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Lisbon rooftops from above.

Fourteen Days from Lisbon to Casablanca

October 4–17, 2025 · Ben and Marta

“Lisbon to Casablanca in a fortnight, mostly by train, because we wanted to feel the distance rather than skip it.”

The ground covered

Lisbon

4 days

Day 1 Arrival

TAP Air Portugal Flight TP204 — Newark to Lisbon

Overnight, landed 8am, and we made the classic mistake of booking a room we couldn’t get into until three.

Time Out MarketLisbon6/10

Where you go when you have four hours and a suitcase. Fine. Loud. We would not go back with a choice.

Journal entry

Slept badly on the plane and spent the first day in that useful fog where you agree to anything. Walked most of Baixa without meaning to.

Day 2 Alfama, properly

Miradouro da Senhora do MonteLisbon9/10

Get there before nine and you have it. After eleven it is a queue for the same photograph.

Cervejaria RamiroLisbon10/10

Garlic shrimp, and then more garlic shrimp. The best thing we ate all trip and we ate very well.

Journal entry

Two hours of getting lost on purpose. The 28 tram went past four times and we never got on it, which felt like the right call.

Day 3 Sintra

Train — Rossio to Sintra

40 minutes, runs constantly, costs almost nothing. Go early; the town fills by ten.

Quinta da Regaleira9/10

The initiation well is the thing everyone photographs. It earns it. The gardens above are emptier and better.

Pena Palace5/10

Beautiful from a distance and a scrum up close. We queued 50 minutes and saw it mostly over shoulders.

Journal entry

Sintra is a day trip that wants to be two days. We tried to do three palaces and did one and a half properly.

Day 4 Belém and the last Lisbon night

Pastéis de BelémLisbon8/10

Yes it’s the tourist one. Yes they’re better warm and they only are here.

LX FactoryLisbon7/10

Good bookshop, good coffee, more gift shops than it needs.

Porto

3 days

Day 5 North to Porto

Alfa Pendular — Oriente to Campanhã

Book a window on the left going north. Comfortable, punctual, and the last hour is worth staying awake for.

Livraria LelloPorto5/10

A beautiful staircase and a hundred people photographing it. Ten minutes inside, and we paid for the privilege.

Day 6 The river

Ponte Luís I, upper deckPorto10/10

Walk it at dusk from the Gaia side. Free, five minutes, and the best thing in the city.

Port lodge tasting, Vila Nova de GaiaVila Nova de Gaia8/10

We learned the difference between tawny and ruby and forgot it by Madrid, but the terrace was worth the ticket alone.

Journal entry

It rained for two hours and we sat it out under an awning with a glass of white port and tonic, which nobody had told us about and which we then ordered every evening.

Day 7 Matosinhos

Metro to the coast, grilled fish for lunch9/10

Twenty minutes on the metro and you are at the Atlantic eating whatever came in that morning. Barely a menu.

Madrid

4 days

Day 8 East to Madrid

TAP Air Portugal Flight TP1094 — Porto to Madrid

Short and unremarkable, which is what you want. There is no good train on this leg, and we checked twice.

Mercado de San FernandoMadrid7/10

The neighbourhood market rather than the famous one. Cheaper, better, and nobody was photographing their food.

Day 9 The Prado, and only the Prado

Museo del PradoMadrid10/10

Three hours, one wing, no attempt at the rest. Best museum decision we have ever made.

Retiro at duskMadrid8/10

Rowing boats, a busker doing Leonard Cohen badly, and the light going orange behind the Palacio de Cristal.

Day 10 Toledo

Train — Atocha to Toledo

33 minutes. Book the return before you go; the afternoon trains sell out.

Toledo old town9/10

Steep, medieval, and almost empty by six when the coaches leave. Stay for the evening if you can.

Day 11 A day with nothing in it

Journal entry

We had booked nothing and nearly filled it anyway. Instead: coffee, a long lunch, a nap, and a walk with no destination. The best day of the trip and the only one with no photographs.

Casablanca

3 days

Day 12 Across the water

AT971 — Madrid to Casablanca

Two hours and a different continent. Get dirhams at the airport; the medina is cash.

Rick’s CaféCasablanca6/10

We knew exactly what it was and went anyway. The piano is good. The rest is the film.

Day 13 Hassan II

Hassan II MosqueCasablanca10/10

Take the guided tour — it is the only way inside, and the scale does not read from the outside.

Old medinaCasablanca7/10

Working, not curated. We bought nothing and it was the most interesting hour of the day.

Journal entry

Thirteen days in and the Atlantic is the same ocean we started on. That took a moment to land.

Day 14 Home

AT200 — Casablanca to New York

Direct, eight hours, and we slept most of it for once.


Highlights What stood out

“Garlic shrimp, and then more garlic shrimp. The best thing we ate all trip and we ate very well.”Best meal — Cervejaria Ramiro, Lisbon
“It rained for two hours and we sat it out with a glass of white port and tonic, which nobody had told us about and which we then ordered every evening.”Best accident — Vila Nova de Gaia, Porto
“We had booked nothing and nearly filled it anyway. The best day of the trip and the only one with no photographs.”Best day — Madrid

Reflection Looking back

Five places in fourteen days is one too many and we would do it again. What we would change: two nights fewer in Lisbon, two more in Porto, and stop booking the first morning after a night flight. What we got right was the empty day, which we nearly cancelled twice.

This is what a week looks like when you keep it.

Yours would look like your week — the ratings, the notes, the photo from the ferry. Free, as many trips as you have.