On the road · Oct 19, 2026 – Jan 15, 2027

Portugal Winter 2026 / 27

Three months following the warm coast south — a week of ADE in Amsterdam, a month living in Lisbon, a detour to Marrakesh for the film festival, December in the Algarve, and New Year's fireworks over Madeira.

Right now
Lisbon, Portugal
Next up
Costa da Caparica, PortugalNov 25, 2026
Stops
8

The route

  1. Amsterdam, Netherlands
    Oct 19 – Oct 26, 2026

    Amsterdam, Netherlands

    Netherlands

    The week is built around ADE — the Amsterdam Dance Event, Oct 21–25 — the biggest electronic music festival on earth, with 300+ venues turning the whole city into one dance floor. Days for the canals and the old city, nights for the music.

  2. Lisbon, Portugal
    Oct 26 – Nov 25, 2026Here now

    Lisbon, Portugal

    Portugal

    The city month, timed for the mildest, most golden early weeks. Basing in Alfama, the oldest neighborhood in the city — steep lanes and stairways, tram 28 rattling past the cathedral, rooftops tumbling down to the Tagus, and a serious late-night scene when the mood strikes.

  3. Costa da Caparica, Portugal
    Nov 25 – Dec 2, 2026

    Costa da Caparica, Portugal

    Portugal

    A friend flies in from home, so it's a week across the river on the Atlantic side: miles of open beach just south of Lisbon, surf shacks and seafood, and the city skyline a short hop back over the bridge.

  4. Casablanca, Morocco
    Dec 2 – Dec 4, 2026

    Casablanca, Morocco

    Morocco

    Here because Casablanca is my favorite movie, and some pilgrimages you just have to make. A couple of days in the big, modern city on the Atlantic is plenty: the Hassan II Mosque standing out over the ocean, a drink at the closest thing to Rick's I can find, and a first taste of Morocco before heading inland.

  5. Marrakesh, Morocco
    Dec 4 – Dec 14, 2026

    Marrakesh, Morocco

    Morocco

    The side quest. Ten days of souks, riads, mint tea and the great square of Jemaa el-Fnaa coming alive at night, with the Atlas mountains on the horizon. A fun dose of noise and culture shock after a month of easy, English-friendly Lisbon.

  6. Lagos, Algarve
    Dec 14 – Dec 29, 2026

    Lagos, Algarve

    Portugal

    The December home base — the warmest, sunniest corner of the mainland, gold sandstone cliffs and hidden coves, deliberately saved for the coldest, wettest stretch of winter. Side-trips out to Tavira and Sagres when the mood hits.

  7. Funchal, Madeira
    Dec 29, 2026 – Jan 12, 2027

    Funchal, Madeira

    Portugal

    Flying out before New Year's, then settling in for two weeks. Subtropical and evergreen — one of the warmest, sunniest spots in all of Europe in December — and a record-breaking fireworks show over the bay to ring in the year. Levada walks, sea cliffs, and Madeira wine.

  8. Lisbon, Portugal
    Jan 12 – Jan 15, 2027

    Lisbon, Portugal

    Portugal

    A few last days back in the city to wrap up — a final round of the places that made the first month.

From the journal

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