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Who We Are

START YOUR
ENGINES.

Prepare to get gloriously lost.

We're not a travel agency. We're not a tour operator. And we're definitely not here to hold your hand. ChiefCups is a crew of adventure addicts and logistics nerds on a mission to bring back the kind of travel that makes your pulse race and your stories legendary.

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Who we are

We set the stage.
You write the story.

We design offbeat and unscripted overland experiences in some of the wildest corners of the planet. No fixed routes, no 5-star fluff, just a challenge-based format where creativity, grit, and questionable decisions pave the way to glory.

Behind the madness? A small team working out of backpacks and 4x4 trunks, fuelled by maps, instant risottos, and the belief that the best memories are the ones you make along the road.

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Carlo Avati
Carlo Avati
Founder · Chief Adventure Officer (The CAO)
The CAO

Built to explore.
Wired to build.

Carlo Avati, aka The CAO, is the engine behind every Cup, ridiculous challenge, and wild checkpoint you'll stumble into. Former tech founder turned chaos architect, he's the one pulling the strings behind the scenes and occasionally pulling your car out of a sand dune at 3AM.

He's crossed the Andes by horse, ridden a busted motorbike from Rome to Bhutan, and shared feasts with fishermen and yak herders alike. His travels have been featured on National Geographic. If there's one thing he takes seriously, it's making sure you have the adventure of your life.

Featured on National Geographic
IG: @_TheCAO
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Questions & answers

Everything you've been
afraid to ask.

A challenge-based 4x4 adventure rally company. We run multi-day overland events in some of the wildest corners of the planet. You get the vehicle, the road book and the challenges. Where you go, and how much trouble you find on the way, is entirely yours.
No, and yes. Nobody wins by driving fast, and there is no chequered flag at the end of a straight line. What there is: a scoreboard. Every challenge you complete is worth points, and the team with the most points at the finish line takes the Cup. So take the long way. Get lost on purpose. The team that detours three hundred kilometres for one absurd challenge usually beats the team that drove sensibly, and always tells the better story.
People who are done with organised tours and packages with the word "adventure" in the brochure. Most participants are 23 to 35 year old. You need a valid driving licence, some confidence on rough ground, and a high tolerance for uncertainty, discomfort, and joy arriving in unreasonable quantities.
Every Cup has its own set of challenges, built for its destination. Some are physical, some are creative, some exist purely to see whether you will actually do it. Each one is worth points. The full list is only revealed at the launch briefing the night before you drive out, so nobody plans their way to the Cup from a hotel room. Most points at the finish line wins.
No. You need to be a confident driver. If you have never driven on gravel, sand, or a track that has not been used since your grandparents were young, you will learn in the first afternoon. The road book and the support crew are there for the rest. What you do not need: rally experience, a 4x4 licence, or the faintest idea what you are doing on day one.
No. The vehicle is in your entry fee, along with the insurance, the paperwork and the camping gear. You show up and drive it into the unknown.
Less than you think. You are living out of one vehicle, so every extra bag is a bag you will be moving twice a day. We supply the camping gear, and a basic tool kit that will get you out of most trouble. Bring layers, a head torch, a spare light, and a tolerance for wearing the same shirt on day six. A roll of duct tape and a handful of cable ties have saved more Cups than any spanner. The full list is in the Adventure Handbook, which lands in your inbox the day you sign up.
Your phone is enough. Most teams navigate on a mix of the road book, an offline map, and asking someone at a petrol station to point. When you sign up you get access to our tracking app, which puts your position on the live map so everyone at home can watch you take the scenic route. If you want a dedicated satellite device, check the law first, because some countries treat them as restricted equipment and will take them off you at the airport. Ask us before you buy one. Honestly, the winging is half the point. The teams who always know exactly where they are tend to come back with the shortest stories.
Yes. It is mandatory, and we check. Get a policy that covers remote travel, and tell your insurer exactly what you are doing. One detail worth repeating to them, because it changes both the quote and the cover: this is not a race. Standard holiday cover will not carry you here, and finding that out from a hospital bed a long way from home is an expensive way to learn it.
This is a genuinely risky adventure, and we would rather say so than sell you a version where nothing can go wrong. You will be driving in remote areas with patchy signal and roads that change with the weather. We run support vehicles, checkpoint camps, local guides, and satellite phones on some events. It is not a controlled environment. That is the point. Travel insurance is mandatory. We take safety seriously. We just do not pretend the adventure comes without risk.
The entry fee covers a team of two to four, so most people arrive with their own crew. If you are on your own, message us. We can sometimes put you in touch with a team that has a seat free, and the solo travellers who take that gamble tend to be the ones telling the loudest stories at the finish.

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