The perfect 2-week Portugal itinerary

On my trip to Spain the year before, I knew I wanted to come back to region, and there was no better plan than to spend 2 weeks in Portugal. Is it too much time – well, no. 2 weeks is the perfect amount of time to explore the best highlights of the country but also go off-beat and expand your itinerary into visiting some of the most unique destinations you’ll ever come across. Portugal encompasses everything – from charming, timeworn cities, to postcard perfect coastal towns, stunning beaches, medieval villages, fairy tale castles, rich history and culture, authentic and sumptuous foods and desserts, amazing wine, and some of the best hiking paths, lakes, and hot springs you’ll ever see, Portugal will not disappoint you.

The perfect 2-week Portugal itinerary will combine a little bit of everything – because there’s nothing that I don’t like to experience. As much as ticking the boxes by visiting the popular areas is for me, going off the beaten path and looking for hidden gems is equally important. I highly recommend renting a car to make the most of your time, but the infrastructure of the city and the connectivity is quite amazing so if it’s impossible for you to drive for some reason, worry not, you’re well covered by alternative ways of getting to these places!

Here’s my recommended perfect 2-week Portugal itinerary.

Day 1 & 2: Lisbon (overnight Lisbon)

Click here to read the detailed itinerary for 48 hours in Lisbon.

Day 3: Day trip to Cascais & Sintra (overnight Lisbon)

For this day, I highly recommend renting a car from Lisbon. Although you may choose to take a train (it’s only 30 min by train from Lisbon to Cascais), renting a car gives you the flexibility to cover more ground in lesser time.

Cascais, a famous coastal town known for its beautiful beaches, picturesque streets and charming vibes is worth a day trip from Lisbon. The two most popular sites are Cascais Citadel, a fortress built in the 15th century, and the stunning Boca do Inferno, a coastal rock formation that overlooks the beautiful deep blue ocean, making for a great spot for taking photos.

Keep about 2-3 hours for visiting these 2 places before heading for Sintra, where you shall visit your highlight of the day – the famous Pena Palace. Another 30-minute drive from Cascais is this famous red and yellow palace sitting proudly on top of a jagged rocky hill, above the town of Sintra. One of the most famous monuments to visit in Portugal, I had heard that the tickets usually sell out months in advance during the peak season, but we were lucky to get tickets for the same day, even though we decided it was best to book online beforehand. Its possible that this was because it was still spring and the year right after Covid had hit, which already had impacted a lot of people’s travel plans. The palace is equally majestic from the inside as it is unique from the outside. Keep aside 2 hours to explore it in detail and account for the hundreds of photos that you’re going to want to click! Do take the audio guide for the tour to make your visit insightful and meaningful.

I suggest grabbing a quick meal at the café in Pena Palace because your visit to Sintra isn’t over yet! About a 10-minute drive from Pena Palace is one of the most underrated monuments of Portugal – Quinta da Regaleira. An enigmatic architecture in a picturesque setting, this estate is romantic to say the least. A network of lanes and tracks, hidden walkways and winding paths take you from one enigmatic sight to the other, so grabbing a map at the entrance to this extensive layout is an absolute must. An opulent palace hidden in a forest is bound to create a mystery – as do the various sites it houses such as the Initiation Well, Promenade of the Gods, and the Chapel. All in all, the estate is fascinating and a contrast to the architecture of the Pena Palace which begins to seem crass & tasteless when compared to the enchanted themes and stunning Manueline-Gothic structures strewn across

After a visit here, you may grab a quick bite in Sintra town before heading back to Lisbon for the night.

Day 4 & 5: The Algarve

I recommend keeping the car that you rented in Lisbon for your trip to The Algarve and then returning to Lisbon to return the car before you take your flight to Azores Islands.

Click here to read about How to make the most of 2 days in The Algarve.

Day 6, 7 & 8: Azores Islands

In your 2-week Portugal itinerary, I highly recommend including The Azores Islands or Madeira. We chose the former.

From Algarve, drive back to Lisbon and return the car, and board the flight to Azores Islands. In Azores Islands, you can rent a different car from the airport on your arrival.

Click here to read about How to spend the perfect 3 days in Azores Islands.

Day 9: Óbidos & Peniche (overnight Obidos)

Once back from Azores Islands, I recommend renting a car from Lisbon Airport to continue with your journey.

Today, you will drive to Óbidos, about an hour from Lisbon, known to be one of Europe’s most well-preserved medieval towns. The walled historical center can get extremely busy during the day, thanks to the day trippers from Lisbon. Although there’s not a lot to do in Óbidos, the labyrinth of cobbled stone streets nestled beautifully in the fortified town make for a charming experience. You will come across several small boutiques, whitewashed houses, patio cafes and restaurants, as you walk these mazed lanes. Stop at any one of the flower-decked, vividly painted shops to buy yourself a souvenir and local handicrafts or the famous chocolate and sour cherry-liqueur (Ginjinha de Obidos). I honestly couldn’t get enough of those! You can also walk along the imposing walls of the citadel and enjoy gorgeous views of the vineyards across.

While Óbidos is a delightful place to explore, you can only spend 2-3 hours strolling along the area. Make use of the day and head to Peniche, a very off-beat, unique coastal town in Portugal known as one of the best surfing locations. A very laid-back small town, Peniche is a good break from most other places on this itinerary, thanks to its appeal only to the locals and lack of popularity amongst tourists. This is where you need to be to experience the slow, Portuguese lifestyle. You can also take a speedboat to Berlengas, a UNESCO listed archipelago that was classified as a Nature Reserve in 1981 due to the importance of its unique ecosystem. The boat trip is only 20 minutes and there are several options that allow you to book a return trip with a waiting time of about 3 hours on the island. The island is stunning; make sure to visit the São João Batista Fortress for the most Instagrammable views.

At night, return to Obidos. You’ll be pleasantly surprised to see how the town transforms once the day trippers are gone!

Recommended overnight stay in Obidos: Patio das Margaritas

Day 10: Nazare, Coimbra, Aveiro (overnight Aveiro)

On this day of your 2-week Portugal itinerary, you’ll drive through some lesser-known, quieter towns of Portugal. About 40 minutes from Obidos, is a town called Nazare. A picturesque fishing village with beautiful beaches and traditional culture.

One of the most popular attractions in Nazare is the Praia da Nazare, a large beach with a distinctive curved shape known for its high waves, sometimes reaching a height of up to 30 meters, making it a popular spot for surfers. I recommend you try the delicious and fresh seafood here, such as the traditional Portuguese dish caldeirada, a fish stew, or the famous Nazare-style sardines, while you watch the surfers tame the crazy high waves. Nazare is a great destination for those looking for a quieter, more traditional experience in Portugal. If you find that the town is right up your alley, you can spend more time visiting Vila Velha, where you can see the traditional houses and narrow streets, and the famous Nazare lighthouse.

About an hour’s drive from Nazare, is the historic university city of Coimbra. While there’s nothing very unique to experience in this small laidback town, the university is said to be inspiration for J.K. Rowling’s Harry Potter Series! So, if you’re a Potterhead, then it might be of interest for you. Entry to the university is not free of charge, but if you do go, then visit the Baroque Library, known to be its most wondrous and beautiful feature. After the university visit, head for a meal to Loggia, adjacent to the Machado de Castro National and enjoy gorgeous views while you dine.

Coimbra

After a stopover at Coimbra, it is now time to move on to your next destination, which is less than an hour away, Aveiro. Yet another laidback town, Aveiro is known for its lagoon and network of canals, where the traditional moliceiro boats take tourists on a little tour of the town. The Art Nouveau buildings and tiled facades make for a unique architecture that is characteristic of the town. Locals often call Aveiro the Portuguese Venice. The bakeries located along the canals are bound to pull you in with the aroma of their freshly baked Artisan breads, buns, and sweets. Don’t be shy, you’re on vacation!

Depending on how long you plan to spend in each of these off-beat Portuguese towns, you could either choose to stay overnight in Aveiro or head to Porto, which is about an hour by road.

Click here to book your overnight stay in Aveiro.

Day 11 & 12: Porto (overnight Porto)

Porto is only an hour by road from Aveiro. Your last 3 days in the itinerary are slightly relaxed.

Click here to read about What to do in Porto in 3 days (including Douro Valley).

Day 13: Douro Valley (overnight Porto)

No 2-week Portugal itinerary is complete without at least a day in Douro Valley.

While some people choose to cover Douro Valley in a day, many prefer to spend a few nights there, experimenting with different types of wines, roaming the vineyards, enjoying leisurely meals at the numerous wineries, offering excellent views anc rusing along the Douro River. If you only have 1 day, you can cover the highlights – Quinta do Pôpa winery for wine tasting with a view, Pinhão and a 1 hour cruise along the river. The detailed 1-day itinerary can be found above, with my Porto 3-day itinerary, where the last day covers Douro Valley.

Pinhão

Day 14: Return

On this day, you have some time to spend either at Douro Valley, if you plan to stay overnight at a winery, or at Porto, or return to Lisbon, depending on where your flight back home is booked from. This active 2-week Portugal itinerary might leave a little exhausted but in love with the country and its diversity!

Don’t want to DIY? Then why not find Portugal Group Tours that’ll fit your requirement?