Naomi Weisman is a Canadian-Australian and mother of three, who loves to Ramble with her dog, cook for family and friends, and laugh whenever possible.
Earlier this year, my partner Brian and I celebrated our 10th anniversary. Since neither of us is big on material gifts, we decided to mark the occasion in a way that felt more meaningful—a trip, just for us.
The last time I was in Portugal, I was 18 and backpacking around Europe. I remember thinking the country was absolutely heavenly… though, truth be told, I can’t recall exactly why! At that age, I was probably more focused on beach-hopping and how tanned I could get than on soaking up the culture or history.
Then last year, one of our Sole Sisters, Colleen O’Neill, started posting photos from her trip to Portugal—and it all came rushing back. Her pictures were stunning, and her joy was contagious. When it came time to plan our anniversary getaway, I reached out to Colleen, who generously shared her itinerary with me.
Now, I want to return the favour and share ours with you, but first things first:
Choosing the right season to visit Portugal is key. The country can get extremely hot and crowded, especially in the summer, so it’s worth doing a bit of research to figure out what time of year suits you best.
For us, we knew we wanted to avoid the peak summer months when the heat and tourist crowds are at their highest. While winter is cooler, it has its own charm—fewer people, a more relaxed pace, and ideal conditions for Rambling and exploring without the hustle and bustle.
We chose to travel in mid-May for three weeks. Knowing that tourist season starts to pick up around then—and gets noticeably busier by June—we booked our accommodations well in advance. For most of the trip, we stayed in Airbnbs. Partly because we needed two bedrooms for some of the time, but also because we really value having a kitchen and laundry facilities on hand.
That said, it’s worth noting that in response to the growing challenges of over-tourism, some European cities are starting to restrict short-term rentals like Airbnb. So, this kind of accommodation might not be as widely available in the near future!
Traveling in midlife and beyond has given us a new appreciation for pacing. Gone are the days of changing locations daily—we’ve learned that a slower rhythm makes for a much more enjoyable experience. So, we made it a priority to stay at least two nights in each spot, with some places deserving three or even four.
Once we mapped out a rough itinerary of where we wanted to stop, it became much easier to organize the rest—flights, car rental, and accommodations all fell into place.
So, here goes…the itinerary:
We flew overnight from Toronto to Lisbon, arriving early and heading straight to the rental car pickup. From there, we hit the road and drove about an hour and a half north to our first stop: Nazaré.
Famous for its record-breaking waves in the winter, Nazaré draws elite surfers and spectators from all over the world. Even outside of surf season, it’s a stunning beach town, with golden sand, dramatic cliffs, and a lively atmosphere filled with charming restaurants, cafés, and little shops to explore.
Óbidos, a postcard-perfect walled city dating back to the Christian conquests of the 12th century, is best visited early in the day—before the tour buses arrive—to truly appreciate its quiet charm. One of my favorite moments was rambling along the ancient ramparts, which offer stunning panoramic views of the countryside.
That said, the walk is not for the faint of heart—it's high up with no guardrails, so those with a fear of heights might prefer to stay on the ground and explore the cobblestone streets below. Inside the walls, you’ll find a lovely mix of artisan shops, cozy cafés, galleries, and a beautiful historic church that’s well worth a visit.
Not far from Ă“bidos is Tomar, another gem often overlooked by tourists. This town is home to an exquisitely preserved Knights Templar castle and the Convent of Christ, founded in 1160 following the Christian reconquest of the region.
The site is a UNESCO World Heritage treasure, and wandering its grand halls, cloisters, and stone corridors feels like stepping back in time. Together, Óbidos and Tomar make for a fascinating day trip—easily accessible from Nazaré—and offer a deep dive into Portugal’s medieval and religious history, all surrounded by breathtaking scenery.
From there, we made our way to Coimbra, another historic gem known for its medieval charm and home to one of the oldest universities in the world. It might sound odd to tour a university, but trust me—there’s a lot to see.
We were especially fascinated by the Room of Curiosities, filled with 18th- and 19th-century specimens collected during Portugal’s age of exploration. It offers a glimpse into a complex and controversial chapter of history, when Portuguese explorers were bringing back treasures—and plunder—from the so-called “New World.”
That said, after exploring the university, we felt ready for something different. I had read about the Lousã mountain range and its ancient villages built entirely from local Xisto (schist) stone. So off we went! Let me tell you—the drive into the mountains was absolutely nerve-wracking.
Hairpin turns, narrow roads, and dizzying drops had me white-knuckling the whole way. I honestly don’t know how people live in those remote villages—or how they ever managed to build them in the first place. Was it worth it? Absolutely. But it’s not for the faint of heart!
PortoÂ
I’m so glad we gave ourselves 4 days to enjoy this vibrant city. We stayed in a fantastic apartment in a walkable neighborhood, which made it easy to explore at our own pace.Â
Pro Tip: While there, we met up with fellow Sole Sisters, Jill Thomas and Jane Witherspoon, who tipped us off about the free walking tours available daily, both in the morning and afternoon. For the cost of a tip at the end, you get an incredibly informative experience and a great introduction to the city’s layout and history. I can’t recommend it enough—just Google “free walking tour Porto” and you’ll find several options.
Porto is bustling during the high season, so if you’re planning to go then, it’s smart to book certain experiences in advance—like a Fado performance (Portugal’s hauntingly beautiful folk music), a Douro River boat tour, or popular restaurants. We absolutely loved our time in Porto and would go back in a heartbeat.
The Douro Valley
This place is pure magic! One breathtaking vista after another, with terraced vineyards and rolling hills stretching in every direction. We based ourselves in Peso da RĂ©gua on a vineyard just outside of town, replete with donkeys and sheep, a perfect hub for exploring the region with a couple of easy day trips.
Since Brian is a train enthusiast, our first adventure was a scenic ride along the Douro River to the final stop, Pocinho. The retro-style train, straight out of the 1960s, was charming and offered gorgeous views along the way.
From Pocinho, we took a taxi up to the town of Foz Côa (pronounced Fosh Coa), a modest little town rich in history and almost entirely supported by its almond industry. While the journey was lovely, I’m not sure Foz Côa is a must-see unless you’re particularly interested in the region’s rural culture. Still, the ride itself—and the landscapes—made it a memorable outing.
The next day brought a stunning boat trip on the river and an unforgettable dinner to celebrate a birthday. The food and wine in this region are truly world-class!
The Alentejo Region
The Alentejo region is a place deeply rooted in rural traditions and known for its world-class wine, sprawling cork forests (which produce about 90% of the world’s cork), almonds, and beautifully crafted pottery.
We stayed in Évora, a captivating medieval walled city and designated as a world heritage site, with sections of its walls and aqueduct dating back to Roman times. It’s remarkably well preserved and absolutely packed with historical interest—an ideal destination for history lovers.
As we did in Porto, we sought out a free walking tour upon arrival to get our bearings and learn about the key sites. Once again, it proved to be a fantastic way to start our visit.
Every town or city we visited in Portugal seemed to have a central square—typically anchored by a church, lined with charming shops, and dotted with inviting cafés. Évora was no exception, but its main square had an energy all its own.
The night we arrived, it was buzzing with a wine tasting festival, and the following evening, the entire town seemed to gather there to watch a football (soccer) match. The cheering crowds and the jubilant parade of honking cars that followed were absolutely epic—such a fun way to experience the local spirit!
The drive from Évora to Faro was both easy and scenic. Along the way, we made a quick detour to Evoramonte to check out an intriguing castle we had spotted from a distance the day before. Like so many of Portugal’s castles and walled towns, Evoramonte has deep historical roots dating back to the 12th century, when the Moors were defeated by Christian forces.
After a devastating earthquake in the mid-1500s, the castle was rebuilt into the distinctive form we see today. It’s a striking sight, perched high on a hill, and definitely worth the stop. Just be sure to park outside the walls and walk up, as the narrow streets at the top are extremely tight!
The Algarve
Faro, the main city of the Algarve, sits on the eastern edge of the region, close to the Spanish border. With its international airport, charming old walled city, pedestrian shopping streets, and scenic waterfront, it made a perfect home base for our week of exploring the Algarve.
The one drawback? Faro itself doesn’t have a beach right in town. But that’s easily solved—there are plenty of beautiful beaches nearby. We took a ferry to Ilha de Faro (you can also drive, though parking is limited), where we found a lovely stretch of sand and several great beachside restaurants.
Another day, we headed east to Tavira, just a 30-minute drive away, where you reach the beach, Praia do Barril, via a delightful vintage train. Both spots offered a perfect mix of sun, sea, and local charm.
The Algarve is home to one of the most breathtaking coastlines in Europe, and we made the most of it by booking two unforgettable tours. The first was a small boat tour departing from Albufeira—about two hours long, a bit crowded, but very well organized.
The guides were knowledgeable and engaging, pointing out key landmarks and sharing insights into the unique geology and history of the area. It was a great introduction to the dramatic cliffs, hidden beaches, and iconic sea caves that define this stretch of coast.
Our second outing was a 3-hour kayaking excursion, and it was truly the highlight of our time in the Algarve. Paddling into the stunning sea caves—like the famous Benagil cave—and gliding past secluded beaches only accessible by water felt absolutely magical.
It’s hard to capture in words the awe of floating beneath towering rock formations, with crystal-clear blue water below and brilliant skies above. It was an experience we’ll never forget.
Other highlights of the Algarve included Carvoeiro, a picturesque seaside town near the famous Benagil caves; PortimĂŁo and the stunning Praia da Rocha, known for its expansive beach and vibrant promenade; and Lagos, with its rich maritime history and dramatic coastal cliffs (and a surprise visit with a local Sole Sister Rambler).
We also ventured inland to Silves, a beautifully preserved Moorish walled city nestled in the hills, and to Monchique, a charming mountain town full of character and surrounded by lush landscapes. One of the most memorable experiences was taking a fabulous traditional Portuguese cooking class—a hands-on and delicious way to connect with the local culture.
As we said goodbye to the Algarve, we made our way to its last stop, Sagres—a place where the Mediterranean Sea and the Atlantic Ocean meet in a breathtaking display of natural power. It’s an incredibly dramatic spot to spend a few hours, with surfers and windsurfers carving through the waves below towering cliffs.
We explored the historic Sagres Fortress, home to the fascinating Chamber of Sound and panoramic views that stretch endlessly across the sea. Wind-swept and exhilarated, we dipped our toes where the two great bodies of water merge—a symbolic and unforgettable moment at the edge of the continent.
Lisbon
On our way to spend three days in Lisbon, we stopped to explore Sintra, an unforgettable destination. Sintra is absolutely magical, with its fairy-tale palaces, lush gardens, and misty hills.Â
ProTip: There's no need to drive there yourself, as we did. Direct trains run regularly from Lisbon, and once you're in Sintra, a hop-on-hop-off bus makes it easy to visit all the major sites. It's a bit pricey, but well worth it for the convenience and the incredible sights you’ll see along the way, like the Moorish Castle and the Palace of Pena.Â
Lisbon, oh Lisbon, how we loved you! There is far too much to see in Lisbon for just 3 days, but we did our level best!Â
Pro Tip:Â Make sure you go to the Metro station to buy a 24-hour public transit pass. It is 11 Euros and well worth it. We bought two days' worth and activated the second one when we needed it.Â
We stayed in a fantastic central location, right along the route of the iconic Tram 28—perfect for rambling around the city. Lisbon’s hills can be a workout, so we made great use of the tram system when we needed a break from climbing.
Pro tip: Tram 28 is a major tourist attraction, so if you want to ride the full route and actually get a seat, aim to board early in the morning. Otherwise, avoid the main departure point at Martim Moniz, where crowds tend to be the biggest—hopping on a few stops later can make all the difference. Alternatively, Tram 12 is the next best thing, with fewer people.Â
Things you shouldn’t miss in Lisbon:
Self-guided walking tours are easy to find online, though we followed routes from our trusty Lonely Planet guidebook. It felt like a treasure hunt as we rambled through the city, searching for the “oldest,” the “most significant,” or the “hidden gem” of the moment. Lisbon is full of nooks, crannies, and surprises around every corner.
Time Out Market is an absolute must—we loved it so much, we went twice! The energy is fantastic, the food choices are endless, and it's a great place to sample a variety of Portuguese flavors. Just behind the market is a beautiful area to wander, and if your legs need a break, hop on the charming, vintage Elevador da Bica funicular to ride back up the hill.
Be sure to have a meal on Green Street Lisbon (and the surrounding area), a lively stretch lined with funky, artistic cafés and restaurants. The atmosphere is vibrant and unmistakably Lisbon.
Finally, no visit would be complete without a trip to the historic district of Belém, now a suburb of the city. It's the birthplace of the beloved pastel de nata (Portuguese custard tart), and home to several must-see sites, including the Jerónimos Monastery and the Belém Tower. It's a perfect blend of history, culture, and sweet indulgence.
Portugal captured our hearts in every way—from its sun-drenched coastlines and ancient cities to its rich culture, incredible food, and warm, welcoming people. Traveling at a slower pace allowed us to truly soak it all in, savoring each stop instead of simply checking it off a list. Whether we were wandering through medieval towns, kayaking into sea caves, or enjoying a glass of wine in a lively square, we felt completely immersed in the magic of the moment.
If you're considering a trip to Portugal, take it from us—go. Plan ahead, but leave room for spontaneity. Eat the pastry. Ride the tram. Wander without a destination. Portugal has a way of surprising you when you least expect it—and those moments become the ones you remember most.
We will go back for sure!
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