Cobblestones & Custard Tarts: Navigating Portugal’s Off-Season Charm
There is a specific kind of magic in Portugal during the off-season. The sweltering summer heat has vanished, replaced by a refreshing breeze that makes every uphill climb a pleasure. Our journey began at Lisbon’s Humberto Delgado Airport, where we picked up our rental car and traded the city lights for the southern horizon, heading toward the quiet, sun-drenched shores of the Eastern Algarve.
Coastal Calm in Monte Gordo
We spent the heart of our trip based in Monte Gordo, a coastal retreat that feels worlds away from the typical tourist trail. It was the perfect home base for a few days of slow living. We did venture into nearby Vila Real de Santo António a couple of times—not just for some dental work, but for a bite to eat and a bit of well-deserved pampering. Interestingly, that city was built in 1774 in just five months; a “model city” designed to mirror the grid-like streets of downtown Lisbon.
Fun Trivia: We weren’t the only ones drawn to the charm of Monte Gordo. Back in 1963, Hollywood legend Ingrid Bergman famously vacationed here to unwind after filming Hedda Gabler. It’s easy to see why she chose this corner of the world to escape the spotlight.
We also made sure to spend a day in Olhão, the Algarve’s fishing heart. Between shopping for local treasures, grabbing a great meal, and wandering the waterfront, we logged plenty of steps to balance out the incredible food.
The Measured Fork: A Mediterranean Balancing Act
As any of my readers know, traveling is the ultimate test of glucose management. Thankfully, Portuguese cuisine is a delicious “minefield” of Mediterranean staples—fresh fish, olive oils, and lean meats—which is actually a dream for someone looking to balance their levels.
Our Valentine’s Day dinner was a true highlight: Cozido à Portuguesa. This traditional “Portuguese Stew” is a powerhouse of boiled meats, sausages, and vegetables. It was hearty, satisfying, and surprisingly easy on my blood sugar. Over the course of the trip, we navigated a beautiful array of local flavors:
- Bifanas: The classic, garlic-marinated pork sandwich.
- Choco Frito: Tender fried cuttlefish.
- Feijoada: A rich, comforting bean and meat stew.
We even detoured for Indian food a couple of times and grabbed some pizza when the craving hit! Even with the occasional Pastel de Nata (those iconic egg custard tarts) and the extra carbs from the crusts, I managed to keep my levels remarkably steady. A few spikes here and there, but nothing that caused concern—proof that with a bit of “measured” planning, you can enjoy the full experience.
Carnival Spirit & Cobblestones in Loulé
After our Valentine’s celebration, we shifted gears and drove to Loulé. If Monte Gordo is the Algarve’s soul, Loulé is its heartbeat. We stayed right in the heart of downtown, trading the ocean breeze for the rhythmic energy of Carnaval. The festivities were in full swing, with the town’s famous cobblestone streets echoing with music and laughter.
Between the parades, we took in the local history, exploring the medieval Loulé Castle and the iconic neo-Arab Mercado Municipal. One of the most memorable parts of our stay was the breakfast spread at our boutique hotel; it was a visual feast that gave us the perfect fuel for a day of exploring the winding, historic alleys.
Fairytales and Masonic Mysteries
We saved the most dramatic landscapes for our final days as we headed back toward Lisbon. We spent our second-to-last day in Sintra, a place that feels pulled from a storybook. We climbed to the vibrant, multi-colored Pena Palace, and while we caught glimpses of the rugged Moorish Castle from a distance as we passed by, our real adventure lay further down the hill.
The hike led us to the enigmatic Quinta da Regaleira, the historic estate of António Augusto Carvalho Monteiro. We descended into the famous Initiation Well, a 27-meter “inverted tower” with a spiral staircase leading to a labyrinth of underground tunnels.
Historical Trivia: These tunnels and the well were never actually meant for water. They were designed for secret Masonic initiation rites, built to represent a journey from the darkness of the earth toward the light of the sky. Exploring those damp, stone passageways felt like stepping into a hidden world of symbols and secrets.
A Final Toast in Cascais
Before flying home to Canada, we headed to the seaside town of Cascais for a wonderful afternoon luncheon with family and friends. It was the perfect bookend to a trip that really began the night we arrived in Lisbon, catching up with fellow Canadian friends in Bairro Alto. Seeing them “living their best life” in such an enchanting city reminded us why we travel: for the connection, the culture, and the stories we bring home.
Portugal, you were delicious, historic, and utterly enchanting. Until next time, I’ll be keeping my fork ready for the next adventure.
