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in: Travel, Travel & Leisure

• Last updated: October 7, 2020

Turning Vacations into Adventures – Part I

Boy looking at airplane flying in the sky.

Editor’s note: This is a guest post from Erik D. Kennedy.

According to contemporary accounts, there were few things Teddy Roosevelt would rather do after a good dinner party than sit around and tell stories. Guests to his White House were amazed by the absolute breadth of tales he could tell about his past adventures—chasing horse thieves across the Dakotas, leading cavalry charges, and hunting bears, just to name a few standbys. People who spoke with him report that his charm was so captivating, one had to “wring the personality of your clothes” after being around him.

Now I have always thought that there’s something undeniably awesome and manly about being able to tell good stories. In a sense, they are a sign of a life well-lived. And while day-to-day existence can be a salient source of decent yarns, it seems to me that travelling is perhaps the great mother lode of storytelling gold.

So that raises the question: how can a man travel so as to later be able to tell as many awesome stories about his trip as possible? Or, simply, how can one turn vacations into adventures? I’ve been thinking about this concept for a while, and after having done some field-testing of my own, I’d like to share what I’ve found. This is by no means a comprehensive list, so I invite you to add your own comments below for turning conventional vacations into swashbuckling escapades.

Stay with Residents

One of the single best ways to raise the likelihood of finding adventure during travel is to stay with residents. Hotel rooms allow you to wallow in solitude; residents don’t. If you show the least interest in doing anything, most people can recommend a pretty hefty list of stuff to do, see, eat, drink, and visit around their hometowns. Not to mention, there are just some perks that come from staying in a house. There’s the occasional home-cooked meal, and then there’s always that time I was stumbling around a house in Delhi, still deliriously food-poisoned from a home-cooked meal, while a group of Christmas carolers/drum band marched through our living room smiling and singing, all the more joyful to see the confused white guy hunched against the far wall.

So, how do you partake in such pleasures? I have three ideas.

Friends (and friends of friends)

There’s no hard and fast rule for how well you should be acquainted with someone before you ask if you can stay with them, but I’ve found that if it’s slightly uncomfortable to ask, you probably should. For politeness’ sake, you might want to throw in something about them recommending a great cheap place nearby and seeing if you can at least meet up a few times while you’re there. Even if you’re not close friends with someone, if you’re going to their city, try to make plans to visit them. Not only do you see the city better, but barring any violent personality clashes, you will part as much better friends—and now each of you will have a friend in another faraway place, which is good.


In my relatively few years of travel, I’ve already spent months abroad on the floors, cots, and beds of various religious buildings. I’ve camped out in a convent in the mountains of south India, and I’ve stayed in the choir loft of a church in Mexico. There are a number of reasons why following suit is a good idea. Churches and religious organizations are often heavily involved with service-based groups, and since religious places are usually built for fairly large groups, a few people staying there for a brief period of time can be much less taxing on them than, say, it would be on a house. Finally, many religious organizations have international connections, so keeping an ear out for those sorts of things at your local place of worship can be quite helpful in finding good places to stay abroad.

Couch Surfing

There are a variety of travelers’ networks that work on the principle of mutual reciprocity of couches. You offer someone (usually a stranger) your couch for a night in the hopes that down the road, another stranger will offer you a place to sleep when you’re in their town. From this one-sentence description alone, it’s clear that this sort of thing is not for everyone, but I do recommend trying it at least once in your life.

I have tried it precisely once in my life, and I ended up staying with either a compulsive liar or a highly-intelligent, extremely wealthy, septilingual German playboy whose biggest regret was receiving a Stradivarius for his sixteenth birthday instead of another sports car. Unfortunately, I’m leaning towards “compulsive liar” on that one, but you can bet I was on the edge of my seat the whole time I was with this guy.

Here are some sites to check out, should this sort of thing sound up your alley. Be sure to read up before diving in. There’s lot of great advice you should get before taking part—for instance, always having a backup plan in case things go south.


The Hospitality Club


Warm Showers (for touring cyclists)

Go Easy on the Planning

Whenever you’re looking for adventure, it’s going to find you more frequently than you’re going to find it. The problem is being ready for adventure when it comes.

So go easy on the planning. You don’t have to plan out every hotel you’ll stay at, every restaurant you’ll eat at, or even every travel arrangement you’ll make between destinations. If you’ve planned everything in advance, you’ve effectively chosen what looked best from a distance. Now that you’re on the ground, things might look different, but you’ve already got a schedule locking you into place.

To some, the idea of not reserving hotels in advance seems ludicrous. “But what if they’re all full?” these people whimper. To them, I offer this gedankenexperiment of consolation: think about every event you know of that could book all the hotel rooms in an entire city. Chances are, if you’re going to any place that is having such an event, you will hear about it ahead of time. So the odds that you’ll be stuck in a city somewhere without any option for sleeping are pretty miniscule. You’re pretty much guaranteed something. If you want to play it safe anyways (or if you’re arriving late in the evening), book the first night, and then play it by ear from there.

If you can refrain from booking all your accommodations ahead of time, you can often find cheaper, cooler, or more convenient things when you’re actually on the ground. How?

  • Talk to other travelers. This is simple. Find a tourist site, find a tourist, and strike up a conversation. Ask where they’re staying and what they like/dislike. Yes, some of what they say will be the stuff you could’ve found out online, but a) you can ask them questions and get answers as you speak, b) they are going to have up-to-date information and c) as a rule of thumb, meeting people leads to more adventure than not meeting people.
  • Find local experts. Same gist as above, only with residents. If you find someone who seems to know a lot about whatever you’re interested in, ask them questions for all you’re worth. For every reason you should talk to another traveler, there’s twice as much sense in talking to a knowledgeable resident. Residents also know where’s cheap—most lately, local knowledge has landed me a few nights in a villa on the Adriatic Coast for as little as that can cost.
  • Explore. Heck, just walk into hotels and hostels that look decent. If you’re really on a budget, try this. Walk into the lobby and look at the key rack. If there are a lot of keys on the rack, they have a lot of vacancies. Use this knowledge to your advantage, and see if they will lower the price for you. While you might think that the person at the desk wouldn’t necessarily have the power to do that, they frequently do, and you can save a bundle while practicing your negotiation skills.

With your accommodations and transportation a bit less structured, you can turn a dense schedule of destinations into a series of waypoints (a festival in city X, visiting a friend around Y, and a plane ride home on Z) that allow for the most adventurous paths to be chosen and filled in from on the ground.

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