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3 Day Lisbon Itinerary with a Day Trip to Sintra

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Lisbon is a fantastic city: it has history (it was a departure point for the new world after all!), amazing food and an incredible energy.  With about a ½ million locals, the city feels like a seamless conglomerate of multiple cultures.  We certainly saw the highlights in 3 days and got a taste of the local life. However, it would take substantially more time to see all the special nooks and crannies and I’d love to return.

Below are details for structuring two full days in Lisbon and one day venturing out to Sintra. 

Here are few helpful things to know:

  • The city is very walk-able but I recommend getting a 24-hour pass, which includes the underground trains, buses and trams – including the famous historic tram 28 which is so fun to ride!
  • We used Google Maps to navigate everywhere.
  • It’s helpful if you have a data plan that covers you abroad or at least buy a local SIM on arrival so you can use Google Maps too.
  • We stayed at an Airbnb which is a great way to experience local life.
  • Currency: Euro
  • Main Languages: Portuguese, English
  • Year Established: 800-600 BC – many different indigenous groups have lived here.

Day One: Exploring Lisbon


We arrived mid-afternoon via train from our stay in Porto (read here for a 3 day guide to Porto)! and did the following (all within about a 35 min walk; add time for how much you’d like to spend at each destination):

Visit the S. Jorge Castle – great views of the city and fun to visit just before sunset to get the day-sunset-night views over Lisbon.

Explore the Chiado neighborhood

Snack:  Natas from Manteigaria Fabrica


For dinner, consider Restaurante Mili (reserve in advance – we missed out on this but heard good things) OR Restaurante Floresta de Santana (delicious seafood and house dessert with very kind owners. This is a family operation and they work incredibly hard to provide amazing, fresh seafood.)

Check out Rossio Square – and stop by A Ginjinha in Rossio to try the delicious local drink (cherry-like liqueur complete with olives); fun to drink in the square and listen to live music being played.

Day Two: Day Trip to Sintra

Make sure you pack snacks and water today as you’ll be venturing between a few neat destinations!


To get to Sintra from Lisbon, take the Linha de Sintra 18831 train from Rossio station.  We purchased round-trip tickets from the station the day of for about €5 each.  The trains become very crowded so if you’ve just missed one, don’t despair! That just means you’re more likely to get a seat on the next one. They depart fairly frequently (about every 30 min).

Arrive mid-morning in Sintra.  Take a deep breath because you’ll likely encounter crowds at first as people offer to give you a ride in a tuk tuk to the destinations. We opted to walk/hike everywhere in Sintra but one could take a tuk tuk for more ease if you’d like. If you are able, you can definitely walk to the first couple of stops noted below.

First (and very importantly!) , walk to Casa Piriquita for delicious pastries.  In particular – the travesserio and the queijadas.  A little break from having natas 😊

With (sugar) energy, now walk to Quinta da Regaleira.  This palace is not that old but feels very magical.  Start from the top and work your way down to the exit. There were many people trying to get the perfect picture – don’t forget to enjoy the surroundings real-time.


For lunch, we were still full from the morning pastries and opted to eat snacks we had packed (fruits, nuts, rice cakes). 

Palacio de Pena is the next stop.  Feel free to grab a tuk tuk as you depart Quinta da Regaleira.  We walked/hiked there on a beautiful path (that eventually turned into the forest) via Google Maps and really enjoyed it but it did take about an hour.  Wear good shoes if you plan to do this!

We paid just for the outside entrance which was sufficient because it allowed us to get up close and personal to the entire castle – just not the interior rooms.  As completely castled-out people living in Europe, this palace restored our energy in visiting castles because of how playful it is.

Walk back to train station and head back for dinner in Lisbon.  We walked according to a Google Maps path – lots of tuk tuks stopped us along the way to offer discounted rides but we decided to save the €’s for more natas and enjoy wandering around the local streets on our way back.


Around dinner time, we stopped by the Time Out Market Lisboa, since it gets rave reviews, and found it overpriced and touristy.  So many local spots offer the same/better food for more affordable prices, so we skipped it.  We were also starving so hanger may have had a play in our opinion. Instead, we decided to take a break from Portuguese food and ventured nearby to have tacos at Pistola y Corazon Taqueria.

Day Three: Exploring Lisbon


Use your 24-hour pass and take the tram to Belem.  This distance is really not walkable from Lisbon proper.

For breakfast, head to Pastelaria de Belem (even if you are completely nata-ed out, try them again here. We also had sandwiches and quiche which were delicious.

Visit the Jerónimos Monastery – definitely worth paying to walk around.  Vasco de Gama and his fellow explorers spent the night before their departure to the Orient at this spot (not in its current form) in prayer in 1497 – It also has an interesting history of the world exhibit.


Walk to the Padrão dos Descobrimentos – I loved this monument commemorating some of the Portuguese explorers.  I enjoyed looking out to the west and imagining what the explorers were thinking as they set off along that route to the new world. It’s also a good location to enjoy the views to the East – it looks a bit like Rio with the Cristo statue on the hill mixed with San Francisco’s Golden Gate Bridge.

Walk to the Belem Tower – maybe not worth paying for (we didn’t and heard from those who had that it wasn’t worth it) but definitely worth checking out.

If you have time/interest, check out the Botanical Gardens.  They’re very beautiful and reminded me of similar gardens in Rio.  

Train back to Lisbon.


Ride the Tram 28 around the city with your pass.  A great way to take in the nightlife. Hop off if you see a neighborhood you’d like to spend a little more time in or check out a Fado performance in a local restaurant.

For diner tonight, go to Ramiro for seafood. Get there early – they do not take reservations and it gets busy since it’s so popular. Highly recommend the king prawn and the Green wine. You will have no clue what anything costs until the bill comes but expect to pay around €70 for a couple splitting two mains, a starter and a bottle of wine. A special way to end your time in Lisbon!

Happy Planning!

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