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Jill Schildhouse
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- I made mistakes on my first trip to Lisbon, but I also got a few things right.
- I'm glad I did a guided day trip to Sintra and tried a tram, even though it wasn't very efficient.
- Visiting in late winter was a smart move to dodge crowds, but I wish I'd spaced out our itinerary.
My dad and I went to Lisbon on a last-minute whim in February.
We landed with no real plan beyond "eat, walk, repeat," which the Portuguese city rewarded — and then promptly humbled us with hills, staircases, and a few rookie mistakes.
This is the playbook I wish I'd had: what mattered on the ground for a first visit, where we accidentally nailed it, and how I'd structure the days if I could do it again.
It's important to wear the right shoes and give yourself extra time to navigate hills.
Lisbon's beauty stacks vertically. I learned to start days "up" and wander "down," saving energy and time.
When it rains, those calçada stones turn slick. Grippy shoes helped us get around, but the real hack was planning routes that flowed downhill.
Also, pad your itinerary because Lisbon's miles are sneaky. Everything seemed close by until we came across a staircase.
Eventually, we started adding a buffer between activities and stopped trying to pinball across the city. One great meal, one big sight, one slow neighborhood wander — that's the winning tempo.
The trams were cool, but they weren't the most efficient mode of transportation.
The vintage cars are adorable and fun to ride, but I found them to move quite slowly. They're not ideal if you're trying to cross town on a tight schedule.
We rode them when we weren't in a rush — otherwise, we walked or grabbed those wonderfully cheap Ubers.
If you want to grab one, try the yellow Tram 28. It's known for its scenic route through iconic neighborhoods like Graça, Alfama, Baixa, and Estrela.
Some of the famous pastry shops are great, but you don't need to wait in line to get tasty tarts.
On our trip, we made sure to try the area's famous pastel de nata tarts. One night, we got them at the famous pastry shop Manteigaria.
Though the place is popular, we were able to head right inside after dinner without waiting in line. The tarts were warm, creamy, and perfect.
We also had lovely versions of the treat at the famous Pastéis de Belém. Both places lived up to their hype, and I suggest visiting them.
But don't be afraid to try a lesser-known spot — especially if there are long lines to get in. Throughout our trip, we stopped at several different neighborhood pastelarias to grab pastel de nata, and the tarts were all tasty.
However, I learned not to believe all of the hype I see online about certain eateries.
I'd seen a viral TikTok of someone saying the pork sandwiches at As Bifanas do Afonso were life-changing, so I told my dad this was a must-visit spot on my list.
Once we arrived on a Monday afternoon, we were met with a wildly long line. My dad's immediate reaction was to suggest going somewhere else, but I talked him into staying.
It took us about 45 minutes to make our way to the counter and place our food order. After all that, we didn't even think the sandwiches were particularly special or memorable.
Ultimately, the time we spent in line is just time we could've spent seeing more of the city. My dad will never let me live this one down.
Now, I know not to believe all the hype I see online and will reconsider how long I'm willing to wait to try any new restaurant.
It turns out that late winter is a perfect time to visit Lisbon.
We visited Lisbon at the end of February and felt like we'd hit the jackpot: blue skies, mild temperatures in the 60s Fahrenheit, and only a few drops of rain one afternoon.
Since our trip wasn't during Lisbon's peak, busiest season, the city also felt breathable and not overly crowded.
We didn't have to wait in long lines for certain attractions and felt had room to actually enjoy the streets without elbowing through tour groups.
Knowing a few dining basics (and recommendations) can save you time and money.
While eating our way through Lisbon, we picked up a few helpful tips.
First of all, it's common for servers to offer to bring couvert (bread, olives, and cheese that you can nibble on before your meal) to your table. However, keep in mind that they typically are not free.
Turn them down if you don't want them added to your check.
Also, if you want to try as much as possible without ordering too much food, lean into petiscos, which are Portuguese small plates.
And if sardines are in season, order them once and thank me later — just be aware that the bones can make mealtime a lot of work.
Sintra was perfect for a day trip, and I'm so glad we paid extra for a guided tour.
During our trip, we made plans to visit Sintra, a town located at the foot of Portugal's Sintra Mountains, about half an hour from Lisbon.
We booked a full-day guided tour with pickup and drop-off in Lisbon that stitched together a greatest-hits loop: Sintra's Pena Palace, Quinta da Regaleira, Cabo da Roca, and a stroll through the town of Cascais.
The real win wasn't "seeing more," it was not having to juggle the schedules of trains, buses, and shuttles, or worry about grabbing tickets — the guide sequenced everything and kept us moving.
I'd definitely book this day trip again for how easy it made navigating all of the logistics.
