Where the wild trails start: Getting off-the-beaten path in Castilla-La-Mancha

One of Spain’s most fascinating cities, Toledo is as marked by diverse cultures as much as it is by its history as an Imperial City. Centuries-old synagogues, mosques and cathedrals jostle for space with cosy eateries serving carcamusas and puchero, all while the majestic Alcázar looms above.

No visit is complete without visiting the Toledo Cathedral and the Monastery of San Juan de los Reyes, but don’t miss the Moorish-era Mosque of Cristo de la Luz and the 14th-century El Tránsito synagogue. After all, there’s a reason Toledo is known as The City of Three Cultures.

You might feel like you’re living life on the edge in Cuenca, as the city is famous for its clifftop houses that seem to almost levitate over the Huecar river. The ancient, dream-like vibe is strong here, especially when you wander the cobblestone streets and narrow alleys of the World Heritage City.

Head to the Spanish Museum of Abstract Art to see paintings from some of the country’s most important modern artists, then enjoy a different kind of view on one of the city’s most romantic spots: the San Pablo Bridge, where the gravity-defying Hanging Houses sprawl out before you.

Designated a Historic-Artistic site, Sigüenza in an architecture buff’s dream, with a mix of contrasting styles and centuries-old buildings offering a fascinating look at a city of contrasts.

The Cathedral of Sigüenza showcases Romanesque and Gothic elements, with an interior that recalls a medieval fortress, while the Renaissance-style Plaza Mayor is the perfect spot to grab lunch, shop, or level up your Instagram grid with some snaps of the ‘houses of the cannons’.

Sierra del Segura beckons to visitors who want to see a side of Spain that’s just as spectacular as the more visited areas, but without the crowds, noise and high prices. In other words, you’ll find plenty of breathing space here (along with some absolutely gorgeous photo-opps).

Head to Parque Natural Los Calares del Mundo y de la Sima to wander the trails, take in the sweeping views, get face to face with some Iberian ibex and just commune with nature. It’s a bit of a walk from the main car park, so wear comfy shoes, but you’ll be rewarded with memories that last a lifetime.

Even if you’re not a great lover of 17th-century literature, you’ll find plenty to appreciate on The Don Quixote Path, which retraces the steps of Miguel de Cervantes’ famous knight errant.

The path crosses through 13 towns and stretches over a week, carrying you through some of the country’s most magical (and crowd-free) towns. From Cervantes’ birthplace of Alcalá de Henares to Ciudad Real – home of the Don Quixote Museum – you’re in for an awfully adventurous amble.

One of the charms of Castilla-Le-Mancha is that it seems ageless, and there’s no better opportunity to step into the past than at Almadén Mining Park, where you can explore mercury mines that date from Roman times.

The Almadén Mining Park is now part of a UNESCO World Heritage Site – think of it as the Stonehenge of the mining world – and offers a learning centre and a mercury museum, as well as the chance to physically descend into an underground mine.

Almagro may not be Spain’s Broadway – the brightest lights here are the stars over the Plaza Mayor del Almagro – but it’s reputation as a cradle for world-class theatre is legendary.

Visit at the right time (July) and you’ll find yourself in the middle of the International Festival, a stunning event dedicated to the Golden Age of Spanish theatre. If you miss that, fear not: you can visit the Open Air Theatre and the National Theatre Museum any time you’re feeling dramatic.

Perched on a sleepy hillside overlooking a bend in the Júcar River, the gorgeous village of Alcalá del Júcar feels an awful lot like the type of place an Iberophile who’s never been to Spain might imagine: think labyrinthine caves, cliffs and whitewashed houses.

Besides being one of the country’s most beautiful locales, it houses the Alcalá del Júcar Castle, a medieval Arab fortress that offers sweeping views of the surrounding area.