From City Streets to Fairy-Tale Peaks: Lisbon & Sintra with the Family

We started our Lisbon adventure with a tuk tuk tour of the city with our excellent guide, Alex. The streets of Lisbon are very hilly, so riding around in a tuk tuk is the best way to get around. Alex took us to the very best viewpoints in the city, historical spots, cathedrals and made sure we stopped for the best desserts in town. Pro tip: When enjoying a pastel de nata from Pasteis de Belem, make sure to skip the long line and go into the quick serve cafe right next door. We decided to change the name of the tour from “Best of Lisbon” to “ The Oh, Wow Tour” because I have never heard my boys say “oh, wow” so many times in one day, and its not easy to impress three teenagers and a seven year old. Alex made sure to keep the day exciting and engaging. The tuk tuk tour was a great way to get a lay of the land for our first day in Lisbon, and I highly recommend doing this on day one.

After our tour ended, we stopped at Time Out Market for a late lunch, then walked to Pink Street to see the hanging umbrellas, and then enjoyed some gelato outside at Praca do Comerico. We ended our day buying last-minute tickets to the Sporting Club of Lisbon football match, which was a lot of fun!

We began day two with a full-day tuk tuk tour of Sintra and worked our way down the coast to Cascais. Once again we had a wonderful guide, Claudia, who kept us entertained and well fed with traditional Portuguese pastries and a full lunch spread. Sintra is hard to describe with words; it is such a quaint town with beautiful palaces and castles that pop up throughout the hills. We loved the bright red and yellow colors of Pena Palace, seeing the traditional castle walls of the Moorish Castle and fell in love with the grounds of Quinta da Regaleira. The famous well and hidden tunnels at Quinta da Regaleira were the real showstoppers of the day.

From Sintra, we headed to the coastline and visited the most Western point in all of Europe. The boys loved playing along the rocky cliffs of the beach in Cascais and seeing all the rock formations and tunnels the strong waves have created over time. Downtown Cascais was the perfect spot to end our long day; it almost feels like you are in a beach town in Florida.

On our third day in Lisbon, we decided to explore the town like we were locals, without a real plan in place. We enjoyed walking the cobblestone streets and going to all the shops along Avenida da Liberdade. On our way over to Chiado, we made a quick stop to see the Santa Justa lift, which is currently inoperable. We explored more shops and were able to keep the boys satisfied with multiple stops for gelato.

Our day ended in Belem with a delicious dinner out by the water followed by a sunset catamaran cruise. We were the only family with kids on the catamaran, but it didn’t seem to be frowned upon. Seeing Lisbon from the Tagus River gives you a new perspective of how beautiful the city is. The cruise ends with a perfectly timed sunset view with the iconic red suspension bridge in the background, which makes this activity a “must do” in my book. It was the perfect way to end our little getaway in Lisbon before we headed to the Algarve.