We Visited Portugal Twice in Two Years… Here’s Exactly Why We Couldn’t Stay Away
Some trips are incredible.
Others quietly work their way into your heart until, before you know it, you’re booking another flight back.
That’s exactly what happened with Portugal.
It’s beautiful without feeling pretentious.
Historic without feeling crowded (outside of a few hotspots).
And somehow still feels like one of Europe’s best values.
After our first trip, we couldn’t stop talking about it. The people. The food. The coastline. The slower pace of life. So when it came time to plan another European adventure, there wasn’t much debate—we were going back.
Now, after exploring Portugal twice, we’ve discovered our favorite towns, made a few travel mistakes, and found places we’ll return to again and again.
If you’re planning your first trip, here’s exactly how we’d do it.
Trip One 2024: Porto and Northern Portugal is the perfect starting point
We flew into Porto on a red eye from New York, and the best decision I made was booking the night before at our first stop so we could sleep for a few hours once we arrived and freshen up.
Best decision ever.
Where to Stay? Downtown Porto and Historic Old Town (Ribeira and Baixa)
By noon, we were ready to go and had plenty of time the rest of that first day to wander through:
🌸 Jardins do Palácio de Cristal
📚 Livraria Lello (usually a wait and line – we just walked by and did not go in)
⛪️ Igreja das Carmelitas + Igreja do Carmo
⛪️ Igreja e Torre dos Clérigos
👣 Rua das Flores
🍽️ Cantina 32 for one of our favorite meals
👣 Escadas do Codeçal
By day two, Porto had already become one of my favorite cities in Europe.
🚊 Standing inside São Bento Station (arguably the most beautiful train station in the world).
⛪️ Watching a wedding at Porto Cathedral.
👣 Rua de Santa Catarina (Cafe Majestic + Cappella das Almas)
🌉 Crossing the iconic Luís I Bridge
🚠 Taking the Gaia cable car down toward the port wine cellars for a port wine tasting
🎶 Listening to street music on the Douro River while the city glowed in golden light
🍨 Gelato on the walk home…just walking everywhere in general
Porto simply has a magic to it.
Don’t Skip the Douro Valley
One of the best decisions we made was renting a car.
The drive into the Douro Valley is spectacular. Rolling vineyards. Tiny villages. Endless river views at Miradouro de Sebolido.
Biggest mistake – not making a vineyard reservation before we got there.
One of our favorite memories? Stopping at Meandro Restaurant for panoramic views and enjoying delicious local wine for about $1.50 a glass.
One of our best meals of the entire trip? Sirga Wine and Bistro, right at our hotel, the Dourwin.
Sometimes the simplest moments become your favorites.
The Fairytale Town Everyone Should Visit (it’s not Sintra)
Óbidos looks like it belongs inside a storybook (and we preferred it over our 2026 visit to Sintra 10/10).
Cobblestone streets. Flower-covered walls. Whitewashed buildings. Ancient churches. A castle towering above the town.
It’s small enough to explore in half a day, but every corner feels like a postcard.
⛪️ St. Martin’s Chapel + St. Peter’s Church
👩⚖️ Town Hall
⛪️ St. Mary’s Church
⛲️ Town Portico + Pillory
🏰 Castle + Royal Palace
📚 St. James’ Church + Bookshop
This was the perfect one night stop between the Duoro Valley and the coast.
Ericeira Was the Biggest Surprise
If I had to choose one town to return to tomorrow, it would hands down be Ericeira.
This laid-back surf town completely won us over. We only had two nights here in 2024, and knew that if we came back to Portugal again, we would stay here longer.
We were so close to Peniche, which was a bucket list stop for Adam, so we made the quick drive after a day exploring Ericeira over to Peniche for a Father’s Day dinner. It was worth it!
🌊 Praia do Portinho da Areia do Norte
🚙 Scenic drive along Estrada Marginal Norte
🤙🏼 Supertubos
🍤 Dinner at Xakra Beach Bar
🌅 Sunset overlooking Farol de Peniche
Our next day was devoted to the beach and surf in Ericeria before we headed further south.
🏄🏽♂️ Board rentals with Activity Surf Center
🌊 Beach day at Praia de Sao Julião
🍽️ Incredible tapas dinner at Mar das Latas
Ericeira was relaxed. Authentic. Unforgettable.
The Algarve Really Is That Beautiful
Photos honestly don’t do it justice, and our biggest mistake when we came back to Portugal in 2026 was not coming back to the Algarve again.
The Algarve — One jaw dropping beach after another.
Day 1: ⛱️ Praia Sao Rafael
Day 2: 🥾The Seven Hanging Valleys Trail (📍This hike is best done from east to west, from Praia da Marinha to Praia do Vale de Centeanes)
🍽️ Stopped in Benagil for scenic lunch
⛱️ Afternoon beach day at Praia da Marinha
🍣 Dinner at Odessa
Day 3: ⛱️ Praia da Falesia (The Gold Coast of Portugal 🌝 … worth renting chairs + shade!)
🍽️ Restaurante Cafe Oceano overlooking Praia dos Pescadores
Every beach somehow looked more beautiful than the last.
Trip Two 2026: We Slowed Down—and Loved Portugal Even More
Our second visit felt completely different.
Instead of trying to see everything, we spent more time trying to experience each place.
We flew into Lisbon (which was a crazy crowded airport, and I would choose Porto airport over it any day) and drove straight to Ericeira.
Four nights.
No rushing.
No checking boxes.
Just enjoying one of our favorite places. Check out my instagram @tailoredwithtanlines for more photos and our favorite spots!
We stayed at Ericeira Prime Villas, which I would absolutely recommend.
Sintra Is Worth the Climb
Everyone talks about Pena Palace.
Pro Tip: I would skip Sintra and go to Óbidos instead, but if you must join the hype and check out Sintra, here is my advice:
Walk.
Skip the shuttle.
Yes, it’s about 45 minutes straight uphill.
Yes, you’ll question your decision halfway up.
But hiking through the forest before arriving at the colorful palace makes the experience even more memorable.
Getting there is part of the adventure.
Cascais: Beautiful… but honestly less quaint than I was expecting
Cascais is stunning, but it is much more of an urban city vibe than the charming streets of Porto I was imagining.
It is very walkable with beach alcoves right in the heart of the city, but it was missing the overall charm I was hoping for. If you are love a more urban area with museums and shopping, then you will love Cascais. Parking was also a little tricky since you have to pay to park really anywhere in the downtown area, which is where we stayed.
We loved Guincho beach! This large beach is about a 15 minute drive from downtown, had big beautiful sand dunes that reminded me of Jockey’s Ridge in Nags Head back home, and is great for surfing and local people watching.
We did find a few truly authentic Portuguese restaurants where we got freshly caught sardines (big ones…not like from the can) that were right within walking distance of our adorable studio rental.
Would I visit Cascais again, probably not just knowing there are other spots in Portugal I treasure more.
Comporta Felt Like Portugal’s Version of the Outer Banks
Comporta was very quiet, and we felt like we could never bring our 3 wild boys here as they would disturb everyone’s peace. 😂
The beaches reminded us more of home than anywhere else in Portugal. Wide stretches of sand. Clear, swimmable water. Natural dunes. Relaxed atmosphere.
Comporta itself is tiny, upscale, and definitely more expensive than most of Portugal—but if you’re looking for a peaceful beach escape, it’s a great option. If I were to do it again, I would have skipped Comporta (maybe even Cascais as well), and headed back to the Algarve and its stunning landscape for a few days.
One Night in Lisbon and it was just enough for us
We only had about 18 hours in Lisbon before flying home. We decided to turn our rental car in early instead of driving into the city itself and then returning it just before our flight the next morning. THANK GOD we did that. We drove straight to the airport to return the car and then took an Uber into the city and quickly realized driving into Lisbon ourselves would have been a nightmare. Uber is the way to go to and from the airport, in and out of Lisbon.
We stayed in Chiado, which I’d absolutely recommend for first-time visitors. It is an older, more charming part of Lisbon and very walkable. Instead of making plans, we simply wandered and loved getting lost in this city.
Portugal happened to be playing its opening World Cup match that same day, so we joined thousands of people packed into downtown Lisbon to watch together on giant outdoor screens … a VERY cool experience, and one of our favorite trip memories.
Our perfect 2 week itinerary if we were to do it again?
Fly into Porto (3 nights)
Rent a car and drive to the Douro Valley (1-2 nights)
Day trip to Óbidos on way South
Ericeira (4-5 nights)
Algarve (4 nights)
But honestly, you can’t go wrong in Portugal! 🇵🇹
