One Of Spain's Most Walkable Cities Is A Well-Preserved Medieval Paradise With Majestic Charm

If you wanted to make a movie of "Don Quixote," the classic story of a delusional knight riding across the Spanish countryside, you could film the entire thing in Cuenca, Spain. The walled city stands on a series of hills, its sun-bleached stone walls overlooking rocky chasms. From its centuries-old parapets, the views are among the most glorious in Spain; within its gates, much of the city looks unchanged since the Middle Ages. Put an actor in armor and have him ride a horse down these narrow streets, and you'd think he traveled back to the 17th century. Author Miguel Cervantes would be proud.

In fact, the city of Cuenca is only a 60-mile drive from La Mancha, where the protagonist of "Don Quixote" is said to have lived. This is the very countryside that inspired Cervantes, and on winding roads around the city, you can imagine the aging warrior and his passive sidekick, Sancho Panza, trotting along in search of adventure. Indeed, there are even whitewashed windmills nearby, the very structures Quixote mistakes for dragons.

This region is steeped in history and folklore, and it's an achingly beautiful side-trip from Madrid, the largest nearby city, about two hours away by car. Cuenca is your basecamp for some of Spain's most romantic countryside, and also a walkable community with lots of amenities and plenty to do. You could easily add it to a bucket list of underrated destinations in Spain.

Cuenca is much older than Cervantes, dating all the way back to the Roman Empire, when it was known as Conca. The Moors controlled Cuenca for some time, until the Castilian Christians conquered the city in 1177. To celebrate their victory, the new rulers commissioned a Gothic cathedral, the first of its kind in the Kingdom of Castile. This structure took over 100 years to build, and additions and renovations took place over centuries. You can visit this stone masterpiece, and book a tour, on the north end of the old city.

Equally spectacular are the "casas colgadas," or hanging houses. These buildings balance on the edges of cliffs, and they almost seem to levitate over the precipitous drops that circumscribe the old town. Many will feel squeamish standing on their balconies, but the views from their railings defy belief, especially during golden sunsets. This architectural style probably reached its zenith around the 15th century, underscoring the impressive topography.

Speaking of which, Cuenca stands just 16 miles or so from the Ciudad Encantada, or "Enchanted City." Rather than a manmade skyline, this metaphorical city is actually a series of gravity-defying rock formations, shaped over time by the erosion of passing waters. Located within the Serranía de Cuenca Nature Reserve, this natural wonder is easily visited from Cuenca, the closest sizable town. This is a beguiling region in any season, and a budget-friendly side trip during a fall getaway to Madrid.

Today, travelers get to experience a historic city of about 56,000 people with spectacular vistas and a maze of medieval streets. Many are angled and even steep, but designed for pedestrians and have little auto-traffic. A footbridge, known as Puente de San Pablo, spans the river gorge and provides one of the best views of town. Up above, you can hike to the Mirador Cerro de Socorro (Hill of Succor Lookout Point), which overlooks the valley and is topped with a sculpture of Jesus Christ.

Flying into Madrid provides the easiest access to Cuenca, thanks to a scenic two-hour drive or an 80-minute train ride that costs only $10 one-way. The latter option is better for travelers who don't feel like renting a car, since they can easily navigate the town and surrounding highlands on foot; Madrid itself is seamlessly connected with an efficient train system.

If you prefer to drive, there are lots of places to stop along the way, including the storied neighboring town of La Mancha, as well as those iconic windmills. Cuenca is absolutely packed with hotels, most of them costing less than $100 per night.