I take my first steps down the Initiation Well here at the Quinta da Regaleira in Sintra. This deep hole in the ground has a spiral staircase around the edge and I continue down, deeper and deeper.

It gradually gets darker. Looking up, I can see the circle of light at the top where I came in. It’s 27 metres above me. This strange inverted tower, full of symbols of ancient cults and mysticism, has me in its grasp.

I am now truly underground and a tunnel has opened up in front of me. I decide to follow it, head bowed, through the darkness, not quite sure where it will lead. All I know is that this is a part of the Sintra day trip experience – a mysterious journey into an almost-magical realm with constant marvels and surprises.

Thankfully, though, most of the journey in Sintra is above ground, not in the long dark tunnels of the Quinta da Regaleira. Because the highlights of Sintra are found in its lush green mountains full of romantic palaces and fairy tale estates.

The history of Sintra

To understand what Sintra is, think of it as a huge district (about five times the size of Manhattan) where the royals and wealthy of Portugal have built grandiose homes over the years.

For centuries, they have created their own little domains with opulent buildings and vast gardens full of amusements. Many of them are still privately owned today. But the best ones are now open for us to explore.

Although you can find more than 1000 years of history at Sintra, I think it’s easiest to think of its development in three important stages.

The Moors

The first stage in the history of Sintra that’s worth mentioning is the few hundred years from the 9th century. This is the period when the Moors occupied different parts of the Iberian Peninsula and were in constant conflict with Christians.

With battle after battle, the region of Sintra changed hands back and forth between the Moors and the Christians. Many of the buildings constructed during this period would form the foundations for the palaces that would come later. The most famous sites left from this period is the Moorish Castle, which I’ll talk about shortly.

The Royals

The second important period is from approximately the early 1400s until the 1600s. This is the time when the Portuguese Royal Family decided to make Sintra their holiday retreat.

It doesn’t take long to get from Lisbon to Sintra, even back then, and so the cool hills were the perfect summer escape from the heat of the capital.

Different rulers left their own marks on the landscape of Sintra and used the palaces and gardens for various purposes. The most important construction of this time was, without doubt, the iconic National Palace of Sintra in the centre of the town.

The Romantics

Perhaps the period that most defines Sintra these days is the period in the 18th and 19th centuries when the idea of Romanticism took over the area. It became the first centre of European Romantic architecture as a new generation of wealthy and artistically-minded people moved here and created new estates.

With a mix of design influences from across the world, with bright colours, and with some playful artistic embellishments, Sintra was transformed into a playground. I think it’s this period that has come to define the fairy tale land that visitors are looking for on a visit to Sintra… including the Initiation Well where I began my tale.

How to see Sintra in one day

So, as you may be able to tell by now, there is a lot to see at Sintra. The large area takes a while to get around and there are impressive sights scattered throughout it all.

It would be very easy to spend two or three days seeing the main attractions – but I know that many people only have limited time to spare and a Sintra day trip from Lisbon is the only option.

With that in mind, I have put together my suggestions for the best way to spend a day in Sintra. This itinerary will take you to all the biggest sights and explain the easiest way to do it independently.

The only word of warning I would give is that most visitors do a very similar itinerary because it is the best and most obvious way to see Sintra in one day. If you are prepared to leave knowing you didn’t see the biggest attractions, you can still see some amazing sights but with much smaller crowds.

Still, I’ll concentrate now on the best way to spend a day in Sintra and see all the main sights. I’ve put all the locations I’m going to talk about on the map below.

How to get to Sintra from Lisbon

I’m going to assume that you’re coming from Lisbon. It’s really easy to get from Lisbon to Sintra and I would recommend you take the train.

It leaves from Rossio station and takes only 40 minutes. There are relatively regular departures but some are direct and some will involve a change. You can see the timetable here.

The trip costs €2.25 each way but you’ll need to buy a transit card for €0.50 if you don’t have one already, making it a return cost of €5 total.

This train line is included for free in the Lisboa Card. The Lisboa Card will give you some other savings if you’re going to Sintra for the day, because some of the sites offer discounts. If you just get the 24 hour card, the whole day will cost you €58.90 as opposed to €48.50 if you pay for each ticket individually (these calculations include all the transportation as well). So it’s not worth doing it that way, but you may like to use it on the third day of the 72 hour card.

If you are also doing some sightseeing in Lisbon – maybe following my guide to the best things to do in Belém, for example – then the 48 hour or 72 hour card could be a great idea!

>> Get your Lisboa Card in advance here

Bus 434 Sintra

Once you arrive at Sintra train station, you’ll see that some of the sights are walkable. However, to see some of the best things in Sintra, you’ll need transportation.

There will probably be lots of tuk-tuks or other private companies offering transportation. I think it’s better to use the special tourist bus that will take you around to the main areas.

You’ll see the signs for the Bus 434 Sintra at the train station. Here you can buy a loop ticket for €5.50 that lets you get on and off at each stop of the loop, right back to the train station. You can see the schedule and other details here.

Things to do in Sintra

I’m going to recommend four main sights to see during a Sintra day trip. It’s very manageable to do all of these without rushing but it will be a long day. However, there isn’t any one particular sight that I would suggest skipping if you’re in a hurry. Just try to get to Sintra early enough in the morning to fit it all in (the first sight opens at 09:30).

Although I have suggested a particular itinerary, I will mention one caveat. If you go on a day when there are lots of tourists, many of them will also follow this same itinerary.

So, if you want to avoid some of the crowds, you can skip straight to my second or third suggestion and then come back and do the others in the afternoon (and then walk back to the train station when you’re finished).

National Palace of Sintra

Starting from the train station, you can get the bus 434 to the National Palace of Sintra to begin your loop trip. However, the walk is only about 20 minutes and it’s a nice way to start to get a sense of the atmosphere here in the mountains.

Although there were structures on this spot from the Moorish period, the palace that you see today is mostly from the start of the 15th century when the Portuguese kings began to spend more time at Sintra as a holiday destination.

From the outside, the most remarkable feature of the National Palace of Sintra is the two enormous chimneys that give it an unusual shape. When you go inside, you’ll realise that they are there for practical reasons and sit above the enormous kitchen.

Inside, the rooms are decorated with furniture and art from the periods when the palace was used the most. The tile decorations are particularly interesting and worth taking note of. One of the most famous parts is called the Swan Room because of the painted swans on the ceiling.

Quinta da Regaleira

The Quinta da Regaleira is not on the bus loop so you have two options. I would recommend just walking along the street because it’s only 15 minutes away and there are some nice views. However, a different bus – number 435 – will take you there. It costs €2.50 per trip.

Quinta da Regaleira has a ‘palace’, which is really just a grand house. But the reason you would visit is for the incredible park around it. When a wealthy man called Carvalho Monteiro bought the estate in 1892, he decided to turn this park into a collection of oddities.

As you walk around, you’ll find towers, fountains, sculptures, bridges, and terraces. Even if you use the map provided, you’ll probably get a bit lost and just discover new things as you wander.

I think the highlight is the well (or inverted tower) that I told you about at the start of this story. You can climb down the 27 metre deep spiral staircase and then follow the underground tunnels to pop up at a second well or further down the garden.

The Moorish Castle

From Quinta da Regaleira, walk back to the centre of Sintra town and catch the 434 bus from outside the National Palace up to the Moorish Castle.

The castle was built at the top of a peak by the Moors in the 10th century. Although it was presumably used for residential and official purposes, it was also part of the fortification effort of Sintra. In the centuries afterwards, the location and foundations were used by various Portuguese rulers who added to the structures but none of them lasted.

The Moorish Castle is in ruins these days and there aren’t many actual buildings to see. What makes a visit to the castle so special is being able to climb up and walk along the defensive walls. You will get incredible views across the region from here, including a great angle of Pena Palace.

Pena Palace

From the Moorish Castle, you can get the bus to Pena Palace or just walk along the road for 10 minutes.

This is another one of the most iconic buildings in Sintra, high on a hill with its yellow and red towers and turrets and dome. Once you go through the entrance gate for the park, you’ll walk up the hill to the castle (or you can pay a few euros to take a transfer bus).

One wing of the palace is an old monastery that was built in 1511. Work to change it into a modern and luxurious structure started in 1838 under the direction of King Ferdinand II. He then added the second wing to make it even bigger and more opulent.

Around the building is a wall that is all about aesthetics rather than defences. It’s a fantasised version of a medieval castle wall that has battlements, watchtowers, and even a drawbridge.

Pena Palace is a perfect representation of the Romantic movement that swept through Sintra in the 19th century and stands as the ultimate symbol to this style.

Sintra tours

Hopefully I’ve explained well enough how you can do a Sintra day trip from Lisbon. But, as you’ve probably realised, there are quite a lot of logistical issues to deal with for the day.

I think Sintra is the kind of place where doing a day tour is actually quite a good idea. Not only will it save you a lot of hassle, but you’ll appreciate having a guide to explain all the background to the palaces and show you some of the features that you might miss if you were just looking around on your own.

There are lots of options for day tours to Sintra from Lisbon. I would recommend any of the following. Have a careful look, though, because they each go to different sites.

However you choose to explore Sintra, I hope you find the time to make the trip from Lisbon. The Moors, the Royals, the Romantics – none of them made this for us. They made it for their own amusement because they appreciated how special this land was.

The fact that we can now enjoy what they have left for us just shows how much care they took in the creation of this fairy tale playground.

Where to stay in Sintra

While I have put together this guide to help you plan a one day trip to Sintra from Lisbon, there are also quite a few accommodation options in Sintra and it is a wonderful place to stay if you want to explore the area for a couple of days without the hassle of catching the train back and forth each time.

This is a UNESCO World Heritage Site. For more info click here. You can see all the UNESCO World Heritage Sites I’ve visited here.