Portugal Itinerary

My 6-day Portugal itinerary

My 6-Day Active Itinerary - Lisbon, Algarve, Sintra, Cascais

Berlim cake, pastel de nata, people dancing in the streets, beautiful architecture, friendly people, delicious meals….these are some of the few things that made my first solo trip in Portugal an adventure I will always remember with love.


I packed my hand luggage on a breezy November night and headed to Lisbon. I arrived in Lisbon around 10am, headed to my hotel, and you know the first thing I did after relaxing for about an hour? I ordered a Bolt ride, and headed to Praça Luís de Camões, a landmark in the city of Lisbon, to meet the tour guide for a free tour of Lisbon.


It was a cool afternoon in Lisbon, beautiful colored buildings lined the streets at Praça Luís de Camões, and the city center was bustling with tourists. 

Day 1: Free Walking Tour of Lisbon

I found this free walking tour on Guruwalk. The walking tour was a great introduction to Lisbon on my first day.  Our tour guide was a friendly and fun guide who led our group (17 tourists from around the world) through the streets and history of Lisbon. The weather was beautiful, and I met some amazing people. We walked, we talked, we laughed, and had a great experience.

I recommend you book a free walking tour anytime you visit a new city. It is a great way to enjoy some sightseeing and learn some history. Don’t forget to tip your tour guide.

Activity: Walking for 3 hours, with a few stops to enjoy pastel de nata and ginjinha.

Food: After the walking tour, I walked back to a street lined with restaurants. How did I find myself back there? I took a picture of a bakery we stopped by on our tour, and I used google maps to find my way back to where the bakery is located. I randomly picked a restaurant and enjoyed grilled sardine with potatoes and a side of fries.

Walking Tour of Lisbon
Walking Tour of Lisbon

Day 2: Hiked the Seven Hidden Valleys Trail while taking in the coastal beauty

This was the highlight of my trip. I took a two and half hour train ride from Lisbon to South Portugal to experience this trail with amazing coastal views. If you ever find yourself in Portugal, do yourself a favor and visit Praia de Marinha to hike the Seven Hidden Valleys trail. If you don’t want to hike, you can still enjoy the gorgeous views. Read more about my Seven Hidden Valleys hike here.


Activity: Hiking for 3 hours, with some stops to take pictures.

Seven Hidden Valleys Trail
Seven Hidden Valleys Trail

Day 3: Captured the heart of Old Lisbon on a Photowalk.

I booked this experience on AirbnbExperience. I met with the photographer on a beautiful partially cloudy day in Old Lisbon. I was lucky enough to be the only one on the tour. The wonderful photographer customized my tour, and I had a great afternoon capturing the heart of Old Lisbon with an experienced photographer. Read more about my photowalk tour of Old Lisbon here


Activity: Walking up and down stairs and hills of Lisbon for 3 hours with these comfortable sneakers.

Photowalk Old Lisbon
Photowalk Old Lisbon

Day 4: Joined a group to enjoy hearty Portuguese meals on a ‘Tastes and Traditions of Lisbon’ Tour

This was an experience to remember. I booked my tour with Devour Tours. The tour group consisted of eight wonderful people and an amazing tour guide. We enjoyed berlim cake, pastel de nata, ginjinha, bacalhau bras, and so much more.

The best part, we learned about some traditions of Lisbon too. If you want to enjoy great meals as you learn about traditions, then book a Taste and Traditions tour when you visit a new city. I know I will book another one on my next trip.

Activity: Walking around Lisbon for about 3 hours, minus the few minutes we sat down to eat. I also walked to my hotel after the tour, which was 35 minutes away. This gave me the opportunity to explore Lisbon some more.

Read more about my Tastes and Traditions experience here.

Berlin cake
Fernando Pessoa

Day 5: Explored a beautiful castle and historic sites in Sintra, and enjoyed yummy ice cream in Cascais

I joined a tour group to visit the beautiful Pena Palace, and also walk around historic Sintra. It was a rainy day, and we had to make the best of the day. We also visited the beautiful town of Cascais, where I enjoyed a delicious ice cream from Santini.


Activity: Walking up the hill to Pena Palace, around historic Sintra, and exploring Cascais on a rainy day. My comfortable shoes came in handy again, since we walked for at least 4 hours.


Day 6: Zipped through the streets of Lisbon riding a tuk tuk 

My last day in Lisbon was bittersweet. I wanted to explore Lisbon for a few more hours before I said goodbye, so I booked a tuk tuk tour with Filipe on AirbnbExperience. He took us through the narrow streets of Lisbon, across the street from some beautiful attractions, and behind buildings to enjoy delicious pastel de nata. My favorite part, cruising through the streets of Lisbon in a tuk tuk.


Activity: This was a light activity. We mostly enjoyed the tour riding in the tuk tuk for two and half hours, with a few stops to walk around attractions. After walking up and down hills in Lisbon, a tuk tuk ride is a great way to relax as you take in the city.

Tuk Tuk Tour
Tuk Tuk Tour

Tip: Don’t forget to be very flexible with your itinerary. Things happen on vacation, don’t let it ruin your experience. Smile and move things around. 

My hike on Day 2 was initially planned for Day 5 with a tour group, but I had to quickly switch my days around after I checked the weather. It was the best decision I ever made to hike solo on Day 2. It was a gorgeous day for a hike in South Portugal on that day, and it rained almost all day on Day 5.

Here are a few things that made my trip easy to navigate:

  • Guruwalk app: I used the app to book my free walking tour.
  • Bolt app: When I wasn’t walking, I used this app to order a ride. My Bolt car always arrived within 5 minutes (except for my last day in Lisbon 🙂 ).
  • Comboios De Portugal: This app was a lifesaver to find train routes and schedules, and to purchase train tickets.
  • AllTrails app: Great app to access trail maps for hiking.

Questions about my itinerary? Email me at choosingopenroads@gmail.com

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