Two weeks in Portugal

Planning a trip for two weeks in Portugal can be almost as much fun as taking the trip…

I go to Portugal for two weeks with my wife and two friends.

I come back.

I get the usual questions.

1) How was your trip?

2) Where did you go and what would you recommend?

The answer to the first was “Great!” The answer to the second is as follows.

I hope to do more in-depth summaries of each location soon so you can know the specifics of what we saw . But this provides an overview of our two weeks in Portugal, a trip taken in mid-October, 2025.

Getting there and getting around

We flew into Lisbon and out of Porto. We rented a car in Sintra (which lies on the outskirts of Lisbon) and dropped it off at the Porto airport before visiting Porto so we didn’t have to drive in Lisbon or Porto. Because of that, driving for two weeks in Portugal was both convenient and easy.

Because there were four of us, before and after we rented the car, we took Ubers almost everywhere. They were cheaper and more convenient than both taxis and even public transportation (e.g. an Uber ride from Lisbon to Sintra is about 25 euros whereas four train tickets would have been around 30 euros (without even counting getting to the train station in Lisbon). We tried the local version of Uber, Bolt, but either the app had issues or their drivers weren’t as available, so we mostly stuck with Uber.

We didn’t visit the south of the country or the eastern part, but you can only do so much in two weeks in Portugal and our itinerary was intended to be a combination of seeing some highlights while not rushing all the time. I think it worked in that regard (despite the fact that we were one night in several locations).

We could have made places like Porto and Coimbra hubs and have done day trips from each to locations such as Braga, Guimaraes, Cerdeira, and Tomar. But we wanted to minimize driving for our two weeks in Portugal and experience as many places in the mornings and evenings, both for better photos and to minimize the crowds. You’ll quickly note that avoiding crowds is a key objective of mine.

I’ve included links to some of my favorite reference sites that we used when planning our trip so that you have additional resources. Three in particular stood out as helpful: Earthtrekkers, We Travel Portugal, and Discover Portugal.

Here’s a map of our destinations for a visual reference. It wasn’t a straight line from south to north, but pretty close. Our only backtracking was bypassing Porto on the way to Braga and Guimaraes then circling back to Porto to end our trip.

Now on to the step by step of where we went on our trip for two weeks in Portugal…

Lisbon

Lisbon is Portugal’s capital and largest city, so you could spend a long time here. Still in our three days in Lisbon, we managed to see quite a bit and would say that three nights is enough to get a good feel for the city.

Famous tram 28 on trip for two weeks in Portugal — *The famous tram number 28 passing through a typical Alfama street*

We stayed in the oldest area, Alfama, visited the more downtown areas of Chiado and Bairro Alto, and ventured out one afternoon to Belem to visit the famous Jeronimos Monastery and have one of our favorite meals of the trip at O Frade restaurant for dinner.

Jeronimos Monastery on trip for two weeks in Portugal — *The Jeonimos Monastery in Belem*

Sintra

This small town of fantastical palaces is often done as a day trip from Lisbon.

Initiation well at Quinta da Regaleira on trip for two weeks in Portugal — *The Initiation Well at Quinta da Regaleira*

We stayed overnight, and I’m glad we did, not least of all for the hotel and cafe (Chalet and Cafe Saudade) which we loved. Breakfast was included with our room, but we enjoyed it so much, we went back there for lunch as well.

Pena Palace in Sintra on trip for two weeks in Portugal — *Pena Palace in Sintra*

We didn’t venture out to the coast from Sintra, but that’s another option with a bit more time. Instead, we visited five of the main sites there in this order: Montserrate Palace, Quinta da Regaleira (on our first afternoon after leaving Lisbon), and then Pena Palace, the Moorish Castle, and the National Palace of Sintra (not shown here) the following morning.

Moorish Castle near Sintra on trip for two weeks in Portugal — *The Moorish Castle in Sintra*

Obidos

This small, walled town with it’s own castle (now a fancy hotel), is pretty and fun to wander.

As in Sintra, we stayed overnight in Obidos to minimize the daytripper crowds. And also as in Sintra, there’s a strong Disneyfication factor here. It can feel as if the whole place has been turned into a tourist experience.

Obidos street scene on trip for two weeks in Portugal

But we also had a wonderful overnight stay in a small guesthouse (Obidos Patio House). That allowed us to experience the town in a more relaxed manner with no crowds.

Dining at night in Obidos on trip for two weeks in Portugal

Alcobaca, Batalha, and Tomar

We drove from Obidos to Tomar stopping along the way at two incredible monasteries. The first was at Alcobaca. This church and monastery (as well as our next two stops) rival the Jeronimos Monastery in Lisbon as extraordinary architectural marvels.

Alcobaca Monastery exterior on trip for two weeks in Portugal — *The entrance to Alcobaca Monastery*

Alcobaca has less ornamentation, but the sheer size and the number of different rooms, courtyards, tombs, and other elements make this a definite place to visit if you’re in the area.

Alcobaca courtyard on trip for two weeks in Portugal — *One of the many courtyards and cloisters at Alcobaca*

Gargoyle at Alcobaca Monastery on trip for two weeks in Portugal — *Some of the architectural details at Alcobaca Monastery*

Next, we stopped at Batalha. As with Alcobaca, we came to this small town for the monastery and it didn’t disappoint.

Batalha Monastery exterior on trip for two weeks in Portugal — *The ornate facace of Batalha*

Started in the late 1300’s, it took over a century to complete.

Tomb of Joao 1 in Batalha on trip for two weeks in Portugal — *Tomb of D. João I (1357-1433) and his wife, Queen Philipa of Lancaster (1360-1415) in Batalha Monastery*

The surprise delight of our time here in Batalha was a wonderful late lunch at Sopas e Companhia (Soup and Company). We probably spent more time eating wonderful food and talking to our server, Dolce, than we did at the monastery. But we did love the monastery.

Inner cloister in Batalha Monastery on trip for two weeks in Portugal — *The details here at the Baltalha Monastery add to the beauty of this place*

Finally, we arrived at Tomar and stayed the night in this charming city.

Tomar old town on trip for two weeks in Portugal — *Ancient mills and wineries in the old town part of Tomar. Though dating back centuries, they look like contemporary architecture.*

Our goal was to get a fresh start the next morning visiting the amazing Convent of Christ and the surrounding Knights Templar castle, a UNESCO World Heritage site. The highlight, to me, is the rotunda (round church). The photos here capture only a fraction of what is there.

Convent of Christ ceiling in Tomar on trip for two weeks in Portugal — *The incredible rotunda at the Convent of Christ (looking up toward the middle)*

Convent of Christ interior on trip for two weeks in Portugal

Cerdeira (Schist Villages)

In the mountains of central Portugal are a number of villages built from the local schist stone. Most of these villages were abandoned by the middle of the last century due to lack of employment opportunities in the area. But in recent years, many homes and villages are being restored. We stayed in one of the more renovated villages, Cerdeira. We’d planned on three leisurely nights there, hiking, taking a workshop on making small versions of a schist house, and just relaxing. Unfortunately, two days before we arrived, we received an email informing us that a few months earlier, a fire had burned through miles of the forest surrounding Cerdeira. The village itself was unscathed, but the blackened hills, the challenging driving conditions, and having to bring our own water to one of the more expensive places we stayed on the trip led us to leave after two nights there.

Cerdeira village — *The lower part of the village of Cerdeira*

Schist wall in Cerdeira — *If you’re thinking, “OK, so it’s a photo of rocks” you would not be wrong. But this is what all the buildings are made of here.*

Coimbra

All four of us agreed that Coimbra was our favorite place on the whole trip.

It’s the home of the oldest and most prestigious university in the country with a famous library that houses bats at night to keep the books free from insects. Alas, you’re not allowed to take photos there. But nearby is the Cabinet of Curiosities, which, while not as ornate, was actually more interesting.

Cabinet of Curiosities in Coimbra — *I personally thought the miniature six-legged donkey was the coolest item here in the Cabinet of Curiosities, but its just one of may oddities that make this such a cool place to visit in Coimbra.*

Coimbra also has a remark able art museum (we had lunch at the restaurant there whose terrace has great views over the city), and a beautiful main shopping street (Rua Ferreira Borges) that is a delight for the architecture as much as the stores.

Main shopping street in Coimbra on trip for two weeks in Portugal — I’m not really much of a shopper, but I so loved this main shopping street, just for the architecture and people watching. Plus, students from the university (just up that slope to the left) come down in their Harry Potter-like black robes and play music and sing songs along here.

Oh, and we the second of our two of our favorite meals of the trip here at Arcada Comes e Bebes. We stayed one night in Coimbra and I wish we’d stayed more.

Rua Fernandes Tomas in Coimbra — *Our favorite restaurant, Arcada Comes e Bebes, is behind me and to my right as I took this photo of this charming street, Rua Fernandes Tomás*

Braga

We only had an afternoon in Braga on our trip for two weeks in Portugal, but it was definitely worth taking the time to see the old town and the ancient cathedral with probably the biggest organ I’ve ever seen.

Organ in Braga cathedral — *The organ in the Braga Cathedral*

But the highlight is the pilgrimage site, Santuário do Bom Jesus do Monte just outside of town.

Steps looking up at Bom Jesus near Braga on trip for two weeks in Portugal — *This is about halfway up the mountain looking up*

Steps looking down at Bom Jesus near Braga — *The view from Bom Jesus du Monte looking down (from about 2/3rds up the hill.*

We didn’t ascend the 381 feet of zigzag steps on our knees as many pilgrims do, but we did enjoy all the sculptures and the views.

Guiramaes

Street in Guimaraes on trip for two weeks in Portugal — *One interesting street in Guimaraes…*

We stayed two nights at this small city not far from Braga. The highlight to me of Guimaraes was just exploring its medieval core.

Woman with umbrella on street in Guimaraes — *And another.*

Old stone building with arches in Guimaraes — *This is one of the two adjacent main squares in Guimaraes*

OK, that’s not true. The real highlight was spending a rainy afternoon in a food court in a shopping mall eating Brazilian food and simply relaxing. Not something on the tourist maps, but our server there made our day.

Porto

We ended our trip with three nights in Porto. As with Lisbon, it is overtouristed. We hated the crowds and all the construction (most of the major squares were torn up as the add new metro lines). But I still loved Porto.

Church in Porto — *The Church of St. Ildefonso is similar to many other beautiful churches in Porto that are covered in the blue and white azulejos (tiles)*

Before it became famous with tourists, it was a gritty port town. But one with great bones. The architecture is beautiful, and while the whole area down by the river now caters to tourists, there’s still the opportunity to get off into the small streets and alleys and just explore.

Night shot of Ribeira waterfront in Porto on trip for two weeks in Portugal — *Looking down on the Ribeira waterfront area of Porto from the Luis I bridge*

Plus, you have Gaia across the river with all the port wineries. It rained most of the time we were there, but there’s much to see inside as in the cathedral (below) and other impressive churches and buildings. Plus, you’ll never run out of options for wine tastings since Porto is all about their most famous product, port wine.

Porto cathedral cloister — *The cloister of the Se’ (cathedral) in Porto*

In summary

That’s it. As noted, I’ll do more in-depth summaries of most of the places noted above. But this should give you a good sense of what you can accomplish in two weeks in Portugal. Overall, I’d say it was one of my favorite trips in the last several years.

My wife and I have never traveled with anyone other than family before (at least for a vacation trip), but it turned out that being with friends added to the enjoyment. I still get readers of my book, Hidden Travel, who cite back to me their favorite line in the book which essentially says that a great place with the wrong traveling companions can be a nightmare and a bad place with the right people can be a dream. It’s true. And in Portugal, we had a great place with the right people, so win win.