Dearest gentle reader,

Wait, sorry, it has been so long since I’ve written a travel blog that I think I may have forgotten how to even start. Sigh. Believe it or not, “write blog post about Portugal” has literally been on my agenda pretty much every weekend since April 2023.

Since April 2023, dear reader, is when our most recent European adventure concluded. I’ll give you a moment here in case, like me, you need a moment to remember that the year is currently 2024. 

(AND THIS IS WHERE I INTERJECT TO NOTE THAT I CAME TO THIS WEBSITE TO WORK ON A POST ABOUT OUR 2025 TRIP TO EUROPE, AND NOTICED THAT I HAD ALREADY MOSTLY FINISHED THIS POST BUT NEVER ACTUALLY POSTED IT. SO ADHD KASEY’S BRAIN SAYS, FINISH THIS ONE INSTEAD AND THEN MOVE ON TO GREECE/ALBANIA/NORTH MACEDONIA/SICILY/AMSTERDAM.)

ANYWAY. Portugal. Lovely Portugal. This trip was known as the “one that got away,” as we were meant to go to Lisbon as a family for Spring Break in MARCH 2020. Anyone else remember what we ended up doing instead? I’ll give you a hint: it rhymed with schmockdown.

As you may recall, we moved back to the United States somewhat unexpectedly in January 2022. We are now living in Ohio, in a lovely community with many fine points but which is unfortunately very short on volcanoes, castles, beaches, granita, and many other things we adore. Do not even get me started on how much we missed our friends as well. All this is to say, that homesickness got channeled into planning another European vacation for 2023. Of the trips that had “gotten away” during Covid, Portugal felt like the obvious choice, in part because flights were so affordable. Originally, we intended to stay for about nine days because we were trying to ensure the kids did not miss too much school. Then the airline changed the return flight and they would have been missing five days of school instead of three, so we said screw it and changed the flight so that they ended up missing six instead. Sorry, school.

Our itinerary for two weeks in Portugal with our kids, then age 10, 8 and turned-4-on-the-trip, was roughly the following:

Day 1-3: Porto, day trip to the Duoro Valley

Days 4-6: Sintra

Day 6-11: Lisbon with friends!

Days 12-13: The Silver Coast

Obligatory How-Points-Factored-Into-This-Trip Round Up
My usual caveat: fancy points people will not be impressed by my airline choices. I might choose differently now, two years after making reservations, but honestly I still think we got a pretty great deal for economy.

Flights: Washington D.C.-Porto, Lisbon to Columbus, roughly 250,000 Capital One points (around $500/each)

Rental cars: Used Capital One travel credit for a rental car in Portugal, Chase points for a one-way Columbus to Washington D.C. rental car.

Hotels: We burned six Marriott free-night certificate for two connecting rooms at the FABULOUS Penha Longa resort near Sintra. 10/10 would recommend. We used a Chase credit for one night in Lisbon (we ended up staying longer there than expected because of our flight change). We also used a free night certificate for a Washington D.C. hotel, but that ended up getting refunded entirely because they accidentally charged my card instead and could not figure out how to fix it. All told, we paid cash only for our Porto Airbnb, Lisbon AirBnB and Silver Coast AirBnB (9/15)

And now — onto to the trip itself. 

A little oddly, we actually started our trip from Washington, D.C. for various reasons (money). We made the six-hour drive on Thursday night, even though our flight was not until about 4 p.m. Friday.  Thus, our trip started by marching our kids for literally six miles to see various monuments in D.C. Our theory was that if we got them tired enough, they would sleep on the plane and thus be in good shape to stay awake until a normal bedtime in Porto, thus destroying jetlag. Happy to report this plan actually worked great.

We arrived in Porto without incident mid-afternoon, rented a car and drove to our AirBnB in Villa Nova de Gaia, just across the river from Porto. In a whole trip of great accommodations, this one was probably my favorite because the entire back wall of this place was windows looking onto the fantastic balcony. You guys know how I feel about places with this kind of windows from the Romania trip, ha. The location was not the most central, but Ubers were so cheap that we just parked our car and grabbed an Uber when we wanted/needed to go downtown.

I had made restaurant reservations at Vila Nova de Gaia’s “World of Wine” district, which included a ton of great places to eat. Since I was not sure whether my anti-jetlag plan would actually work, I wanted to make sure we could feed them at an-earlier-than-normal-for-Portugal time and then send them to bed early if needed. Thus, I booked at the only place that took reservations for 6 p.m., resulting in them calling me, concerned, to ask if I really wanted to come at that absurd hour. Sure did! And that, my friends, is how we ended up being THE ONLY PEOPLE IN THIS ENORMOUS RESTAURANT FOR TWO HOURS. It was called T&C, and it was lovely.

Our plan was to potentially go to the nearby Pink Palace, one of several themed World of Wine mini-museums. Pink Palace is rosé theme, but it was kid-friendly with ballpits and fun stuff to look at. However, tiredness won out and we did not go that evening, instead heading back to the AirBnB to sleep.

DAY TWO dawned with more pre-planned jetlag-killing adventures! I arranged for us to do an e-bike tour at 11 a.m., as our previous e-bike adventure (in Puglia) remains an all-time favorite. As usual, it was a bit tricky to find a place that would allow kids Owen and Fiona’s ages, but we ended up doing a tour with BlueDragon, booked through GetYourGuide. Fiona was juuuuust tall enough for the bike (happy days!) and Lochie sat in a baby seat on my bike.

The first half hour of the trip was pretty alarming as we watched the kids trying to figure out the e-bikes, but mercifully someone else on the tour was struggling with their bike so we were shockingly NOT the troublemakers of the group. The three-hour trip ended up being a perfect way to see a lot of the highlights of the city and learn some history too.

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Afterward, we had a fabulous lunch by the river, where I sampled the Porto specialty,  francisinha, a sandwich that is sort of like a meat-filled grilled cheese covered with tomato soup. It was not my favorite, but I was glad to try it at least.

We spent the rest of the day walking around, including venturing back across the river to the Gaia side to pop into various port cellars. As you may know, port is a fortified wine made specifically in the Duoro valley. Until the late 1980s, it could only be exported from Vila Nova de Gaia.

We wrapped up our day with a visit to World of Chocolate in the WOW district, followed by a fabulous dinner at PIP in the district. The World of Chocolate was not quite as exciting as we hoped (we were picturing a ton of chocolate samples) but still worth a visit if you have kids with you.

DAY THREE in Portgual was tour day! We wanted to see parts of the Douro Valley, especially the wineries, but struggled to decide on a tour since many of them were all-day or multi-day affairs (not good with the kids) or were cost-prohibitive. We ultimately booked a half-day tour with Portugal By Wine, and tour guide Joao was exceptional! It was a group tour, but we ended up being the only people signed up so that worked out great for us. We drove our rental car to a pickup in Peso de Regua, then toured some small towns in the Douro Valley and one winery. Joao was extremely kind and informative, and even volunteered to take the kids on a nature walk while we did a winery tour. I cannot recommend him highly enough!

By the time we got back to our AirBnB, it was pretty late so we went with a take-out and TV kind of evening. Chris and I stayed up way too late watching IU get murdered in the second round of the NCAA tournament on one of the kid’s iPads. SIGH.

Day Four was driving about three hours to a resort near Sintra. We thought about stopping by Aveiro or Coimbra on the way, but ultimately decided against it.

PHASE TWO OF THE TRIP: PENHA LONGA RESORT

This phase of the trip was inspired by 1) Chris and I each having five free-night certificates from a Marriott credit card promo, and 2) seeing a lot of people on my points groups talking about this hotel as being a great bargain considering it had a lot of amazing restaurants on site (including two Michelin starred ones!). We decided to treat ourselves for this particular occasion. Good experience, but probably not something we’ll make a habit of.

Since European hotel rooms have stricter occupancy  rules than American ones typically do, we had to book two connecting room instead of a single to share. This was AMAZING and I wish we could afford to do it every time. Practically a whole wall opened up between the two rooms, so we were plenty close to the kids when we wanted to be. But also, it was a door. That closes. Yay!

The Penha Longa is near the city of Sintra, on a huge property with a lot of fun stuff to offer. While we were there, we enjoyed the pools, rented a golf cart to drive around, played giant chess and spent a lot of time in the kid rec-room areas. Chris and I decided to splurge on our first-ever Michelin restaurant experience while there. We booked a babysitter through the hotel to watch the kids for a few hours while we went, as we certainly were not bringing them with us. It was the most amazing meal I’ve ever had, but also took an insane turn. If you want to hear more about this MASSIVE FIRST WORLD SITUATION and also about how we are idiots, please see the very end of this post.

Our last day at the Penha Longa was Lochie’s 4th birthday (note from 2026 — he turns 7 in two months ahhhh), and we opted to go see Sintra. This was kind of a should-we-or-should-we-not thing because we planned to do a whole tour of Sintra with our friends when we met up in Lisbon, but we decided to go for it anyway. On a few trips, we’ve left the thing we wanted to see the most until the very end of the trip, and something random has come up to make us miss it. So we decided not to risk it, and headed for the Pena Palace. It was a bit of a hike to get where we needed to go, but it was gorgeous!

Afterward, we ended up at a Pizza Hut because that was what the birthday boy wanted. After our experience at the Michelin restaurant the night before (see below) we were not complaining.

Phase 3: Lisbon with friends

As I mentioned early on, we were (and still are!) missing our friends from Sicily as we were planning this trip. After we booked it (about six months ahead of time), I mentioned what we were planning to my Motta Mamas group chat. Two of my girlfriends ended up deciding to come along too, along with their families! All told, we had six adults and seven kids with us, ranging in age from 10 to 4 at the time.

I ended up finding an AirBnB that was described as being three apartments that can be combined. It was supposed to be nine bedrooms and six bathrooms, which we assumed meant each apartment had three bedrooms and two bathrooms — perfectly even. Instead, it ended up being a 4bed/3ba, 3bed/2ba, and 2bed/1bath. Whoops. It was nice to have some separation but all still be together in the same place though, especially for my little introverts.

First stage of our grand reunion was a meal at Lumi, a rooftop bar near our hotel that was just gorgeous. It also had the advantage of being one of the very few that a) would take a reservation for a very large group, b ) was serving food very early. I was dying to go to one of these rooftop bars, but I will say that one thing I did not consider was that it might be hot up there, given that it was March. It did indeed get very hot up there, but we had an excellent time catching up anyway.

On the way back, we looked around for a while and then ultimately headed to the AirBnB to hang out.

For our first full day in Lisbon together, we had a great time visiting the zoo with our pack of animal enthusiasts and visited the Time Out market in downtown Lisbon.

And a meal at the Time Out market! I will say this place was a fairly chaotic option to choose with kids, but everyone could get what they wanted. On the other hand … everyone expected to get what they wanted, and to tour the whole damn place to figure out what they wanted. Yeahhhhhhhh. I actually think this would be kind of great now (2026) because the bigs could go order and collect their own food.

After a kid-centered day, however, came PARENTS NIGHT OUT! For this, we booked a babysitter through the Mary Poppins Agency, which sent two lovely babysitters to handle the crew. This is another way the combined AirBnB came in handy. We did this a second time too, on Monday night.

For our night out, we chose a restaurant that our friends Matt and Christine (the two on the left) had visited about 10 years before, O Chaido, for the famous “steak on a stone.” This place theoretically did not have space for us when we tried to book online, but reaching out to explain the situation led to them agreeing to set up a table for six. The people there could not have been nicer! We adored this place.

Funny story — Matt and Christine remembered loving this place and loving the steak on the stone, but did not remember all the details. Trusting them, I went ahead and just ordered that anyway. When they did not ask me for a temperature for my steak, I joked that it better not come out raw. So, it was pretty hilarious when this was served to me:

Turns out, the thing is that you cook the meat on the stone yourself. It was fun and super delicious!

Sunday, we booked a private half-day tour to Sintra. I am quite certain there are public transit ways to get there that would have been cheaper, but we wanted to make things as simple as possible since we were traveling with seven kids. We booked a private, full-day tour that picked us up right at the AirBnB in a pair of vans. We had a bit of a rocky start with a car-sick kid, but once we reached Sintra things had pretty much chilled out.

We briefly looked at the Sintra National Palace, then most of the group went to Pena Palace. Since we had already been there, we look some time to look at the Moorish Palace in Sintra instead.

Afterward, we hit the Quinta da Regaleira, an estate built by an eccentric millionaire and naturalist. This property had a gorgeous house and grounds, but the most interesting thing is the “Initiation Well,” the purpose of which is entirely unclear even now.

After this, we headed to a nice lunch set up for us in the seaside community of Cascais, complete with wine tasting. We stopped by the beach briefly, at the kids’ request, and most of the adults (including MY HUSBAND) opted to stay off the sand. Those of us who did not got to fish the two youngest, Lochie and Lucy, out of the water after a COMPLETELY ROGUE WAVE attempted to claim them.

Fortunately, the kids had changes of clothes with them. Shockingly, I did not think to bring clothes for myself, so I just got to be all wet from carrying a sobbing Lochie off the beach and to the car.

Our final stop was Cabo Da Roca, the westernmost point of Europe. The kids all got very expensive documentation of their visit, which they have never looked at since. Do not recommend, haha.

On Monday, we spent time at local parks, followed by a visit to the amazing Oceanarium da Lisboa.

Our final adventure of the day with the kids was a ride on the Hippoboat, an amphibious vessel that takes you on a tour of Lisbon that involves periodically plunging into the river. It was a little cheesy, but the kids got a big kick out of it and it was an easy way to see some sights.

We got the nannies back that evening, and the adults went out on another adventure. This time, we did not have reservations but we got lucky enough to snag the last spot at another gorgeous rooftop,Java.

Originally, my family was supposed to be leaving Portugal entirely after this, but our flights got unexpectedly changed. By then, it was too late to add another night at our Airbnb, so we all booked at nearby hotels. It was a pretty low-key day for us, just spending time together.

Part Four: The Silver Coast

Since we were originally planning to leave two days earlier and from Lisbon, we had a couple days to fill after our friends left. We considered a ton of options, but did not want to drive far so we ended up heading toward Portugal’s Silver Coast. We stayed at a super cool Airbnb that had an indoor pool in the basement, then pretty much just chilled out. We did a walking tour in Obidos, which was lovely, and had dinner in Nazare, a town famous for enormous waves.

I am a huge fan of walking tours when traveling with children, as they are usually pretty short and are a good way to see the highlights and learn some things. Obidos was a gorgeous city!

Most importantly, we also picked up a bunch more ginja, a gorgeous cherry liquor often served in chocolate shot glasses. We had it all over Sintra and Lisbon, but it was particularly good in Obidos.

The Torre Branca apartment near Obidos, it was in a very small town and the owners were extremely nice.

Our final meal in Portugal was at Pangea by the Sea in Obidos, which was amazing! In addition to this blue sangria, we had amazing calamari — and this is coming from someone who is not a fan of that at all.

The next morning, it was back to the airport for our return to reality (SOB).

And now, for the promised bonus content.

IN WHICH WE EMBARRASS OURSELVES IN “HIGH SOCIETY,” or

OUR MICHELIN STAR EXPERIENCE AT LAB BY SERGEI AROLA

I will preface this by saying that I am aware that we were aware we were signing up for an extremely extravagant meal experience, and also that it is was an absolutely incredible meal. I am not really complaining, merely sharing this story because it is a fun illustration of our idiocy …

With that warning, here goes.

Going to a Michelin star restaurant was part of the draw  of staying at the Penha Longa, one we justified by thinking, we aren’t paying for the stay anyway, so why not? We chose LAB by Sergei Arola. Originally, I figured we’d just do the set menu and not pay for the wine pairing, but Chris happened to win a $500 prize through this Lions Club drawing my dad enters us in every year, and we decided “fuck it.” With the wine pairing, the meal was going to be something like 450 euro. I made my peace with that, even though it is OBJECTIVELY INSANE to my mind.

So going into this, my preoccupation was with psyching myself up to eat everything put in front of me. I am historically NOT an adventurous eater, something I’ve been trying to correct in myself for a while now. So on the way over, I’m giving myself a little pep talk about how EVERYTHING IS EDIBLE, JUST EAT WHAT THEY TELL YOU, YOU WILL BE FINE. That’s where my focus was. (Already making excuses here).

So when we arrive and our reservation is not going to start exactly on time, the maître d’ invites us to go to the bar and have a glass of champagne. He recommends one in particular and I’m thinking, ok, you are the expert. I’m also thinking, pretty sweet that we get an extra glass of wine because they are running late.

Ha. Hahahaha. SOB.

So the meal starts with this “tour” of Portugal with seven insane presentations of little tapas from various regions in Portugal and one from Spain. One was a shrimp that looks like a fossil and has to be excavated from sand made of some kind of spices (that one was the only one I thought was gross, and sadly was the very first one, so cue panic haha). Everything else ended up being very delicious and unique, and when it finished we were brought into the tiny dining room for our actual meal. It was amazing, but the theme seemed to be: why does this thing taste completely different than I would have guessed, and why is it more delicious?

For instance, the “cookie” on top of this gold kiwi bird was in fact filled with blackberries and MEAT.

So with each course, there is new wine. We did notice that most other patrons in this place were not drinking the whole wine brought to them, but we paid for the wine pairing, damn it. We are NOT leaving wine on the table. This is one of our core values as a couple.

So at various times during the meal, the waiter tells us that the sommelier recommends another specific kind of drink to go with a specific course, and do we want that? I remember thinking, why ask us? We paid for the wine pairing, you are the experts, I do not need to get real involved with this decision.

As you have probably already gathered, we should have obviously clocked that for some drinks they ASKED us if we wanted it versus just pouring it into the glass like with most of the rest of the wines. This should, perhaps, have tipped us off that there was something different here. On the other hand, we were finishing those glasses of wine so our judgement was, ahem, impaired.

I’d like to emphasize that this was a pretty small dining room, just a handful of other tables and you could easily hear other people talking at their tables. Including one woman who bitched at length about how she had to fly economy to get here. The “cozy, intimate” vibe kind of backfired on us, however, when they brought Chris the bill and he quietly handed at me to look at it.

“WHAT?!?!” -Kasey, a million wines deep, after being presented with the bill. I literally gasped. Loudly enough for basically everyone in the restaurant to hear.

In my defense, I had just been handed a bill for MORE THAN EIGHT HUNDRED EURO.

Chris was mortified. Not my finest moment. Luckily I collected myself and went back to trying to pretend this is just a NORMAL EXPERIENCE because we TOTALLY BELONG HERE. But I’m pretty sure the damage was done at that point.

It seems that since we are total rubes, we missed the unspoken rule that if you are ASKED if you want something, it means there is a price attached. The “complimentary” champagne was like 50 euro a glass. The additional drinks (and I think one of the desserts?) were also outrageously expensive. Since we blindly said YES to everything offered, things, uh, added up.

I am still a little traumatized.

That said, we’d already pre-paid the babysitter and had like 45 minutes to kill, so Chris and I did the only thing we could.

Went to the hotel bar for 15 euro gin and tonics.

Fin.