. On the many sunny clear days you can see the Bay of Cadiz. It is located in a lovely square in the historic centre of Medina Sidonia.

Each tastefully decorated apartment has its own living area and basic cooking facilities, flat screen tv and hairdryers. The hotel has varied small terraces and gardens where you can relax and enjoy the stunning views. The hotel serves a hearty breakfast and does have a restaurant if you prefer not to venture into town.

Further details on the hotel website, and independent reviews on Trip Advisor.

Local facilities:

  • Mastercard accepted
  • Swimming pool
  • Hairdryer
  • Wifi hotspot
  • Television

Nearby facilities:

  • Shops
  • Market
  • Banking / cheques cashed
  • ATM / Cash machine

Hospederia Convento de San Francisco, Vejer de la Frontera   (3 Star)

Hotel Convento

This C17 converted convent has just been renovated to create a lovely hotel mixing old and new, the rooms whilst large and airy can give the feel of what it was like to live in a convent. All come with great views of the beautiful town of Vejer de la Frontera.

There are large sitting rooms and a lovely roof terrace, and the restaurant is said to be one of the best in town!

Further details on the hotel website, and independent reviews on Trip Advisor.

Local facilities:

  • Mastercard accepted
  • Hairdryer
  • Wifi hotspot
  • Internet access
  • Television
  • Minibar

Nearby facilities:

  • Shops
  • Market
  • Banking / cheques cashed
  • ATM / Cash machine

Las Cortes de Cadiz, Cadiz   (3 Star)

Reception of Hotel las Cortes

This C18 palace is a typical building from the period, its rooms are themed telling the story of the 1812 constitution of Spain.

It has a wonderful roof terrace with great views over the city, a small spa area and nice cafe bar with outdoor street seating.

The rooms are a good size some with Juliet balconies some with city views some with interior windows.

Further details on the hotel website, and independent reviews on Trip Advisor.

Local facilities:

  • Mastercard accepted
  • American Express accepted
  • Hairdryer
  • Wifi hotspot
  • Internet access
  • Television
  • Minibar
  • Safe

Nearby facilities:

  • Shops
  • Market
  • Banking / cheques cashed
  • ATM / Cash machine

Extra nights and stop over hotels

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 Becquer, Seville   (4 Star)

Hotel Becquer, Seville

The 4-star Hotel Becquer is a lovely hotel, with lots of original features, and is just a 10-minute walk from the historic old quarter and cathedral. There is a large airy lounge with plenty of seating, a breakfast room and attached tapas bar.

Please note the hotel's pool, solarium and terrace are closed until 30 September 2016.

Further details on the hotel website, and independent reviews on Trip Advisor.

Local facilities:

  • Shops
  • Banking / cheques cashed
  • Mastercard accepted
  • American Express accepted
  • Swimming pool
  • Hairdryer
  • Wifi hotspot
  • Television
  • Minibar
  • Air conditioning

Gallery Hotel Molina Lario, Málaga   (4 Star)

Hotel Molino Lario - rooftop pool

The Molina Lario is perfectly situated in the old town just a stone’s throw from the Cathedral, known as ‘the one armed lady’, and within easy walking distance of the other key sights.

The recently built hotel is formed of one new building merged with 2 19th Century buildings, retaining their original façade. The rooftop pool and bar is perfect for relaxing after a days sightseeing, with views over the city and harbour.

The 103 rooms exude comfort and tranquillity, with robes, slippers and a pillow menu to ensure you have a good night’s sleep. Tea and coffee making facilities and complimentary mineral water are available in all rooms.

Breakfast is a hot and cold buffet which can be taken in the central courtyard.

Further details on the hotel website, and independent reviews on Trip Advisor.

Local facilities:

  • Mastercard accepted
  • American Express accepted
  • Diners Club card accepted
  • Swimming pool
  • Hairdryer
  • Wifi hotspot
  • Television
  • Minibar
  • Air conditioning
  • Safe
  • Tea/coffee facilities

Nearby facilities:

  • Shops
  • Market
  • Banking / cheques cashed
  • ATM / Cash machine

Travel options

Transfers included from Jerez airport at 13:05, and back to Jerez airport at 11:15.

Please call our sales team on 1-800-567-6286 or email to arrange connecting flights.

Customer reviews

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.

Reviewed by Mr Wall on 25/02/2016

Excellent Rep in Marita and driver in Diego.It was nice to have the same driver all the time. Bikes were excellent, much better than the ones we had in the Asturias holiday earlier in the year when half the gears slipped. Every hotel, except in Cadiz gave us freshly brewed wonderful coffee for breakfast. We have never had that before in a Headwater holiday .Hotels marked down for food was not because there was anything wrong with it just that breakfast was very at Medina di Sidonia just bread with those awful sachets of packaged jams and spreads. Comfort marked down for a couple of hotels because it was difficult to get a good night's sleep because of noise outside. At Medina Sidonia some sort of machinery going all night .The hotel in Cadiz has the best rooms at the front as they have large French doors and a little balcony over a pedestrianised street. It is actually fine until after midnight when the bars from the square down the road empty out and revellers pass by the hotel until the eary hours. We had an extra night so changed to a room at the back where there is only a small nonopening window over the door. Slept very well though so it was worth it.Very scenic area. I think grading is 2 plus not a 2.

Reviewed by Dr Morris on 23/11/2015

Exhilarating and exciting cycling holiday in wonderful locations; good mix of town and country; typical Spanish scenery and food; good choice of evening restaurants; breakfasts a bit skimpy..bring snacks along to keep you going.

Reviewed by Ms Heard on 07/11/2015

Cycling in Andalucia, excellent and, having experience of other Headwater Cycling holidays, would judge the grading to be spot on. It was very hilly in parts and maybe a couple of hills needed a 2+ grading but overall we thought a 2 bikes to be accurate grading. At nearly 70 and cycling at home approx. twice a month I managed the hills very well - one just has to remember it is not the Tour de France' there is no yellow top for the first one up the hill...... We flew from Heathrow and due to a missing passenger the flight to Madrid was delayed resulting in us missing the onward connection to Jerez. However, it all adds to the adventure! The hotels were excellent and all very central with a great many options of restaurants in the towns for evening meals; apart from Medina. All of the towns we visited were lovely, very interesting and very different, Andalucia is the most attractive area of Spain we have visited. If possible it is well worth having an extra night in Jerez which we did - don't miss seeing a Flamenco show and sampling the sherry! Cadiz old town was delightful and again we added a couple of extra nights, well worth it. We ended our holiday with three nights in Seville - the icing on the cake. The cycling was, as usual, great, good bikes, well written cycling instructions and wonderfully quite roads and tracks. Two negatives, we did find it difficult to find good picnic spots and we really missed not having map holders - apparently they hadn't arrived from England and the rep wasn't able to access them from elsewhere. Overall an excellent holiday, we would certainly recommend it.

Reviewed by Mr Hadden on 30/10/2015

A very enjoyable holiday. We felt that the grading system does not have enough levels and that some of the cycling was quite challenging, particularly the three days that end with a climb to the finish. We found that we could get very good dinners/lunches at a reasonable price. The Spanish drivers were very considerate to cyclists; the best that we have found anywhere.

Reviewed by Mrs Leslie on 22/10/2015

A completely unjustifiable cost for the quality of holiday provided

Reviewed by Mr Hooton on 03/10/2015

Cycling is not the main part of the holiday; it gets you through the county side and build up your appetite to enjoy food and drink in the towns and villages along the way. The break days enable you to take in the places along the way; it is well worth taking the time to explore and find out about the places, you'll discover the convent nuns who sell biscuits through a hatch in Arcos de la Fontera, and the 16th Century competition between the churches for supremacy through acquisition of increasing old a decaying bodies of saints.

Reviewed by Mr Tagger on 26/09/2015

We enjoyed the holiday. The variety was v good. Medina Sedona was poor location poor restaurants and poor hotel. Suggest find another venue. Access to beaches was nice change to cycling. Some routes were boring and occasionally v busy. The worst point was the poor quality bikes. Marita kept pointing out that everything worked . This was not true. But as I said too her - everything worked on my grand mothers bike but I would not care to travel across Spain on it. Shame about bikes as it is the one point that would stop me going on another of your holidays On a brighter point transfers and luggage movement was excellent ! Also maritas help in getting back some left clothes was v good and thanks to her for that. Find another hotel in Cadiz . Apart general points already expressed electrics in the room were not up to E U HEATHY AND SAFETY in my opinion.I would definitely have this check out if I was your company - 3 black outs in 1 night plus arrangement of balcony quite dangerous
Headwater response:
Dear Mr Tagger, Thank you for taking the time to complete your post-holiday feedback. It was lovely to see you enjoyed your holiday overall. We were however sorry to read of your disappointment with the bikes provided. Ordinarily, we have received positive feedback in this area, however, please be assured that we realise we cannot afford to let our standards slip, so with this in mind, we will continue to monitor the feedback we receive and work closely with our suppliers to ensure they are providing the high quality products and service our customers expect. We were also sorry to hear of your dissatisfaction with the hotel in Cadiz, since receiving your concerning feedback regarding the electrics tripping in your room, we have investigated this with the hotel owners, our local agent and the electricity board. They advised us of a maintenance issue that occurred on the 21st, which caused sporadic power outages throughout the town. As reported in the local press. This fault has since been resolved; and no further feedback received on this issue. In closing, we would like to thank you for bringing this matter to our attention and for your constructive feedback. We look forward to welcoming you on another of our holidays in the future. Yours sincerely, Headwater Customer Service Team

Reviewed by Mrs Brown on 06/05/2015

Well organised, good fun, overpriced.

Reviewed by Mr Jaffe on 05/05/2015

This was our 10th Headwater cycling holiday and it lived up to expectations. We loved this area of Spain particularly at this time of year when the countryside is so colourful. The cycling was challenging but really enjoyable particularly the off road parts of the route. The climbs up to the hill top towns were tough but doable if taken at your own pace, and a great sense of achievement when you reach the top! The busy roads especially coming out of Jerez on the first day were a bit daunting though. All the hotels were of a good standard with very helpful and friendly staff. All were well located although Hotel Cortes de Cadiz was a bit noisy at night.We particularly liked the flexibility of choosing where to eat in the evenings as there were plenty of tapas bars and restaurants at each location. Overall we had a great time and would recommend this holiday to people who enjoy cycling and want to explore a beautiful and historical part of Spain.

Reviewed by Mr Brown on 13/03/2015

An excellent and historic area to explore with some lovely rides and options for increasing the mileage if desired. The hill top white towns are wonderful and evocative of a previous age and are full of interest.

Reviewed by Mrs Hughes on 24/02/2015

The first couple of days felt like a boot camp - it was more strenuous than we'd anticipated, and the weather was a bit overcast and chilly too. The odometer on the bike didn't work and we had to estimate distances. By Day 3 however we were used to it all and really started to enjoy it. Once the sun came out and we had met several very hospitable and generous bar owners and enjoyed several delicious lunches and dinners we really warmed to it and felt ourselves getting so much fitter too. Our eventual verdict was that we would definitely do it again - there was so much to see and experience and the cycling was superb. The baggage deliveries always worked too, like clockwork, and we really appreciated the service running so smoothly.

Reviewed by Mr Smeeth on 05/01/2015

Disappointing, poor value for money, will not be booking future holidays through Headwater or recommending to family, friends or work colleagues
Headwater response:
Dear Mr Smeeth, Thank you for taking the time to complete your post holiday feedback questionnaire. We were sorry to read that this holiday did not meet your expectations and that you do not feel you could recommend this holiday. So far the overall feedback we have received from this holiday has been positive, however, as it is a new holiday there have been some areas which have required improvement. Please be assured that we have passed on your feedback to our local agent and we are working closely with him to ensure all our customers have an enjoyable holiday. We would like to thank you for your feedback. Yours sincerely, Headwater Customer Service team

Reviewed by Mr Barnes on 29/10/2014

A thoroughly enjoyable trip. Vejer and Cadiz were the highlights for us. (We added two nights in Seville. If you do the same, do not miss the Casa de Pilatos). We felt very well looked after by the local rep. The trip notes were detailed and included distances that could be matched to the supplied bike computers, as well as post-turn indications, that gave reassurance (or warning) that we were on the right track (or not). These notes had a few inaccuracies that were still being ironed out at the time of our trip (we were the second set of Headwater clients). The hotel in Jerez had apparently dropped a star, and we were taken instead to a very comfortable 5 star hotel at a golf resort out of town. That was an ideal hotel to return to after a week of cycling, but not such a good hotel to start from, as it was a long way into town (~EUR20 taxi ride) for any who might wish to visit Jerez.
Headwater response:
Dear Mr Barnes, Thank you for taking the time to complete your post-holiday questionnaire following your recent holiday to Spain, Please be assured that all of the feedback we receive whether complimentary or critical is valuable in helping us to continue to improve and develop our holidays for the future and is well received. I was pleased to see you rated your holiday overall as good to excellent. I am sure that you have brought back some great memories to treasure. Since you travelled, we have made some improvements to the holiday in relation to your constructive feedback. We have changed the first hotel back to Jerez centre to ensure it is more convenient for customers wishing to visit the town. We have also corrected the inaccuracies you highlighted with the route notes. Thank you once again for your feedback, we look forward to welcoming you on another of our holidays in the future. Yours sincerely, Headwater Customer Service team

Departure dates & prices

October 2016 departuresTour only 
Oct 1$1439
Oct 2$1439
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Oct 30$1437
Oct 31$1437
November 2017 departuresTour only 
Nov 1$1394
Nov 2$1394
Nov 3$1394
Nov 4$1394
Nov 5$1394
Nov 6$1394
Nov 7$1394
Nov 8$1394
Nov 9$1394
Nov 10$1394
Nov 11$1394
Nov 12$1394
Nov 13$1394
Nov 14$1394
Nov 15$1394
Nov 16$1394
Nov 17$1394
Nov 18$1394
Nov 19$1394
Nov 20$1394
Nov 21$1394
Nov 22$1394
Nov 23$1394
Nov 24$1394
Nov 25$1394
Nov 26$1394
Nov 27$1394
Nov 28$1394
Nov 29$1394
Nov 30$1394
December 2017 departuresTour only 
Dec 1$1394
Dec 2$1394
Dec 3$1394
Dec 4$1394
Dec 5$1394
Dec 6$1394
Dec 7$1394
Dec 8$1394
Dec 9$1394
Dec 10$1394
Dec 11$1394
Dec 12$1394
Dec 13$1394
Dec 14$1394
Dec 15$1394
Dec 16$1394
Dec 17$1394
Dec 18$1394
Dec 19$1394
Dec 20$1394
Dec 21$1394
Dec 22$1394
Dec 23$1394
Dec 24$1394
Dec 25$1394
Dec 26$1394
Dec 27$1394
Dec 28$1394
Dec 29$1394
Dec 30$1394
Dec 31$1394

Holiday details

Holiday type

Self-guided cycling, hotel-to-hotel. Managed by Headwater appointed agent.


Daily from 25 Oct '16 to 31 Dec '17, for 8 days (7 nights). Non standard transfers can be arranged at no extra charge from both Jerez airport and Jerez rail station.


All continental breakfasts included.

Other details

Please see our Planning your holiday and What's included in the price? pages for additional information. Please call us for single room supplements, room upgrade options and child prices.

Starting your tour

Transfers included from Jerez airport at 13:05, and back to Jerez airport at 11:15.

Enquire about this holiday

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 additional information.

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We can call you when it's most convenient for you, or contact you by email if you'd prefer. Morning calls will be between 9:00-13:00, afternoon calls between 13:00-17:00, and evening calls after 17:00.
Let us know any queries you might have about departure dates, similar holidays or tailor-made options.


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  • ATOL Protected (No. 9957)
  • IATA Registered
  • ABTA Member (No. W1593)
  • Relaxed activity holidays since 1985

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call us: 1-800-567-6286 or email:

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