If you’re thinking about taking a trip to Portugal, stop right now and book your flights! This was one of the best trips that I have done, and although I was super nervous about my first solo trip, it was amazing. I went in peak Summer, and while this was VERY hot, I have no regrets. Everything is open, the streets are full of music and dancing, the sunsets are beautiful and it stays light until quite late. So let’s get into some details:

When to go?

Like I said, I went in Summer (August) and loved it, BUT:

Spring (March to May): pleasant weather, wildflowers blooming, and less tourists.

Summer (June to August): Hot and dry, can be more expensive and crowded. However, Summer is festival season with many cultural events, great beach weather.

Autumn (September to November): Fewer crowds but still pleasant weather. This is a great time for wine tours because it is harvest season.

Winter (December to Feb): Mild weather but can be rainy. Not all tours will be open and some shops and restaurants may be closed.

Itinerary Overview

Lisbon- 3 nights
Porto- 1 night
Duoro valley- 1 night
Algarve- 2 nights
Madeira- 2 nights

Lisbon

I arrived quite late on my first day, landing at 20:00 and only getting into Lisbon around 22:00. From the airport, I took an Uber to my hostel: Home Lisbon Hostel. I highly recommend this hostel, it is in the city center, very conveniently located. I chose a hostel because I was travelling alone and thought that it may be a good opportunity to make some friends have have a more social atmosphere. I stayed in a private room with an en suite bathroom and this was very clean and comfortable. There is a simple breakfast included, which was plenty for me. The music from the streets can be quite loud but I was able to sleep and I am generally a light sleeper. I realized that I actually didn’t take any pictures of the room that I stayed in, but it looks just like the photo on Hostelworld, which I have put in. Since I arrived late and it had been two long flights, the first night was a write off.

Day 1

The first full day in Lisbon!

I started the day by visiting the Arco da Rua Augusta, which was built to commemorate the city’s reconstruction after the 1755 earthquake. This gets super crowded throughout the day, I got there at 7:30am to get this photo alone.

After this, I went to the Pink Street. This is beautiful to see early in the morning, when it has just been cleaned from the night before.

We then went to two popular neighbourhoods: Chiado and Baixa. Chiado is home to the Rue Garrett shopping avenue with high-end boutiques and restaurants. Baixa is in the historical center of Lisbon.

We then went in search of the famous number 28 tram. I had read that tram 28 is really a tourist trap, completely crammed and comes with a high risk of pick pocketing. For this reason, I snapped a shot of the tram but did not actually catch a ride. The Bica Furnicular is a railway line that has been recommended to get up the hill, instead of taking the crowded tram, however I did not go on this.

We then stopped at the Jeronimos Monastery. This is a UNESCO World Heritage site and was commissioned by King Manuel I in 1501 to commemorae Vasco da Gama’s voyage to India. It serves as a spiritual center and symbol of Portugal’s Age of Discovery.

I was now borderline hangry and decided to take a trip to the Time Out Market for lunch. It was here that I had my favourite Pasteis de Nata of the whole trip (and I tried one in every town). The Time Out Market has an amazing variety of food, but it was super difficult to find seating, so maybe try to avoid peak lunch hour. The Pasteis de Nata place is called Manteigaria- I cannot recommend enough.

I then continued on to the Monastery of São Vicente de Fora. This is a 17th century church and monastery containing the royal pantheon of the Braganza monarchs of Portugal.

I then ended the day with cocktails and dinner at Topo Martim Moniz, which had a nice view but was otherwise nothing special.

Day 2

Today was an early start because I had booked a private tour of Sintra. Sintra is an amazing town and UNESCO world heritage site, famous for its palaces, villas and historical sites. I booked a private tour for a few reasons. The first is that I wanted someone who was knowledgeable about the different palaces and could give me a detailed history about the town. Another reason is that I did not have my car yet and I was unsure if I took the train to Sintra, how would I get between the different places. It turns out that it is actually quite easy, there are buses and tuk-tuk drivers once you get to Sintra and it is very well mapped out. I took a private tour because I was hoping that I could personalize it, with the intention of going to Pena Palace first because it is the most crowded, so that I could get photos there before everyone arrived. However, the tour guide informed us on the morning of the tour that we needed to book a timeslot for Pena Palace, which we did not realize, and quite a lot of the earlier slots had been booked out by this time. We started at Quinta da Regaleira, which is a very impressive estate built by a Free Mason and is filled with Pagan and occult symbols.

We then went to the Pena Palace, which dates back to the 12th century and has been a home to the Royal Family. Pena Palace was classified as a National Monument in 1910 and ranks as the single most important site in the Cultural Landscape of Sintra, classified by UNESCO as World Heritage in 1995. The palace has a surrounding park, which is EXTENSIVE. Our guide took us on a beautiful walk through the park- note that I was wearing very impractical clothing and that most people wear hiking shoes for this. That being said, I did make it through the hike, holding my dress off the ground and occasionally slipping in my wedges. The guide took up to a “secret spot” which had a beautiful view of the palace in the background.

It was a LONG walk to the palace. You can only drive so far and then the rest is a very long and very hot walk. The palace is absolutely stunning when you do finally make it to the top, covered in sweat. You are only allowed inside when it is your time slot, but you are allowed to explore the park beforehand. I really enjoyed the tour inside the palace, the interior is beautiful and the guide was very informative.

I would recommend spending a night in Sintra. There is so much to see and do and it would be amazing to be in this town without any of the day tourists. If possible, it would be great to do a private tour, making sure to book the first slot at Pena Palace well in advance, and then stay the night. That way you get both the information and secret spots from the tour, but also get the peace and quiet in the evening and the following morning. I booked my tour through Jump In Tours. After Sintra, they also take you to Cascais, which is a very pretty seaside town. I was beyond tired at this point and think that this could be missed. It may be worth seeing if they could give you a better rate if you stay over in Sintra and skip Cascais.

Day 3

This was the last morning in Lisbon before heading to Porto. On this day, I took a trip to Belem. This is most famous for two things: the tower and Pasteis de Belem. I bought an online “skip the queue” ticket for the tower. The tower is is 16th century building which was a point of embarkation and disembarkation for Portuguese explorers. Unfortunately, the line was SO LONG (it turns out that everyone buys a “skip the queue” ticket online), so I decided to skip this and rather get ice cream and check it out from the outside. The Pasteis de Belem are not the same as your average Pasteis de Nata. They come from the monks of the Jeronimos Monastery, who needed to sell the recipe in order to survive after the dissolution of the monastery. The recipe is STILL a secret, making it different from a normal Pasteis de Nata but no one is exactly sure why because we don’t have the recipe. Honest opinion: I preferred the Pasteis de Nata at Time Out Market, but these were really good!

Porto

And onto Porto!

I took a Flix bus to Porto. This was very convenient, cheap and comfortable enough. I then used Uber to get to my hotel. I stayed at Descoberta Boutique Hotel by Aspasios, because it was reasonably priced and had an amazing location within walking distance to the river. Porto is split into two regions: North Bank and South Bank. North Bank is the historic city center, while South Bank has most of the port wine cellars. There is a bridge across the river connecting the two banks and it is very easy to hop between. I stayed on the North bank.

Places I recommend visiting in Porto North Bank:

Sao Bento Station: this station is a UNESCO world heritage site and a National Monument of Portugal. The murals represent moments in the country’s history.
Livraria Lello: this is one of the most famous bookstores in the world, but when I went, the queue was trailing all the way down the street and around the corner. Given that I only had one night here, I decided not to wait.
Igreja do Carmo & Igreja dos Carmelitas
Santo Ildefonso Church
Chapel of Souls

I stopped for lunch at one of the restaurants along the river bank and tried the Polvo à Lagareiro- which is octopus with olive oil, potatoes, grelos and garlic. I then walked across to South Bank for a port tasting at Quinta do Noval, which was great.

After this, I wanted to go to the well known Kittie’s Rock for sunset. However, on the way, I realized that it was jam packed with people and I was not going to get a great sunset view. So I backtracked a bit and found a place to stop along the dirt road. To get to Kittie’s rock, I found Google maps misleading: there is a dirt road above R do Casino da Ponte- this is the correct road to take. Don’t forget to bring some drinks and a snack for the sunset. After sunset, I walked along the river bank, there are musicians and acrobats and all kinds of incredibly talented people. Porto was one of my favourite places in Portugal.

Duoro Valley

The following day, I went to a car rental to pick up what I thought would be a Fiat 500 but turned out to be a slightly less photogenic Fiat Panda. I ubered from Porto for about 20 minutes to Francisco Sa Carneiro Airport and rented with Alamo. I found the process fairly straightforward. I then drove to my accommodation in the Duoro Valley, Quinta da Gricha. I cannot stress enough how amazing the drive was through the valley and how renting a car was NB. There were no buses or trains that could get to this area and a taxi would be okay but its an awkward two hour drive and you won’t be able to stop on the side of the road to take photos. I have no regrets about the car rental, even though it was my first time driving on the right hand side of the road and I was alone. That being said, the roads in the Duoro valley are narrow and the drive could get a little hairy but I recommend 100%.

Quinta da Gricha was absolutely beautiful, clean, comfortable with warm and welcoming hosts. I cannot recommend it enough.

Because I only had one night there (big regrets- stay at least two), I decided to visit two port wineries on the day of arrival. I booked transport with Taxis do Duoro and they were super effieicnt, they picked me up from the hotel on time and drove me to both the wineries, while waiting for me, and then back to the hotel. I first went to Quinta de la Rosa, where I did a cellar tour, port tasting and then had lunch. It was a killer 34 degrees! But still an awesome experience.

After that, I went to the famous Croft Port for a tasting, which was great. I then got back to the hotel safely and enjoyed the evening by the pool with the most beautiful views.

Algarve

I then woke up the next morning to start a very taxing 6hr 30minute drive by myself down to Lagos. Honestly, I would not recommend doing this, I would have rather drive back to Porto (which I anyway needed to backtrack to and drive through), drop off the car and then take a bus. At least with the bus I could have read a book or something other than focusing on the very confusing road, signs and toll roads without understanding any of the signs because they are obviously all in Portuguese. I then called a friend to keep me entertained and then ran out of data, which meant that my Google Maps cut out. I then had to find a petrol station where no one spoke English and tried to explain to them that I needed data. This ended with me buying a new SIM card. Overall, an entertaining experience but maybe book the bus. I (finally) arrived in Lagos and stayed at the Carvi Beach Hotel. This was nice, but I think my expectations were really high after Quinta la Gricha and the Duoro valley. Overall, I found that there was a lot of construction, broken buildings, graffiti etc in Lagos. It was not quite the idyllic beach town that I imagined. I also found that there were bugs in the sand, so it is quite unpleasant to sit on the sand itself. You can rent a lounger, which I did and that was lovely but also quite expensive.

On my second morning, I woke up and went to Praia do Camilo. Although I complained bitterly (to myself) about getting up so early, I will admit that the sunrise was absolutely worth it. I managed to get a table at Restaurant Camilo, which is famous for its seafood. It was tasty, but I wasn’t blown away by the prawns- maybe order something else.

Madeira

The next morning, I left Lagos and drove up to Lisbon. I then flew from Lisbon to Madeira. Ryanair takes their luggage limits VERY seriously, which resulted in me being way over the limit (thanks so some port purchases) and having to sacrifice snacks, shampoo and conditioner and my hairdryer. In case you wonder (like I did) why people are clapping upon landing: the landing strip at Madeira is considered to be one of the most difficult in the world due to the short runway, unpredictable winds, as well as cliffs. There is specialised pilot training required to make this landing.

I arrived in Madeira and stayed with a friend and her family. They took me for a drive around the island, we went to the Porto Moniz natural pools and in the evening went out to the festival activities. The next day, they had rented a boat for us to cruise around the bay and swim. While in Madeira, I highly recommend trying poncha- the local alcoholic drink. This is made with aguardente de cana honey, sugar, and either orange juice or lemon juice. There are also some beautiful hikes around the area, which I did not get to try, but they did come highly recommended.

Home!

From Madeira, I flew back to Lisbon and then spent a night at the airport hotel before my flight early in the morning back to Cape Town. Portugal was without a doubt one of my favourite holidays thus far!

A solo trip around Portugal!