4 Days in Lisbon, Portugal - The Longest Weekend

Lisbon, Portugal is a city that has been high on my travel wishlist for years. and despite making the rounds to most of the big spots in Europe, I had yet to go. We spent 4 days in the Lisbon this fall, and I’ve created this itinerary to help guide your trip through this amazing city.

It seemed like everyone I knew had been to the Portuguese capital this year, and I wanted in on the action.

My husband and I spent one week here, but we easily could have stayed for a month. Between the pastel buildings, the incredible wine, and the Portuguese hospitality, we were in heaven.

Did I mention the pastries?

Lisbon feels like the European sister to San Francisco: the hills, the trams, the red bridge, the hipsters… It has an atmosphere that draws you in, makes you feel right at home, and entices you to stick around for a while.

To experience all that this vibrant area has to offer, allow yourself four days. Can you do it in less? Sure, but four days are just right to both explore Lisbon and experience the gems that lie outside of the city proper. And trust me, there are plenty.

So grab a cup of coffee and read on for my take on how to spend an amazing 4 days in Lisbon…

Contents

How to Spend 4 Days in Lisbon, Portugal

Day One – The Alfama + Bairro Alto

Day Two – Sintra

Day Three – Chiado + Belém + Principe Real

Day Four – Cascais

Rooftop views of Lisbon’s skyline from São Jorge Castle

Day One – Explore Lisbon’s Alfama + Bairro Alto

Morning

Kick off your 4 days in Lisbon with a strong cup of Portuguese coffee and a delicious brunch – both are beloved past times in Portugal. A few of my favorites include…

Nicolau Lisboa – For healthy power bowls, eggs benny and gluten-free pancakes, look no further.
Graça 77 – For vegetarian fare in the heart of the Alfama, head here after checking out the Miradouro da Graça.

Mid-Day

After brunch wander up, down and around through the narrow streets of the Alfama, the oldest neighborhood in Lisbon. Take in the old winding streets, beautiful tiled buildings and many lookout points for great views of the city.

The lookout at São Jorge Castle, the tiled facade of Graça 77, and a tuk tuk weaves through the Alfama

Walk up to the Miradouro de Santa Luzia and São Jorge Castle for epic views of the city. Drop into Portas do Sol for drinks on the terrace, or if you’re up for lunch check out Alpendre, a family-run establishment serving up traditional cuisine.

Continue wandering down the hill to the Praça do Comércio, the main square in Lisbon. Brush up on your Portuguese history by jumping on one of the tours that typically leave from here, like one of these options through GetYourGuide:

The Praça do Comércio and nearby views from the waterfront

Evening

Spend the evening in Bairro Alto, where we based our week in Lisbon and one of my favorite spots in the city.

Lisbon is known for its rooftop bars, and at sunset there’s no better place to be. Here are some fun places to start off your night:

The Lumiares Hotel – Hit up their rooftop bar for great craft cocktails and an uninterrupted view of the water.
Miradouro de São Pedro de Alcântara – This lookout point has extensive city views along with a bar and mini farmer’s market. It’s the perfect low-key spot for sunset and people watching.
The Insólito – An eclectic but intimate rooftop bar with great views of the São Jorge Castle
Topo Chiado – Technically not in Barrio Alto but very close, Topo is a great place for sunset cocktails. Skip the admission fee of the Elevator of Santa Justa next door and head here instead.

Tiled buildings and endless stairs in Bairro Alto

Once the sun sets, the neighborhood of Bairro Alto comes alive. Tuck inside one of the area’s cozy restaurants. Some of my favorites include:

Alfaia – For traditional Portuguese fare with a wine list is as thick as a Harry Potter book, head here for a memorable meal.
BOA-BAO – Asian fusion with a hip atmosphere and travel-themed menu. Don’t miss the shrimp dim-sum and lemongrass curry.
Grapes & Bites – Drop in for a tasting of tapas and wines from all over Portugal.

After dinner wander through the streets of Bairro Alto, where the bars spill out into the streets and the party continues well into the night.

If you’re up for a change of scenery, head down the hill to the Pink Street, the heartbeat of Lisbon’s nightlife. You can’t go wrong here, but be sure to check out…

Pensão Amor – A former brothel-turned-bar spans multiple floors and dominates the area.
Pink Wine Point – This flamingo-themed wine bar had me at hello.

Looking for hotels in Lisbon? Click here to see current prices for accommodation.

Day Two – Day Trip from Lisbon to Sintra

If you have 4 days in Lisbon, be sure to set aside a day to visit Sintra. The palaces and mansions of Sintra are straight out of a fairytale… or a Disney movie, depending who you ask. If you’ve made it to Lisbon, factor in a full day to explore the former summer homes of the Portuguese royalty and nobility.

Pena Palace, the Palace of Monserrate, and Quinta da Regalia at Sintra

How to Get to Sintra from Lisbon + How to Get Around Sintra

Sintra is an easy day trip from Lisbon – a quick 40 minute train ride from Rossio Train Station in the Chiado neighborhood. Click here for the timetable.

The sights in Sintra are fairly spread out, with many of the palaces located miles apart. We utilized a mix of options to navigate the area:

Uber – Cheap and readily available, when split amongst our group Uber was cheaper than the bus to hop between the castles.
Tuk tuk – Another fun and efficient way to get around, these little guys are everywhere in Sintra as well as Lisbon. Be sure to negotiate your fare!
Bus – Lines 434 and 435 leave from the train station run between all sights. Be prepared to wait in line!

While it’s possible to see Sintra independently, if you prefer the ease of a tour that’s an easy option as well. Check out one of these options:

Morning + Mid-Day

There are more than ten palaces, villas and convents to explore in Sintra, each with their own distinct architecture and landscape. To maximize your day (and to avoid boring any male travel companions), pick a just few to visit.

Monserrate Palace and the Initiation Well at Quinta da Regalia

Here are my faves, in the order I’d recommend visiting:

Pena Palace – The largest and loudest of the bunch, this former summer residence of the Portuguese royals looks like something out of Shrek. This palace gets the most visitors, so it is a great place to start your day. Arrive by 9 a.m. to be the first in line when the gates open at 9:30.
Palace of Monserrate – Hop in a tuk tuk at the Pena Palace and head here for an Indian-inspired mansion with stunning interiors.
Quinta da Regalia – Get lost in the whimsical gardens and palace of one of my favorite spots in Sintra. Don’t miss the Initiation Well, which feels like it’s out of Game of Thrones.

If you have time, head to the Sintra National Palace and the Castle of the Moors. You’d be hard-pressed to see them all in just a day trip, so pick which ones jump out to you most prior to your visit.

Afternoon

After asking every local that we met in Sintra where we should eat lunch, the answer was unanimous: only tourists eat in Sintra.

For a truly authentic experience, hop in an Uber and head over to the coastal town of Azenhas do Mar, a short 15 minute drive from Sintra. Take in the cliffside vistas of the Atlantic Ocean and head to to Adega das Azenhas for a traditional Portuguese lunch of freshly caught seafood and vegetables.

Freshly caught sea bream at Adega das Azenhas

An extra emphasis on the fresh – four of us shared this sea bream that was caught a mere two hours prior. It was truly one of the best meals we had in Portugal and was well worth the detour.

From Azenhas do Mar, either pop back to the Sintra train station or spring for the surprisingly affordable Uber ride back into Lisbon.