Hippie Playboy

Hippie Playboy

Slow travel, warm winters, and the road ahead.

Active journeys

On the road · Sep 21, 2026 – Sep 28, 2026

Same Same But Different

A week at Lake Perris in two halves — four days building the place as a volunteer, then three days watching everyone else enjoy it. Desert heat, a reservoir the color of a swimming pool, and music running until the sky goes pale. The last stop before the trailer points north for a month on the coast.

Follow the route →
Planning · Sep 28, 2026 – Oct 10, 2026

Nine Nights North

Pasadena to the Oregon coast the slow way — 1,200 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, a ranch above Pescadero, a bluff over the Pacific where you take what you can get, two nights in the Mendocino wind, and the redwoods on the way to a campground my son picked out near Newport. Fires closed Big Sur to sleeping this year, so the plan bent around them. Most of it isn't booked. That's the point.

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 →

From the journal