A Local’s 3-day Lisbon Itinerary
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Seeing Lisbon in three days seems like an almost impossible task. In fact, there are plenty of activities to do, places to visit, and incredible streets to explore in one of Europe's most beautiful capitals.
But if you're coming to Lisbon in a limited time, you should know it's possible to visit the city in just two days. And I'm adding another one to this itinerary so you can go further afield to the mystical town of Sintra.
In Lisbon, we have a saying that we use when we want to represent something almost impossible: "meter o Rossio na Betesga," aka "to fit Rossio [the biggest downtown square] into Betesga [a small and narrow street next to it]."
This Lisbon itinerary is undoubtedly a challenge, but with it, you'll be able to visit some of the city's most important monuments, tour the historic neighborhoods, and let yourself be swept away by the sound of Fado. Along the way, I'll show you some of my favorite spots and give you a handful of reasons to come back.
So, let's get to it because there's just too much to do!
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Table of contents
How long to spend
How to get around
Where to stay
Itinerary overview
3-day itinerary
Day 1 - From Belém to Downtown Lisbon
Day 2 - Historic Lisbon - the city’s soul
Day 3 - Day trip to Sintra, Cabo da Roca, and Cascais
Bonus Day 4 - More day trip options
Tours of Lisbon with Ana Sofia
If you’re looking to explore Lisbon with a local, reach out to Ana Sofia for a guided tour!
Ana is a Lisbon native and she’s been running walking tours, food tours, and day trips to places like Sintra, Évora, and Óbidos for over a decade.
A fully licensed guide with years of university study under her belt, Ana has the knowledge to keep history buffs happy, but still always makes her tours light, entertaining, and fun.
How long to spend in Lisbon
For most visitors, 3 days is the perfect amount of time to spend in Lisbon on a first trip. This gives you enough time to see the all of the major sights and attractions within the city center and Belém area, explore a few pleasant neighborhoods, and take a day trip out to Sintra, Cascais, and Cabo da Roca.
That said, Lisbon is an incredibly historic city that is filled with hidden treasures, pleasant neighborhoods to explore, great museums and cultural center, leafy parks, grand boulevards, and fantastic cafes, restaurants, and bars. Places like Fatima, Alcobaça, Óbidos, Évora, Arrabida park, and the Troia peninsula are also all doable as day trips from the city, so there is lots to keep you occupied.
If you’re coming for a city break, you could easily spend 5 days to a week, combining time in the city with day trips all around the Lisbon metro region.
However, I know that most visitors are coming to Lisbon as part of a larger trip around Portugal, and have limited time. So with that in mind, I do think that 3 days gives you a good introduction to the city.
How to get around Lisbon
You don't need a car to visit Lisbon. In fact, traffic can become really chaotic at rush hour, and parking is scarce and mostly paid (and quite expensive!), so having a car when in the city is not at all convenient.
Walking
Lisbon is quite compact, so if you're in good shape, I suggest walking most places, as the distances are never too far and exploring the city by foot is the only way you'll feel the charm of the old streets, see all the typical stores, and bump into the locals.
Metro and tram
For longer distances, the city has a good metro system that takes you quickly, easily, and cheaply, to all the main neighborhoods and tourist attractions, so getting around is a breeze.
And when you can't get somewhere by metro, you can always take the bus or the traditional streetcars. Tram 28 is the most touristic, as it retains its old appearance and passes through the historic neighborhoods of Graça, Alfama, and Bairro Alto. There are many others.
Tuk-tuk
For those with mobility limitations (and anyone who just doesn’t feel like walking or using transit), hiring a tuk-tuk is also an option. Because they are smaller, Tuk-tuks have an easier time getting around than cars do, and you’ll also get some explanations from the driver about the places you're passing through. You can book a tuk-tuk online - several companies offer the service - or try to catch one directly at Praça do Rossio or Praça do Comércio. However, be prepared to pay quite a lot, especially in the summer. A tuk-tuk can cost up to 80 euros for a 1.5-hour ride.
The Santa Justa Elevator in Baixa/Largo do Carmo, the Calçada da Glória, Rua da Bica, and Calçada do Lavra) elevators/funiculars are also very helpful for some of the steeper climbs.
Taxis
Regarding taxis, there are regular licensed cabs all over Lisbon, and apps like Uber and Bolt also work. Compared to other parts of Europe or North America, cabs in Portugal are very cheap.
A few tips
To get to Belém, take Tram 15 or the train from the Cais do Sodré station, getting off at the Belém stop.
To visit Cascais, just take the same train (not tram) all the way to the end of the line.
To visit Sintra, you’ll need to take a 40-minute train ride from Rossio Station. While Sintra is easy to get to, keep in mind that if you want to visit other interesting destinations nearby, it’s really best to rent a car and make a proper day trip of it.
Where to stay
Lisbon is truly a city of neighborhoods and they’re all quite distinct from each other, each with their own appeal.
I don’t think there’s a perfect answer to the question of where to stay as it really depends on your interests and the type of traveler you are. Anyone who tells you “this is the right neighborhood for 99% of travelers” is either a tourist themselves or just someone who doesn’t know the city very well.
Even so, if you just want a quick answer, I think that most travelers will do ok by choosing a hotel in any of the following 4 neighborhoods:
Baixa and Chiado
Principe Real
Avenidas Novas
Alfama
If you want a detailed guide on how to choose the right neighborhood for your base, have a look at my article on where to stay in Lisbon.
Explore the charming Belem neighborhood and her architectural anbd historical treasures on a guided tour with lifelong resident and local guide Ana Sofia!
Itinerary overview
This 3-day itinerary is intended for travelers coming to Lisbon for the first time. It’s designed to help you understand the city, see the main sights, explore some great neighborhoods, and eat some terrific food. It also includes a day trip out to Sintra and has a list of other potential day trips in case you have a 4th day in the city (or just aren’t interested in seeing Sintra).
On your first day, you’ll explore the Belém neighborhood in the morning, with the Jerónimos Monastery and the Torre de Belém the chief sights. In the afternoon, you’ll have a riverside lunch and then explore the neighborhoods of Baixa and Chiado as well as much of Lisbon’s “downtown”. You finish the day with a sunset cruise on the Tejo river before dinner and maybe (?) a night out in Cais do Sodre.
Your second day is all about historic Lisbon, focusing on the Alfama and Mouraria neighborhoods along with São Jorge castle, some iconic churches, and a few terrific viewpoints. In the evening, you have time to get a little off the beaten path, enjoying a wander in the neighborhoods of Principe Real or Graça. Finish the day with a Fado show in Bairro Alto.
Your third day will be spent outside the city, taking a day trip to the palaces of Sintra in the morning before visiting fantastic Cabo da Roca in the afternoon and finishing the day with dinner in Cascais and a visit to one of Estoril’s lovely casinos.
Day 1 - From Belém to downtown Lisbon
The history of Lisbon and the story of the Portuguese Discoveries are told in the Belém area and the city's downtown. It was from Belém that the Portuguese maritime expeditions set out to explore the world, while downtown served as the city's administrative and commercial center, where wealth obtained abroad was brought and traded.
As you tour the city on this first day, with the Tejo River always by your side, you will experience how Lisbon has evolved without ever losing sight of its heritage.
The Torre de Belém
Morning
Mosteiro dos Jerónimos
Your first stop today is the Mosteiro dos Jerónimos in the Belém neighborhood. Get there from central Lisbon by catching Tram 15 at Cais do Sodré station around 9:00 a.m. or even a little earlier. The journey to Belém takes around 20 minutes and the tram stop is directly in front of the monastery.
Considered a UNESCO World Heritage Site, this is one of Portugal's most visited monuments. To avoid the long queues that usually form, especially during the summer, you'll want to be there when it opens (9:30 a.m.). Buying your ticket online in advance can also save you some waiting time.
The Jerónimos Monastery was built in the 16th century by order of King Manuel I and is located where the ships set sail during the Age of Discovery.
Start your visit with the Cloister and its incredible Manueline architecture. This is one of the most beautiful areas of the monastery, and the details in the columns and arcades are extraordinary.
Then move on to the Church of Santa Maria de Belém, where you'll find the tombs of two iconic figures in Portuguese history: Vasco da Gama, the navigator who discovered the sea route to India, and Luís de Camões, one of the most famous Portuguese poets, author of "Os Lusíadas," an epic work that tells of the Portuguese achievements during the Age of Discovery.
Before leaving the site, be sure to spend a few minutes admiring the South Portal of the building, which is full of details and representations of the saints and monarchs who lived during this historic period.
Mosteiro dos Jerónimos - go early to avoid those lines
Have a Pastel de Nata at Pastéis de Belém bakery
It should be mid-morning by now, and this is the perfect opportunity to try Lisbon’s famous pastel de nata pastry at the iconic Pastéis de Belém bakery. You'll find the famous 1837 factory only 200 meters from the monastery. It produces the best custard tarts you'll ever taste. Be prepared for a bit of a queue at the door, but it will be worth it.
And don't bother asking for the recipe because it's still a closely guarded secret. Believe me, I've tried!
Praça do Império garden
Instead of staying inside the pastry shop or by the door, do as I usually do: take your “pastéis” and go and enjoy them in the Praça do Império garden, which is just in front.
Waiting in line for Pastel de Nata
The line continues…
Visit Belém’s other monuments
With your strength restored, head down to the riverside to see the Padrão dos Descobrimentos (Monument to the Discoveries), a stone monument shaped like a caravel boat, 52 meters high. This symbol of Portuguese expansion is topped by the image of Prince Henry the Navigator, followed by 32 other sculptures of historical figures from the Discoveries.
Finally, follow the river north for 10 minutes to visit the Belém Tower. Considered a World Heritage Site along with the Jerónimos Monastery, it’s a Manueline fortification that was built in the 16th century to protect the port of Lisbon. It also marked the starting point for maritime expeditions from the city.
You may find yourself queuing to get inside, but for me, the real charm of this monument lies in its exterior, full of details, geometric patterns, and maritime representations. The inside is lovely too, but you don’t have to feel guilty if you don’t enter.
Padrão dos Descobrimentos monument
Afternoon
Lunch overlooking the river in Belém or at LX Factory
After you’ve checked out the tower, it should be squarely time for lunch. In the neighborhood, you can continue a bit further north, past the Monument to the Overseas Combatants, and have your meal at Darwin's Café on their terrace overlooking the river.
Alternatively, you could do my personal favorite: have lunch at the fabulous LX Factory closer to central Lisbon. To get there, get back on Tram 15 (in direction of Praça da Figueira) and get off at the Calvário stop.
Occupying a former industrial area, LX Factory is not a restaurant but rather a huge complex that is home to a series of stores, art galleries, restaurants, and cafés. My favorite thing to do here is have a light meal at Chef Nino and then get lost amongst the books at Ler Devagar, a bookstore in the interior of an old printing plant.
Wander around Chiado, but first have a coffee!
After lunch, take the Streetcar 15 back to the center and get off at Cais do Sodré. It's time to see downtown Lisbon; the Chiado neighborhood to be specific.
From the station, walk up Rua do Alecrim to Praça Luís de Camões. Here, you're on the doorstep of the Bairro Alto alto area, but we'll leave that for tomorrow. For now, continue to the emblematic café Brasileira do Chiado for a "bica" (the name Lisboners give to espresso) or a cup of tea. Sitting on a table is a statue of Fernando Pessoa, a tribute to one of Portugal's best-known Lisbon poets, who used his place to write and meet fellow artists.
Praça Luis de Camões
Livraria Bertrand
With a little post-coffee pep in your step, take a walk down Rua Garrett towards the Armazéns do Chiado shopping center, in the direction of the Santa Justa elevator. Along the way, you'll pass Livraria Bertrand, the oldest bookshop in the world (recognized by Guinness World Records in 2011).
Founded in 1732, go inside to browse its seven rooms and feel the atmosphere of this place that was frequented by great names in Portuguese literature, such as Aquilino Ribeiro, Alexandre Herculano, Eça de Queirós, and Antero de Quental.
Santa Justa Elevator
Your walk down Rua Garret will end at a modern shopping center called Armazéns do Chiado, just in front of the Santa Justa Elevator. I wouldn’t bother stopping at the mall, but if you’re in the mood for some shopping, it has all the standard stores.
Once you see the line of people, you’ll know you’ve arrived at the elevator. Built in 1902 by Raoul Mesnier du Ponsard, a disciple of Gustave Eiffel (architect of the famous Eiffel Tower), it’s an impressive feat of engineering made of cast iron with neo-Gothic details and it connects the area of Baixa Pombalina to Bairro Alto. While it serves a functional purpose, I recommend it because of the great panoramic view.
Praça do Rossio (Praça de D. Pedro IV)
After your elevator ride, take a short walk over to Praça de D. Pedro IV (locally just known as “Rossio”), the city’s most noble square. There used to be many old stores and cafés around here, but they have now been replaced by hotels and lodgings, which, in my opinion, has unfortunately taken away some of its charm.
Despite this, it is at the top of the square that you can see the impressive Teatro Nacional Dona Maria, from 1846, one of the city's most important and emblematic theaters.
If you still want to catch a glimpse of the old shops, on the right-hand side of the theater, you'll find Chapelaria Azevedo Rua (the oldest hat shop in Portugal and where my father used to buy his caps!) and A Ginjinha, one of my stops for a ginjinha (sour cherry liquor) when I go to the Coliseu de Lisboa, in the opposite street, to watch a concert.
Praça do Comercio via Rua Augusta
The afternoon is flying by, so it’s time to go to Praça do Comércio, another of Lisbon’s most famous squares. To get there, set off along Rua Augusta, one of Lisbon's main shopping streets. With stores on both sides, be careful as you can quickly lose track of time here.
You'll find the extraordinary Rua Augusta Arch at the end of the street, marking the entrance to the square. I suggest you climb up to its viewpoint for the ultimate view of this grand imperial square which has been the symbol of the city's reconstruction since the earthquake (and subsequent tsunami) of 1755.
Flanked by restaurants and cafés and positioned right next to the river, this is one of the best places to watch the sunset.
Praça do Comercio during an event
Santa Justa Elevator (more lines)
Praça do Rossio
Take a sunset cruise
I know that I just said that Praça do Comércio is a great sunset spot, but because most of today has been dedicated to the memory of the Age of Discovery and Portuguese maritime tradition, how about watching the end of the day from the river on board a cruise?
Several companies offer 1.5 to 2-hour tours, departing from the docks at Terreiro do Paço, Alcântara, or Belém. The tours sail from the Alfama hill to the Belém Tower, passing under the 25 de Abril Bridge.
Evening
Dinner at Time Out Market and some nightlife in Calçada do Combro
It's time for dinner after the boat trip, which has certainly worked up an appetite. Close to Cais do Sodré is Time Out Market. Occupying a former fruit and vegetable market, you'll find a series of restaurants and cafés for a relaxed meal at shared tables. If you want a more intimate atmosphere and are a meat lover, opt for the Sala de Corte restaurant on the other side of the garden.
It's been a long day, and you'll probably want to rest, so I’ll forgive you if you call it a day! But… if you still have the strength to enjoy Lisbon's nightlife, here's a suggestion: start with a drink at Rua Cor de Rosa in Cais do Sodré, and then head up to the Calçada do Combro area to go dancing at Incógnito, an iconic alternative music nightclub (and my favorite since my college years).
Day 2 - Historic Lisbon - the city’s soul
There's something that sets Lisboners apart from the rest of the Portuguese, even though those of us from the city can't quite explain what it is. People from other parts of the country claim we’ve got our own accent, although we certainly can’t hear it!
You might also say the way we invite a neighbor over for an espresso: "Vamos à bica!", is very particular. Or maybe it has to do with how Fado has marked generations, and the word "Saudade" (to miss someone or something) is engraved on our souls.
And while Lisbon is becoming increasingly cosmopolitan and modern, its essence can still be found in its old neighborhoods and in its music. On this second day in the city, this is what we’ll set out to discover.
Overlooking the Alfama neighborhood
Morning
Miradouro das Portas do Sol
Start bright and early at the Miradouro das Portas do Sol. This is a privileged viewpoint over the historic Alfama district, the Tejo River, and the roofs of the typical houses that characterize this area.
In the morning, the sun illuminates this zone with golden hues, a special light that captivates everyone who visits the city.
Take an early morning walk in Alfama
The Miradouro is a good starting point for exploring the winding streets, narrow alleys, and steep, time-worn staircases of Alfama, Lisbon’s most historic neighborhood.
Take your time exploring the neighborhood and enjoying the typical tiled houses with wrought iron balconies and clothes draped over them, drying in the wind. Use all your senses. Listen to the sound of the locals going about their daily lives and stop to smell the homemade food being prepared.
If you visit in June, get ready to see the whole neighborhood decorated with banners and colorful paper balloons as part of the Lisbon Festivities and Saint Anthony celebrations.
Know that Alfama is extremely touristy now though, so expect there to be crowds just about everywhere. Even so, if you come early (or head down the side streets), you can feel the neighborhood as it once was, before the tourism boom.
Alfama backstreets
Wandering in Alfama
São Jorge Castle
As you wander Alfama, keep in mind that your final destination should be São Jorge Castle, which you can reach by numerous routes all involving some steep climbs.
Once you get to the castle, note that the ticket office is on Rua de Santa Cruz do Castelo. There are often lines, so I’d recommend buying your ticket in advance to save some time.
Pass through the entrance gate and climb up to the walls for one of the most extraordinary views of Lisbon. Take some time to explore each of the towers that make up this national monument. Then, take a stroll through the gardens and head to the Archaeological Center, which contains remains dating back to the Iron Age, the Islamic occupation, the Middle Ages, and the Modern Era.
Your ticket includes guided tours of this space and the Camera Escura (Dark Chamber). The latter is housed in the Torre de Ulisses, one of the castle's most emblematic towers, and allows you to see Lisbon in real-time through a periscope that offers a 360º view of the city.
If you still have time and desire, you can also visit the museum in the alcáçova area, which has a collection that reveals the multiple cultures and experiences from the 7th century BC to the 18th century.
Afternoon
Lunch at Gosta do Castelo
Time for lunch! Head to Gosta do Castelo, a friendly restaurant with vintage decor and a relaxed atmosphere. Opt for a brunch menu or try the traditional Bacalhau à Brás or a Pork Belly Bao. Due to its location near the castle, book online to guarantee a table.
Miradouro de Santa Luzia
After lunch, make your way back to Portas do Sol, but this time, turn right to visit another incredible viewpoint in Alfama: Miradouro de Santa Luzia.
The view from here is very similar to the one in the morning, but what makes this viewpoint unique is its romantic terrace decorated with bougainvillea and tiles illustrating scenes from the city's history.
Fado Museum
You'll also find Lisbon's history portrayed, but in comics, in the tunnel that runs under the Portas do Sol viewpoint and connects Rua Norberto de Araújo with Beco de Santa Helena. Follow this lane towards the river and the next stop on this itinerary: the Fado Museum.
This museum is a first glimpse into understanding this Lisbon art form, which has been recognized as a World Heritage by UNESCO. Here, you can learn about the history of Fado and its main protagonists, from the iconic Amália Rodrigues to the current names that keep this musical style alive. From the instruments to the costumes to the interactive studios, get ready to spend a good hour here.
Sé de Lisboa cathedral
Once finished at the Fado Museum, walk about 15 minutes to get to the Sé de Lisboa. Built in the 12th century, this beautiful cathedral, so often depicted on postcards of the city, has stunning architecture both inside and out.
Next door is the Church of Santo António de Lisboa. Known as the "matchmaker saint," locals often throw a coin into the fountain before the church, especially on June 13, St. Anthony's Day, asking the saint to help them find love or ensure happiness in their marriage.
Sé Cathedral
Alleys
See a different side of Lisbon in Mouraria
The end of the day is fast approaching, but there's still time to wander around another historic neighborhood. Mouraria is located next to Martim Moniz Square, and its history dates back to the Muslim occupation of the city. After the Christian Reconquest in the 12th century, this district continued to receive inhabitants of the most varied nationalities and beliefs, making it a center of multiculturalism until this day.
Here, meander through the winding streets and narrow staircases, stopping to pop into any of the countless small local shops. Go up to Largo da Severa square, which is so-called because it was where Severa, the first Portuguese fado singer, was born and lived.
Then, return to Martim Moniz square and enter the Hotel Mundial for a sunset drink on its rooftop, which overlooks downtown Lisbon.
Evening
A wander in Graça or Principe Real (or both!)
In the late afternoon or evening, I’d recommend going for a stroll in the neighborhoods of Graça or Principe Real. They’re quite different from each other, but are both very charming.
Graça is a more historic neighborhood that sits on a hill overlooking Alfama and much of Lisbon. Although it is changing rapidly, it remains a mostly local and middle class neighborhood full of great squares for a coffee or beer, interesting shops, pleasant streets for strolling, and lots of great restaurants. It also has some of Lisbon’s best viewpoints.
Principe Real is north of the historic downtown and is an upscale residential neighborhood with leafy boulevards, fantastic parks and squares, excellent boutiques and shops, and a good dining scene. It’s a great place to go for a leisurely walk, do some window shopping, or grab a drink and people watch from a sidewalk cafe or little bar within any of the nice squares.
The view from Miradouro da Graça in… Graça!
Dinner and a (Fado) Show
Now that you know the history of Fado and have walked through the historic neighborhoods where this musical genre was born, it's time to see a live show.
At Adega Machado and O Faia, both in Bairro Alto, you can dine while listening to the chords of the Portuguese guitar and the melancholy voices of the artists who give their soul to Fado.
Day 3 - Sintra, Cabo da Roca, and Cascais
On the 3rd day of this itinerary, leave the city to discover one of the most beautiful villages you'll ever visit: Sintra.
Located 30 km from Lisbon, its architecture, monuments, and natural surroundings are so relevant and breathtaking that UNESCO has recognized it as a World Heritage Cultural Landscape.
It's no wonder that this town has been a source of inspiration for several artists, such as the English poet Lord Byron or the Portuguese painter Almada Negreiros, or has been the setting for major film productions, such as "The Ninth Gate," starring Johnny Depp, or "The House of Spirits," starring Meryl Streep, Jeremy Irons, Glenn Close, Winona Ryder, and Antonio Banderas.
To visit Sintra, simply take a train from Rossio Station and return to Lisbon at the end of the day. But if you want to make the most of this day trip, rent a car so that you can then visit the other places I'm going to suggest.
Quinta da Regaleira
Morning
*Note that today’s plan, as I’ve described it, needs to be done with a car. So either plan to rent one for the day or book a guided tour. If you want to do the plan with public transport, you can still visit Sintra and Cascais, but not Cabo da Roca.
Have a typical breakfast at Casa Piriquita in Sintra
Wake up early so you can get to Sintra as soon as possible. Car circulation in the historic center is restricted, and parking is limited. Going early in the morning increases the chances of finding a good parking spot.
I recommend trying to get here for 8:30 am if possible so that you can make the most of your day and avoid crowds (to the extent possible).
Because you'll have left early enough (you can do it!), start your tour at Casa Piriquita, a lovely little cafe where you can try the delicious Travesseiro de Sintra, a local puff pastry cake filled with egg and almond cream. I'm not a big fan of almonds, but whenever I go to Sintra, even I still can't resist having one!
Piriquita restaurant
Coffee and a travesseiro (and some OJ!)
Go for a walk in town
Most people think of Sintra as just the palaces that surround it, but the town itself is actually very charming. It’s full of winding cobblestone streets, pretty architecture, and terrific viewpoints.
I very much recommend starting your day with an early stroll around the town so that you can enjoy it before the tour buses arrive with thousands of other visitors.
Sintra town on a quiet night
Palácio da Pena
If you’re ok with crowds, head to the Palácio da Pena (Pena Palace), one of Sintra's most iconic monuments. As it's at the top of the mountain, you can walk there, but it will take a long time and be a very demanding hike. The best option is to take bus 434, near the Sintra Palace (or near the train station), which runs between the historic center and the main attractions.
The Pena Palace looks like something out of a fairy tale, with its red and yellow colors and a mixture of architectural styles and decorative elements that will fascinate you.
I suggest you visit with an audio guide to learn about its history and spaces. The audio guide can be accessed via an app, but you must pay a supplement when you buy your ticket. If you want to avoid making the walk, you can also add the cost of the transfer that takes you from the main entrance of the Parque da Pena (Pena Park) to the palace.
Getting tickets: To enter the Pena Palace, it's best to buy your ticket online, as it's subject to a compulsory date and time reservation. Book well in advance to ensure you have access on the day you're in Sintra and at the time that suits you best, as this is a very busy monument.
Visiting the Pena Palace, especially if you also want to stroll around the gardens, will take you all morning.
Do keep in mind that Pena Palace is Sintra’s most famous site and far and away it’s most visited. The lines can be intense and it can also be extremely crowded. In high season, it’s a bit of a madhouse.
Pena Palace
Palácio de Monserrate
If you don’t want to deal with lines or just want to visit somewhere a bit less touristy, I always suggest Palácio de Monserrate (Monserrate Palace) as an excellent alternative.
It’s a 19th century palace in Arabic style with stunningly beautiful gardens. It’s off most tourists’ radars, so provides a starkly different experience from Pena Palace and Quinta da Regaleira.
Monserrate
Afternoon
Lunch at Tascantiga
When you’ve finished exploring the palace, return to the historic center of Sintra for lunch. Go to Tascantiga, a small restaurant by the Escadinhas da Fonte da Pipa staircase just outside the center of town. Be sure to try some of the wonderful petiscos (snacks/appetizers) served there.
Sintra Mitos e Lendas Museums
After lunch, let’s explore Sintra's more mystical side. Start with a visit to the Sintra Mitos e Lendas museum, located at the tourism office. It’s an interactive center that takes visitors on a sensory journey through the town's myths and legends, often blending reality with fiction. It’s cool.
Quinta da Regaleira
Speaking of blending reality with fiction, this is the perfect motto for a visit to one of the prettiest places in Sintra, Quinta da Regaleira.
I find this to be one of the most intriguing palaces because of its architecture and the myriad symbolism found inside, including references to the Freemasons, Alchemy, the Knights Templar, and even Dante's "Divine Comedy."
The estate consists of several labyrinthine gardens with fountains, sculptures, towers, caves, tunnels, an intriguing palace, and even an Initiation Well, extending 27 meters into the ground, often associated with Masonic rituals.
The mysteries surrounding this estate can be felt as you walk along its paths. I guarantee it's a place that will surprise you.
Although Sintra’s second most famous monument, Quinta da Regaleira is still much less touristed than Pena Palace. The site is very large, so give yourself at least 1.5-2 hours here.
*Before moving on, I have a quick pro tip: if you can get over the feelings of FOMO, I’d actually recommend skipping the morning visit to Pena Palace and instead going to Quinta de Regaleira right at 10:00 am. Then, I’d save Monserrate Palace for the afternoon. I’ll explain why belofew.
If you show up to Quinta da Regaleira early and get in line for the 10:00 am entrance (which is when the sight opens), you’ll beat most of the crowds, at least for your first hour. If you want to see the initiation well, I’d recommend checking your map and making a beeline for it. Entering right at 10:00, you’ll be able to go down it without any line or crowds. If you wait even an hour, you’ll be in line with hundreds of people and the line moves slowly as lots of people are posing for very involved photos.
Then, you can visit Monserrate in the afternoon. It never gets particularly crowded (whereas Quinta does), so an afternoon visit is still fine.
The gardens
The Palace
The Initiation Well
Azenhas do Mar
There's so much to see in Sintra and you really could spend a day or two here, but not this time. The day is winding down and there’s still more to see nearby, so it’s time to leave this magical little town behind.
If you have a car, now we’re headed to the coast (if you’re doing the day trip with public transport, now will be the time to grab a train and head to Cascais, skipping these next two stops).
20 minutes from Sintra is the gorgeous little town of Azenhas do Mar. There are no sights in town, but the town is itself an amazing sight; a little circle of white buildings with red tile roofs all cradled within a rocky ridge jutting out into the Atlantic Ocean. The location and contrast is absolutely stunning.
Azenhas do Mar
Cabo da Roca
Cabo da Roca, 25 minutes from Sintra and 20 from Azenhas do mar, is part of the Sintra-Cascais Natural Park and it marks the westernmost point of continental Europe.
Located 140 meters above sea level and with an imposing lighthouse, the view over the cliffs and the sea is magnificent.
In this place, "Where the land ends and the sea begins" (as you can read on a sign there), stay to watch the sunset, when the golden light changes the color of the cliffs and the sea takes on an even stronger blue.
There are also a series of easy trails and walkways that you can take to access different viewpoints.
The view from one of the walking trails at Cabo da Roca
Evening
Dinner in Cascais and a bit of fun at the Estoril Casino
Instead of returning to Lisbon, drive the coastal road over to the lovely little resort town of Cascais where you can enjoy dinner at the Maré restaurant on Estrada do Guincho. Here, under the signature of renowned Portuguese chef José Avillez, you'll find dishes where fish and seafood really shine.
If you're in the mood for Asian food, another option is the Estoril Mandarin in the Estoril Casino. This is where I’ve had my best Peking Duck to date, but there are dozens of other Cantonese food options.
After dinner, try your luck in the casino or just hang around the lounge for a drink and some live music.
You should plan to arrive back to Lisbon late, having enjoyed a wonderful day.
Visiting Sintra doesn't have to mean spending all day shoulder to shoulder with thousands of other visitors. Beat the crowds and explore better with local guide Ana Sofia!
Bonus 4th day - More nearby day trips
If you have a 4th day in/around Lisbon, you could do any number of things: there’s always more to see in the city itself, Sintra has much more to offer than what you’ll have seen yesterday, and the surrounding area is full of great places to visit within a about an hour’s drive.
Assuming you’re interested in seeing more of what the nearby areas have to offer, here are three classic day trip options, each of which are to places that I really love:
Option 1: Óbidos
Óbidos is one of Portugal's most beautiful and well-preserved medieval villages, and visiting it is almost like taking a trip back in time.
About an hour from Lisbon, this ancient town, surrounded by the walls of its castle, is full of historic churches, little white houses decorated with colorful flowers, and cobbled streets with craft stores and restaurants.
Its beauty is such that it was once a wedding gift from Portuguese kings to their queens.
An itinerary here includes walking on the ramparts, visiting the museums, entering the art-filled churches, visiting the local bookshops, and, of course, tasting the traditional Ginjinha de Óbidos (sour cherry liquor) served in a chocolate cup.
Óbidos is also known for its cultural events, such as the Chocolate Festival, the Medieval Fair, the International Literature Festival, and the Christmas Village. If you're thinking of going there, see if the dates of your trip coincide with any of them.
Medieval Óbidos
Option 2: Mafra and Ericeira
About 40 minutes from Lisbon, you'll reach Mafra, known for its imposing National Palace, one of the largest Baroque buildings in Europe, and a UNESCO World Heritage Site. In addition to the various rooms where the Portuguese kings lived, you'll also see one of Europe's most magnificent libraries.
After visiting this palace, head to the Tapada Nacional de Mafra, an ancient royal hunting grounds, where today you can hike and see deer and wild boars.
After exploring the history and nature of Mafra, continue on to Ericeira, a beautiful coastal town.
Popular among surfers owing to its statues as a World Surfing Reserve, this fishing village also stands out for its picturesque streets, relaxed atmosphere, and excellent fish and seafood restaurants.
The National Palace in Mafra
Option 3 - Setúbal, Arrábida Natural Park, and Tróia Peninsula
Cross the 25 de Abril Bridge to visit the Setúbal peninsula, 1 hour from Lisbon, in a perfect combination of nature, gastronomy, and wine culture.
The Arrábida Natural Park is located here. It is known for its incredible landscapes and crystal-clear beaches. A drive here reveals extraordinary panoramic views of the ocean.
Setúbal is also recognized as an important wine region in Portugal. Among the many local wine estates, José Maria da Fonseca is one of the most renowned, and it offers visits to the winery and wine tastings.
The city of Setúbal has little to see, but it is here that you can taste the best fried cuttlefish in the country. It's also from here that the ferries cross the Sado River (keep an eye out for dolphins) and take you to the beautiful beaches of the Tróia Peninsula.
Coastal views in the Arrábida Natural Park. Photo: Senyrah, CC BY-SA 3.0, via Wikimedia Commons
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