How To Travel Lisbon, Portugal: 5-Day Itinerary with Sintra and Cascais Day Trips
Our 7:00 am flight from Seville, Spain arrived in Portugal’s capital on a Monday morning.
With tired eyes, I looked around and immediately noticed how there seemed to be many more accent marks on signs around Lisbon, which is Portuguese-speaking, than Spain.
My mom, aunt, and I hailed a taxi from the airport. The driver whipped around the streets and eventually dropped us off on the quintessential black and cream-colored cobblestone road outside the hotel.
We made it to Lisbon!
Here is our 5-day Lisbon travel itinerary with day trips to Sintra and Cascais.
Cascais, Portugal
Day 1: Fly into Lisbon early in the morning, spend the day in Lisbon
Day 2: Sintra Day Trip
Day 3: Cascais Day Trip
Day 4: Lisbon
Day 5: Lisbon & return home
Lisbon
Since our time in Portugal was so short - just five days - we stayed in Lisbon and visited nearby towns Sintra and Cascais on two separate day trips, returning to Lisbon in the evening.
What We Did in Lisbon:
Honestly, Lisbon was our last city during our whirlwind 4-city/3-country overseas adventure (we went to Barcelona, Seville, and Tangier) and we mostly wanted to take in the sights and feelings of being in a new city.
Because we packed so much into our Sintra and Cascais day trips, we took it easy in Lisbon instead of checking off a list of “things to do.”
We’d wander around the city’s hills during the day and go down to the water at sunset, stopping at a nice cafe or two along the way and moving with our intuition.
On the way to dinner one night, we happened to walk by the famous, picturesque hill where Tram 28 is. This is probably one of the most recognizable photos you’ve seen of Lisbon: a yellow and white tram moving up or down a narrow hill.
This is one of my favorite ways to travel: wander where you feel called and find the gems along the way.
Looking for a list of things to do in Lisbon? Here are 25 Things to do in Lisbon.
Getting to Lisbon
Fly into Lisbon Airport (Humberto Delgado; LIS). Otherwise, taking a train would be easier than driving in my opinion, though I do know people that have rented cars in anticipation of a Portuguese road trip.
Where We Stayed
We stayed at Hotel Santa Justa.
This hotel was right in the historic center. It was a beautiful hotel and the breakfast (not included) was fantastic. They also helped me arrange a birthday surprise for my mom: a bottle of wine and chocolates.
Oh, and don’t forget to try one of the famous Portuguese egg tarts while you’re in Lisbon: Pastel de Nata! I tried these for the first time in Macau, a former Portuguese colony in Asia.
Sintra
Sintra is a beautiful, hilly town less than hour away from Lisbon by train. You can easily spend a day wandering through from castle to castle, which is what we did.
Bring a camera: the castles - and views from around the hills - are stunning!
The two castles we visited were the Pena Palace and the Moorish Castle.
Getting to Sintra
Take the train from Lisbon Rossio Station (located in the historic center). Note that Lisbon is a large city so there are multiple train stations.
The ticket lines for both paying at the window and paying at a kisok where long, but for both day trips we took, they were about equal in the time we spent waiting.
It takes about 45 minutes to get to Sintra from Lisbon by train. It’s not recommended to drive as Sintra is very hilly and the roads are narrow.
Once you get to Sintra, find a tuk-tuk to take you up to the castles. We are happy we went with a tuk-tuk driver instead of a bus. On the tuk-tuk we’d be able to maneuver the way up by being able to squeeze between the cars and buses. It would take a lot longer in a car or bus.
Here is a helpful article we referred to during our trip on getting from Lisbon to Sintra.
What to wear to Sintra
Bring a jacket! It can get chilly since you’re up in a hilly area. We went in early September and I wore skinny jeans, converse, a short-sleeve top, and brought a long-sleeve chambray shirt to throw on if it got chilly. Having the layer was helpful because we got a little warm walking up the steep hills with the sun, but chilly when we were at the top with all the wind.
Make sure to wear comfortable shoes you can walk in! This is not the day to wear heels.
You’ll be walking up and through hilly terrain (on paved pathways) as you move from castle to castle. The tuk-tuks can’t take you directly to the entrance of each castle as there is no way to do so. You will be required to walk a bit.
Bring snacks to Sintra
The main street in Sintra is lined with cute restaurants and shops, though you won’t find much to eat when you are up in the hills exploring the castles.
Except for seeing one or two restaurants attached to the top of the castles for tourists (in my opinion, these types of restaurants around the world are always so-so and it’s much better to find a more authentic restaurant elsewhere), you won’t see snack vendors or anything.
Bring something like a healthy protein bar, small bag of nuts, or banana to tide you over.
Where we ate: Our tuk-tuk driver recommended his friend’s restaurant to us and took us over there, which was really nice.
Usually this kind of thing is kind of noticeable if the driver/guide was getting commission, but it didn’t seem like that was the case, which was nice.
I wrote down the name of the restaurant but can’t find it anywhere! I guess we’ll have to return to Sintra…not a bad idea. ;)
Cascais
Oh, the beauty of the Cascais! Settled along the sparkling Atlantic Ocean, this summer resort town is only 30-40 minutes from Lisbon by train.
It is a gorgeous place to switch things up by spending a day by the sea after being in bustling Lisbon and hilly Sintra.
Getting to Cascais
Take the train from the Cais do Sodre station. Remember, this is a different station than the train for Sintra.
Get off at “Cascais” about 30-40 minutes later and enjoy the views of the Atlantic Ocean out the window in the meantime.
What to Wear to Cascais
Cascais is much more flat than Lisbon or Sintra. You’ll probably want to walk around town or head to the beach, so wear comfortable shoes or sandals!
It was hot and sunny when we went in early September. I wore a black t-shirt dress and strappy flat sandals. I kept a swimsuit in my bag in case we decided to hit the beach, but we didn’t end up going.
Instead we walked up and down the coast, wandered by the art museum, went into some shops, and settled on a nice outdoor restaurant for lunch.
After a long day in the sun, we hopped on the train back to Lisbon and spent our last night at a restaurant on the water.
Our time in Lisbon was short, but well worth it. I feel like we got a nice taste of the city while being able to visit two lovely towns (Sintra and Cascais) which felt very different than Lisbon itself.
There is much to see and do all over Portugal, so if you have the time to go elsewhere, do it!
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