One of the most popular essays we have published on this website is titled Unconventional Adventures. In it, we make the case for embarking on adventures that deviate from the traditional flight-hotel-dinner-museum tourist itinerary. The essay seemed to resonate with people.

In response, some friends sent me a follow-up question: **How do I design a great adventure?**This is a difficult question to answer, because what constitutes a great adventure for you might be different than what I might enjoy, and because writing out the ‘rules’ for an adventure (like writing a

guide to empathy) feels a bit futile and counter to the whole point of adventuring. Still, I wanted to write this. My friends asked. And if you have not spent much time designing crazy adventures, it’s reasonable that planning them might be daunting.

So the below our my best criteria for designing an unconventional adventure.

If you did not read the original essay, our definition of ‘

unconventional adventure’ is roughly one that is both difficult and, as the name suggests, non-standard; eating at a two-star Michelin restaurant instead of a three-star would not qualify. Our hope is that you consider designing an adventure like this to spend some vacation time on next year instead of whatever it is you currently do :) Then email us and tell us how it went.

Reminder that this is all opinionated thinking from us and is not objective truth about the world! Many great adventures do not follow these criteria.

The ingredients of an excellent adventure

The first ingredient of an excellent adventure is actually an anti-ingredient: money. More money spent does not correlate to you having a fun adventure. Unlike many things in life (say, hotels) where spending more money can objectively get you a higher quality of experience, spending more money on your adventure will not. There might even be an inverse correlation. Money can make things boring.

Besides ‘don’t obsess over money’, below are the best heuristics we can provide. Design your adventure according to the following criteria and we are pretty sure you will have a good time; or if not a good time, an adventurous one.

(i) Your adventure should be difficult or uncomfortable in some way. It could be physically difficult—like hiking 10,000 feet of elevation gain in a single day. It could be mentally difficult—like playing hide and seek across an entire city. Or it could be both—like trying to hike 100 miles without a map. This intentional friction is one of the things that separates adventures from leisure travel. You have to use your brain, or your body, in new and unusual ways. Maybe you even get scared; adrenaline pumps. These are all the makings of an excellent adventure. Embrace the difficulty!

**(ii) Your adventure should have a specific goal. **Sure, the pages of history are filled with wandering adventures that featured no goal at all. Still, I find that it’s easier to land on an exciting adventure if you can think of some goal, however loose. Maybe your goal is to move from Point A to Point B. Maybe your goal is to aimlessly wander with some constraint (see below). Maybe your goal is to do something in a specific amount of time. I can’t decide for you. What I can say is—consider having a goal.

**(iii) Your adventure might be more fun with a constraint. **The easiest way, though not the only way, to find a fun constraint for your adventure is to use the word “without”.

• I’m walking across my city without a map
• I’m circumnavigating the globe without getting on an airplane
• I’m biking 1,000 miles without having trained in advance Of course there are other kinds of constraints, like limitations on time (I’m biking across the UK in 10 days) or limitations on money (I’m traveling from New York to Los Angeles on $50). It helps to think about what you would usually do if your adventure were leisure tourism—what tools would you use? What budget would you have? How much time would you need? Then remove one of those things.

**(iv) Your adventure should be exciting for some narrative reason. **This one is trickier, but humans love

a good story. We tell stories to ourselves all the time; about ourselves, about our jobs, about the world. And so it stands to reason that you will have a better time buying into the ridiculous concept of your adventure if it has some narrative standing. For example…

• A 50 mile hike in the mountains with 11,000 feet of elevation gain = Cool, but no narrative.
• A 50 mile hike from the beach to a mountaintop with 11,000 feet of gain = Now that’s exciting. You may be able to derive your narrative from your goal. If you are crossing a country, that might be narratively interesting enough without any modifications. But, as with the above example, if your idea was to do an exhausting hike then you might want to find an exhausting hike with some narrative appeal.

Other good examples:

source to sea down the Thames, crossing Wales in a straight line.

It’s true that people who post their adventures publicly (like the YouTubers I’ve linked above) have more pressure than most to find a narrative hook for their adventures. You don’t have to do this if you don’t want to, but I firmly believe that a narrative can help you feel more excited about your adventure. It’s easier to give up if your goal is ‘a big hike somewhere’. It’s harder to give up if you started on the beach and your goal is to reach a mountaintop. If none of this resonates, discard this bullet entirely.

If you’re not sure whether your narrative is interesting enough, ask: Would I watch a video about this?

A short list of unconventional adventures we’d like to see (or go on)

I would consider participating in any of these and I would absolutely watch a video—or read a report—from anyone who ended up doing them or something like them. My goal is both to give you some ideas you can steal and to help kickstart your own adventure brainstorming.

• Starting in London, travel around the world in 80 days without getting on an airplane, renting any kind of motor vehicle, or paying for non-public transportation (i.e. no private taxis).

• **Do a bicycle race across Denmark (or similarly-sized country). **There is a Point A and a Point B but you can choose any route you want, like The Speed Project. I say ‘gamified’ because you would likely need to do some game-like balancing to make multiple, diverse routes viable.

• Cross Europe (or a similarly-sized region) with a starting balance of $0 and without breaking any laws. Do it as fast as you can. Could be more fun if you turn it into a race with teams. (I can think of some wildly different strategies to approach this and don’t know which would win!)

• A source to sea kayak adventure down some non-Thames major rivers, like the Nile or the Danube or the Rhine. It would be fascinating to see how things change as you progress down the river.

• **Play sardines across an entire country. **One person hides and, if you find that person, you hide with them. Could be structured and gamified or could be completely freestyle.

• **Cross Poland on a bicycle without a map. **Of course you could choose any country you wanted :)

• Build a boat from scratch and use it to cross the Black Sea from Romania into Georgia. Or really just make and use it to cross any body of water you find interesting.

• Hike, unsupported, from the beach on the Mediterranean in southern Spain to the top of Mulhacén, the Iberian Peninsula’s tallest mountain. Do it in one calendar day.

• Pick a location (say Italy), pick a number of days (say 4) and pick a starting point (say Bergamo). Arrive there with nothing but the clothes on your back and $10 in your pocket. This is a real concept that has been enjoyable to watch and could be fun in all sorts of places.

• Walk across your home city without a map.

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• Land in New York. Buy the cheapest used car you can find and drive it all the way to Los Angeles. ** We could write 100s more ideas here, and many of the ideas on this list could be generalized and used in any number of locations. I recognize that many of these ideas are not feasible without significantly shifting around your priorities. [0] But, then again, I did say they were unconventional.

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[0] I picked dramatic adventure ideas for this essay, but you could absolutely use the same criteria to design fun one-day adventures at home; new ways to explore your city or see your country.

Enjoy these essays?

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