Travel Recap: Lisbon, Portugal (with a day trip to Sintra!)

Lisbon is the capital of Portugal and its largest city, and it was the second stop on my Portugal trip, after Porto and before Lagos. 

Lisbon is one of the oldest cities in the world, and we spent a lot of time just walking the city, taking it all in.

If I'm being perfectly honest, I did prefer Porto and Lagos to Lisbon, although I still loved the city. As I said in my Porto travel diary, I think the reason was because Lisbon had that familiar feeling of being in a city. But it was still a stunning city, with historical sites throughout, and a day trip to Sintra just a short train ride away.

As a side note, it's funny that Portugal was my first European trip because my first trip to South America was Brazil in 2016 with my friend Amy... so we kept joking that we just really loved the Portuguese language! As an FYI, "hello" in Portuguese is "olá"; "sorry" is "desculpe"; and "thanks" is "obrigado" (male speaker) or "obrigada" (female speaker).

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tips and general info:

  • When we were looking for accomodations in advance of our trip, we read that the Baixa and Chiado neighborhoods were highly recommended.
  • We took the train from Porto to Lisbon and caught up on sleep on the way!
  • One word: Cobblestones! I decided to wear my Jack Rogers as we walked all over the city, which did not provide as much support as I needed, but I was determined not to complain because it was my fault for not wearing sturdier shoes (and one of my friends even commented that she couldn't believe I hadn't complained once, haha).

itinerary:

  • We looked at the Portugal Boutique Hotel (in Santa Maria Maior); the 7 Hotel; and My Story Rossio (highly rated and good prices) before deciding on an Airbnb. 
  • We arrived on a Monday; stayed Tuesday and Wednesday (with a day trip to Sintra on Wednesday); and left Thursday for Lagos. We gave ourselves an extra day here as opposed to Lagos because we wanted to visit Sintra and felt like there was probably more to do in a big city than in Lagos (which may have been a mistake -- not because there's not plenty to do in Lisbon but because I would have loved more time to hike Lagos and just gaze at the scenery!).
  • On Monday, we ate at Ibo Restaurante and visited the Carmo Convent ruins and Castelo de São Jorge.
  • On Tuesday, we went to Kais for dinner. During the day, there was a lot of strolling the water and having drinks in the sun!
  • On Wednesday, we took the train to Sintra, which was about 40 minutes each way. There we explored Pena Palace and the Castle of the Moors.
  • On Thursday, we left for Lagos by train.

photo diary:

These photos were taken with an iPhone in 2017, I'm sorry they're not better quality!

The Carmo Convent Ruins and Archaeological Museum -- the convent was destroyed during an earthquake in 1755.


Looking out at Lisbon from Castelo São Jorge
Hat: One I impulsively bought off the street in Lisbon :) | Top: Express | Shorts: BLANK NYC | Sandals: Jack Rogers (affiliate link)


Hahaha clearly I was even worse at taking photos in 2017 than I am today... like why didn't I move my purse out of the photo?




My b-school ladies!

In Rossio Square

Monastery of São Vicente de Fora


Similar hat: Nordstrom (affiliate link) | Dress: Lulus (affiliate link) | Shoes: Jack Rogers (affiliate link)

Belém Tower / the Tower of Saint Vincent


The Palacio Nacional da Pena (Pena Palace) in Sintra!




Sunglasses: Illesteva (affiliate link) | Jacket: J. Crew | Romper: Good Night Macaron | Shoes: Jack Rogers (affiliate link)





Obviously Titanic was my favorite movie growing up...

Pena Palace from the Castelo dos Mouros (Castle of the Moors)



Soooo many steps



On top of the world with my PortuGALS



Quinta da Regaleira


This photo honestly creeps me out... very The Ring.

where to eat and drink:

what to do:

  • Walking tour of Lisbon
  • Tour the Castelo São Jorge 
  • Browse LX Factory (retailers and restaurants)
  • Day trip to Sintra! Personally, I would have been happy with another day here -- there are so many castles and even beaches!
  • Walk the Pink Street (Rua Nova do Carvalho, 1200-372)
  • Day trip to Cascias (we decided against this because we were doing Sintra and added on Lagos)
  • Feira da Ladra Market
  • Cab up Miradouro Da Nossa Senhora Da Graca for views
  • Belem Tower
  • Visit the gardens at the observation point Miradouro de Sao Pedro de Alcantara
  • Visit Igreja da Sao Vicente de Fora
  • Tour the museums
  • Visit Jeronimos Monastery
  • The Lisbon Oceanarium
  • Visit Miradouro da Senhora do Monte for a view of the city

links I used or recommend:

Honestly, while writing this, I started wishing I had a return trip to Lisbon coming up... just thinking about strolling the waterfront or sitting with a drink overlooking the city, it sounds pretty good to me!

Click here to read my travel diary of Porto and click here to read my travel diary of Lagos!

love from


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