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Aug 20, 2026
Chasing the Sun South
Three months, mostly Portugal, built around one embarrassingly simple idea: go where it's warm, and keep going as it gets colder. Here's the whole plan.
Hippie Playboy
Slow travel, warm winters, and the road ahead.
Active journeys
On the road · Sep 28, 2026 – Oct 12, 2026
Nine Nights North
Pasadena to the Oregon coast the slow way — twelve hundred miles of Highway 1 in an 18-foot trailer behind a Jeep, alone. Elephant seals at San Simeon, the whole of Big Sur in one long golden day, ranch country above Pescadero, a bluff over the Pacific where you take what you can get, two nights in the Mendocino wind, and the old-growth redwoods on the way north to meet my son near Newport. Fires closed Big Sur to sleeping this year, so the plan bent around them. Nine nights, and the good ones were never the planned ones.
Follow the route →Planning · 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.
Follow the route →