Turning Vacations into Adventures – Part I

by A Manly Guest Contributor on January 10, 2011 · 28 comments

in Blog

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.

{ 28 comments… read them below or add one }

1 Ben January 10, 2011 at 2:37 pm

Just be aware that if you constantly bore people with your stories, you may come off as narcissistic and tedious. Teddy’s status and charisma probably had as much to do with people’s willingness to listen to him as the stories themselves.

2 Darrin January 10, 2011 at 3:24 pm

Excellent. I’m finally getting a passport and going to work on seeing the world. These ideas will help make sure I’ve got something to say about it when I get back!

3 Mitch January 10, 2011 at 4:19 pm

also check out airbnb.com perhaps — –
a nice medium between couchsurfing and actually knowing whats going to happen

4 Ryan Tyler January 10, 2011 at 6:03 pm

Well done. I haven’t used or hosted couchsurfing, but I know someone who has and they vouched for it as well. I think the most important piece of advice that you’ve given is the final section, particularly the ability to let go of minute to minute planning. Not everyone can reach this state of mind, though. In fact, if you can reach this point and your traveling partner cannot, you are very likely to have a bad time. So choose your traveling companions with care.

5 Tryclyde January 10, 2011 at 6:16 pm

Personally, I think being a good listener is better than being a good storyteller.

6 Mark Safranek January 10, 2011 at 6:37 pm

There certainly is merit in a life well-lived and the ability to tell others about it in a way that inspires and uplifts.

7 Greg M January 10, 2011 at 8:51 pm

I travel overseas often on business and I always end up having a few adventures that amaze my colleagues, even those who are on the trip with me.

1) Make full use of the hotel- Get a map from the desk when you check in and ask the staff for a few areas on interest in the vicinity. Also, ask the staff where they like to dine/hang out in their free time. You can usually get some great tips for free or nearly free activities that don’t show up in any guidebook.

2) Take walks- I wake up early and hit the streets. Likewise, I take nightly strolls after dinner or the last meeting of the day. I’ve managed to bump into famous people, join in unique local activities and see some beautiful sights that my colleagues hanging out in the hotel all missed.

3) Ask people- Ask the restaurant staff for recommended specials. Talk to the staff at local attractions. If you show a genuine interest in learning more about an area, you’ll be amazed at the opportunities that are presented.

That being said, always remember to stay safe while you are out experiencing the world.

8 Gal @ Equally Happy January 10, 2011 at 8:59 pm

A few weeks ago my girlfriend and I took a trip to San Luis Obispo from our homes in the San Francisco Bay Area. We planned very little and spent most of the trip just wondering around this cute little town, exploring everything from the trendy shops to the local art museum. We took a little detour to walk down a creek that we randomly saw besides a street and had a wonderful time in general. On the way back, we decided to stop at every random little town that seemed to be more than just a strip mall. Unfortunately (or fortunately), the very first town we came to was charming to the point where we spent all of our time there instead of seeing other towns.

Lesson learned? Don’t overplan. Taking some random trips makes for a very fun adventure!

9 Dan Smith January 10, 2011 at 9:53 pm

I’ve never done vacations quite like you mention, but in several overseas deployments I met with local churches and joined them in whatever was going on. It was always a great way to underplan and over deliver on a vacation.

10 Liverpoolpaddy January 11, 2011 at 5:19 am

I lov travelling and aside from holidays have been lucky enough to live in Barcelona, Lyon and Queensland, Australia. As my name suggests, I am a Liverpool native and have travelled all throughout the UK and Ireland as well as Rome, Athens and Nuremberg.

I would make a list of must see things before going – what do you absolutely have to see if it is a once in a lifetime trip? Some will be more obvious than others.

I agree though that the key to seeing a city at its best is having an early breakfast then hitting the streets. Don’t forget that the staff at any hotel are there to help you so if you ask them for some suggestions “off the beaten track” they will be happy to oblige. Similarly, they can suggest pubs and clubs for all tastes (I avoid hotel bars like the plague – over priced and full of other tourists! You are much better off finding a city centre dive!)

As ever, be careful. I lived in possibly the worst street in Barcelona for pickpocketing and had my room broken into. Learn the tricks before you go. Learn the scams. There are plenty of websites out there you can find these on. Don’t carry more cash than you need to and keep wallets in a front pocket. Most of it is common sense if you actually think about it.

11 Gwynn January 11, 2011 at 5:32 am

It’s the unexpected things that turn holidays into adventures. Last year I travelled to Turkey for a week and then took the train to Greece for another week. It was quite a long train journey and I vowed not to get on another train for at least a year, haha.

On the day we set to go home to the UK… a volcano in Iceland closed all of the airports in western Europe. Countless boats, trains, coaches and four days of solid travel later… Best holiday ever! I’ve never felt such unity with the people around, everyone was doing the same as us. I made some great friends in that four days. Now that’s an adventure.

12 Angellady January 11, 2011 at 7:45 am

[...]I would make a list of must see things before going – what do you absolutely have to see if it is a once in a lifetime trip? Some will be more obvious than others. [...]

I think like liverpoolpaddy!

13 mikeyyc January 11, 2011 at 10:59 am

As others have alluded to, the single best thing you can take with you when travelling is an open mind. Be open to new experiences, food, people everything. Consider that you may never be in the same situation again, it would be a shame to let it slip by.

I think another addition to the contacts would be various forums on the internet. If you have interests, and are a member, you automatically have people with a common ground anywhere and everywhere in the world, depending on the forum you’re on. Speaking from experience, a simple email resulted in having a loaner motorcycle and a day long adventure in the Philippines that could never have happened in any other circumstance. A lifetime’s worth of stories, and new close friends were the result.

14 Josh January 11, 2011 at 12:32 pm

My wife and I did this on our honeymoon. We went to Charleston, SC and had the time of our lives by just randomly walking around town, hopping on the random bus, and renting a car and randomly driving around to local beach towns. We found a lot of stuff that isn’t advertised online and made a lot of memories.

15 Tys January 11, 2011 at 1:01 pm

Great advice. One thing I’d like to build upon is the staying with residents thing. Yes, the mentioned websites offer some possibilities for connecting to locals, but I would like to recommend the ‘granddaddy’ of host – traveler organizations: Servas. http://www.usservas.org

Founded in 1948, it’s worldwide, open-minded, and does a very good job of screening travelers and hosts for open-mindedness (and trouble).

I personally have had GREAT experiences as both host and traveler. check it out. you can also see the global website at http://www.servas.org


16 adam January 11, 2011 at 1:25 pm

Great advice. I’m always a bit nervous to ask strangers to stay..but my inner boy usually wins out with a mischievous grin. now i just need to acquire the funds and time to do some travel to put this advice to practice

17 Peter O'Reilly January 11, 2011 at 6:40 pm

My suggestion is to take a page from Yes Man and accept anything and everything that comes your way. I’ve had several fun experiences as a result as a result of adapting that attitude.

18 Wilson Davalos January 11, 2011 at 8:48 pm

I’m actually looking to do some major traveling this year. I feel that my last few years this hasn’t been a priority for me and this really needs to change. I’ve looked at some Couch Surfing sites before and would love to plan out a few weeks traveling S. America. The art of conversation is so important and new experiences help with that.

19 Andrew January 12, 2011 at 5:29 am

I have found that even the usual hotel can be the grounds for a good adventurous tale. Just be sure you talk to the clerk or owner as you enter into it. Eventually you will find something interest to gravitate to. It also helps if the hotel is either upscale or unique, but it is not necessary. I recall staying one night at a hotel in the middle of San Francisco. I had an adventure parking my car into the tiny garage below my room…and ruined one of my side mirrors in the process! I spent the night listening to the owner tell tales of living in San Francisco in the 1970s. That was well worth the $50 I spend for a room.

20 Nick January 13, 2011 at 3:07 am

I don’t usually have the money that it takes to rely on “whatever’s available” as far as accommodation goes. I stay in hostels for the most part, and rely on reviews from other travelers.

As a larger habit, I get worried if I don’t know how I’m going to get from point A to point B, etc. Again, a large part of this worry is my extremely limited budget. So what I do is meticulously plan accommodation and transportation, and absolutely nothing else. That way, I know I’m not going to wind up being forced to stay in a $200 a night hotel, or pay three times the pre-booking cost of a flight or train ticket, but I still get to be adventurous. I’ll stay three days in a foreign city and have only the vaguest idea of what I want to do when I get there. For instance, I went to Madrid and I knew that I wanted to visit the Prado Gallery, but for the remainder of my three days my friend and I spent most of our time just walking around and exploring the city.

Walking leads me to another tip–always look for walking tours. This is fairly easy when hosteling, since many of the hostels keep track of cheap walking tours in the city. It’s by far the best and most informative way I’ve found to get a feel for a city in just a few hours, and a good guide can show you hidden gems and courtyards and alleyways you never would have found with a guidebook.

21 Vincent January 13, 2011 at 8:22 am

Simple advice for great adventure: travel alone. No slacker will hold you back whatever you want to do, no conflicts over what city/museum etc to visit, and a great enticement to meet (precisely because you’re alone) and be met (locals would rather host 1 person than 2 or 3 of them).

Book a return flight with ten days in between, take a backpack with nothing but clothes, have a go at the language, talk to locals, and do what you normally don’t. This mindset got me talking to a Syrian millionnaire in a shabby café at 11.30pm in South Eastern Turkey, among other things.

22 Tim Raveling January 13, 2011 at 11:14 am

Good post Erik! I’d like to vouch for couchsurfing and offer some tips as to how to make it work better. I’ve couchsurfed “officially” in Belfast, Paris, and Athens, and had great experiences in all 3. The trick to getting the most out of couchsurfing is understanding the system. By looking at profiles to check descriptions, friend connections, comments by other travelers, etc., you’ll be able to find those people who are really integrated into the couchsurfing network, as opposed to just unconnected hosters who may or may not be kosher. The people who are integrated, who’ve had profiles for a few years, who attend CS meets, etc., tend to be real travelers and are generally good to stay with.

While I do enjoy staying with locals I meet on the train when given the chance, couchsurfing (when it goes well) is a bit more relaxing, as your hosts are usually easily financially able to afford a guest, and are travelers themselves, giving you something in common.

23 Jonny January 15, 2011 at 8:09 pm

This is all good advice, but I read with a sense of irony your hesitant endorsement of couchsurfing (I tried it precisely once…) because you had a single unnerving experience. What happened to the sense of adventure you were espousing? The character you stayed with may have had a penchant for embellishment, but so what? Did he try to murder you in your sleep? If you you only want to stay with people like you, you’re going to have the same adventureless vacation you have always had. Adventure isnt comfortable. What makes great storytellers is not the adventures they had, but the way they relate those adventures to their audience. They know which details to put in a story and which to leave out.

24 Jonny January 15, 2011 at 8:26 pm

Here are a couple of other tips:

- If you are staying in a hotel, make friends with the concierge, bartender or other hotel staff. Be up front and say you dont want to spend a lot of money but just want to do what locals do. Even a guy in a suit takes it off once in a while and has some fun.

- Even if you dont use a site like couchsurfing, contact some local members to meet up for a drink. Couchsurfers love to meet new people, even if they arent actually hosting them. They’ll have a good idea of where adventure is lurking.

- Peter already said it, but it’s worth repeating. Say “yes.” Most of your real adventures won’t be planned. They will be impromptu encounters with a local stranger (ie a future friend) who wants to introduce you to something new.

25 Ben January 16, 2011 at 6:14 pm

If you are younger, hostels are a great place to meet people and keep your trip interesting. I studied abroad last semester and met so many amazing people at the hostels. Definitely better than sitting alone in your hotel room!

26 Sean January 17, 2011 at 5:49 pm

Great info on going easy on the planning. I find that a little research on the area and a willingness to meet the locals and talk to people tends to open up loads of opportunities. When at all possible I avoid large hotels and look to smaller hotels, B&Bs or villas. I find that the opportunities to meet the locals is much better in these areas.

27 Daniel January 19, 2011 at 1:33 am

When my wife and I moved from Orlando to Seattle a few years ago, we were given the option to fly out. We turned it down and took the opportunity to drive – partly because it might be a once-in-a-lifetime event, and partly because we had a dog that I couldn’t see sticking in the belly of plane. So, we packed us, two suitcases, a dog bed and a dog into a Mini Cooper and headed out. Things were going fine until I decided that we should get off the Interstate and take the back roads through Colorado and into Utah. After nearly 10 hours in the car, 2 of which we saw almost no signs of human life outside of the road we were on, we arrived in the small town in Utah we planned to stay the night in. Except, they didn’t have any rooms. So we drove for another two or three hours north to Rock Springs, WY. As we arrived at nearly midnight we were informed that there were no rooms. The closest places would either be Denver or Salt Lake City. Exhausted from the day’s travel, we pulled to the side of the road and tried to sleep… in a Mini Cooper.

After only a few hours of “sleep”, I decided to just drive toward Jackson, WY. At 8am we arrived, only to find that there were no rooms there, either. So we “showered” in a restaurant’s restroom, had breakfast, and left to find a place to stay. We finally found refuge in Missoula, Montana. What originally turned out to be a disaster turned into one of our favorite adventure stories to tell!

So, yes, more often than not adventure finds you. Just be willing to stick yourself in the middle of the possibility, and have humor if your adventure isn’t exactly what you thought it would be.

28 Carter January 21, 2011 at 1:44 pm

This is basically the focus of my blog.

My favorite criterion when trying to pick a vacation spot is to pick somewhere new you have never been before. That is how you get stories in your life and avoid that rut that people get stuck in where they go to the same place and do the same things every year.

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