Between the Deadlines and the Deep Blue
Some trips are about adventure. Some are about relaxation. Ours was a challenging mix of both—equal parts spreadsheet deadlines and seaside sunsets, work calls and winding coastal roads, city squares and silent mountain trails. It was a work-slash-pleasure kind of journey, which meant balancing productivity with the simple joys of discovery.
Portugal—especially the island of Madeira—had long been on our radar. The promise of natural beauty, rich culture, and an easygoing atmosphere made it the perfect place to blend business with moments of pure escape. We traveled between the mainland and the island, choosing accommodations with a strategy: good first meal (fuel for exploration), a walkable location, and if possible, proximity to an airport or office—because nothing kills travel magic like a stressful commute.
We expected a great trip. What we didn’t expect was how deeply Portugal would settle into our souls.
Landing in Madeira: Where the Ocean Hugs the Mountains
We arrived in Madeira the way all travelers do—through Cristiano Ronaldo Airport, named after the island’s most famous son. Even before stepping off the plane, we were greeted with Madeira’s most famous welcome gift: wind. Pilots earn their stripes landing here, where the sea crashes against steep cliffs, and gusts test their precision. Fortunately, ours must have been a pro because we landed smoothly.
Our first stop was Santa Cruz Village Hotel, chosen for its perfect trifecta: close to town, near my office, and walkable to the airport. That last one wasn’t just a theory—we actually did the walk, suitcases rolling along behind us, skipping the 5€ BOLT ride like champions.
Santa Cruz felt like a town caught between the past and present—small but lively, with traditional homes, family-run cafés, and a sunlit promenade tracing the coastline. It also happened to be festival week—the Santo Amaro celebration, the final farewell to Christmas. Locals filled the streets with music, laughter, and food stalls selling sweets, ponchas and espedata. It was the kind of warm welcome that instantly makes you feel like you’re part of something.
But the real star of Madeira? The scenery. No matter how many photos you see, nothing prepares you for the scale of it—mountains so steep they seem to fold into the ocean, clouds hanging low over green cliffs, roads that wind through landscapes that belong in a dream. And, of course, water everywhere you look, being surrounded by the North Atlantic Ocean.
Porto Moniz: Where the Ocean Carves Its Own Pools
We set aside a weekend to drive west to Porto Moniz, a place where nature and the Atlantic Ocean have done something truly spectacular. Here, lava flows once met the sea, cooled, and formed natural swimming pools—little pockets of turquoise where waves crash against black volcanic rock. It’s the kind of place that looks straight out of a fantasy novel.
We stayed at Aqua Natura Bay Hotel, just a five-minute walk from the pools. A rooftop pool, an ocean-view restaurant, and a cozy room—not bad for a winter getaway. Sure, it was too cold to swim outside, but just standing near the pools, watching the Atlantic breathe in and out, was an experience on its own.
We also tracked down a little hidden curiosity—the “Hobbit Bar” at Casas Da Levada. Tucked away in the mountains, this place felt like stepping into another world. The owner was kind enough to let us peek inside, and we immediately made a mental note to book a stay here next time.
Funchal: A City Wrapped in Christmas Lights
Returning to Funchal, Madeira’s capital, felt like stepping into a Christmas postcard—even though it was January. The decorations were still up, and the city glowed with lights and festive cheer. There’s something about the way Madeira does Christmas—it lingers just a little longer, like the warmth of a good meal or a long conversation with an old friend.
We took the airport shuttle (6.40€, cash only) straight into town and checked into Five Design Rooftop by Storytellers—a no-frills apartment but perfectly located near grocery stores and the pedestrian-friendly Old Town. This was where we split up for a bit—sometimes working, sometimes wandering solo. That’s the thing about balancing work and travel: you make space for both, and somehow, it all evens out.
Back to the Mainland: Lisbon, Then the Road
Flying back to Lisbon was uneventful—though let’s be real, airports are never fun. No matter how smoothly things go, they’re always the hardest part of any trip—the lines, the security checks, the general loss of time. At least in Lisbon, we found Cosy Rooms, a shared apartment near the airport. We ended up chatting with the other guests, which was a reminder of why we love travel—the unexpected connections, the shared stories over coffee in unfamiliar kitchens.
Then came the road trip.
We visited Alcobaça, Nazaré, and Óbidos—a mix of history, coastal cliffs, and medieval charm. Óbidos, in particular, was a time machine—a walled town where cobbled streets led to ginginha (cherry liquor) shops and old bookshops. But fair warning: parking is outside the walls, which meant dragging luggage over stone paths (a fun workout we didn’t ask for).
Coimbra: Breakfast Worth Writing Home About
Of all the places we stayed, one truly nailed breakfast—Coimbra Monumentais B&B. The homemade spread was so good it deserves its own paragraph—fresh pastries, warm bread, cheeses, jams, and a cozy setting that made it feel like a meal made just for you. It was the kind of breakfast that makes you linger a little longer, the kind that makes you think, why don’t we eat like this every day?
Coimbra itself was steeped in history, with its ancient university, narrow streets, fado music and buildings that whispered stories of centuries past. But it was the food—simple, fresh, made with care—that really stayed with us.
Douro Valley & Porto: A Perfect Ending
For the wine leg of the trip, we stayed in the Douro Valley at Quinta dos Padrinhos, surrounded by rolling vineyards and misty hills. Even though it was too cold for the pool, the views were worth every mile driven.
And then, Porto—the grand finale.
We stayed at Hotel Jaguar Oporto, where they welcomed us with complimentary Port wine (as all hotels should, honestly). The staff even offered to drive us closer to the Old Town, sparing us a long walk. Porto had a certain energy—more laid-back than Lisbon, but buzzing in its own way—and we soaked it in, knowing it was our last stop before heading home.
Coming Home, But Never Really Leaving
As the trip wound down, the usual feeling settled in—the bittersweet pull of leaving a place that had, in some way, changed us. There’s comfort in heading home, in familiar routines and your own bed, but there’s also a quiet sadness in knowing you won’t wake up to the sight of Madeira’s cliffs, or the smell of fresh pastries in Coimbra, or the hush of Porto’s Douro River.
We’ll go back someday. Maybe in summer, when Porto Moniz’s pools are warm enough to swim in. Maybe to finally stay at that Hobbit bar. Maybe just to wander the streets of Funchal at Christmas again.
Portugal lingers. It doesn’t let go easily. And honestly, I wouldn’t want it to.
