
Want more tips on travel in Portugal? Here’s the Douro River train, a 10 day itinerary, and hiking in Geres National Park. There are additional Portugal itineraries on my Itineraries page.
Special Note About This Itinerary
Because I used to live here, and because it was Mr TravelObservation’s first trip to Portugal, I selected all of these destinations for a specific purpose. This isn’t necessarily the itinerary I’d recommend for all clients, depending on your travel style – that’s why I like to talk to potential visitors to Portugal to see what they want to do.
This might seem like a lot, but I can assure you that we also had time for amazing long Portuguese dinners and coffee/pastry stops and wandering the streets of the city getting lost and enjoying the view.
I’ve included the hotels that I stayed at if I liked them – when I travel for personal reasons I try to only stay in hotels I’d recommend to clients, since my motto is “planning your trips as carefully as I plan my own!”
Day 1 – arrival in Lisbon
We stayed at the adorable Janelas as Verdes which means Green Windows. It’s in the Lapa residential area of Lisbon, halfway between Belem and Lisbon center.

Would I put clients here? It depends on their expectation. If they want to walk out their door and by right by Rossio train station or Praca do Commercio, no. But if they are used to traveling in cities and understand you can’t be close to everything (ever tried to pick a hotel in Paris?) and are comfortable taking a tram/bus or a longer walk, than absolutely. The roof-top library and patio, free pasteis de nata, sumptuous breakfast, and amazing staff made this hotel a true 5-stars. I’d recommend it without reservation, as long as clients understand its location (which I loved because it was all family restaurants and typical lifestyle in that area – no tourists!)
It’s a luxury boutique hotel in an 18th century townhouse, and every evening they replenish the port wine in your room!

Day 2 – Exploring the city
The Belem area is kind of my go-to to introducing newbies to Lisbon because everything is easily clustered together. It’s a “WOW!” introduction to Lisbon history filled with perfect postcard photo opportunities.
We took a bus straight from our hotel to the Belem area. You can also take a trolley (tram) as well.
Our first stop was the Jeronimos Monastery. Entrance to the church is free, but the cloisters were closed this day. The Maritime Museum is now housed in one portion as well, so we stopped by. The Maritime Museum is definitely worth a trip and can sometimes by overlooked by visitors, but it’s a great explanation of Portugal’s relationship with the sea and has an impression collection of royal barges.
The Tour de Belem and Monument to the Discoverers are also in this area. The Tour De Belem was actually closed today too (these are closed normally on Mondays, but since Christmas Day had been a Monday, they apparently decided observe their closure on a Tuesday) but we were able to see it from the outside. At least this saved us a bit of time, and we decided to go back into Lisbon center instead of back to the hotel.
We took the bus from the Praca da Figuoeira up to St George’s Castle. We ate lunch in a delightful restaurant just opposite the entrance (and surprisingly the prices were not inflated either). We thought about walking back down from the castle through the Alfama district, but our feet were already hurting and we decided to jump on the bus, since we had bought an all day pass.
Back in town, we decided to go the “Lisbon Story Centre,” a new museum that is on the Praca da Commerco. What a lovely experience! It’s a guided tour with earphones that is controlled by GPS. In this multimedia experience, the narrator will start whenever you are at a new “chapter” of Lisbon’s story. The section on the Lisbon earthquake, for instance, will actually start trembling to replicate the earth moving. The section about Lisbon’s growing importance as a sea port has barrels and fake sea gulls and a model ship. The museum is about 45 minutes with the guided narration, and I think it’s a wonderful stop at the beginning of your stay to get acquainted with Lisbon’s history (most other sites in Lisbon and Portugal don’t do that good a job of explaining their history).

Day 3 – Sintra
There’s sooo much to see and do in Sintra, and as you know from my previous itineraries I often recommend that you consider staying two or three nights there instead of basing yourself in Lisbon. I hope to do this next time if we are there during warmer weather.

We took the train up from Lisbon and within 40 minutes we had arrived. Since it was winter, many sites didn’t really open til about 10am, so even though we arrived at 10:30am we still were able to beat some of the crowds (until lunchtime, and then the tourist buses rolled in).
We went to Pena Palace (hint: don’t pay for the inside, the parks and exterior are stunning enough. Another hint: take your time exploring the grounds. Many tourists are there to snap a photo of the palace exterior but won’t ever venture into the extensive gardens, so you’ll find some peace and quiet there), the Moorish Castle, and Quinta Da Regaleira. I don’t really recommend three in one day, especially if you have any mobility issues or tire easily, but all these places are special to me and the cry of the day was “Must show Mr TravelObservations!”
In the evening, after returning to Lisbon, we went to the Povo Restaurant, a fado restaurant that doesn’t charge a cover and which doesn’t feel too touristy (although there were plenty of Americans in the restaurant!) What a great evening! There were three sets of music, none of the sets were too long, and the tapas-style food was tasty (and they had the biggest glass of sangria I’d ever seen). It’s important to be familiar with fado etiquette: They won’t seat you if the music has already started and you’ll be asked to wait till the set finishes. Also, talking is not permitted during the music. It is meant to be an immersive experience. The servers will not come and take your order while the music is playing, so be sure to catch their eye during breaks. If you want to pay (esp. with a credit card) just go to the back of the room where their credit card machine reader it.

Day 4 – Estoril and Cascais
We had a leisurely morning because we were still pretty tired from yesterday. After packing up, we took the train (the station was very close to the hotel) to Estoril, where I had a free night certificate to use at the InterContinental Estoril. The hotel is right on the beach and kindly upgraded me to a oceanview balcony room, where we could sit and overlook the beautiful Estoril coastline.

After admiring the view, we decided to walk the boardwalk from Estoril to Cascais. It started pouring with rain, so as we were hungry anyway we took refuge at the Hotel Albatroz (this was probably the most expensive lunch we had the whole trip, but the rain was pouring so hard that we didn’t want to search elsewhere). By the time we finished lunch the rain had stopped, so we continued our walking tour of Cascais, going to Boca Da Inferno and through the Parque Marechal Carmona.


I had thought about renting the electric bikes that are everywhere and convincing Mr TravelObservations to bike to Guincho Beach, but the clouds were still pretty threatening and we decided not to risk getting caught in another downpour.
For dinner, we decided to seek out a non-touristy spot and that meant going deep into Estoril away from the ocean. About 15 minutes walk from the hotel was a delightful family run restaurant that served us a ridiculous sized “seafood and rice” dish – we couldn’t even finish it.
Day 5 – Roadtrip through Central Portugal
We picked up the car and embarked on a fabulous road trip! The interior of Portugal is great to drive – I would just never advise anyone to drive INSIDE Lisbon or Porto since it’s quite alarming for many Americans!
Our first stop was the famous beach town of Nazare, where some of the world’s highest waves are recorded. We took the cable car up to the hillside town of Sitio, which has a beautiful overlook onto Nazare, although it was quite foggy so I can’t share photos. However, there was something quite magically about walking around in this little cliff village surrounded by mist. Old ladies in their traditional costumes were gamely sticking it out, selling nuts and cookies from their carts, and we ended up ducking into a shop and buying handmade wool hats from a grandma-like shopkeeper.
After a stop for coffee and snacks in Nazare, we then headed to Alcobaca, merely 20 minutes away. Alcobaca is a beautiful monastery where Ines and Pedro, the “Rome and Juliet of Portugal,” are buried. You can pay a modest fee to enter the cloisters, which is well worth it. (You can enter the cloisters at Batalha, our next stop as well, but I decided I didn’t want to confuse Mr TravelObservations so we only did cloisters at Alcobaca).

Batalha, also close by, was next. This stunning gothic cathedral commemorates an important battle and is an important part of history. We also had lunch and I ordered a bifana (beef sandwich) for Mr TravelObservations.

I had wanted to take Mr TravelObservations to Almourol Castle too, but as we were still 2 hours from Porto, we decided to head to Porto so that we could miss the traffic into the city.
We returned the car that same day – no need for a car in big cities like Lisbon and porto. It’s great for the day trips or in-between transportation. If you can drive stick transmission, you’ll save a lot of money. We dropped the car off at the Oporto airport and then took an Uber into town.
Our hotel here was the InterContinental Porto which blew us away with their service – and we appreciated it even more when they upgraded me as a Platinum Ambasador member to their duplex 2-floor suite! As a Platinum Ambassador I also received a substantial discount off of breakfast, which was well worth it.

I took Mr TravelObservations for a walk after checking into the hotel because there’s something special about your first introduction to Porto being at night. The cathedral is all lit up and the river restaurants are playing music with candles in their windows. We found a lovely restaurant by the river and took our time reminiscing over the great day we had had.

Day 6 – Geres National Park
I had originally planned to go to Braga and Guimaraes which are much more well known for day trips from Porto – but I’d never been to Geres National Park and when I realized there was an amazing small group tour leaving from Porto, I jumped on the chance. What a great chance to show Mr TravelObservations the “wild” Portugal! I wrote a separate blog post about this experience, you can read it here.

Day 7 – Last day in Porto and overnight in Lisbon
Our last day in Porto. I paid for the hotel night so that we didn’t have to check out early, so we were able to relax and enjoy ourselves.
We walked past the Lello bookstore but decided not to go in because there was a line. I’ve been in it when it’s empty, though, and it’s well worth going if you can time the crowds right.
If you look up things to do in Porto you will of course see the port wine cellar tours and tastings – this is definitely worthwhile, we just chose not to do it since Mr TravelObservations does not drink so it seemed a little silly to pay for him.

New Year’s Eve day was also Sunday in Porto so I was a little concerned about thigns being closed. There were some sites that were closed that I had planned to go to, such as the Casa do Infante (House of the Prince) which is where Prince Henry the Navigator was born. But we were able to ride the Funicular dos Guindais, an elevator from the Ribeira riverfront up to flat ground, as well as explore the Crystal Palace Gardens, which were a beautiful surprise and I’m sure must be lovely in the springtime when everything is in bloom.

Porto is an amazing city – this was my second time to Porto (I lived in the Lisbon area) and every time I wish I could spend more time there. In the summer, be sure to visit the Douro river valley or even consider staying on a quinta there (you can also read my blog from a previous trip about how to take the train down the Douro for one of the most scenic trips in the world)
Around 6:30pm we went to the airport and checked into our flight… which had a layover in Lisbon! So we landed in Lisbon at 9:30pm and immediately went to our amazing hotel, Palacio do Governador in Belem. It’s a converted palace that was the governor’s home. It’s a boutique luxury hotel, and suitable for someone who loves the Belem area (you’re still about 20 minutes from the “real” center of Lisbon by public transportation).
We were able to walk two minutes down to the banks of the river, near the Tour de Belem, and watch some fireworks. It was a wonderful way to ring in 2018!

Day 8
Departure! After celebrating NYE in Lisbon, we left for the airport for our 11am flight, and got back home in the evening on New Year’s Day
I know I have a lot of articles about Portugal and that’s cause I love it so much! I hope this blog was useful in seeing how you can see a lot of Portugal in one week and even see sites like Geres National Park which many first-timers never go to. If you’d like to reach out for more advice and help with booking some of these, be sure to reach out via the form on my Contact page!