So far, life is the longest trip I’ve ever taken. The challenge of this question is knowing what counts as a “trip.” I lived in India for over 12 years? Was that a trip? It didn’t feel like it. It felt like my home was in a different country. I think I once spent about two months one Summer in Hungary back in the 90’s? Was that a trip or family time? I’ve spent about a month (just under what would be required to do a “visa run” — more of a fresh stamp run) in Thailand. I suspect the latter is what the question aims at. While I’m pretty far toward the traveler end of the Traveler – Tribesman continuum, 30 days moving about without being someplace that feels home-like is where it starts to wear on me. (Of course, being a traveler, any place can feel homelike if I don’t need to think about where to eat on a daily basis or how to do laundry on a weekly basis.)
Of course, maybe the question is drug related. In which case, I once had psilocybe mushroom tea, and that trip lasted about five hours?
Tiger Riding for Beginners 