Phone us  01392 441245  |  E-news sign up
& weddings
Honeymoons and weddings abroad are tailor-made by Expressions Holidays. Contact us for a range of honeymoon and wedding destinations around the world and an amazing choice of honeymoons from island-hopping to visiting cultural sites.

With Authentic Experiences from Expressions Holidays you enter a world of genuine holiday and travel experiences within the framework of one of our tailor-made holidays, be its significance culture, gastronomy, wine appreciation, wildlife, sports or special occasions.

Expressions Spas opens a world of tailor-made spa holidays that allows you to choose according to region, type of treatment desired, product type and recommends for your party type, whether it be for couples, singles or perhaps mothers and daughters travelling together.

Expressions Families affords you an amazing choice of sophisticated resorts ideally suited to families in selected destinations worldwide. You can also choose according to required facilities in resort and we suggest holidays for families with grandparents and single parent families too.

Expressions Holidays offers you tailor-made rail holidays and journeys by train, including luxury trains, scenic journeys and classic rail tours.

Tailor-made journeys and tours for individuals and small groups to selected destinations around the world from Burma to Italy, from Vietnam to India.
  • History & Heritage of Extremadura


    Parador de Toledo

    Parador de Trujillo

    Parador de Trujillo

    Parador de Merida

    Parador de Merida

    Parador de Caceres

    Parador de Caceres

    Parador de Plasencia

    Parador de Plasencia

    History and Heritage of Extremadura

    Fly-drive – 9 night and 10 days
    Discover the unspoilt countryside and Roman heritage of the remote Extremadura region in western Spain, staying in five historic Parador hotels along your route. This touring holiday enables you to visit the UNESCO World Heritage Sites of Toledo, Mérida, and Cáceres, as well as the towns of Plasencia and Trujillo, also deep in important history. Extremadura is an off-the-beaten-track destination which gives an authentic experience of rural Spain; a land of rolling hills with historic and atmospheric towns dotted throughout.

    Arrive in Madrid and drive southwest to Toledo for your first two nights in Extremadura. This luxury tour begins with the Parador de Toledo, a building of exceptional history that sits just across the river from Spain’s former capital. Spend two days exploring the City of Three Cultures, visiting such landmarks as the exquisite Gothic cathedral, and the Cristo de la Luz mosque. The intriguing amalgamation of such different cultures gives Toledo a unique edge. From here, drive into Extremadura for one night at the Parador de Trujillo, the former Convent of Santa Clara. Trujillo is an important stop on the Ruta de la Conquistadores, due to its status as the birthplace of some of the people responsible for the discovery of the New World. This important history is evident in many of the town’s streets, though nowhere more clearly than in the museum. Base most of your exploration of Trujillo in the Plaza Mayor, one of the most beautiful squares in Spain, which is lined on all sides by enchanting historic buildings. Drive on after a night in Trujillo to Merida. This town is renowned for the depth of its Roman heritage, once the capital of Roman Lusitania. Navigate the quaint streets seeking out the theatre, amphitheatre, aqueduct, and other monuments, finishing off each day with a night of relaxation at the Parador de Merida, situated within another convent. Your next stop, Caceres, is a mediaeval town riddled with evidence of both its Moorish and Christian heritage. Stay at the Parador de Caceres for two nights, a 14th century palace, while you explore this picturesque town and everything that is encased within its old walls. Your final port of call on this luxury touring holiday is at the Parador de Plasencia, a charming 15th century convent. Spend your last two days exploring the incredibly diverse architecture of Plasencia held within its mediaeval walls, brought about by its multicultural history, and taking the opportunity to uncover the smaller settlements and landforms that punctuate the surrounding landscape. From here, drive back to Madrid to return your hire car and catch a flight to home.
    Click here to download a pdf with details about this touring holiday.


    Prices start at £1,390 per person.

    What’s included:
    • Scheduled flights with British Airways, from London Heathrow to Madrid-Barajas return. Flights from other UK airports can be arranged.
    • Group C car hire for ten days
    • 2 nights bed and breakfast in a standard double room at the Parador de Toledo
    • 1 night bed and breakfast in a standard double room at the Parador de Trujillo
    • 2 nights bed and breakfast in a standard double room at the Parador de Merida
    • 2 nights bed and breakfast in a standard double room at the Parador de Caceres
    • 2 nights bed and breakfast in a standard double room at the Parador de Plasencia

    Click the tabs above to view our suggested day-by-day touring itinerary and to find out more about the hotels featured.
    Click here to find out more about how our touring holidays work.

    Client testimonial: "Enjoyed very much. All 5 hotels were excellent". Mr H, June 2017

    History and Heritage of Extremadura

    Day-by-Day Itinerary

    DAY ONE: Arrive in Madrid and drive southwest to Toledo, where you stay for two nights
    Begin your Spanish touring holiday by flying into Madrid, where you collect a hire-car. Drive about 50 miles southwest towards Toledo, a historic city in the region of Castile-La Mancha. Stay for two nights in the Parador de Toledo, a four-star hotel across the river from Toledo’s old town. Best visited mid-week to avoid the crowds, Toledo is known as the City of Three Cultures due to the co-existence of Christianity, Islam and Judaism. Built into a wide meander of the River Tajo, this spectacular city combines the spires of its Gothic cathedral, and the domes and archways of synagogues and mosques, with the impressive landscape of central Spain.

    DAY TWO: Toledo
    Toledo was made famous by El Greco, a Greek painter who made the city his home in the 16th century. The 13th century Gothic cathedral, the crowning glory of the town centre, was built on the site of a Muslim mosque and now houses a rich collection of paintings by the likes of Rubens, Raphael, and Titian, in the Sanctuary. Enter this formidable building through the Puerta de Mollete, from which food was once distributed to the poorer residents. Inside, 88 columns support the vaulted roof, and some of the stained glass windows date back to the 13th century. Admire the craftsmanship of the marble tombs in the Capilla de Santiago, and the artistry of the Retablo of the New Testament in the Capilla Mayor. For a taste of the exotic, perhaps move on to the Cristo de la Luz, decorated with keyhole archways and colourful stone. The Iglesia de Santiago de Arrabal is the most stunning example of Mudéjar architecture in the city, constructed out of dark brick, with curved, indented walls. The Puerta Vieja de Bisagra is the only remaining section of the Moorish town walls, and the Iglesia de Santo Tomé resembles the minarets of Marrakech. The Alcázar of Toledo sits at the highest point of the city, overlooking both the river and the bustling streets. Now, this 16th century palace houses a military museum, which sheds valuable light on Spanish military history. These are just a few of the eclectic architectural and historical delights that Toledo has to offer, and a few hours wandering around the city are sure to throw up infinite treasures, including the baths and caves. Do not miss out on the local products sold in the many small shops tucked away on the side streets; admire the damascene metalwork, and indulge in the Toledo marzipan. From the balconies of the Parador de Toledo, you have views across the spires, towers, and higgledy-piggledy roofs of the city. The rooms and public spaces are luxurious and comfortable, with traditional Mudéjar designs, wooden beams, and beautiful staircases acting as the signature features. The restaurant offers a unique opportunity to sample intriguing dishes inspired by the Castile-La Mancha cuisine.

    DAY THREE: Head west to Trujillo and stay overnight
    Leave Toledo to travel west to Trujillo, a journey of just over two hours. The small town of Trujillo is centred around one of the prettiest squares in Spain, the Plaza Mayor, and overlooked by the 13th century Arabian Caliphate Castle with outstanding views of the Extremadura countryside. Begin your exploration of this town in the Plaza Mayor, admiring the many important buildings that line it, and the bronze-cast statue of Francisco Pizarro at its centre. Take in the distinctive architecture of Trujillo, best seen in the angular balconies, the temple with Renaissance side chapels, the classical portico and Tuscan columns of the Palace of the Dukes of San Carlos, and the ‘Bread’ colonnades and segmented arches of the Palace of the Marquis of Piedras Albas. The Palace of the Marquises of the Conquistas is the most magnificent building on the square, with Plateresque decorations and two alabaster columns. As the birthplace of colonisers such as Francisco Pizarro (conqueror of Peru), and therefore a key point on the Ruta de la Conquistadores, Trujillo is home to a number of elaborate palaces and manor houses built with gold from the New World. The Coria Museum illustrates the story behind the discovery of the New World, and introduces you to the key Spanish figures. In the evening of your night in Trujillo, taste some of the local specialities, including bean soups and meat dishes, particularly Iberian pork. Stay for one night in the Parador de Trujillo, a peaceful four-star establishment set within the former convent of Santa Clara, with two beautiful cloisters, one of which dates back to the Renaissance. This stop on the tour offers a brief introduction to one of Spain’s most beautiful towns, and a night of relaxation in another historical Spanish property.

    DAY FOUR: Drive southwest to Mérida and stay for two nights
    Drive approximately one hour southwest to Mérida, the capital of Extremadura. Stay two nights at the Parador de Mérida, an attractive four-star hotel in an 18th century convent, which boasts a verdant inner courtyard and beautiful gardens. Like the white-washed exterior, the rooms are light and airy, with traditional furnishings and the occasional splash of colour.

    DAY FIVE: Mérida
    Explore Mérida, home to some of Spain’s finest examples of Roman architecture, and once the capital of Roman Lusitania. Begin with the 1st century theatre and amphitheatre, the former of which is built around a stage set of 2 stacked rows of columns decorated with sculptures of deities and imperial figures. The amphitheatre also retains some of its original features, including the box, gallery, and grandstands, and is still in use today. In the city centre, through the Arch of Trajan, stands the Temple of Diana. Scattered throughout the city are the ruins of Spain’s longest Roman bridges, one of which extends to over 800 metres, with 60 arches, the stony paving of an excavated Roman Street, and the Acqueduct de los Milagros, all of which establish a distinct atmosphere in this historic town. Across the river is the Alcazaba citadel, the fortress of which preserves an underground Roman reservoir, now decorated with Visigothic pilasters. The National Museum of Roman Art is the perfect stop after a day of exploring the ruins on the streets. Marvel at the excellently preserved sculptures, columns, and mosaics, all of which are housed in a striking contemporary building that, in its arches, tall halls, and Latinate marble name plate on the front, harks back to the Roman architectural structures that it honours. In the evenings, return to the Parador de Mérida to relax in the luxurious public rooms, before dining in the hotel’s restaurant on local delicacies, accompanied by Ribera del Guadiana wines. Finish off your meals in Mérida with desserts made by the expert pastry chefs. After dark, head back into the town centre to see the ruins and quaint streets lit up by atmospheric lighting.

    DAY SIX: From Mérida to Cáceres, where you will stay for the next two nights
    Head northwards to the walled city of Cáceres, approximately one hour’s drive away. Stay two nights at the Parador de Cáceres, a 14th century palace with a historic ambience, located in the heart of the old town. The rooms have harnessed the beauty of the building’s original splendour, with columns and arches, and arcaded courtyards downstairs. The furnishings of the rooms are contemporary and chic, which serves to highlight the legacy of the building itself, as well as establish a relaxing sense of comfort. There is plenty of time on your two days in Cáceres to discover the authentically mediaeval old town, which appears almost unchanged since its 16th century heyday, complete with cobbled streets and a convent selling traditional candied egg yolks.

    DAY SEVEN: Cáceres
    With an extremely high concentration of historic buildings, Cáceres’ prosperous history is evident in its Renaissance palaces, ancestral houses, towers, and plazas, many of which date from the 15th and 16th centuries. The history of battles between the Moors and the Christians has left its mark on these mediaeval streets, which are now a blend of Roman, Islamic, Gothic, and Italian Renaissance styles. There are over 30 Islamic towers, though the most famous is the Torre del Bujaco, a 12th century tower that overlooks the pretty Plaza Mayor. The Concatedral de Santa María, situated on a plaza of the same name, dates back to the 15th century. Its imposing austere façade gives way to a luminous interior, with a brilliantly carved cedar altarpiece as the centre point. This impressive building now houses several noble tombs, an ecclesiastical museum, a series of chapels, and a bell tower which offers fantastic views over the Old Town. The Roman heritage of the town can be seen in the Arco del Cristo, a Roman gate that links two sloping streets together. On the Plaza de San Jorge stands the Iglesia de San Francisco Javier, an 18th century Jesuit Church. Though a more modern addition to the town, its white towers have become somewhat iconic; inside, its golden altar, in contrast with its bright white walls, is mesmerising. The pathways and sights in Cáceres are incredibly rewarding and varied, crossing bridges, and rising up small hills, passing buildings that mix the typically Spanish white-washed houses with those of warm stone. The best times to enjoy the magnificent city that lies within these mediaeval walls are either on a quiet day, or in the evening. At these times, the peaceful beauty of the place can be enjoyed, as well as the horizon sculpted by the roofs and sculptures of Cáceres’ religious and historic buildings.

    DAY EIGHT: Drive further north to Plasencia for your final two nights
    Drive approximately one hour northeast to Plasencia, a medieval walled town strategically located along the Ruta de la Plata, one of the pilgrimage routes to Santiago de Compostela. Stay two nights in the Parador de Plasencia, a Gothic-style hotel set within a 15th century convent in the heart of the town’s historic quarter. This irregular building has undeniable charm, with mottled stone walls, windows of varying sizes, and picturesque cloisters and courtyards.

    DAY NINE: Plasencia
    Take the time to explore the riverside town, famed for its weekly market dating back to the 12th century, as well as its two cathedrals, towering above the town, which are back-to-back. The Old Cathedral was built in the 13th century, in-keeping with the Romanesque style which had only just reached Plasencia due to its position on the Christian and Muslim border. The New Cathedral was built in the 16th century with Gothic, Renaissance, and Plateresque elements on both the interior and exterior designs. The Cathedral Museum nearby houses some of the greatest artworks that have been on display in the cathedral, from the Gothic panel of the Caná Wedding, to the works of Baroque painters such as Gregorio Fernández and the Brothers Churriguera. The Palacio de los Monroy is the perfect example of Palatine architecture. For those looking for something a little different to end your tour, perhaps visit the Ethnographic-Textile Museum near the cathedrals, the Hunting Collection at the Palace of Mirabel, or the Sanctuary of the Virgin of the Orchard. From here you can easily venture into the surrounding countryside to discover the farmsteads among the waterfalls and twisting rivers, the wildlife of the Monfragüe National Park, the pretty villages of the Sierra de Gata, and the Jerte Valley which is filled with cherry blossom in spring. Dine at the Parador de Plasencia in the evenings, on delicacies such as partridge, lamb, pork, figs, trout, and local favourites such as cheese from La Serena, and cherries from the Jerte Valley. You may want to plan your visit for early in the year to see the Plaza Mayor at Plasencia fill with lively celebration on Shrove Tuesday, or simply aim for the heat of summer to witness the landscape around the Jerte River at its most splendid.

    DAY TEN: Return to Heathrow from Madrid-Barajas
    Depart Plasencia and drive about two and a half hours back to Madrid Airport, to drop off your hire-car and catch a flight back to the UK. If your flight is in the evening, you may wish to take a detour to Salamanca, adding only another hour to your drive. As the capital of the Castile region, Salamanca has much in the way of historic architecture to offer, including two cathedrals, a grand square, and an ancient convent, as well as a lively and infectious atmosphere.

    Driving times for this touring holiday:
    Madrid to Toledo: 35 minutes
    Toledo to Trujillo: 2 hours
    Trujillo to Mérida: 55 minutes
    Mérida to Cáceres: 55 minutes
    Cáceres to Plasencia: 55 minutes

    Click the 'Hotel Information' tab to find out more about the hotels featured in this touring itinerary.

    History and Heritage of Extremadura 2

    Hotel Information

    These are the historic hotels that are featured in this touring holiday. Alternative hotels are available in some destinations – please contact us for full details.

    Parador de Toledo
    Located across the river from Toledo’s old town, guests staying in this historic building can enjoy panoramic views from the swimming pool, terraces, and guest rooms. This four-star establishment balances the perfect blend of homely detail with luxurious comfort and service. Beamed ceilings stretch across canopied beds. Wicker armchairs sit beside the large outdoor pool. Excellent food is served alongside breath-taking views on the terraces and balconies. Walk along cosy corridors to seek out comfy spots to sit and read, or take a drink in the bar. This marvellous hotel offers convenience and comfort, with the necessary touches of luxury.

    Parador de Trujillo
    A peaceful and tranquil hotel housed within the Convent of Santa Clara, the Parador de Trujillo allows you to explore the historic town of Trujillo, relax beside the pool, or sample the best of local cuisine in the restaurant. The interior spaces of this four-star establishment are structured around the original layout of the convent. The breakfast room is topped with a dramatic stone ceiling, and the glass-roofed courtyard is lined by the thin pillars of the original cloister. The bedrooms, too, complement the building’s heritage, some with artistic headboards and furnishings to match. For your one night in Trujillo, this hotel surpasses all expectation and embodies the concept of a luxury Spanish hotel.

    Parador de Mérida
    An attractive hotel set in the heart of the city, the Parador de Mérida boasts an inner courtyard and beautiful gardens, as well as a selection of artefacts that illustrate the building’s rich history. The shape of this white-washed building maximises the potential for each room to have stunning views. Its regal doorway introduces guests immediately to the sense of luxury that is continued within. Cloistered courtyards mingle beautiful historic spaces with contemporary relaxation, and the bedrooms master the fine balance of indulgence and rustic homeliness. The central hallway, which resembles the cavernous belly of a Romanesque cathedral, and corridors lined with ancient pillars, pay testament to the area’s history and create interesting points of interest within the hotel itself. This four-star hotel also has an excellent restaurant serving local food.

    Parador de Cáceres
    This Gothic-style building combines a historic atmosphere with a high level of modern luxury, boasting original features, such as vaulted ceilings and a cloistered inner courtyard. A building of many corridors, arched rooms, and attractive stairways, the Parador de Cáceres offers an intriguing and captivating setting for your exploration of the town. Stay in rooms defined by their pillars and arches; dine in the light, airy, wooden-ceilinged restaurant, whose vast windows overlook the verdant exterior. Locate small outdoor courtyards, or sit under trees to avoid the heat of the midday sun. This four-star hotel captures the essence of this tour of Extremadura, and gives you direct access to the town centre, but with the feeling of total exclusivity, created by the impressive stone structure, and the surrounding trees.

    Parador de Plasencia

    This former convent, with Gothic-style interiors, is excellently located in the heart of Plasencia’s historic quarter. Walking through this four-star Parador is a similar sensation to being cast back in time and walking along the corridors of a mediaeval castle. Its grey-stone walls ironically add a sense of chic contemporary living to the sitting areas and gym, while the wooden beams and chandeliers in the dining room elegantly remind you of the building’s true age. The bedrooms retain the castle-feel, with canopied beds, stone arches, and comfortable soft furnishings, whilst ensuring the highest standards of comfort and relaxation are possible.

    • BOOK NOW

      Complete a simple booking form and e-mail it to us.

    • CALL US 01392 441245

      We are open Mon-Fri 9-17.30 Sat 9.30-16.00.


      Let us know a convenient time to call you back to discuss your holiday.



    • Rail holidays

      Rail holidays and train journeys, tailor-made.

    • Garden holidays

      Italian garden holidays and tours for individuals and small groups

    • Family holidays

      Visit our selection of tailor-made family holidays to selected hotels and resorts around the world.

    • Cookery holidays

      Tailor-made cookery holidays in Italy

    • Spa holidays

      Rejuvenating, relaxing, refreshing, good for the body and the soul; spa and well-being worldwide

    • Authentic experiences

      Our selection of authentic experience and special interest holidays.

    • Worldwide journeys

      Luxury tours for individuals around the world


  • New Marine Biology Centre at Kanuhura

    A new Marine Biology Centre as opened at Kanuhura in the Maldives.

    Find out more Read more

  • New Grand Suites for the Venice Simplon Orient Express in 2020

    Three new Grand Suites will be introduced for 2020 on the Venice Simplon Orient Express

    Find out more Read more

  • Six new Cinnamon suites at Mount Cinnamon

    Mount Cinnamon will be introducing 6 new Cinnamon suites in time for the festive season.

    Find out more Read more

  • Renovated Crusoe suites at Soneva Fushi

    Ten newly refurbished Crusoe Suites at Soneva Fushi will be ready to welcome guests in December

    Find out more Read more

  • Hotel Botanico introduces new Wellness Programme June 2019

    The Hotel Botanico in Tenerife is introducing a new ‘Slim and Wellness Programme’ from June 2019

    Find out more Read more

  • Luxury Al Andalus rail holiday departure dates 2020

    The luxury Al Andalus train departure dates for 2020

    Find out more Read more

  • Cookery Holidays at Eremo della Giubiliana Sicily

    The Eremo della Giubiliana has announced the themes for its cookery lessons

    Find out more Read more

  • New Family Aqua Park at the Westin Resort Costa Navarino

    The redesigned Aqua Park at The Westin Resort Costa Navarino opens end of April 2019.

    Find out more Read more