.“Fail to prepare, prepare to fail”—a phrase that’s been drummed into me over decades of working life, and apparently, I can’t shake it even on holiday. If I were still in my twenties, I’d probably be throwing caution to the wind and letting the universe sort out the details. But I’m not twenty-something anymore, and I’ve long accepted that I need the comforting illusion of control that comes with knowing exactly where I’m sleeping and how I’m getting there.
I’ve also never packed lightly in my life—a character flaw I’m now forced to confront head-on. Whittling my belongings down to “essentials” feels like an impossible task, mainly because I’m convinced everything is essential. And let’s be honest: I may be taking a backpack, but I’m absolutely not staying in hostels. I have limits. That said, I will be embracing buses and trains with the enthusiasm of someone who’s watched too much Race Across The World and is determined to prove they’re still adventurous. We’ll see how that goes.

Latest adventures in the Caribbean