We've been to Iceland three times — in September, October and February — doing the kind of things that make travel insurance less of an afterthought and more of a genuine necessity. Driving remote roads in the dark chasing the northern lights, hiking across lava fields and glaciers, navigating weather that changes faster than any forecast predicted.

Iceland is small but mighty. It's one of the most geographically dramatic countries on earth, and a lot of what makes it worth visiting — the interior highlands, the glacier lagoons, the black sand beaches — is also genuinely remote. The nearest hospital to some of the places we've been is a long drive or a helicopter ride away.

That changes the insurance conversation.

Most travel insurance policies are written for people who stay on paved surfaces. The fine print tends to assume a hotel, a beach, maybe a city tour. If you're the kind of traveller who plans trips around trails, summits, and carrying everything you need on your back, that fine print deserves more than a skim.

We've hiked in Abisko National Park in freezing temperatures, climbed in the Lofoten Islands, walked alongside icebergs in Greenland, snowshoed through Swedish Lapland, and spent time in some of the more remote corners of Iceland. We've been close enough to needing a claim — a snowmobile incident in Svalbard being the most memorable — to know that having the right coverage matters a lot more than saving €20 on a policy.

Here's what to actually look for when buying travel insurance for hiking and backpacking.

We run a travel blog, and before that, we worked as freelancers. Which means at some point we crossed the line from "people who travel a lot" to "people who work while traveling" — and that changes the insurance conversation in ways that most standard guides don't address.

When you're working abroad, the stakes are different. You're not just covering a two-week holiday. You need health coverage that works for months at a stretch, potentially in multiple countries. You're carrying equipment — laptops, cameras, hard drives — that represents your income, not just your entertainment. And if something goes wrong, you can't just cut the trip short and go home, because the trip is the job.

The good news: there are plans built for exactly this. The less good news: not all of them are worth the money, and the distinctions between them matter more than most people realize before they actually need to make a claim.

For years we bought travel insurance the way most people do: per trip, every time, slightly begrudgingly and always wondering if it was worth it. A policy for Iceland. A policy for Norway. Another one for Portugal. By the time we were taking five or six trips a year — which added up faster than we expected once travel became our job — without even considering the time factor.

The switch to an annual plan travel insurance felt obvious. One policy, one payment, covered for every trip we take that year — including the spontaneous ones, the long weekends, and the press trips we sometimes get a short notice for.

But an annual multi-trip travel insurance isn't the right answer for everyone. If you're planning one long continuous trip — a three-month slow travel stint through Southeast Asia, a working season abroad, a sabbatical — a long-stay policy is a completely different product and usually a better fit. Here's how both work, and how to figure out which one applies to you.

We often get asked if a travel insurance is necessary.

Good question!

Keep reading to find out, to learn all the benefits of a travel insurance, and to enjoy 5% discount — up to 15% off with seasonal offers — exclusive to Penguin Trampoline readers if you do need one.

When we travel, be it the arctic fjords of Norway or the hidden beaches of Portugal, one thing stays constant: our insurance. We’ve used Heymondo for every trip and in this Heymondo review you’ll see why we keep going back to it — especially because of its value for cancellation coverage and outdoor-activity protection.