As told by Danielle Rudic, Vice President of Marketing and Product
At Travelive, we take product testing very personally. When we say we try everything before offering it to our travelers, we mean it in the most literal way possible. We bring the family. All ages. All opinions. Very little filtering. If something works for a well-traveled, fun-loving, occasionally stubborn group traveling together, we trust it will work for anyone.
Each year, my family picks one destination to reunite in, since we live in different parts of Europe. This year, Portugal got the honor. It was my umpteenth visit and everyone else’s first, which meant expectations were high and commentary was constant. Five nights. Six days. Best of Portugal, plus a few surprises. No padding. No rushing.
Portugal understood the assignment.
Nights 1-2 | Lisbon
We began in Lisbon, staying in a family apartment at Torel Palace. I insisted on this property, and within minutes, everyone stopped questioning my decision. Historic palace. Big views. Actual character. The kind of place that makes you slow down without asking your permission.
Breakfast deserves a mention because it became an event. Generous, relaxed, and dangerously easy to linger over, it powered us up for Lisbon’s hills and encouraged unnecessary second cups of coffee. Then there was the resident cat. She appeared, assessed the group, immediately identified the animal people, and claimed us. Within an hour, she was checking on us regularly with a casual “s’up” look, as if she were management and we were doing fine under her supervision.
Our first afternoon was dedicated to walking. Alfama. Bairro Alto. Side streets. Staircases that felt personal. Everyone wanted to feel the city, which led to an impressive step count and a shared realization that Lisbon does not recognize flat terrain as a concept. Winter helped. Crisp air, fewer crowds, and Christmas markets glowing with twinkling lights made even the uphill climbs feel festive. Almost.
Day two started early and in proper Travelive style. Our rental car was waiting for us directly at the hotel. No offices. No lines. No stress. Bags in the trunk, coffee secured, and we were on our way.
First stop was Belém. Specifically, pastéis de nata from Pastéis de Belém. Still warm. Gone immediately. Yes, those pastries. But Belém was not just a sugar stop. We explored Jerónimos Monastery, admired its intricate Manueline details, and walked along the river to the Monument to the Discoveries. History had its moment. Dessert still won.
From there, we headed toward Sintra, stopping at Cabo da Roca, the westernmost point of mainland Europe. Windy, dramatic, and perfect for photos that make everyone briefly philosophical.
In Sintra, Pena Palace delivered exactly what you expect. Bold colors, towers, and romantic excess in every direction. Then came my personal favorite, Quinta da Regaleira. Mystical gardens, secret tunnels, symbolism everywhere, and the Initiation Well that somehow convinces every visitor to whisper, even when no one explains why.
Important note from someone who has learned the hard way. If you are self-driving and visiting Quinta da Regaleira, park at the last official parking lot before entering old Sintra. It is a 15-minute walk. If you decide to push your luck and drive farther in search of something closer, Sintra will reward you with a completely unnecessary 20-minute scenic loop around the entire town before returning you to the exact same parking spot, slightly older and significantly wiser.
Nights 3-4 |Alentejo
On day three, we headed south into Alentejo, my favorite region in Portugal and the place where time simply behaves differently.
We paused in Alcácer do Sal for traditional fritters with chickpea jam and coffee, followed by a relaxed stroll along the river. Lunch came in Comporta, where winter sun, quiet beaches, and sand underfoot immediately reset everyone’s pace. We also stopped to see the upcoming Na Praia hotel, opening this summer and created by the same visionary behind São Lourenço do Barrocal. Expectations are officially high.
Just before reaching Évora, we visited the Chapel of Bones. Sobering, fascinating, and oddly bonding. Nothing brings a family together quite like contemplating mortality before dinner.
Our home for the next two nights was Octant Évora, and it felt like a deep exhale. We stayed in a two-bedroom villa with a pool, which in winter became the ideal spot for sunset wine and long conversations.
The next morning explained everything. The grounds are vast and beautifully spaced, with areas for children and adults, swimming spots in the water reservoir, farm animals, herb gardens, lakes, and miles of greenery; with no crowds in sight. Even my adult children reverted to age six, petting animals and riding around in a golf cart with serious enthusiasm. The wine vault inside the hotel impressed them just as much, which says a lot.
Later, we visited the Cromlech of the Almendres, often described as Portugal’s Stonehenge and notably older. Dating back more than 7,000 years, the stones sit quietly among cork trees and open skies. No fences. No spectacle. Just a stillness that makes everyone instinctively lower their voice.
The afternoon took us to Monsaraz, and it was there that plans completely fell apart in the best possible way. Whitewashed houses, sweeping views over Alqueva Lake, and nativity scenes created by local artists filled every corner. We explored every lane, lingered at every viewpoint, and lost track of time entirely. Lunch at São Lourenço do Barrocal disappeared into the afternoon siesta. We mourned briefly. Local sangria helped.
Dinner was at O Moinho do Cu Torto, a deeply traditional spot with a spectacularly bad relationship with Google Translate. Our glowing review kept getting rejected for “inappropriate language,” thanks entirely to the restaurant’s name, which translates to “Crooked bottom (to put it mildly) mill. Inside, menu translations promised things that sounded alarming and bore absolutely no resemblance to what arrived at the table. We ignored the phones, trusted the kitchen, and were rewarded with generous, slow-cooked dishes that tasted like centuries of tradition. Laughter filled the room.
Night 5 | Back to Lisbon
Our final night brought us back to Lisbon and into Pousada de Lisboa on Praça do Comércio. Elegant, central, and exactly what we needed after a week on the road.
The rental car vanished seamlessly, collected directly from the hotel. Bags dropped, we met my favorite tuk tuk driver for one last photo tour of Lisbon’s viewpoints. Golden light, familiar jokes, and a final look at a city that had delivered far more than expected in a very short time.
Final Thoughts
Portugal proved that even a bite-sized itinerary can feel rich, layered, and genuinely memorable. At Travelive, we test everything before offering it to our travelers. Sometimes that means skipping lunch. Sometimes it means upsetting Google Translate. Always, it means sharing experiences we believe in because we lived them first.
