The long one. Often after something: a sale, a retirement, the kids leaving, a year that asked too much. The shape of the trip is what makes it work or doesn't.
A sabbatical isn't a holiday with more days in it. The rhythm has to change. After two weeks of moving, most people break. After three weeks of stillness, most people get restless. The trip that lands is the one that builds in the right ratio of motion to rest, and the right unspoken permission to do less than the brochure suggests.
The work is mostly about pace. Where you start, where you end, where the trip changes register. A month through Japan and northern Thailand. Six weeks split between southern Italy and the Greek islands. The South American loop done slowly: Buenos Aires, the Iguazú border, Salta, into Bolivia. Africa and the Indian Ocean combined, with ten days on safari, ten days at sea, and no flight in between you can't recover from.
The properties matter less than the through-line. A sabbatical with three brilliant hotels and the wrong order between them is a worse trip than one with two competent hotels and the right shape.
It is the trip type where having someone who knows you across multiple journeys earns its keep most quickly. The second one is materially easier than the first, because we've already learned how you actually travel rather than how you say you do.
The other five
When you're ready