Portugal is no secret anymore. Lisbon’s hills, Porto’s riverside charm, and the Algarve’s beaches are firmly on the global travel map. But beyond these headline destinations, there’s another Portugal – one of medieval towns, Roman ruins, Templar legends, and sun-drenched landscapes where life moves at a slower pace.
If you’re looking for a more authentic, off-the-beaten-path experience, three places stand out: Óbidos, Tomar, and Évora. Each offers history, atmosphere, and depth, without the crowds and intensity of Portugal’s busiest cities.
Here at Overland Portugal, we make sure to visit these towns on our Small-Group Tours of Portugal. And we’re here to tell you why they deserve a place on your itinerary…
Óbidos – A Medieval Town Worth Savouring
Just an hour north of Lisbon, Óbidos is often described as picturesque, which it absolutely is. But it’s far more than a pretty postcard. This small town is brimming with history, literature, and its very own cherry liqueur.
This small walled town dates back to Roman times and flourished during the Middle Ages, when it was given to Portuguese queens as a traditional wedding gift. Walking through its gates feels like stepping into another era. Stroll along the medieval walls for sweeping views of the countryside and explore cobblestone streets twisting between traditional houses, with the old castle towering overhead.
More than a historic attraction, Óbidos is a cultural gem. Step inside the Igreja de Santa Maria to admire its azulejo tiles. Browse independent bookshops, tucked away in wine cellars and churches, that define this UNESCO Creative City of Literature. And of course, savour the ginjinha. This local cherry liqueur is traditionally served in a small chocolate cup — a simple yet indulgent pleasure you won’t want to miss.Is there any wonder why it’s on our list of the Best Places to Visit in Portugal?
Tomar – The Legacy of the Knights Templar
Founded in the 12th century by the Knights Templar, Tomar became one of the most important religious and military centres in Portugal. Its skyline is dominated by the extraordinary Convent of Christ, a UNESCO World Heritage Site that tells the story of the Templars and, later, the Order of Christ.
The complex itself is vast and layered. The Charola — a round church inspired by Jerusalem’s Church of the Holy Sepulchre — is richly decorated and unlike anything else in Portugal. The Manueline window, carved with maritime motifs, reflects the wealth and ambition of the Age of Discovery. Cloisters, chapels, and passageways reveal architectural styles spanning several centuries.
Yet Tomar is not just about its monument. The town centre, built along the Nabão River, is relaxed and inviting, built along the Nabão River. Locals gather in Praça da República beneath the statue of Gualdim Pais, the Templar Grand Master who founded the town. Small cafés line the streets, where you can sip on a coffee and watch life unfold. Tomar is ideal for travellers who want history and depth, not just a quick photo stop!
Évora – The Heart of Alentejo
Further south, in the wide-open landscapes of the Alentejo, lies Évora. Encircled by medieval walls, Évora’s compact historic centre is a UNESCO World Heritage Site. But unlike some heritage cities, it doesn’t feel staged, but lived in.
The Roman Temple of Évora stands dramatically against the sky, a reminder that this was once an important Roman settlement. Nearby, the cathedral rises above whitewashed houses and narrow lanes. Climb to its rooftop terrace for panoramic views across the city and rolling plains beyond.
Then there’s the Chapel of Bones, perhaps Évora’s most famous site. Lined with human bones and skulls, it’s both sobering and thought-provoking, built by Franciscan monks in the 17th century as a meditation on mortality.
But Évora’s appeal extends beyond its monuments. This is the heart of the Alentejo, a region known for vineyards and a slower, more grounded way of life. A particular highlight of this region is its delectable olive oil — and tasting it is one of the Best Things to Do in Portugal.
Discover the Underrated Places of Portugal with Overland
These are places where you can walk without rushing, where conversations linger over coffee, and where centuries of history feel close enough to touch. They’re ideal for travellers who have already seen the big cities or for first-time visitors who want their introduction to Portugal to feel authentic rather than hurried.
Of course, reaching these towns independently requires careful planning. Transport connections can be limited, and the real value in visiting them comes from understanding what you’re seeing.That’s why our 7-Day Portugal Explorer Tour is the perfect option. We travel overland, linking iconic highlights with remarkable towns like Óbidos, Tomar, and Évora. You won’t just pass through, but have time to explore properly, guided by local experts who bring each place to life. For travellers willing to go beyond the obvious, we offer a sense of discovery that stays with you long after the journey ends! If you have any questions or want to book your tour, feel free to get in touch with us.
