The Best of Central Spain’s Medieval Heritage: A Road Trip Through Castile

Make sure to take advantage of the hotel’s breakfast as you will want plenty of energy for your first full day in Madrid. Hit the ground running as you head out this morning with an English-speaking local resident to see the city through a native Madrilenian’s lens. The walk is spontaneous, relaxed and tailored to your fancy. Are you a culture buff? A gastronome? An outdoor enthusiast? A football fanatic? A shopaholic? Madrid certainly has enough to fuel your passions (or even ignite new ones). For the afternoon you have a couple of options. You can continue exploring on your own now that you have a feel for the city, or you have the option to head out for another private tour, this time with a focus on discovering Madrid’s rich heritage as a melting pot of writers, artists and creative spirits.

Madrid is a cradle of some of the world’s best pieces of artworks and, naturally, some if its best art galleries. Today is dedicated to the Prado Museum, which houses one of the largest and most comprehensive collection of Spanish artworks. Masterpieces on display include Goya’s The Third of May 1808, Caravaggio’s David and Goliath and Velasquez’s Las Meninas.

After one last breakfast at your hotel, it is time to bid farewell to Madrid. Today you will pick up your rental car and drive one hour south of the city to beautiful Toledo. Along the way you can make a cultural pit stop at the Royal Palace of Aranjuez, one of the official residences of the Spanish royal family. Your home for the next two nights is an elegant hotel in the historic centre of Toledo. You can spend the rest of today settling in. When your tummy starts to grumble, head to the lovely on-site restaurant to sample some tasty Toledan gastronomy.

The former Spanish capital of Toledo is awash with beautiful remnants of the three major religions that co-existed here in the Middle Ages: Islam, Christianity and Judaism. It is no surprise then that UNESCO has recognised the city on its prestigious World Heritage list. Today, you will have the opportunity to admire all of Toledo’s absolute must-sees with a private guide. There is the 13th-15th century Cathedral of Saint Mary, which combines French gothic architecture with Spanish ornamentation; the 14th-century Santo Tomé church, with its Islamic-style bell tower, which houses the Burial of the Count of Orgaz painting by El Greco; and the 12th-century Santa Maria la Blanca synagogue, which became a church in the 15th century and later a museum. You will also have time at then end of the tour to visit some other sites in the city, such as the Alcázar of Toledo, a fortress which played host to battles of the Spanish Civil War in the 1930s.

Today you will hop back into your rental car and drive just under two hours to Avila. You just have one night in Avila and there’s not a moment to waste, so once you’ve checked into your centrally-located hotel it’s time to get out exploring. There are plenty of sites to keep you busy in Toledo. The Cathedral of Avila is the first Gothic church in Spain, while the Basilica of San Vicente is an exceptional example of Romanesque style. However, the star of the show is certainly the Convent of Saint Joseph, whose foundations were first laid by Saint Teresa of Jesus back in the 16th century. You can enjoy dinner out in town or back in the hotel. We recommend tucking into some classic Castilian cuisine: Barco de Ávila beans (a hearty bean stew) and tasty cold cuts.

After fuelling up on breakfast at the hotel, it’s time to bid farewell to Avila. The bulk of today will be spent driving to Salamanca, which takes around three hours. Your destination in the city is a boutique hotel in the heart of the historic centre. The rest of the day is yours to enjoy at leisure. You can head out for a wander in town or simply kick back and relax in your new home.

After a day of travelling yesterday, it’s time to get moving. After a tasty breakfast at the hotel, you will be met by one of our top local guides to head out for a private cycling tour of Salamanca. Discover the charming suburbs and the tranquil River Tormes before heading into the old town. The Plaza Mayor (central square) is the beating heart of the city. Here you can admire two immense Catholic cathedrals which speak to the cultural evolution of Salamanca. During the 16th century, the city wanted to prove itself as a real intellectual and economic power by building the Catedral Nueva (new cathedral), moving away from the austere forms of the Romanesque church. However, the cathedral wasn’t completed until nearly 200 years later, in 1733. Other must-visit sites include the Dominican monastery of San Esteban and the famous house of las Conchas, which is decorated with as many shells as there are days in the year.

Today you will embark on a pleasant two-hour journey to your final destination in Spain: Segovia. Your hotel is located in the heart of the historic centre, so once you’ve settled in and freshened up you can spend the rest of the afternoon getting a taste of your new surroundings.

It is your last full day in Spain and there’s not a moment to waste. After tucking into a hearty breakfast at the hotel, turn your nose to a spot of sightseeing in town. Perched on the imposing Sierra de Guadarrama, at the confluence of the Eresma and Clamores rivers, Segovia is a city of exceptional architectural heritage. The dominating castle, Alcazar de Segovia, is one of the city’s most prized possessions, while the huge medieval aqueduct is an impressive example of Roman engineering. Other sites include the 13th-century Vera Cruz church and the Gothic-style Segovia Cathedral. We can arrange for you to head out with a knowledgable local guide to learn the historic significance of the city’s most important sites.