Some people mark the moment their kids leave home by redecorating a bedroom. My wife Briana and I marked it by getting on a plane to Portugal with our friends and fellow empty nesters Maurisa and David. We apparently decided the best cure for a suddenly quiet house was to fill it with two weeks of laughter and port. This is our Portugal trip summary: the whole two-week journey, tied together in one place.
We landed on this plan after more than twenty years of school pickups, sports schedules, and college move-ins — the kind of calendar that runs your life so completely that you forget what its like without. Then, all at once, it was empty. Portugal seemed like the responsible response. By the time we hit the airport lounge, we’d already swapped “our kids schedules” for whether four grown adults could reasonably justify a second round of drinks before a transatlantic flight. We could. We did.
Porto: Where the Plan Was to Have No Plan
Porto did not care that I’d spent months watching YouTube videos and scouring the internet about it. It simply handed us the Ribeira district — cobblestones, laundry lines, the Dom Luís bridge looming overhead — and let us feel appropriately small and touristy about the whole thing.
We settled into the Exmo Hotel by Olivia, a 16-room boutique spot where the staff treated us like slightly lost relatives who needed pointing in the right direction, which, in fairness, we did. They sent us to Bacalhau for our first taste of proper Portuguese cooking, and from there Porto did what it does best: let us wander without a schedule, through Mercado do Bolhão’s stalls, into a port cellar at Sandeman where David officially converted to Team Port, and eventually into Livraria Lello — a bookstore so famous it requires timed tickets, a fact I found ridiculous right up until I was inside it, staring at a carved wooden staircase like it owed me money.
But the real surprise was the Church of Saint Francis. Unassuming outside, absolutely dripping in gold on the inside — the kind of place where you forget to take a photo because you’re too busy standing there with your mouth open. (I may have snuck one anyway. No regrets.)
The Douro Valley: Two Nights of Doing Almost Nothing, Beautifully
If Porto was about motion, the Douro Valley was about slamming on the brakes. Two hours upriver, the roads narrowed, the hills turned into a staircase of vineyards, and we rolled into Ventozelo Hotel & Quinta — 400 hectares of working vineyard that happens to also have some of the nicest rooms we slept in the entire trip.
We hadn’t even unpacked before we were doing a private wine tour, which I’d assumed would feel redundant after Porto. It did not. Ventozelo’s pours might have been the best of the whole week. We hiked the vineyard trails, spent a golden hour at the infinity pool watching light change over the valley, and ate two consecutive “best meals of the trip” at the estate’s restaurant — a claim I recognize we made about four different meals on this journey. Portugal, it turns out, does not care about the integrity of your superlatives.
Lagos: Cliffs, Calamari, and an Anniversary in the Sand
Six hours south — and somehow the easy six hours, compared to those Douro switchbacks — Lagos traded vineyards for whitewashed buildings and cliffs that plunge into water so blue it looks photoshopped even when it isn’t. We set up camp at The Salty Lodge, then wasted no time getting on a boat.
Our guide Marta took the four of us — no crowd, no rushing — past sea caves and cliffs with beer and wine in hand, and handed us the trip’s best restaurant tip almost as an afterthought: Camilo, perched above its own cove, where a seared tuna nearly caused a fight over the last bite. We walked it off along the Ponta da Piedade boardwalk, stopping every few feet to declare a new “best view yet,” which the next bend would immediately disprove.
Then came the beach day — Praia da Dona Ana, sunbeds be damned (30 euros for two, and well worth the price) — which also happened to fall on our 23rd wedding anniversary. Two decades-plus of marriage, celebrated by doing absolutely nothing on a beach. I’d argue we’ve never made a better decision.
Lisbon: A City That Punishes Ambition
Lisbon greeted us with hills that treat “15-minute walk” as more of a suggestion than a fact, and a lunch at Estaminé — a two-table restaurant run by a husband-and-wife team who fed us, hosted us, and briefly made me emotionally compromised over shared plates. We chased it with cocktails at Secret Garden, the highest bar in the city, with the whole of Lisbon sprawled out below us in a way that made the climb feel, for once, entirely fair.
Not everything landed. Jerónimos Monastery’s “timed entry” turned out to mean “the time you begin waiting in the sun,” a lesson learned the hard way and one I will not be quietly letting go of.
Sintra: The Grand Finale, Guarded by a Well and Some Aggressive Wind
We closed things out with a day trip to Sintra, a town that looks like someone asked several architects to design a fairy tale and refused to let any of them compromise. Our guide Pedro walked us through Quinta da Regaleira’s inverted, water-free well — nine spiral landings, Masonic legend, and a floor tile that has launched a thousand conspiracy theories. From there it was on to Pena Palace, where 20-to-30-knot winds turned a leisurely castle stroll into something closer to an extreme sport. The views, to be fair, were worth every gust.
The Portugal Trip Summary: Two Weeks in Review
Two weeks, four empty nesters, and one very good excuse to stop talking about carpool lines. That’s the Portugal trip summary in full: Porto’s wandering streets, the terraced vineyards of the Douro, Lagos’s cliffs, Lisbon’s hills, and Sintra’s wind-battered castle. Turns out the house wasn’t the only thing that got a little quieter — so did the part of us that used to worry about schedules at all.
My Take: If I Had a Portugal Do-Over
If I were planning this trip again, I’d add more days in Porto and the Douro Valley, and trim a bit off Lagos and Lisbon to make room for it. Porto rewarded slowing down more than we expected, and two nights in the Douro was cruelly short — we’d barely learned where the good wine was kept before it was time to pack the car again. Lagos and Lisbon were both fantastic, but a day less in each wouldn’t have hurt us, and my calves would have filed no complaints. Call it a lesson learned in hindsight, which, as far as I can tell, is the only place lessons ever get learned.
Thinking about a trip of your own? That’s exactly what Why Not Just Go is for. Every post here comes from real travel, real mishaps, and real regrets about not booking another night. So pick a place, pack the comfortable shoes, and stop overthinking it. Why not just go?
