From Porto to Lisbon: The Famous Sights and the Secret Stops you should add to your list!

Let me start by saying this: if you’re heading to Portugal, pack good shoes. Not “cute for a city stroll” shoes—actual walking shoes. Especially if Porto is on your list. The city rises in two layers tied together by steep hills, stairs, and cobblestone alleys that will challenge your calves and reward you with postcard views at every turn. We clocked serious mileage (think 56 flights of stairs our first day) exploring both the riverside Ribeira district and the higher-up historical center. Porto doesn’t play around.

Day 1: After arriving in Porto we hit the ground running and headed towards the Livraria Lello bookstore—yes, that one. The one often rumored to have inspired the Hogwarts library. It’s been listed as one of the most beautiful bookstores in the world, and walking up its famous red staircase feels like stepping into a fairytale. Even if you're not a Harry Potter fan, you’ll be spellbound. We also stopped for a Francesinha. It was big enough for the both of us! This is a sandwich with layers of meats like ham, steak, and sausage, between two slices of bread, topped with melted cheesee and covered in a tomato-beer sauce and served with french fries!

Day 2: Our second day was all about the Douro Valley—a small-group day trip that took us deep into wine country. We visited three different wineries, each with its own personality, then cruised down the river on a boat tour that made us feel like we’d stepped into a painting with rolling hills and terraced vineyards.

Day 3: The next day we kicked things off with a walking tour led by our guide Diogo, who was hands-down one of the best guides we’ve ever had. Funny, passionate, and full of stories that made Portugal’s long and winding history actually stick. We booked this through Guru Tours. Guru tours is a free tour app, and you pay your guide what you think the tour was worth at the end. We’ve done this in a few different locations and have had fantastic guides and others that were just ok. But it is always a great way to get the lay of the land and insider tips! (Book your Guru Tours here!)

That afternoon we walked over the river, took the Gaia cable car down to the waterfront, and wandered through distillery shops where port wine is practically a religion. If you’ve ever wondered where all those Douro River cruises dock—this is the spot.

We rode the cable car back up, grabbed a spot near a local street performer, and waited for Porto to light up. The whole city starts to shimmer after the sun goes down. Total magic.

To Lisbon

Day 4: Leaving Porto, I chose to do a private transfer from Porto to Lisbon (you can book the same one here). Yes, you can take the train, or fly, but there is just so much to see! So we splurged. I really wanted to stop in Aveiro, sometimes called the Venice of Portugal. It’s a charming little town full of canals, and those bright, gondola-style boats called moliceiros. We wandered through the streets, took a canal cruise, sampled sweet ovos moles (a local egg-yolk treat), and felt like we’d stumbled into a storybook. The canals are lined with friendship bridges! Instead of the locks that people put on bridges (often called locks of love), Aviero has people tie ribbons. It’s lighter and even more beautiful with all the colorful ribbons waving in the breeze!

Friendship Bridges in Aviero

I also wanted to stop in Costa Nova, the little fishing village known for its vertically striped houses. This charming town is full of character and is often very busy during the summer, but quiets down after the beachgoers and tourists leave. The houses were painted so the fishermen could find them through the fog, the other story we were told was that they were painted so the fisherman knew which one was theirs when they were drunk…. Either way it created a cute an adorable backdrop for us to see! The beauty of having a private driver, he was happy to take us and make this short detour so we could stroll and snap a few pictures!

After leaving Costa Nova we ventured to Nazaré, a fishing town famous for its massive winter waves from November through January. Although we didn’t get to see anyone surfing the big waves, it gave us something even better: lunch at Pangeia. The octopus was served three ways, and every single bite was perfection. If you love bold, beautifully cooked seafood (and don’t shy away from tentacles), this place is a must.

Our last stop on our private drive was in Obidios, a medieval town straight out of a storybook. Once a wedding gift to Portuguese queens, it’s still wrapped in 14th-century stone walls. We entered through the arched Porta da Vila, its blue-and-white tiles a hint of what was inside: narrow cobbled lanes, whitewashed houses trimmed in bright colors, flower boxes spilling over, and tiny shops selling books, art, and liqueur. Everywhere you turn feels like a painting. We sipped ginjinha, the local cherry liqueur, served in little chocolate cups, and climbed parts of the wall for sweeping views of red-tiled roofs and vineyards rolling out into the countryside. It’s small enough to see in a few hours but packed with history and charm.

Day 5: Our first morning in Lisbon we did another guru walk. This time through the Baxia and Alfama neighborhoods. Seeing all the portugese tiles up close was so cool.  We then headed to the absolute best thing I feel we ever booked, a tile painting class with a local artist at Art of Azulejos. Here we got to see and try our hand at making our own tiles! I love these so much and they are hanging in our kitchen. I love art and items that we collect from around the world to decorate our house. After our class we decided to walk back and stop at the National tile museum. It is breathtaking to see these tiles and the detail that goes into them after just experiencing how hard it was to paint one tile, let alone a series of custom images!

We ended our time in Portugal in Lisbon, staying at the sweetest little boutique hotel: Pousada Alfama. It sits right in the heart of the Alfama district, which feels like the soul of the city—winding streets, fado music drifting from doorways, and enough old-world charm to make you forget what year it is, with the historic Tram 28 running right in front of it.

Day 6: We took a day trip from Lisbon to Pena Palace in Sintra. Wear good walking shoes—you’ll need them for the 10–15 minute uphill walk to the palace. There’s a shuttle if you’d rather skip the climb, and plenty of grounds to explore once you’re there. You could easily spend a full day wandering here! From there we visited the city center of Sintra where we wandered the streets. Of course we had to stop at the famed Casa Piriquita is known for being one of the oldest and most famous bakeries in Sintra and for its Travesseiros, a puff pastry you must try! We then wandered to Tulhas, where I can’t even tell you what we ate. We took the manager’s meal recommendation and talked with him during our meal. It felt like being welcomed into a friend’s home.

After Sintra we continued on to Cascais, a wealthy seaside town once known as a retreat for royalty. Today it’s polished but still relaxed, with wide beaches, a marina full of gleaming yachts, and palm-lined promenades perfect for strolling. 

Back in Lisbon that night we walked down the Pink Street, and headed to dinner. One of my favorite meals of the whole trip? At Time Out Market Lisboa, of all places. Yes, it’s a food hall. Yes, it’s touristy. But also? It’s packed with incredible local chefs, and I had a salad that I’m still thinking about: crisp greens, juicy berries, tangy goat cheese, a drizzle of honey, and—wait for it—ice cream. On a salad. And somehow it worked. Wildly flavorful, totally unexpected, and the perfect bite to end the day. But what made this meal even more spectacular was the camaraderie of other travelers. At Time Out Lisboa, you sit at a long communal table. People often ask about what you are eating or share stories. We ended up talking to two girlfriends from Dublin for 3 hours that night! I love meeting people from all over the world and swapping travel stories that inspire my next trip!

Day 7: We ended our time in Lisbon touring Belem district where we went to see the Belem tower and the Monument to the Discoveries. We strolled along the riverfront and then wandered over to the Mosteiro dos Jerónimos.  As we strolled back to our hotel, we walked on the roof of the MAAT museum (museum of art, architecture, and technology) where we admired the view of the Cristo Rei (Christ the King) statue in Almada, across the Tagus River from the city, which is inspired by the Christ the Redeemer statue in Rio de Janeiro.

I knew I’d love Portugal. I just didn’t expect to fall for it so hard—the people, the history, the quiet power of this little country, the food, the views… and my husband’s new obsession with port wine.