Insider tips for Toledo, Cuenca & La Mancha Spain! 

Join us in our travels to the amazing La Mancha region in the heart of Spain!… We will start with the highlights of beautiful medieval Toledo! From here we will jump into the celebration of the San Isidro festival in Las Mesas, where we were hosted by our good friend Maria! With her as our local guide we stopped at various highlights and ended our trip in Cuenca!… Read all about our great experience and local tips to make the most on your journey through the land of Don Quixote!… 


Spain’s La Mancha Region 

La Mancha is the natural and historical region in the heart of Spain and comprises the provinces of Albacete, Ciudad Real, Guadalajara, Toledo and Cuenca. On this trip we mostly focus on the latter 2 regions! The dry lands of La Mancha are well known for its wines (more on this later) and of course the setting for the adventures of the famous Don Quixote of La Mancha. When driving around the region you will see the many distinct windmills that the literary hero was ‘fighting’. 

La Mancha Windmills

Highlights of Toledo

Toledo is a marvelous medieval city set on a hill overlooking the La Mancha plains. Obviously the city has many sites of interest, unfortunately most with slightly overvalued entrance fees. Therefore, do some research upfront, but in my opinion you do not need to visit that many churches & museums anyway! The key highlight of Toledo is to get lost in the maze of historic narrow covered medieval alleyways. Especially when avoiding the crowds you feel like being thrown back centuries into medieval times! 

Toledo Alleys


Getting to Toledo

As Toledo is situated on a hill and has many narrow alleyways to navigate through, I advise to pack light for your stay. (Leave unnecessary belongings in your car, or pre-drop these at your hotel). 

Top Tip: Assuming you arrive by car, park at the free public ‘Safont Parking’ Which is opposite the Bus Station. 

From the Car park (and from various other sides of the city) you can take the convenient escalators up the hill! So even when you are not the most fit you do not have to climb all the way up! 

La Mancha Toledo Highlights
Creating your own Toledo walking tour

With those logistics out of the way, you are all set to discover Toledo! I advise to add the following key sights in your navigation and ‘get lost’ via the various alleyways connecting these!… 

  • Puerta Del Cambron
  • Mirador del puente
  • Puente de San Martin
  • Monasterio de San Juan
  • Sinagoga de Santa Maria
  • Iglesia Catedral Primada de Toledo
  • Alcazar de Toledo
  • Mezquita del Cristo de la Luz
  • Puerta de Bisagra

La Mancha Toledo Bridge
Of course there are many more sights to discover! However, these will give you a great walking tour past many more interesting shops, restaurants and museums. Remember, as said, in my opinion most entrance fees (especially for the churches, in Toledo and the wider La Mancha region) can be a bit overpriced, so do check if you feel it is worth your money before you enter. When in doubt stroll on!

Toledo Dinner

Top Tip: You can avoid the entrance fee for the Iglesia Catedral Primada de Toledo by entering via the ‘back-entrance’ (on the Calle Chapineria). This gives access to the prayer area ‘only’. However, from here you do not have full access to the church but can see most of it. 

La Mancha Toledo Catedral

Top Tip: You can visit most sights in Toledo in a day, however it is nice to stay overnight, especially to beat the crowds in the morning and at night!

La Mancha Toledo Catedral

Toledo Alleys

On top of the above, I like to emphasize a few key highlights and hidden gems that you must include in your Toledo itinerary!…


Churreria Chocolateria Santo Tome 27

How better to start your Spanish Toledo adventures, than with an early coffee and churro! The best place to enjoy these delights is the quaint Churreria at Santo Tome 27. It is only open in the early morning (until 11am). Bring cash as no cards are accepted. Say hi to the lovely lady that works here, who let me pay later (as I found out too late about this cash-only policy).

Churreria Toledo

Hacienca del Cardenal

Hacienda del Cardenal is a beautiful spot for any meal or coffee! Found at the bottom of the hill next to one of Toledo’s escalators. 

Toledo Hacienda del Cardenal

Puente de San Martín

A short stroll out of the city (and already part of the highlights listed above) make sure to check out Puente de San Martin. (Or the similarly beautiful Puente de Alcantara, on the other side of the city). The entire picture of the historic arching bridge over the Tagus river with the backdrop of the city is just spectacular!… 

La Mancha Toledo Bridge

Mirador Toledo

Only a short drive out of Toledo, the Mirador offers unparalleled views over the entire city

La Mancha Toledo Mirador

Celebrating the San Isidro festival in Las Mesas, La Mancha

San Isidro is the patron saint of Madrid and that of farmers. Given that La Mancha is an important farming region and San Isidro’s miracles are connected with well-needed water in this dry region, the celebrations are a very important part of life. The San Isidro festivities date back to the 12th century and take place during mid May. 

Las Mesas San Isidro Festival La Mancha


Our friend Maria grew up in Las Mesas, and invited us to join the open-air celebrations in her village. Obviously a great opportunity to dive into (very) local heritage with a local guide to tour us around! The celebrations take place at a church in the middle of the La Mancha fields. This church only used for these yearly occurring festivities. Many people camp in the surrounding fields during this multi-day celebrations complete with music, dances, games and (very important) lots of drinking!…

Las Mesas San Isidro Festival La Mancha

Las Mesas San Isidro Festival La Mancha

Las Mesas San Isidro Festival La Mancha


How lovely and welcoming were the Las Mesas people and Maria’s family, with an amazing paella lunch and later that night an invitation to a friend’s barbecue at a friend’s tent!… 

Las Mesas San Isidro Festival La Mancha

Las Mesas San Isidro Festival La Mancha

Las Mesas San Isidro Festival La Mancha

Las Mesas San Isidro Festival La Mancha


Most people speak limited English, making it a great occasion to catch-up on our rusty Spanish!… The free-flowing Sangria certainly helped here!… 

Las Mesas San Isidro Festival La Mancha

Other La Mancha highlights!

After a ‘busy’ day of drinking and celebrating we woke up in our Palacio Infante Don Juan, overlooking the Belmonte Castle. Today it was time to explore the wider La Mancha region. La Mancha is the largest delimited wine region, not only in Spain but in the whole of Europe. So how better than to further examine one of the main (export) products? 

Belmonte Castle

Finca Antigua wine tour

There are countless wineries. However, not all are open (all days of the week), some require a pre-booking and not all offer tours in English, so do some online research before your visit. As we visited on a Sunday, and during the San Isidro festival we had limited options. Nevertheless, we found a great winery where we had a multi-hour tour and tasting experience; Bodega Finca Antigua.

Finca Antigua Bodega

We have had our fair share of wine tastings and tours all over the world, but I must say Finca Antigua has one of the nicest tasting tour experiences! Mainly as the tastings take place on multiple locations on the tour throughout their property (as opposed to the typical ‘tour first, tasting after’ approach). 

Finca Antigua Bodega

Restaurante Casas de Lujan

Enroute to Cuenca, we stopped for a fabulous lunch at the landmark restaurant Casas de Lujan! Whenever traversing the La Mancha region make sure to stop here for their famous steaks and other Spanish culinary highlights!

Casas de Lujan Restaurant

Highlights of Cuenca

Before heading to Madrid, we end this La Mancha tour in Cuenca; yet another wonderful historic hilltop city! The historic center of Cuenca is smaller than Toledo’s but definitely not less impressive. Cuenca is most famous for its ‘hanging houses’ that seem to dangle above the cliffs. We stayed in one of these, offering beautiful views over the surrounding nature. 

La Mancha Cuenca


Top Tip: Cuenca is also great for a day trip! Park for free at Parking del Castillo Gratuito at the very hilltop and make your way down via the walking trails and through the historic city. (Save energy for your way up! There are no escalators as in Toledo!)

La Mancha Cuenca

A few highlights that you certainly should not miss are listed below (link them together in a GPS for your explorations): 

  • Mirador Cuenca – beautiful views over the ‘hanging’ city and the walking bridge
  • Catedral de Santa Maria – Largest church of Cuenca
  • Casas Colgadas de Cuenca – most famous hanging houses
  • Puente de San Pablo – for great views
  • Grotte del Huecar – Great for food and drinks in a Grotto 

La Mancha Cuenca

La Mancha Cuenca

Top Tip: Keep in mind that Cuenca is situated higher up in the Spanish highlands and is therefore colder, so bring a sweater or jacket. We were a bit underdressed for an (a-typical) colder period in May. 

La Mancha Cuenca

Onwards to Madrid

As said, our visit to Cuenca marked the end to this Don Quixote adventure through La Mancha, full of culture, celebrations and history!… However our Spanish adventure did not end here, as we traveled onwards to Madrid! This is city was above expectations, so do read all about my tips & tricks!… 


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