It seems that everyone has an opinion on Portugal, amirite? You've seen dozens of Lisbon and Porto "must do" Instagram reels for this uber-popular (and rightly so!) country. So, what's this free guide gonna offer you? My own bossy opinions on what to do, where to eat, what not to miss, and where to stay. That's it. Covers top recommendations for 4-5 days in Lisbon and about 10 days on a road trip north to Cascais, Sintra, Aveiro, Porto, and The Duoro Wine Region. I've spent 10 weeks in Portugal on three separate trips and these are my tips.
We’ve been three times (2014, 2019, 2022) and it truly just keeps getting better and better.
Popular for a reason
1. Castelo de S. Jorge — On everybody's "must do" list, this landmark offers great views over the city and ancient castle ruins to explore. But the journey is as important as the destination. There is a walk up via stairwells and alleys full of street art that offers visual stimulation and local culture while you climb. You can find an entry point near Miradouro do Recolhimento.
Terrific views over Lisbon. Historical context. Little carts selling wine. A visit to the castle has it all! And the uphill walk to reach it is the true joy IMHO..
An overlook full of street art that also marks an entry point for a colorful climb up to the castle.
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2. When you walk back down into Alfama, just stroll the tiny streets and eat grilled sardines!
3. Fado — seeing Fado singers and guitarists is a must and good music can be had all over the Alfama and in Barrio Alto as well. The best we’ve ever seen, though, was at a tiny, adorable place called Mesa de Frades in Alfama.
Go late at night (skip the reservations and mediocre food) and just get wine, close your eyes, and let the music wash over you. In 2022 I was with a group of friends and saw a young singing phenom who blew all our minds.
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4. Museu da Marioneta (puppet museum). Small and awesome. Easy to do in an hour or so and have lunch at Heim (see dining section) a half block away.
This tiny but chock-full museum traces the history of puppets and marionettes through different origins and traditions. And, it's just wicked weird. I love it. Special exhibitions over the years included a spectacular Wallace & Gromit display in 2019. Located in an old monastery.
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5. LX Factory. Hipster vibes in a reclaimed factory warehouse area.
Essentially a shopping and eating area under a soaring highway bridge. LX Factory is a bit "too cool for school" (i.e. very Instagrammable) and can get crowded, but its still fun to walk around and grab a beer or bite. Don't be too picky about where you nosh or imbibe. Everything is quite good and the key is — who has the shortest line?
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6. Jardim Botanico de Lisboa. Sweet mid-city botanical gardens, this is a great place to sit and read awhile or write in your journal.
A shady respite on a hot day. Also a quiet place to meander or hang after brunch with free entrance on Sunday mornings. Don't miss the cactus section. Water features and sculpture installations throughout add to the charm.
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Day-Long Waterfront Stroll & See
Uber out to the Torre de Belem and walk (or scooter or electric bike) back the 5 kilometers to central Lisbon along the waterfront.
Enjoy a stroll through this 16th Century limestone tower offering views across the Tagus River. Built to protect Lisbon from incoming raids, it also marked the last sight of land for outgoing sailors. Sit a spell and listen to the ever-present buskers. Then, grab a refreshing drink, ice cream, or glass of wine from a food cart in the neighboring park before you meander back to central Lisbon along the water.
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On your way back:
A. Stop at Padrao dos Descobrimentos (take the elevator to the top for the views).
MAAT stands for Museum of Art, Architecture and Technology and the exhibits here are wide-ranging and eclectic. Tickets include entrance to both the newer (very modern), sleek building and the former power plant next door. Vast spaces and striking, bold art.
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C. Continue walking under the Ponte 25 de Abril bridge (the one that looks like the Golden Gate) where you can sit down for an aperol spritz or grab some ice cream before learning about the bridge's construction (more interesting than it sounds) and taking in the expansive views at Pilar 7.
While often compared to the Golden Gate Bridge in San Francisco, (even I did in my narrative above!) because of its orangey red color, Ponte 25 de Abril actually is 30 years younger and more similar in design to SF's other bay-spanning bridge, the Bay Bridge. In fact, it was built by the same company (American Bridge Company) that constructed the Bay Bridge, explaining the similarity in design.
The multi-media trip through the history of the bridge's construction may be a bit tedious, but it's worth it to end with an elevator ride up to a panoramic viewing point over the river.
I have a weird affinity with this museum full of dramatic renaissance and ancient art. Many classic oils depict biblical scenes ranging from the serenity of the Virgin Mary to violent torture. Housed in a 17th century palace, the walls and halls overflow with paintings, sculpture and decorative arts. Don't miss the museum's most famous resident — Temptation of St Anthony by Bosch.
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Where to Stay in Lisbon
If you are going the Airbnb route and are looking for night-time quiet, I recommend staying either near the Botanical Gardens in the Principe Real area or in the area south of Jardim da Estrela (also worth a visit!) near Heim and the puppet museum. Barrio Alto, Chiada, and Alfama stay pretty loud into the early morning and are just much more crowded in general.
For Hotels with sound-proofing, however, I highly recommend staying in Alfama as the best bougie boutiques are there — many with river views. Although hardly inexpensive, my too faves won't completely break the bank, either:
The reviews don't lie. Large fabulous rooms (many with patios), and just about the best staff in the city. Superb breakfast, a small, chic bar, and splendid public terraces. Historic and lovely with tasteful decor and a truly top-notch housekeeping team.
This special place features modern rooms with a clean design, but the best reason to stay here is the splendid rooftop pool deck. While the shallow, dyed-red pool cools you off on a hot day, the true joy is watching cruise ships drift by while sipping a glass of vinho verde. Pure heaven.
This truly wonderful breakfast/brunch restaurant has 3 locations, but the best is near the famous Bica street car. SUPER solid. Everything is great and fresh, but their take on huevos rancheros is delicious.
Tiny family-run joint in an odd, outer part of Alfama (you’ll think, where is Dawn sending me?!). The squid ink pasta is out of this world. All other dishes here are fabulous as well. Really great prices on bottles of Vinho Verde!
Great for brunch or lunch. Trendy "avo toast vibe" kind of place, but everything on the menu is consistently delicious. Pair a visit with the puppet museum. Fauna & Flora nearby also is good, but has gotten SUPER popular and overrun.
Go for the tapas and drinks. The charcuterie and cheese are spectacular. Sit in the vast, beautiful space and sip wine or an Aperol spritz. It's oh, so Lisboa.
Don't be put off by the weird parking ramp entry to this rooftop bar, the views are THE BEST. A bit trendy and overrun as well, but with sprawling decks it doesn't feel too crowded and is a great place to grab a beer and photos at dusk and sunset.
Large food court near the waterfront. It’s not nearly as cool as it was a decade ago, as it’s gotten super touristy, but it really is a must visit spot. My friends swear by the octopus hotdog and oysters. I always try something new. The last time I devoured a wonderful half grilled chicken. Stop by the terrific wine shop and also the gelato stall for a decadently rich and creamy dark chocolate.
Small and charming. This is one of my fave places for an intimate lunch and linger. Great grilled fish and an impressive wine list.
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Road Trip North — Cascais, Sintra, Aviero, & Porto
When you are ready to leave Lisbon, hit the road north. The toll roads and highways in Portugal are beautifully maintained, fast (the Portuguese are a bit lead-footed), and a tad pricey, but worth it for cutting off time. In fact, consider renting one way and flying into Lisbon and out of Porto for a leisurely, stress free, two-week vacation.
Stop One: Cascais
Stay in Cascais for a night (or two) to relax from the hectic pace of Lisboa. Book a room at the Farol Hotel and just chill by the pool until you are inspired to stroll through the nearby Parque Marechal Carmona. I can't really recommend a specific dining experience that will blow your socks off, but all the seafood restaurants are solid and feature fresh catch.
Cute little boutique art hotel with a great pool located waterfront and right by the famous lighthouse. Rooms are clean, modern and simple.
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Drive up the coast by Cabo da Roca Lighthouse (the westernmost spot in Europe). Take in the rugged cliffs and turquoise water, then continue on to Sintra.
If you are familiar with northern California, you'll catch Mendocino vibes while gazing out at this stunning coastline. Craggy outcroppings covered in blooming ice plant and a vintage lighthouse complete an idyllic picture.
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Stop Two: Sintra
Sintra is Portugal’s Newport, Rhode Island (or more accurately, the other way around) and I recommend staying 2 nights here. Also like Newport, Sintra is primarily about touring castles and mansions. All are worth a visit, but my advice is that you don’t miss at least these two: Quinta de Regaleira and Pena Palace. Plan a long, late lunch or dinner at Romaria de Baco.
While the interior is worth a meander, the garden-filled grounds and grotto are where it's at. Separate yourself from the influencer hordes, follow a quieter path, and explore.
Yes, the red and gold palace exterior is sublime and supremely photogenic, but don't miss the opportunity to hike around the extensive park's grounds and walkways. You'll discover a giant ancient cross, mossy grottos, and moody little nooks where no one else goes. The interior is the least interesting thing about Pena Palace, but still worth doing.
Traditional Portuguese cuisine with a modern twist. This is the kind of place to linger over your meal (I seem to do that a lot!) and start chatting with nearby tables. Blackened slow-roast pork is my fave and goes down delicious with a bottle of Touriga Nacional.
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Stop Three: Aveiro.
Continue up the coast to Aveiro (Portugal’s mini Venice) for a night or two and stay on the canals in an Airbnb if you can. This place we stayed this last time (see below) was super adorable, but it’s right over a cafe/bar that stays open until 2 am and it was LOUD. I was fine with my noise-canceling headphones tapped into the Better Sleep app. The owner gives guests a 20 euro gift certificate for the bar to mitigate the situation, and it goes a long way as wine is so cheap in Portugal!
Averio’s Old Town area is very art nouveau and you can get a map that takes you on a self-guided walking tour all over town and through the lovely Parque de Santo Antonio. The canal boats also are worth a spin, as well. Aveiro is hands-down one of Portugal's most photogenic towns.
Portugal’s wine region is truly lovely with terraced hillsides of vines and lots of still wine and port houses. I know nice hotels exist throughout the region but we’ve stayed in the same Airbnb both times. If you are traveling with a small group or just want a special spot, this 3-bedroom place on the river is a rare combination of simple and spectacular.
Unlike many international wine countries, you can’t just drop into the quintas (wineries). Reservations are vital. One of the best experiences we had in 2022 was a tour, tasting and lunch at Quinta do Tedo. It’s set in a truly stunning spot overlooking both the Duoro and Tedo rivers. Another great experience in 2014 was at Quinta de Napoles (Vinhos Niepoort) nearby. We even had lunch onsite with the owner!
If you want to try the traditional portuguese dish of bacalhau (salted cod), the best I’ve had (anywhere in Portugal TBH) is here in the Douro region at Restaurante O Tonel, a weirdly wonderful little local’s joint made to look like you are in eating inside a giant port barrel.
If the incredible location and views aren't enough, this quinta offers a tour for every interest level — ranging from simple to the Harvest Experience immersion tour. Hint: you get to blend your own tawny port. Lovely wines and ports and a terrific onsite restaurant satisfy your tastebuds. And, Quinta do Tedo even features a hiking path through the vineyards so you can stretch your legs.
The Duoro home of the venerable Niepoort winery, a Dutch family who settled in Portugal in the mid 1800s. The winery offers a spectacular tasting and deck with views over the valley.
Very local, very weird, and sooooo worth a visit. You enter what seems like a small store and wait to be invited into the dining hall. When beckoned, you walk through a door in the back left corner into a large room designed to look like the inside of a massive port barrel. Kitschy yes, but it's a hoot. And, the food is truly delicious.
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Stop Five: Porto
Portugal’s second city is a bit grittier, edgier, and artier than Lisbon and has gotten more so over the years. I think that only increases its appeal, even if it is less fashionable than its big sister.
During our most recent visit we stayed at this super-affordable and cute 2-bedroom Airbnb right near the Ponte Luis I bridge and the Jardim do Morro park (great place for sunsets). The owner was a total darling and left us Pastel de Nadas (the famous Portuguese egg custard pastry), beer, port, and coffee. EVERYTHING is super walkable from here.
1. The port houses are right below the Airbnb and you can walk down and wind among them (most need reservations, but some, like the venerable Kopke you can just walk into). Take the sky cab back up to the park.
Walk down to the port houses via the charming stairwells, but this view-enhancing cable car is a fast way back up. Well. . .if the line to ride isn't too long, that is. Do it once just for the experience.
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2. Walk over the bridge and the rest of central Porto is at your feet. NOTE: Porto has a beautiful central square, but when we were there late June 2022, it was totally ripped up by construction. Reports are that it is mostly (but not completely) finished a year later — so keep that in mind.
3. Climb the Torre dos Clerigos and check out the museum. Great city views and beautiful historic church.
This baroque bell tower is an architectural masterpiece, and the view from the top is breathtaking — capturing Porto from all angles. The cramped stairwell leads you up a few levels, offering an interesting bird's eye perspective into the attached chapel, before continuing to the top. Also includes a surprisingly interesting museum documenting the tower's history and importance to all of Portugal.
Sidewalk cafes, buskers, and tents full of artisan wares share space in this riverside passageway that stretches for blocks. A carnival atmosphere prevails.
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6. Peek into the Sao Bento train station. It’s 1800’s tile facade is beautiful
One of the most beautiful train stations in Europe. Twenty-two thousand hand-painted tiles by artist Jorge Colaço grace the walls and ceiling, and it is simply glorious.
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7. Also pop into Livraria Lello, a lavishly designed historic bookstore.
With ornate architecture, intricate stained glass windows and a remarkable staircase, it's not an overstatement to call this the most beautiful bookstore in the world. Sadly, the word is fully out and it gets CROWDED as folks jostle for a photo on the stairs. You must purchase a ticket online to get in, but you can use it as a voucher to buy a book
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8. Two MUST-EAT dining spots:
A. Ze Bota. This tiny place down a secluded street simply rocks.
Super fresh and elegantly prepared traditional cuisine. Delicious veal and fish. Order both the octopus and green salads and share everything. Go for lunch right at noon and (yes, I'm gonna say it again!) linger over wine. Now run by the kids of the owners we first encountered in 2014, Ze Bota is truly a MUST. An old custom was to take polaroids with international customers and mount them on port crate panels to the wall. As of our last visit (late June 2022), our 2014 photo with our friends was still gracing the lower part of the restaurant's entryway (see photo).
Go hungry and share a selection of tapas and one Francesinha. This traditional portuguese sandwich features layers of beef steak, cured pork, and fresh sausage, topped with cheese and a spicy beer sauce. Ridiculous, yes, but fabulous!
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Bonus Destination: Evora
Another place we really loved in Portugal was the historic town and region of Evora. Sites include The Chapel of Bones and Templo Romano Evora. It’s a land of cork trees and where almost all wine corks — worldwide — are from. If you venture this way, visit the amazing medieval village and castle of of Monsaraz and the Almendres Cromlech, a series of neolithic standing stones (kinda like Stonehenge). It’s a magical place and definitely worth 3-4 nights if you have time.
Literally a chapel built with the remains (skulls, leg bones, hand bones, etc.) of thousands plastered into the walls. It's a poignant reminder of the impermanence of human existence and the broader importance of humanity.
Beautifully preserved Roman ruins in central Evora. Photogenic and surrounded by other historic structures, such as a chapel. Includes a lovely park and good wineries and restaurants nearby.
One of the largest stone circles in the world. Thousands of years old and believed to be an astronomical calendar to mark solstices and equinoxes. Though largely unknown outside Portugal, it may be older than the famous Stonehenge.
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We stayed at this terrific Airbnb right in the middle of a cork farm in Redondo, another quaint village 30 minutes from Evora.
The Evora region also is a fantastic first stop if you are planning a road trip into southern Spain (a trip I'm happy to help you plan. See my services).
My free and for-purchase itineraries and guides are action-packed and lean heavy on wayfaring (enjoying destinations by foot) and road trips. I specialize in travel for active, 40+ traveling couples who neither spend extravagantly nor journey on a shoestring. I know where to splurge and where to save, and will advise on the best way to thrive when on the road. I live and work from abroad 8 months of the year with my husband, Adam. The other four, I explore every last hiking trail in my home of Sedona, Arizona, USA. FYI — we rent out our home nightly via Airbnb and VRBO. Check out at sedona-vacation-home.com. I'm food-motivated and passionate about weird, little museums; explore by foot whenever I can — clocking miles on pavement, sand, and single track in places as diverse as Kyoto, Cartagena, and Tallinn. I balance my travel time returning to favorite spots (ANYWHERE in Japan; Oaxaca, Mexico; Siem Reap, Cambodia) and peeling back the layers of somewhere new. I'm available for hire as a travel consultant and I will continue producing very opinionated travel guides here on Thatch and publish my travel musings via posts and stories on Instagram via @wayfarerdawn and on my website wayfarerdawn.com.
