Where to Go in Portugal: Five Places I'd Build a Trip Around

I keep meeting people who "did Portugal" over a long weekend in Lisbon. Lisbon's worth it. It's also maybe a tenth of the story. Give the country another few days and it keeps changing on you: a medieval river city up north, a fog-bound hill stacked with palaces an hour from the capital, then two sets of Atlantic islands that barely feel like the same nation.

These are the five I'd plan a trip around, with the practical notes I wish I'd had the first time. The deeper destination guides and most of the tours I mention live on our Portugal sister site, Guidekin, if you want to dig into any one of them.

Lisbon — start here, but pace yourself

Most trips start in Lisbon and there's no shame in that. The airport sits twenty minutes from the centre on the red metro line, which spoils you for day trips later.

What gets people is the climb. The city is draped over a row of hills, and you earn your views one calf-burning lane at a time until you hit a miradouro and the whole tiled mess of rooftops falls away to the river. Senhora do Monte is the one I send people to first. Go at golden hour, bring a beer from the kiosk, fight for a spot on the wall.

Alfama is the old soul of it, the quarter that mostly shrugged off the 1755 earthquake, and it's best after dark, when fado leaks out of doorways and you stop bothering with the map. Ride Tram 28 if you must, but board it early; by nine it's a sardine tin of selfie sticks. Out in Belém, queue for a custard tart at the place that's been making them since 1837 (the copies elsewhere are fine, this one is better), then walk it off around the monastery.

Fair warning: Lisbon tries to keep you. People book three days and stay nine. If you want to spread out past the obvious, the run-down of Lisbon tours and day trips is a useful way to see what's actually within reach of the city.

Sintra — book before you go, seriously

Sintra is the day trip everyone takes, and half of them do it wrong. The fix is simple: buy your palace tickets online before you leave Lisbon, and catch the first train out of Rossio (about forty minutes). Show up on spec at eleven and you'll spend the day in queues instead of gardens. If timed entry stresses you out, guided visits to the Sintra palaces bundle the tickets so you're through the gate before the coaches arrive.

The headliner is Pena Palace, a red-and-yellow thing on the ridge that looks like a child designed it and a king paid for it. I actually prefer Quinta da Regaleira down the hill, mostly for the Initiation Well: a moss-slick spiral staircase that bores straight down into the ground like a set from a myth. The ruined Moorish castle earns its walk on the wall-top views alone.

Then there's the weather. Sintra makes its own, cooler than Lisbon and often socked in with fog before noon, which is either atmospheric or maddening depending on your mood. Bring a layer. If you've still got light, push on to Cabo da Roca, the cliff where mainland Europe just runs out of land.

Porto — the one I'd go back to first

If I had to repeat a single Portuguese city, it'd be Porto. Steeper than Lisbon, rougher around the edges, and it wears its history without buffing it first.

The postcard is the Ribeira waterfront and the double-decker Dom Luís I bridge, but the good stuff is across the water in Vila Nova de Gaia, where the port houses have aged their barrels for a couple of centuries. You can walk between cellars — Graham's, Taylor's, Cálem — and most pour a tasting with a view back over the old town. Lock in the port-lodge tastings and a Douro cruise ahead of a weekend; the better lodges fill up.

Back on the Porto side, step into São Bento station even if you've nowhere to be, just for the twenty-odd thousand blue tiles narrating Portuguese history across the walls. Then eat a francesinha. It's an absurd sandwich, meat and melted cheese under a beer-and-tomato sauce with an egg on top, and it's exactly what you want after a day of stairs. Porto is also the front door to the Douro Valley, which is a trip of its own, and probably your reason to come back.

Madeira — not the cruise-stop cliché

People file Madeira under "cruise stop" or "where my grandparents went," then they actually go and quietly shut up about it. It's a volcanic island ninety minutes by plane from Lisbon, green and near-vertical, with a spring-ish climate that barely shifts all year.

The walking is the reason to come. Levada trails follow centuries-old irrigation channels into the mountains along near-flat ledges, so you get alpine scenery without the alpine suffering. For one big day, the ridge route between Pico do Arieiro and Pico Ruivo runs along the island's spine, usually above the cloud; start before dawn and you'll watch the sun break over a sea of mist. The ancient laurel forest it threads through, the Laurisilva, is a UNESCO site, and there's a decent primer on Visit Portugal if you want the background. Prefer something gentler on the knees? The guided levada walks and Madeira tours run from easy strolls to full-day scrambles.

Funchal, the capital, deserves a slow morning at the market, and yes, do the wicker toboggan run down from Monte at least once for the sheer silliness of it. Close the day with a poncha — honey, sugarcane spirit, lemon — and then don't drive anywhere.

The Azores — go now, before everyone else figures it out

The Azores are nine volcanic islands sitting alone in the middle of the Atlantic, and they're the wildest, greenest stretch of Portugal by some way. São Miguel, the biggest, is the easy first island. Stand at the Vista do Rei and look down on the twin crater lakes of Sete Cidades, one supposedly blue and one green (whether you can tell depends entirely on the cloud that day). In Furnas, dinner comes out of the ground: cozido lowered into the geothermal soil in the morning and dug out, falling apart, by lunch. There's an iron-stained hot spring the colour of weak tea nearby to soak it off.

This is also one of the best places anywhere to see whales. Sperm whales and dolphins are out there most of the year, and the whale-watching boats and island tours leave from a few different harbours, so one's usually easy to slot around the forecast. And you will plan around the forecast here. The Azores do four seasons in an afternoon; that's the tax on all that green.

With more days, hop over to Pico, where the volcano of the same name is the highest mountain in all of Portugal. Most people never get past São Miguel. That's fine by me. More hydrangea-lined road for the rest of us.

Fitting it together

So how do you actually combine this lot? The clean first trip is Lisbon for three days with a Sintra day folded in, then a fast train north to Porto for two more. That's a week, and a very good one. The islands are a different commitment. Madeira and the Azores each want their own stretch rather than a bolt-on, so I'd hold them for a second trip instead of cramming everything at once.

Whatever you choose, my one rule for Portugal: book the few things that sell out, and leave everything else loose. The place is better when you're a little bit lost in it.