3 Enchanting Overnight Trips Near Madrid

by Last updated Sep 7, 2023 | Published on Aug 2, 2023Europe, Madrid, Spain, Travel

Everyone raves about day trips from Spain’s capital, but there are also overnight trips near Madrid that are worthy of your wanderlust. Madrid is a wonderful city, not only because it’s so centrally located (literally in the center of Spain), but also because, well… It’s Madrid. Enough said. After years of living here, we’ve lost count of how many times we’ve traveled through and stayed overnight on our way to exploring other parts of Spain. We never run out of things to do in Madrid.

But there is much more to enjoy in this heart of Spain than just its capital. You don’t have to go far to discover a treasure trove of enchanting towns. While many of them can be great day trips from Madrid, you and I both know that once you’re there a day is not enough and you want to stay overnight. Whether you’re arriving into Madrid, or passing through it like we frequently have, consider these three enchanting overnight trips near Madrid that are ideal for deepening your experience of Spain.

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Cuenca for an Overnight Trip Near Madrid

Above ImageThe hanging houses of Cuenca.

Top Sites in Cuenca

For some time, we had been hearing great things about the UNESCO World Heritage Site of Cuenca. The Moorish-found walled town is most famous for its casas colgadas (hanging houses). As you can guess from the name, they are built on the very edge of rock cliffs with balconies hanging over the edge. Today, the most famous and well preserved house is home to the Museo de Arte Abstracto Español (Spanish Abstract Art Museum). Not only do you get to view some amazing art, but the setting is also incredible with its traditional spaces and gorgeous views of the gorge it hangs over.

Above ImageA spectacular view of Cuenca old town on the right and the San Pablo Convent on the left, now a Parador hotel.

While there is a modern part of the town, the old town is where you want to be. Situated high on a limestone ridge, it has two rivers on either side, the Júcar and the Huécar, forming spectacular rock formations. The cobblestone streets are steep and in many areas rock stairways form the path. Be prepared to do a lot of stairmaster walking. Our legs were so sore after the first day!

There is plenty to do and see in Cuenca, from its romantic cathedral and Medieval castle ruins to a historic still functioning seminary that you can stay in. There are also countless trails for hiking in the beautiful nature that surrounds the town. Another main site is the San Pablo iron bridge, a pedestrian bridge which crosses high over the Hueca River Gorge to connect the town to the San Pablo convent (today a Parador hotel).

Above ImageThe view of Cuenca from the other side of the San Pablo bridge.

How to Get to Cuenca

Getting to Cuenca is ideal by high speed train from Madrid or Valencia, being only an hour away from each city. If you’re going between the cities, it makes for a great additional visit, like we did when taking the high speed AVE train from Valencia to Madrid. Or, you can drive but from either city it takes about two hours by car. Keep in mind as well that driving and parking in the old town will be tricky.


  • It’s ideal to have at least two nights and one full day in Cuenca, but if you have more time, there is plenty to see and do with two to three full days.
  • We recommend visiting Cuenca in the fall or spring since summer time can get very hot and the winter is known to get really cold.
  • Cuenca is also known for impressive Easter celebrations but be warned that it gets very crowded and should be planned far in advance.
  • For a variety of great tours in Cuenca, click here

Segovia for an Overnight Trip Near Madrid

Above ImageThe castle (Alcázar) of Segovia.

Top Sites in Segovia

Ah, Segovia… I love thinking back to our visit there because it has one of the most beautiful castles I have ever seen in Spain. It’s also one of the most visited sites in Spain. The iconic castle, also referred to as the Alcázar de Segovia, sits at the highest point of the old town and features impressive towers and even a moat. You can tour inside the castle and also enjoy learning about its history and admiring the incredible rooms and antiques.

Above ImageThe Roman aqueduct of Segovia. There was a beautiful classical music concert when we had dinner there during our visit.

Segovia’s old town sits on a ridge, similar to Cuenca, but here the views of the surrounding countryside are more open and gentle, although spectacular nonetheless. The stone, narrow streets, Romanesque churches, and especially the Cathedral of Segovia, culminate for a captivating experience.

But the other most famous historic site is the Roman aqueduct of Segovia. With over 160 arches, it truly is impressive to stand beneath this relics that was built with no mortar around the first century AD! It was even in use to deliver water until 1973. You can catch views of the aqueduct from various places in the town. I highly recommend having dinner just below it in one of the various restaurants in the Plaza del Azoguejo. To enjoy dinner on a terrace, gazing at the aqueduct as the sun sets and the arches are lit up, is a beautiful experience.

Above ImagesThe charming streets and the Cathedral in Segovia.

How to Get to Segovia

Segovia is north of Madrid and can be reached in just over 30 minutes by train. Beware that some maps only show slow trains that take longer, but there are 30-minute trains that go quite frequently throughout the day from Madrid Chamartin Train Station to Segovia. It’s also quite inexpensive. To drive there from Madrid, it takes just over an hour and driving and parking are limited in the historic center. Expect to walk to really enjoy the old town.


  • Segovia is popular as a day trip from Madrid, but it’s so worth spending at least two or more nights there. We spent only one night there and would have preferred more time.
  • Summer time gets hot in Segovia but we were there in late June and the evenings were pleasantly cool. We still recommend going in a shoulder season, like the fall or spring.
  • To find various tours for enjoying Segovia, click here

Toledo for an Overnight Trip Near Madrid

Above ImageOne of the many churches in Toledo’s historic old town.

Top Sites in Toledo

And yes, of course I have to include Toledo. This historic city is probably the most popular destination near Madrid to visit and can be done in a day trip as well. But where’s the fun in that? This town is popular for a reason and there is so much to see. It is stunningly beautiful with its old world architecture and rich culture that results in the Medieval Arab, Christian, and Jewish monuments that line its cobblestone streets.

Famous for its Greco Museum, Alcázar fortress, and astounding Cathedral, it is also magnificent to wander among its old neighborhoods. You’ll want plenty of time to see sites which are best discovered on foot. The town also sits on a hilltop with a river curving around three sides, affording beautiful views of the surrounding countryside.

Above ImageOne of the original entrances to Toledo in its Medieval walls.

How to Get to Toledo

Getting to Toledo from Madrid takes only 35 minutes by train and about an hour by car. And I know I sound like a broken record, but be careful trying to drive and park in the old town. It will not be easy.


  • Toledo is definitely best visited in the shoulder seasons so you can avoid the summer crowds and heat.
  • Staying three nights so you can have two full days in Toledo is highly recommended.
  • For various tours in Toledo, click here

Ideal Itinerary for Traveling from Madrid

Above ImageThe Crystal Palace in El Retiro Park in the center of Madrid.

While all three of these destinations are great to visit from Madrid, Cuenca and Segovia can make for an ideal itinerary when traveling from Valencia to the northern region of Asturias. We enjoyed this on a recent trip in late June when I crafted the following travel plan.

  • From Valencia train to Cuenca for 2 nights
  • From Cuenca train to Madrid for 2 nights
  • From Madrid train to Segovia for 1 night
  • From Segovia train to Oviedo, our final destination for a couple of weeks


Central Spain Travel Itinerary

This central Spain travel itinerary worked great for us to enjoy Cuenca as a new destination. Then we stayed two nights in Madrid so we could enjoy a full day to tour the Reina Sofia Museum and visit our favorite park, El Retiro. Our last morning there, we met some of my family who flew in from the US. From Madrid, we then traveled together to Segovia for our first time. The only thing we would do differently is to stay two or even three nights in Segovia instead of just one.

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Written by Amalia Maloney Del Riego

Written by Amalia Maloney Del Riego

Fora Advanced Travel Advisor & Content Creator

I love living in Denia, Spain and traveling worldwide. My idea of a great time is ‘eating and drinking’ my way around a new place and meeting the people. As a Fora Advanced Travel Advisor, I specialize in custom travel planning for trips throughout Europe, as well as scouting trips for moving to Spain. Here on you can enjoy our Europe travel resources to experience Europe and live in Spain.


  1. Amanda

    You are the best, your tips and insights are spot on and informative.
    We are now planning our next trip which will be Cuenca.
    Thank you for your detailed explanation for our next trip from Valencia.

    • Amalia and Eric

      Hi Amanda! You are so welcome. We’re so glad that you enjoy our blog and find it helpful. You’ll have to let us know how you enjoy Cuenca and of any other trips we can help with. Have a great time!


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