A 5 Day Madrid Itinerary: Flamenco, Day Trips and More!
A 5 day Madrid itinerary using 4.5 days of PTO! Madrid is a beautiful, clean European city, but one of its best perks is that it often has super affordable flights and has amazing small, Spanish towns close by!
And, trust me, you are going to want to visit some of those small towns. They are so charming and are a good contrast to the hustle and bustle of Madrid!
We opted to spend two and a half days exploring Madrid, one day for a day trip to Toledo and one day trip to Segovia. Toledo is a beautiful, walled city located high on a hill and Segovia is SO picturesque with its incredible aqueduct and Disney-inspiring castle!
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Summary of Your 5 Day Madrid Itinerary
This 5 day Madrid itinerary includes two and a half days to explore Madrid in addition to a day trip to Segovia and a day trip to Toledo. Both of these towns are within an easy train ride making it easy to spend a full day in each town.
In all honestly, I thought Madrid was great, but the more I visit smaller European towns, the more I love them! I highly suggest you do at least one day trip while in Madrid!
For planning purposes and PTO preparation (because thats what I do!), we used half a PTO day to leave on Thursday afternoon and returned on Wednesday, getting us back to work on Thursday. Again, a perk of Madrid is that it is easy to get to with several direct flights from the US!
Friday: Explore Madrid- Parque de El Retiro and Palacio de Cibeles
Spend your first day (once you land in Madrid) exploring the east side of Madrid! This side of Madrid is a bit farther out than some of the more centrally-located places, so hop on public transportation and make your way to Parque de El Retiro!
Parque de El Retiro is a large park that consists of a beautiful pond, gardens and the Palacio de Cristal. You can spend a lot of time here due to its size, but if you only have a few days in Madrid, don’t spend TOO much time here!
- The Palacio de Cristal is a 19th century observatory that is now used as an art museum
- Price: 12 euros
Palacio de Cibeles is also on this side of town. It is a government building with INCREDIBLE architecuture, but, also, has a great view of the city from above!
- There is a restaurant located at the top of the building, or you can just opt to go to the observation deck to watch sunset and have a drink while you are over there!
For dinner, head to Gustos at the Plaza Mayor. It may be in the “tourist” section of town, but it had a beautiful inside downstairs section or a patio option, the food and sangria were amazing and the price was affordable!
Saturday: Day trip to Segovia
There are two day-trips from Madrid on this 5 day Madrid itinerary. I suggest going to Segovia on Saturday due to it being a less-common day trip and may be cheaper and less crowded on a Saturday.
Why visit Segovia?
- Segovia is one of my favorite day-trip cities I have ever visited! It is quaint, but there is SO much beauty squished into the small city.
- The alcazar de Segovia is phenomenal; built into the side of a cliff with symmetrical architecture, it is something to see! Along with the alcazar, Segovia has clean, beautiful streets and an iconic aqueduct at its entrance.
What to do in Segovia?
You will arrive just outside of the aqueduct of Segovia, so start here! The aqueduct is picturesque, but its even more impressive in person! Don’t miss the views that are up the stairs to the right of the aqueduct!!
From here, you will walk down the beautiful streets of Segovia toward the Plaza Major. Here you will find the beautiful gothic-style cathedral of Segovia, which you can admire from the outside or pay 3 euros to see the inside.
Continue on to the other highlight of Segovia, the Alcázar de Segovia! This castle is truly INCREDIBLE and its no wonder it was an inspiration for Disney!
- The castle is about a 25 minute walk from the aqueduct and you can also opt to either see the castle from outside or tour the inside!
A Day Trip to Segovia!
To get to Segovia, you will train from Chamartin Station in Madrid directly to Segovia
Where is Segovia?
Sunday: Explore Madrid- Walking Tour, Royal Palace, Flamenco Show and More!
Continue with explorations of Madrid on Sunday!
Start with a walking tour in the morning. I love a walking tour to get some history of the city and to get a better idea of the layout of the city!
Many walking tours end at the Royal Palace and Almudena Cathedral, so explore these after your tour!
- The cathedral is free unless you want to go into the dome.
- To get into the dome of the cathedral you have to purchase a ticket to the cathedral museum.
- You also have to pay to enter the palace. If you want to see the inside, I suggest purchasing a skip-the-line ticket with a guided tour!
Following your waking tour, head to Plaza Mayor and Puerta de Sol, the heart of the city center! This is where you will find loads of restaurants, shopping and entertainment.
Do a Flamenco show with dinner included to top off the day!
- The flamenco show was a highlight of Madrid for sure! My recommendation is to choose one that includes dinner and drinks (we didn’t do this option and we regretted it).
Monday: Day Trip to Toledo
Your 5 day Madrid itinerary should really include Toledo as well! It is easy to get to and such a neat city!
Why visit Toledo?
- It is only about a 30 minute train ride from Madrid and so worth it!
- Toledo was once the capital of Spain and is a beautiful city on a hill surrounded by a wall. The winding streets, terracotta roofs, friendly locals and history really make it worth visiting.
Do note, though, siesta time is taken seriously here, so you may have trouble finding open restaurants between 1pm to 4 or 5 pm!
What to do in Toledo?
Once you arrive in Toledo, you can take a short walk to the city center. Know, though, that you will need to take escalators to get to the top of the city!
Be sure to take in the views from the overlook that is just to the right when you come up from the escalators.
From here, head to the main square, Plaza de Zocodover, where you can find a bite to eat or some sangria!
Don’t miss the Cathedral at Plaza del Ayuntamiento and Monastery of San Juan de los Reyes which both have incredible architecture and history!
You will also want to see the city walls up close, which you can do as you walk down the road from the monestary. Here you will see the gate of the city, the walls and plus get another view of the valley below!
A Day Trip to Toledo!
Madrid has two main train stations, so whereas you go to the Chamartin station to get to Segovia, you will go to the Atocha station to get to Toledo!
Toledo is closer to Madrid than Segovia, which is good because it is also larger! You could even consider staying one night in Toledo if you wanted.
Where is Toledo?
Tuesday: Explore Madrid- Go Tapa Hopping and Take a Cooking Class
You have several options of things to do on your last day in Madrid, however, I suggest delving into the food and drink culture and doing a tapa and sangria hop!
- These two were some of my favorite things about Madrid!
- You can do this on your own by trying out different restaurants and bars who will offer tapas and sangria or you can opt to take a guided tour.
- The perk of a guided tour is learning all of the BEST spots from a local!
If you are enjoy cooking or getting your hands dirty, you can still delve into the food culture by doing a Spanish cooking class!
- Here they will show you how make Spanish dishes and tapas on your own!
Book a wine and tapas walking tour or a Spanish cooking class!
Did you know the oldest restaurant in the WORLD resides in Madird?
- Sabrino de Botin was founded in 1725 and is the oldest restuarant in the world according to the Guinness World Records.
- Have dinner or at least stop by for drinks because there isn’t another in the world older than it.
Alternative to Day Tripping on Your Own
As I have said, I HIGHLY suggest visiting both Segovia and Toledo. However, I know navigating multiple trains can be a bit overwhelming. Another option to seeing both towns is to do a guided tour of Segovia and Toledo from Madrid.
This will allow you to see both towns, but with the comfort of being picked up and dropped off in Madrid. You will also have a guide who will have some insight on the history of both cities!
Where to Stay While in Madrid
Be sure to stay in a pretty central location while you are in Madrid, especially if you only have a few days in Madrid. Staying on the west side of Madrid will get you closer to many of the highlights of Madrid and also close to metro stations to get you to Atocha and Chamartin stations for your day trips.
5 day Madrid Itinerary Recap
Madrid is a beautiful city, but just outside of Madrid is even more beauty! Yes, you can spend a lot of time exploring Madrid, but if you are working and trying to save PTO days, this itinerary gives you a taste of the big city as well as small city life of Spain!
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