Bikepacking Planning

The Hidden Headaches

So we have our dream: set off on a grand adventure with nothing but our bikes, a sense of wanderlust, and the open road stretching ahead. A trip that started in my mind and flows into reality with a series of simple (scary!) decisions. How hard can it be, right?


On the whole, it’s been relatively easy to plan our intrepid bikepacking trip. We have a route (or at least the rough outline of one), the gear, the excitement and we are crazy enough. The thrill is in the details, after all!

But then… then we were introduced to two monsters: booking flight sand insurance.


Booking Flights: Not Quite So Easy

Booking a tour? Piece of cake! You book a pre-designed route, get a flight, and voilà! You’re on your way to your pre-planned adventure dreamland. But we don’t have an “endpoint” or “official dates” for this endpoint. Well, then we entered ‘the hard basket’.


I want the freedom to follow the road less travelled, but getting to that road means we have to navigate airlines, flights, and a little bit of uncharted chaos. Think: limited routes to remote destinations, tough time syncing travel with gear, and always the nagging question: where do I even fly into?!


Insurance: A Whole New Level of Fun

Now, if we were into cruises or biking tours, insurance is no problem. We can practically get it with a click of your mouse. Book a hotel, stroll around a couple of plazas, maybe pop a bike into a tour group and boom—we are covered. But take it to the wild, remote places above 3,000m, where the only things nearby are our bikes (and the odd llama or two!), and our spirit of adventure. Good luck with that.


Trying to get insurance for that? It was like trying to get a yes from a toddler who has discovered the power of the word “no.”


We called up insurance companies and explained our journey—crossing mountain ranges, peddling remote backcountry, biking through places where the concept of roads is more of a suggestion than a reality. And they talk at us like you’ve asked to ride our bikes straight into a firing volcano.


Hot Tip 1: Get yourself a travel agent—a creative one! They’ll know the workarounds and who to call when the ‘normal’ options don’t cut it. Don’t just pick any agent. Go for the one who thrives on getting those special travel paths to align. Trust me, this doesn’t cost you a thing but it could save you days of stress and sleepless nights!


Hot Tip 2: Get an insurance broker—one that knows the loopholes. This is key. You’re not just looking for basic coverage for typical trips. You’re hunting for a broker who gets the remote, above-3,000m, “we’ve never been to this place before” kind of insurance. They’ll understand your request, know the right questions to ask, and, if you’re lucky, help you avoid banging your head against the wall. Literally.


Don’t Let the Details Ruin the Dream

Was planning an intrepid bikepacking trip a piece of cake? Well, sort of… Until we added flights, insurance, and logistics into the mix. But with the right travel agents, the right insurance broker, and a bit of tenacity, we made it work without to much bashing our heads against a brick wall!!


I think the adventure isn’t in perfecting our plans—it’s in the chaos of getting it all together and making it happen. With a little help and the right prep, our wild ride to South America is just around the corner.