Inspiration for your own tailor-made trip

A Tale of Two Cities
Art, History and Heritage in Madrid and Toledo

Madrid - Toledo

Starting from between £1,330 to £2,000 per person for 6 days depending on the time of year, type of accomodation and activities

Itinerary Highlights

  • See the sights of Madrid through the lens of a local before discovering the distinguished Prado Museum
  • Admire the sweeping landscapes of central Spain on your train ride from Madrid to Toledo
  • Discover the must-see sites of medieval Toledo with a private guide
Madrid and Toledo: two neighbouring cities that display the impressive cultural heritage of central Spain. This six-day getaway kicks off in Madrid, where you’ll be getting a behind-the-scenes experience of the city on a walking tour with a local guide before admiring the iconic masterpieces housed at the Prado art museum. Then you’ll catch the train to Toledo, a medieval city home to a mixture of Christian, Jewish and Muslim religious heritage. Our team will be on hand along the way to guide you towards your passions – a football game in Madrid? Shopping in the finest neighbourhoods? Eating in historic tapas bars? You name it, we can arrange it.
Madrid - Espagne © Ben Roberts/PANOS-REA
Madrid - Espagne © Ben Roberts/PANOS-REA
Madrid - Espagne © Salva Lopez
Madrid - Espagne © Salva Lopez
Madrid - Espagne © Salva Lopez
Madrid - Espagne © Salva Lopez
Madrid - Espagne © Ben Roberts/PANOS-REA
Madrid - Espagne © Ben Roberts/PANOS-REA
Musée Reina Sofia - Madrid - Espagne © Ben Roberts/PANOS-REA
Musée Reina Sofia - Madrid - Espagne © Ben Roberts/PANOS-REA
Palais Royal - Madrid - Espagne © Monica Gumm/LAIF-REA
Palais Royal - Madrid - Espagne © Monica Gumm/LAIF-REA
Alcazar - Tolède - Espagne © Getty Images / iStockphoto
Alcazar - Tolède - Espagne © Getty Images / iStockphoto
Musée du Prado - Madrid - Espagne © Gianfranco Tripodo/The New York Times-REDUX-REA
Musée du Prado - Madrid - Espagne © Gianfranco Tripodo/The New York Times-REDUX-REA
Musée du Prado - Madrid - Espagne © Jose Vega/stock.adobe.com
Musée du Prado - Madrid - Espagne © Jose Vega/stock.adobe.com
Madrid - Espagne © Salva Lopez
Madrid - Espagne © Salva Lopez
Madrid - Espagne © Hotel NH Collection Palacio de Tepa
Madrid - Espagne © Hotel NH Collection Palacio de Tepa
Tolède - Espagne © Yvann K / Adobe Stock
Tolède - Espagne © Yvann K / Adobe Stock
Monastère San Juan de Los Reyes - Tolède - Espagne © LAMBERTOJESUS / Adobe Stock
Monastère San Juan de Los Reyes - Tolède - Espagne © LAMBERTOJESUS / Adobe Stock
Musée Reina Sofia - Madrid - Espagne © Ben Roberts/PANOS-REA
Musée Reina Sofia - Madrid - Espagne © Ben Roberts/PANOS-REA
Tolède - Espagne © ziggy / Adobe Stock
Tolède - Espagne © ziggy / Adobe Stock

Itinerary

100% customisable for you

Your cultural escape to central Spain starts today. Head to the airport, whizz through security and enjoy some down time in the airport lounge with some nibbles and refreshments as you await departure. Flight time to Madrid is two-and-a-half hours, just enough time to practice some handy Spanish phrases before touchdown. A private driver will be waiting for you on arrival to whisk you into the heart of the city centre. Your first accommodation is an elegant hotel located within easy walking distance of the main sites, where you’ll be staying for the next three nights. The rest of today is yours to spend settling into your new Spanish surroundings. We recommend heading out for a stroll through town to find some tasty eateries. One of our favourite spots is the Mercado de San Miguel, an upmarket food hall offering traditional fare, but you’ll also be armed with our coveted destination-specific Dossier, which is full of tried-and-tested recommendations for wining and dining.

It’s your first full day in Spain and what better way to spend it than discovering the capital in the company of a friendly local resident who knows the city inside out. The walk is relaxed and totally based around you, so before heading out you can discuss your tastes – are you a culture buff? A gastronome? A football fanatic? A fashion obsessive? Whatever it is, Madrid has plenty to fuel your passions and maybe even spark some new ones…. The rest of the afternoon is yours to play with. You can continue exploring the city at your own leisure or we can arrange for you to head out on a second walking tour, this time to discover Madrid’s fascinating history as a hub of writers, artists and intellectuals.

Today is all about soaking in Madrid’s grand cultural splendour. You’ll be armed with entrance tickets to the Prado Museum, one of the world’s most important art galleries. You can admire Velasquez’s ‘Las Meninas’ (1657), Charles V at Mühlberg’s ‘Titian’ (1547), Goya’s ‘Tres de Mayo (1814), Fra Angelico’s ‘Altarpiece of the Annunciation’ (1426), Caravaggio’s ‘David and Goliath’ (1605), Rogier van der Weyden’s ‘Descent from the Cross’ (1435), Hieronymus Bosch’s ‘The Garden of Earthly Delights’ (1504) and Greco’s ‘Portrait of Jeronimo de Cevallos’ (1613), just to name a few. The rest of today is yours to spend as you please, and there are plenty of other museums and sites worth visiting. We could also arrange for you to head out this evening with a knowledgeable local guide to discover the oldest taverns and tapas bars in Madrid, one of which dates back to at least 1787.

Your journey through central Spain continues today. After a hearty breakfast at your hotel, head to the beautiful and very green train station in Madrid to board a thirty-minute train to Toledo. On arrival, settle in for two nights in a characterful hotel in the heart of the UNESCO-listed historic centre. The rest of today is yours to spend getting your first taste of life in Toledo. We recommend simply getting lost in the labyrinth of bustling streets that make up the centre: admire impressive architecture before tucking into some indulgent culinary delights at one of the many inviting tapas bars.

Set atop a gorge overlooking a peaceful river, Toledo is a city that dazzles with scenic, cultural and historic delights. For centuries it was known as the ‘City of Three Cultures’ for being a place where Christians, Jews and Muslims co-lived, for the most part, harmoniously. Today you’ll be discovering the many sites that reside within the old city walls in the company of a knowledgeable local guide full of fascinating tales. Toledo’s treasures include Saint Mary's Cathedral, which dates back to the 13th century and displays a mixture of French Gothic and Spanish ornamentation; the 14th-century Santo Tomé church, with its Mudejar-style bell tower; and the 12th-century Santa Maria la Blanca Synagogue (now a museum), whose name indicates the Christianization that took place here in the 15th century. The rest of the afternoon is yours to continue exploring. You could head over to the Alcazar, which was the place of iconic Civil War battles in the summer of 1936, or we can arrange for you to pair up with another local guide to discover the city’s hidden gems. For dinner this evening, follow your nose to find a classic little tapas bar in town or, once again, turn to our destination-specific Dossier for inspiration.

Sadly the time has come to bid farewell to Spain and embark on the journey home. This morning you’ll be collected by a private driver and transferred back to the airport in Madrid. After whizzing through security, settle into the airport lounge to enjoy some nibbles and refreshments before taking off on a two-and-a-half hour flight back to the UK.

Suggestions

Everything in this itinerary is entirely customisable, down to the smallest details. Here are some more suggestions of what could be included

DISCOVER THE CREATIVE HISTORY OF MADRID



From the Golden Age to the Movida, Madrid has long been a haven of artists and writers looking for inspiration. Cervantes, Pedro Calderon de la Barca and Federico Garcia Lorca are just a few of the Spaniards that speak to the city’s creative nature. But there are also great foreigners that have flocked here: Hemingway, John Dos Passos and many others. Head out today with a private guide to discover the works and places that evoke Madrid’s fascinating creative history.



VISIT MADRID’S OLDEST TAVERNS



Madrid is home to a collection of charming old taverns that haven’t changed in centuries. Today you’ll be visiting three of them in the company of a knowledgeable local guide. Your first stop is Casa del Abuelo, a tavern founded in 1906 that is known and adored for its delicious prawn-based tapas fishes and traditional decor. Then you’ll head over to Casa Alberto, which dates back to 1827 and is said to have been frequented by Cervantes. Round off your day with a visit to Taberna Antonio Sanchez, which, dating back to at least 1787, is the oldest restaurant in Madrid. A longstanding meeting place for big names in the worlds of bullfighting and the arts, this spot serves traditional cuisine in an even more traditional setting.



THE HIDDEN GEMS OF TOLEDO



After visiting the must-sees of the city, it’s time to go beneath the surface. Head out with a friendly local guide to discover the sites of the city others might overlook. You’ll start at the remains of the thermal baths of Toletum, where you can learn about the importance of baths for Roman sociability. Continue on to the Church of San Salvador to admire a rare Visigothic pillar, on which scenes from the life of Christ have been carved, such as the healing of the born blind and the resurrection of Lazarus. Round off your walk with a stroll through the old Jewish quarter and the Casa del Judio. The Jewish community of Toledo were very prosperous: in the 14th century, there were ten synagogues and seven yeshivas in the city.

Why visit Spain with Original Travel ?

Each of our trips is entirely tailor-made with originality, quality and cultural immersion in mind. Our team of destination specialists will craft itineraries based on your tastes, using their first-hand knowledge and the help of our in-country team of Concierges and guides. All trips are accompanied by a wide range of additional services, including a 24-hour helpline, the Original Travel app, fast-track airport services and much more.

ENQUIRE NOW

A few of the benefits of travelling with us to Spain

  • Our local Concierges
  • The Original Travel app
  • Airport lounge access
  • Destination Dossier
  • 24-hour helpline
  • Expert guides
  • 100% carbon absorption

You might also like

A rough idea of the price

Depending on the time of year, type of accommodation and activities

The estimated cost for this trip starts from £1,330 to £2,000 per person. The final cost of the trip depends on the way we tailor it especially for you. The final cost varies according to several factors, which include the level of service, length of trip and advance booking time. The exact price will be provided on your personalised quote. The average starting price for this trip is £1,650 per person.

100% tailor-made holidays

Understanding Your Needs

Our team of destination experts will get to know you and your unique requirements for your holiday

Personalisation

We work with you to build an ultra-personalised holiday itinerary with your choice of accommodation, experiences and activities

Our Services

All of our holidays include little extras designed to make a big difference to your trip, from fast-tracking you through airport check-in and security to our network of local Concierges