Óla friends! I’m finally back with a new itinerary! This summer I traveled to Ireland, Scotland, Austria, Israel and Romania however most of those were to visit friends and family so I didn’t have full itineraries for any place. However if you have any travel questions for these places shoot me an email!

This December for my parent’s 25th wedding anniversary my whole family went to Portugal for a week. Because I made a kick-ass itinerary when the family came to visit me in Paris at the end of my study abroad, my family entrusted me with making the full itinerary. I actually chose the cities and airbnbs the same day we booked the plane tickets because we booked a bit late and I wanted to make sure we could find good 5-people airbnbs so while making the itinerary I had to work within the time constraints I had actually brought upon myself. Looking back I don’t know if I would have broken it up differently because everything ended up pretty great, but if we went in the summer I absolutely would have changed our scheduling.

Fast Tips

+ It’s about 55 every day in Portugal in December. We all were good to go with a fall jacket and walked so much we ended up ditching our outerwear halfway through the day anyway.

+ If you stay in Lisbon it is easy to make a few day trips. I would highly recommend renting a car to get around if you want to hop from city to city like we did. Portugal is pretty tiny so the longest drive we had of the trip was 4 hours and it was from the almost top to almost bottom of the country.

+ We were in Portugal on Christmas and everything was closed. About 3PM on Christmas Day stores started opening up, but I would plan on buying food for breakfast and lunch the day before (before things close early for Christmas Eve).

+ Food was not the highlight of the trip for my family. Normally when we travel we insist on eating only food from that country (eating at only Portuguese-food restaurants) but honestly after a few Portuguese food meals I wouldn’t feel like you have to stick to that if you are feeling as “eh” about the food as we were. Their breakfast, on the other hand is stellar and you should make sure to try as many pastries as possible. A very important note on dining out in Portugal: Europe is notorious for taking their time with dinner, but Portugal was horrendous. We waited over an hour just for our food to come out multiple times and then spent on average 30 minutes at each meal trying to flag down a server just to get the check (which you must ask for, they won’t bring it to you). If you’re in any type of time constraint, just grab food to go.

+ On the other hand, the cost of living in Portugal is very cheap. For breakfast we never spent more than 15 euros for the whole family and most dinner entrees were 10-15 euros and wine about 3 euros. Also there’s a family discount at most museums (around 15 for the full family) so if you’re with a 4+ person family make sure to tell them!

+ As always, I recommend you buy a European SIM card in the airport. I think for most American plans its $10 a day, but if you buy a European SIM it’s 20 or 30 euros for unlimited call, text and 5G of data (more than enough for your trip). Plus you can save the SIM and use it the next time you’re in Europe! European SIM cards, no matter what country you buy in, work across all of Europe. I used my Irish SIM from the summer with no problem (just reactivated it and paid for the month when I arrived). You have to call your carrier to unlock your phone before you leave to put in a different SIM card.

Itinerary

Day One

We arrived in the Lisbon airport at 6AM. It took us about an hour and a half to get through the customs line (maybe because we were with all the other first flights of the day?) then picked up our Sixt rental car right in the airport. This all took about 3 hours (including buying my dad a SIM card in the airport) which was fine because nothing opens in Sintra until 10AM.

We drove up to the parking lot for Palace de Pena and started there. We paid for the grounds and inside – I don’t know if it was so worth it to go inside although it was cool to see the old kings and queens rooms.

The view of the Moorish Castle from Palace de Pena

We walked from there to the Moorish Castle (Castelo dos Mouros) which was very awesome. There were no inside parts but you walk along the rampart and get a gorgeous view.

I heard from many friends that their favorite part of Portugal was Sintra. For my family it was none of our absolute favorite place but we really loved it and it was a great way to start off the trip. I agree that it’s a must see and if you are staying the whole trip in Lisbon it’s an easy day trip on the train.

We drove to eat lunch in Sintra proper at the only open restaurant (this is Christmas Eve day) then drove an hour and a half to Obidos to check into our Airbnb then immediately go to sleep. We picked up some groceries on the way for breakfast and lunch the next day. We loved our Airbnb in Obidos (and it’s especially great in the summer for large groups - they have 3 guest houses on the property and all can be rented out). The next morning we took a little driving detour to a nearby beach “Praia de Bom Sucesso” and collected beautiful shells before heading into Obidos. As it was December it was way too cold to even put our feet into the water but the beach was stunning.

Day Two

Video from my sister’s GoPro heading up the rampart

Obidos has an adorable little Christmas Village that we really wanted to go to on Christmas morning, however it wasn’t open until 4PM. We decided to go into Obidos to wander around regardless and boy are we glad we did. I heard from locals that in the summer Obidos is so crowded you can’t even move (the streets are teeny tiny), but it was almost empty when we went which was incredible. For my family, wandering around an empty Obidos was one of the highlights of our trip (and my absolute favorite).

There’s a parking lot right next to the village (you can’t drive on the tiny streets) and when you enter there’s a staircase to your right with a “Danger” sign. This staircase leads up to the rampart around the city and we walked along the whole outside of the city on the rampart and ended at the other end in their big fortress/castle. We then descended and walked back through the little city. Things were just starting to open and we stopped into one of the many Ginja stores. Ginja, the classic cherry liquor of Portugal, is produced in Obidos and served as little shots in chocolate cups. It’s delicious and way higher in alcohol content than you think so be careful not to have too many! (It also makes great souvenirs).

One of the cute colorful side streets of Obidos

From Obidos we drove 2 hours north to Porto. Our Porto is divided into north and south with a river in between. All the Porto “destinations” are in the north and some wine tasting is south of the river (it was closed when we went so we weren’t able to go). We stayed south of the river in Afurada and got to see the gorgeous sunset walking along the river.

Day Three

We spent day three in Porto. I’d recommend doing most of your souvenir shopping here since the shops are abundant and the prices aren’t as expensive as Lisbon. We ate breakfast at Confeitaria Serrana, which was recommended to us by a friend and was wonderful. Here we tried our first bola, quejida and pastel de nata. The patisserie is right near the Sao Bento train station, which we stopped into to view the gorgeous tile inside the station. Porto was absolutely the tile capital of Portugal in terms of how beautiful all the tiling was. We spent a silly amount of time outside the Catholic Church (Igreja do Carmo) taking photos in front of the gorgeous tile.

We walked up the Clerigos tower to get a gorgeous view of the city (this is an absolute must-do, and only 240 steps).

We wanted to go into the Livaria Lello (Harry Potter book store) but didn’t know you had to 1. pay to get in and 2. wait in a very long line and we eventually decided not to. We also didn’t have time to see the Jardins do Palacio de Cristal which is supposed to be wonderful. We did walk along the Rue de Ribiera Negra and then over the Ponte Luis I for the most incredible views of Porto. This bridge is another must visit. You could take enough panoramas in Clerigos Tower and on the bridge to last the year!

Porto is a great city to wander around and I would recommend a full day or a day in a half in the city. We only had the morning until 3PM and didn’t get to see everything on our list, especially because lunch took 3 damn hours (see quick notes above). Obviously port wine is widely available in the country but it feels cool to drink it in Porto (especially if you don’t love port and only want to drink it once for the experience).

We then drove 2 hours to Evora and ate dinner around the corner at Dona Laura (a cute tapas restaurant across the street from Laura’s husband’s fine dining restaurant Dom Joaquim). We loved our meal and would highly recommend anyone eat there. Their puff pastry dessert was especially incredible as was their cheese tasting plate with their homemade jam. (I bought a jar to take home!)

Day Four

We spent the morning in Évora. This town was another highlight and favorite of our trip. It’s the sweetest town but with the coolest monuments.

We started in the Chapel of Bones – equally cool and creepy and a must-see. Next door is Igreja e Mosteira de Sao Francisco which is a great quick stop in because it’s very beautiful. We walked to the Praca do Giraldo to get breakfast at a cafe. Again, every different pastry was absolutely amazing. We ate at Cafe Arcada Evora.

We’re not a regular family, we’re a cool family.

We went to Evora Cathedral, our favorite monument of the trip. We immediately went up to the roof (about 150 steps) and spent a lot of time taking bomb-ass photos. When you walk in the cloisters make sure not to miss the spiral staircase to the upper level opposite the bathroom.

View from the cloisters in Evora Cathedral

We went to Rota dos Vinhos do Alentejo for a wine tasting before we left. It’s 3 euros to try 6 wines with a full explanation of each. And we were lucky that one of their special wines made in a terra cotta urn was on the tasting menu for that week and we got to try. This awesome tasting shop can get really crowded in the summer and in the evening so it’s best to try to go during an “off” time/hour.

On the way out of Evora we drove to the Cromleque Dos Almendres - the prehistoric stone circle. It’s really, genuinely, just a bunch of big neolithic rocks (as is Stonehenge) but in a huge cork tree grove which was very cool. We even cut off a few little pieces of the cork bark for ourselves which was amazing.

Cutting cork off a cork tree

After this we drove 2.5 hours far south to Faro and checked in to our Airbnb. We actually didn’t do anything in the city of Faro, and if that’s the case for you and you have a car I would highly recommend our Airbnb. It was enormous and so clean. We had dinner a 10 minute drive away at Flor do Ameiro which had such a cozy local vibe – we spent a lot of the dinner talking to the owner who was so sweet.

Day Five

Day five we spent in the Algarve. If you go in the summer, you absolutely can spend a whole week in this region (the far south, beaches on beaches). There’s not very much to do in the winter, but we still had a fabulous time.

We got to the Benagil Beach really early, not realizing that boat tours of the cave didn’t start until 10. But we took some great photos on the beach while waiting then did a super cool boat tour of all the nearby caves. This was a trip highlight for many of us and highly recommended. (We went with Taruga tours.) We went during low tide which was also great because we got to boat inside some of the caves. We stayed in the boat but in the summer I believe you stop in a cave to swim a bit and take photos.

We drove from there to Cape Sagres, the southernmost point of Portugal. We started at the Sagres fortress, which is absolutely worth the 3 euro (I think) entrance fee. We ended up spending over an hour at the fortress taking photos by a gorgeous white building. I wanted to give my parents some gorgeous photos for their 25th anniversary and we took those here in Sagres.

When approaching the fortress, on the right hand side you will see this amazing view with a path to the edge of the cliffs. This is absolutely the very best view! And you can take an alternate route to descend down to the beach, which is just teeming with surfers (we didn’t have enough time to do this).

That amazing view

We drove from here to Lisbon, our final destination. We returned our car early because it was made clear to us that a car would just be a hinderance in the city. Our Airbnb in Lisbon was in Alfama which was an absolutely amazing neighborhood to stay in. It’s not accessible by car and is all little restaurants and shops on tiny colorful streets. I’d highly recommend staying in Alfama or Bairro Alto – a slightly more commercial area that we spent a lot of our time in. Both are equally convenient in terms of walking distance to most things.

Picking out the fish for dinner at Sea Me

We ate dinner at Sea Me – highly, highly recommended (and recommended to make a reservation if you can!). It’s an amazing Japanese/Portuguese fusion restaurant where you pick out your fish at the back of the restaurant. I had the most incredible sushi.

Day Six and Seven

Another family photo, this time in the little streets of Alfama

I’m packing our Lisbon adventures into one list, because at this point in the trip we were all exhausted and took a lot of breaks at the apartment.

We ate breakfast one day at The Mill, in Bairro Alto, which was recommended to us by a friend. It was a very hip, Brooklyn-style breakfast place with great food and drinks.

We stopped at Bica Funicular, the most photographed street in Lisbon, to… take some photos, obviously! Then we walked to a little outdoor market (which felt seasonal) to get some daytime Sangria.

Sunset view from Miradoura de Santa Luzia

We wanted to go to Castelo de Sao Jorge for sunset but the line just to get in was insane so we watched the sunset from Miradoura de Santa Luzia, which actually ended up being spectacular. “Miradoura” means lookout point in Portuguese and you should definitely be on the “lookout” for them. Haha.

We went to both the Tile Museum and Fado Museum. The Tile Museum was absolutely wonderful and I’d highly recommend. We only actually went to the Fado Museum because it was right by the apartment but it was fascinating to learn about the history of fado (traditional Portuguese music), especially because our dinner on the last night was at a restaurant with live fado music.

One night we ate good dinner at Santo Antonio Restaurante in Alfama. We also loved eating and chatting with the owner at Cantinho Da Rute, right next to our apartment.

Our first night the Praca do Comércio was putting on a big concert series. We were too tired to stay until the fado performer at the end but had a great time dancing in the square.

Final Thoughts

Portugal is an amazing country and an absolute must-visit. The people there are so nice, the food is cheap and every corner is so beautiful. If you’re going in the summer you can probably split your time between Lisbon and The Algarve. We loved the route we took in the winter (although 9 days would have been better for us than 7). You could also spend a whole week just in Lisbon! Our two favorite spots (Evora and Obidos) aren’t so easily accessible if you don’t have a car. Unless you’re staying the whole time in Lisbon I would highly recommend getting a car for the trip. And don’t forget to say “Obrigado/obrigada” (thank you!) to everyone.

Dancing around Portugal

Are you going to Portugal any time soon? Do you have any tips from your own trip? I'd love to see photos!