My mom, her sister, and my two young girls (ages 5 + 10) have been planning a Spring Break trip to Paris and Versailles for nearly a year. If you’ve been following along in the news, you’ll know that protests have been rampant in Paris and Versailles and, while European protests are pretty much a way-of-life, these seemed to be a bit “more” than the usual. Besides, major tourist destinations were being randomly closed depending on how extreme the protests were on any given day, and who wants to go all the way to Paris and not have access to the Louvre?
Since we were traveling with the littles and had booked fully refundable tickets, we decided to make a last-minute change of plans. Portugal had long been on my, my mom, and my aunt’s bucket lists, so we decided to re-route to Lisbon. We had five days to find a hotel, and book flights, restaurants and excursions. I immediately called my brother who had done a Portugal trip recently.
My brother is pretty much always traveling and does extremely thorough (especially culinary) research before his trips. He had lots of great tips and a Google Travel list of Lisbon that he was able to immediately send me. I also turned to Instagram and was very fortunate to get lots of tips from Lisbon locals, Portuguese-Americans, and people who have traveled Portugal extensively. So, after vetting all the recommendations for kid-friendly options, this is what we did (and what I would highly recommend):

HOTEL
We stayed at the Pestana Pousada Lisboa – Praça do Comércio. The rooms here aren’t exactly economical, but for what this hotel offers I was honestly shocked by the $350 sticker price. The location was unbeatable (especially for elderly and young kids – more on that in a sec), the views were top-notch, the food INCREDIBLE (with free continental breakfast and a great restaurant), the rooms well-designed and it even had an indoor pool to boot. The concierge was also clutch. I’m not one to usually turn to concierge for help and advice (as I usually wing it based on previous recs), but because this trip was booked so last-minute, they were able to help us with car bookings and reservations with very little notice.
I usually have some kind of complaint about a hotel. Maybe the food isn’t so great, or the concierge makes bad recs, or the location leaves something to be desired, but I can honestly say our seven-night stay at the Pestana was absolutely flawless. I also mentioned previously how it’s a great hotel for kids and the elderly. I say this because Lisbon is a VERY hilly city (it’s basically the San Francisco of Europe), but this hotel is located right on Praça do Comércio (one of Lisbon’s most important squares).
Praça do Comércio is also right near the (flat, sea level) waterfront which is lovely to walk on, but it also had taxis, tuktuks, scooters and bikes available within 20 yards of the hotel entrance. It’s also worth noting that I linked the tuktuk just so you can see what it is if you don’t know, but I wouldn’t recommend booking ahead of time. They are readily available in Praça do Comércio for less money (even negotiable prices, though I do believe in paying these people ever penny they deserve). There are also loads of shops, churches, restaurants, etc. within walking distance (without having to climb a single hill). And if you’re up for the climb, my favorite area of Lisbon, the Chiado neighborhood, is a very short walk from the Pestana Pousada. Even if you opt to not stay at the Pestana Pousada, they have a very lovely restaurant with very lovely outdoor seating that I would highly recommend for lunch or a late afternoon cocktail!

DAY TRIPS
I’ve done a lot of different types of Euro trips. Some have been “let’s see ten cities in ten days!” while others have been “let’s stay put and really explore this place.” Because we were traveling with young kids, I wanted the pace of this trip to be really manageable. We opted to stay in Lisbon for seven nights, and do a couple of day trips. Honestly, it was such a good call. Lisbon is a much larger city than I imagined it being, with lots to do. Plus, there are several cities and towns that you can reach in less than an hour that are just INCREDIBLE. The first of which was Sintra.

Sintra
We spent about 3/4 of a day in Sintra, though I wish we had more time. We booked a tour guide and a car from Lisbon (via the Pestana Pousada) and that was also a VERY good call. Our tour guide was extremely knowledgable and it made the day very fulfilling.

One of the main places that people visit in Sintra is the Pena Palace. Our tour guide recommended that if we only have one day in Sintra, we should opt out of the Pena Palace and head to the Queluz National Palace. His reasoning was that the lines to get into the Pena Palace are hours-long, and even once you get inside it can be a long wait. If we did Queluz (an extremely underrated gem), we’d be able to see more in Sintra. I’m so glad we made that call because not only did it allow us to see more, the Queluz was just incredible. The Queluz Palace is largely recognized as one of the last important Rococo palaces built in Europe, and it is just an absolute dreamland (with no lines and no crowds to boot). One thing to add about the Queluz is (I think) this would not be an easy place to access via train, so booking a car service would be best.

Next, we took some time on some hiking trails in União das Freguesias de Sintra. It was great having the tour guide because he was able to show us some of his favorite spots on the trails. This was one of my favorite parts of our trips, and if I had more time (and wasn’t with a five year-old), I would have opted to spend a day hiking these trails!
The last thing we did in Sintra was to hit up the Historic Center of Sintra. We didn’t have a ton of time here, but what I can say is it is one of the most romantic and beautiful areas in all of Europe. Our tour guide highly recommended we go to Casa Piriquita to get the Travesseiro and, damn, this pastry has to be in the top 3 best pastries I’ve ever had.

Cascais
I think it’s often debated as to whether Cascais or Sintra would be more worth a day trip from Lisbon (if left with the unfortunate situation of having to choose). Honestly, that’s a really tough choice. While Sintra offers unmatched romanticism and mountain views, Cascais is a stunning beachfront town with wonderful shops and restaurants. While both Cascais and Sintra are accessible by train from Lisbon, I would say that Cascais would be the better location to travel by train as so much of it is easily seen within walking distance of the train station. Sintra, by contrast, is extremely hilly and much of what is great to see there is spread out and better accessed by car (note: there is still a lot to see within walking distance from train, just not quite as much as Cascais).

We went to Cascais two different days of our trip. The first was via car and we were able to see some really stunning locations/beaches outside the town center. We ate at a gorgeous waterfront restaurant called Mar do Guincho that had decent (nearly all seafood) food (but really go for the views). If you pop Mar do Guincho into your google maps, you’ll also see the nearby beaches, which are incredible. We also popped by Cabo da Roca, which is an utterly breathtaking spot that is the westernmost point in all of Europe.

The second trip we made to Cascais was for nearly an entire day. We went to the beach in downtown Cascais which was fun, with some great food trucks next to it. Still, if you’re looking for a beach day, opt for the other beaches near Mar do Guincho. We spent a lot of this day just perusing Cascais and popped by what is often regarded as the best gelato in the Cascais, Santini.
Fátima
My aunt (who is mildly religious, while my mom and I are not) took a day trip by herself to Fátima. While I was not in Fátima myself, I think it might be worthwhile to report the consensus between my aunt, our tour guide and the hotel concierge: if you are not very Catholic, it might be best to skip Fátima.
LISBON RESTAURANTS
I sometimes talk about how I come from a family of foodies. My Italian grandfathers were really the fabric of our family’s food obsessions. As two quick fun anecdotes: my paternal Italian grandfather fought for the Allied powers and was an Italian translator, based at an Italian POW camp in New York. On Sundays, he would stuff as many POW’s as he could into his trunk and his car, and sneak them home for Sunday pasta (priorities!).
My maternal grandfather had a huge garden where he would grow his fruits and veggies and cook as much as possible from it (a tradition my mother inherited). Every Saturday, he would bake about 25 loaves of bread (he went to the grave with that recipe, though some of his last words were trying to dictate it to Billy). On Sundays, he would go from house-to-house of his family members and neighbors to deliver the (highly coveted) loaves.
My brother (basically my maternal grandfather reborn) now owns Southdown Coffee, where his egg sandos and pastries have even made Food + Wine drool.
In short, my family doesn’t f&ck around when it comes to food, so I feel very confident that the recs I am about to give you will be worth your while (mostly because they initially came to me by way of my brother and locals). The food in Portugal also reminds me of the Italian food that I grew up on; made from scratch and the heart, with the freshest ingredients. I have approximately zero food credentials myself (other than having the great fortune of being surrounded by these very talented cooks and love eating perhaps more than any other activity on earth). GIVE ME ALL THE FOOD!

Prado/Prado Mercearia
I’d like to preface this rec by saying that I accidentally made two reservations at Prado Mercearia, and never had the pleasure of eating at Prado. Prado Mercearia and Prado are on the same block and are sister restaurants, with the former being the tapas wine bar to the latter. If you’d like to eat at Prado (from everything I’ve heard, this would be a very good idea), be sure to make a reservation. I did pop into it and all I can say is the interior design alone would make me want to eat there.
Prado Mercearia was also incredible in its own right, and a great spot to pop in for lunch. The wine list is full of local natural wines (including the famous “green” wines from the Verde wine region of Portugal). Aside from having a top-notch wine list, Prado Mercearia has an incredible tapas menu that I believe is ever-changing, and the breads, meats and cheeses are also to-die-for.

Senhor Uva
Senhor Uva is a very tiny restaurant (make a reservation!) at the very top of a very steep hill (take a cab!). It is also vegetarian (not vegan), so if you’re a meat monster, maybe skip this one. Senhor Uva also has an ever-changing menu, but the tapas were INCREDIBLE and this was maybe my favorite meal in Portugal. Senhor Uva is also known for its top-notch natural wine list. We went with the kids and that was totally fine, but I can imagine this being a great date spot, too.

Chef Felicidade – Pharmacia
The food here was really very good, but not quite on the same par as Senhor Uva and Prado Mercearia. Still, the main reason I would recommend this spot is for the ambiance and the views. I would make a reservation here, too, as even for lunch it can be hard to get in. Depending on the time of year you visit, requesting a seat outside isn’t a bad idea as the views are amazing and it’s a really unique setting. Be aware, that most of the tables don’t have shade, so on a hot day, it might be best to sit inside.
While we went here for lunch, I can also imagine this being a fabulous spot to grab drinks and some appetizers before the sun goes down. Be aware that Pharmacia is also at the top of a very steep hill. We opted to tackle the walk from the waterfront, which made us really feel like we deserved those French fries.

Manteigaria
I’ve been told Manteigaria has the best Pastel de Nata (a custard pastry) in all of Lisbon. And, damn, they must be right. Do NOT miss out on popping by ones of their locations and grabbing one warm and straight out of the oven.

Nannarella
This Roman-style gelato spot was hailed by many as the best gelato in Lisbon. The line was long (even late at night), and it’s worth popping by if you’re in the area. Personally, I found Santini (which also has a Lisbon location) to have a slight edge, but I say try both! Never too much gelato, right?

WHAT TO DO IN LISBON
SHOP
Especially in the Chiado neighborhood. There were soooo many incredible boutiques with incredible clothes, accessories and shoes. No one in our group could really be considered a big “shopper,” yet something about those unique, quaint boutiques of Chiado was irresistible to all of us. For kids clothes, be sure to pop into Loja Dada. And just around the corner, you’ll find a bunch of great spots, like 21.pr concept store and the stores surrounding it. Another favorite was a short walk away, but still in Chiado. Unfortunately, I cannot remember the name of it, but if you are facing the Carmo Convent, take a right down the hill and it will be on your right (just before the church, which is also worth popping into!).

VISIT THE CARMO CONVENT
The square outside the convent is visit-worthy in itself for a quick espresso or a leisurely cocktail, but the monastery ruins themselves are really quite amazing and worth the visit. A lot of sights in Lisbon are on the outskirts (like the Belem Tower), but the Carmo Convent is smack in the middle of all the action. Lisbon suffered a devastating earthquake in 1755 and very little survived it. The Carmo Convent is the ruins of this medieval masterpiece, and there is something quite majestic about being in the midst of it.

TAKE A TOUR BY TUKTUK OR HIPPO BOAT
Josie loved our first TukTuk tour so much that she begged for a second (I rewarded her with a second one on our last day for good behavior). The fun thing about the TukTuks is that they have specific routes/themes, so if you do more than one, you’ll see different sites. The Hippo boat was another highlight of the trip. It’s a bit of a pain to get to (it’s near Belem), but worth the trip if you have the time. Our tour guide was wonderful and hilarious, and the boat takes you first around the city, and then into the water. It was cool seeing the city from both perspectives, but the thing that really made the Hippo boat a home run was that the kids REALLY loved it.
VISIT THE LISBON FLEA MARKET
I’ll admit, I wasn’t entirely impressed with the vintage wares at this market but take what I’m saying with a grain of salt because most flea markets are hit or miss. That said, the indoor part of the market has great food and there are tons of vendors. Some have lots of junk, and others have some great stuff. Pricing varied by vendor, but one of the great things about Lisbon is that prices are much more reasonable across the board vs. other major American or European cities.
Keep in mind, this market is only open on Tuesdays and Saturdays, starting at 9am. Also be sure to pop into The Church and Monastery of São Vicente de Fora, a mannerist masterpiece situated immediately next to the Flea Market.
STROLL THE WATERFRONT/POP INTO TIMEOUT MARKET
The waterfront is nice and flat and is a beautiful spot to take a long stroll. The TimeOut Market Lisboa is only about a block from the waterfront, and is worth popping into for some quick bites!

I can’t wait to take another trip back to Portugal as I am so eager to explore more of the country. The people were incredibly kind, the food was amazing, the weather spectacular (we visited early April) and the views just (chef’s kiss). After we returned, my brother asked me what my favorite part about Lisbon was. My answer? “I just loved walking the streets. The architecture is magical and the vibe is infectious.” He responded with, “yep. that was my favorite part, too.”
Thank you so much for this fantastic & detailed guide!! We’re headed to Portugal next month & staying at the same hotel in Lisbon. Your food recommendations are so appreciated. Thank you!
Thank you for sharing! What a beautiful trip with family!!!
I loved seeing Portugal through your eyes! Thank you for writing about your lovely Girls Trip vacation.🌱
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