Money Lessons Learned from Traveling Well

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Several months ago I wrote a post about what traveling while broke taught me about finance. Now, while I certainly don’t travel five-star, first-class all of the time, I’ve reached a point in my life where I can travel comfortably. I no longer have to sleep in a hostel and wait tables in a bar for a week to get enough cash to move on to my next destination.

You wouldn’t think that you’d learn too many money lessons from traveling comfortably. After all, if you’re not scrimping and saving to get somewhere, what financial lessons do you have to learn? Surprisingly, even when you think you have it made, there are still lessons to be learned. Even if you can afford to travel well, here are some things you can still learn:

The experience is often less than worth it

The thing about traveling well is that, while it can be comfortable, the experience is often not worth the money paid. I find when I pay more money to travel that I end up on more scheduled tours that limit my options. Sure, I have a nice bed to sleep on, but I only see what the tour operator wants me to see. Or, I end up eating in “better” restaurants that serve weird food when I would have been happier in the pub down the road. While I enjoy traveling in comfort, I don’t have many outstanding memories from those trips. The outstanding memories are from trips I took when I was younger and broke. Those trips forced me to interact more with the people and partake fully in the culture, rather than travel at the mercy of tour operators.

The Lesson: Paying more doesn’t guarantee you a better experience. Just because I pay more to travel doesn’t always mean that I enjoy it more. Sometimes there’s something to be said for going where you want to go, when you want to go there. Eating in the less expensive restaurant can be more enjoyable than the five-star place. Just because something is expensive doesn’t make it worth it. They key is to figure out what is worth it to you (for me it’s business or first class on an airplane, just for the leg room alone) and only pay for that. If you don’t want the pricey guided tour, figure out a way to travel without it while keeping the things you do deem to be worth it. This applies to things other than travel, as well. When paying for something, don’t get trapped into paying for pricey extras that you don’t want or that don’t add anything to the experience for you.

The best memories often come from stuff that’s free or inexpensive

I can’t think how many times I’ve paid for something that was supposed to be a once in a lifetime experience that I barely remember. The things I do remember most from traveling were free, or close to it. Just seeing the scenery somewhere, watching the people, happening upon a street performer, finding some tiny local museum, or seeing a local theater production have all generated more memories than the pricey tours and once in a lifetime experiences.

The Lesson: An oldie but a goodie…The best things in life are free. While I’ve seen a lot while traveling well, the things I remember most come from trips I took when I was broke. Being broke forced me to appreciate the things that were free and to really seek them out. As a result, I had a more fulfilling experience and enjoyed much more. The things that have stuck with me have all been things that I didn’t pay for, or only paid very little for. This applies to my life at home, too. The things I remember most are things like playing in the snow with my dog, playing games with my family, or watching a sunset at the lake. The things I’ve paid big bucks for (concerts, movies, and the like) don’t stick with me for very long. When seeking something to do or to stimulate your mind, look for the free stuff. It’s likely to be worth more than the expensive stuff.

You become a target for thieves

When I travel, especially if I’m traveling comfortably, I know to try and blend in. This means not looking like the typical American and flaunting pricey jewelry and designer clothes. I also know to keep my money well hidden and not flash it around. Too many people don’t learn this lesson and prance around foreign countries in designer clothes and expensive handbags, all while flashing money clips stuffed with cash. Guess what? This makes you a target for thieves. I’ve known of too many people in my tour groups and on cruises who get robbed and usually it’s because they made themselves an easy target. They looked wealthy and didn’t take proper precautions.

The funny thing is, when I was traveling broke, I didn’t have to worry about this as much. My clothes were a mess and I didn’t have any money worth stealing. (Even so, I took care to protect what I did have.) Nothing about me stood out or marked me as a likely target in most of the places I visited. I couldn’t have looked rich even if I’d wanted to. In retrospect, that kind of freedom was nice. Now, while I’m still not drowning in designer duds, I do have to think more about not standing out.

The Lesson: Whether abroad or at home, take care not to look or act like a target for thieves. Keep your money well hidden and don’t flash a lot of cash. Save your expensive jewelry for special occasions. Don’t flaunt your designer clothes and handbags, especially in places where they will make you stand out. If you drive a fancy car, don’t put personalized plates on it that give away your identity and keep an eye out for people who may try to follow you home. Take care to reduce your appeal to thieves, no matter where you are.

You may also end up feeling like an absolute fool

More than once I’ve felt like a complete fool when I’ve traveled well. When I’m marching around a site with my tour group and the locals are by the side of the road begging for food, I feel like an idiot. I feel like an even bigger idiot when some “typical American tourist-type” that’s in my group says something derogatory or insensitive about or to a local, tries to impose his American values on the local culture, or acts in an entitled, jerky manner. When I was traveling broke, I never felt that way. Sure, I felt bad that the locals didn’t have a lot, but I didn’t feel like the gap was that big (even though it really was, it seemed smaller). I also never traveled with other tourists that were insensitive louts. I was alone most of the time and I took care not to offend anyone or intrude my American-ness into their culture.

The Lesson: When you have money, the gap between rich and poor seems (or should seem) much bigger all of a sudden. You realize that you have so much more than many other people. Even when I was broke I had much more than most, but it didn’t feel that way. Now it almost makes me feel foolish to have so much when others have so little. I feel this way at home sometimes, too, when I’m in the poorer areas of town. Being comfortable or well off can make you feel like a jerk, sometimes, and it can make you appear to be a jerk if you lord it over others or act like they are somehow beneath you.

Traveling well requires sacrifice in other areas

Although I can afford to travel well, I can’t afford to do it all the time. Unless you come into some serious sums of money, you have to pick and choose when and where you travel, and how you will take each trip. Many of my domestic trips are camping trips because I can see much more for much less money. However, when I travel internationally, I try to spring for some extra comforts. To do that, though, requires sacrificing in other areas. It may mean that I don’t take any other trips that year, or that I reduce the number greatly. It may mean that I have to give up something else in my budget to make that dream trip possible. There has to be give and take to travel well, but remain within the budget.

The Lesson: If travel isn’t your thing, you’ve probably experienced this with whatever it is you do enjoy. Unless you have a lot of money, you have to make sacrifices and choices so that you can what you want, get a few extras, and stay within your budget. The trick is figuring out what you really want and what you’re willing to give up (or do, like take a second job) to get it.

Some people will try to take advantage

When you travel well, there are those who assume that you have either no financial sense at all, or that you have so much money that you won’t notice or care if they take a little bit extra. There are shopkeepers who try to cheat you on the prices or give you incorrect change on purpose. There are servers, bellhops, and others with their hands out, angling for tips, even if they didn’t do anything whatsoever. There are vendors who will try to push inferior goods on you at inflated prices. There are cabbies who will cheat you on the fare. Certainly these bad seeds are the minority, but they are there and those with money are bigger and easier targets than the poor student.

The Lesson: Don’t let people take advantage of you, whether you’re on the road or at home. Know your prices, count your change, know what the merchandise is really worth, and question anything that seems inappropriate. If you look like you have money, some people will try to take advantage of you and it’s up to you to guard against it.

Your financial problems pale in comparison to many others’

When I travel I’m reminded that my concerns about funding my retirement plan, paying for health insurance, or figuring out how to pay for my next vacation are “first world” problems. I see many people struggling to put food on the table, put a roof over their head, or even find good medical care. It’s easy to forget, when I’m in my hotel or ensconced on a cruise ship, that not far beyond the doors are people who have a very different definition of “financial problems” than I do.

The Lesson: Perspective. It’s tempting to think that just because I’m okay financially that finances aren’t a big problem for others. It’s easy to retreat into my bubble and forget that other people’s problems are much larger than mine. Traveling well but seeing the hardships that others face is a reminder that my problems often aren’t really “problems” at all. It’s a lesson that carries over to my life at home and makes me more apt to give to charities and to volunteer my time.

I’m learning these days to find ways to travel in comfort while keeping the spontaneity and experiences that I loved when I traveled broke. I’m also learning that traveling well comes with its own set of financial problems that are different from those encountered when traveling broke. There are lessons to be learned and I’m slowly learning them.

(Photo courtesy of timeshare trap)

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5 Responses to Money Lessons Learned from Traveling Well

  1. Jamie says:

    This made me laugh out loud: “The outstanding memories are from trips I took when I was younger and broke” because it’s SO true. Even now, as an older adult, traveling with my kids, it’s the free activities and then spontaneous things we do when we’re traveling that make for the best memories. Maybe it has something to do with a total lack of expectations. I also like what you say about perspective. This is one of the best reasons to travel, especially with kids…to see how many different ways there are to create a life.

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  4. getagrip says:

    This idea of not having fun memories of things you paid well for is one I don’t really get. I have just as strong memories of seeing Blue Man Group, Phantom of the Opera, Styx, visiting Disneyworld, etc. as I do of camping with the kids and watching them pull their first fish from the lake or canoeing one early morning with one of my kids in a local pond. If what you spent your money on holds such little meaning or potential memory for you, was it really something you were looking forward to in the first place, or is it just some form of selective thinking (e.g. it must be better because I had fun and it didn’t cost money).

    I can see that there might be times where you spent money and were disappointed, but how many times did you not spend money to do something, were disappointed or found it mediocre, and brushed it off because it didn’t cost you anything but some time? Could the bais be because you invested yourself more in the “free” thing because you had lower expectations? While not necessarily disagreeing with some of the authors observations, it seems to me the author of the article spent more time watching and being embarrassed by her fellow travelers than enjoying and focusing on the sites she was paying to visit. The site wouldn’t be any different whether with a group or by yourself, it’s the way you interpret the experience that makes the difference.

  5. Elaine says:

    I agree fully with your statements. My husband and I took our most expensive vacation to Hawaii for our honeymoon. Because we had spent so much, we expected much more than our typical $500 roadtrip that creates epic memories. We were disappointed with Hawaii. That being said, our favorite time wasn’t the expense “excursions” but the free drive to Hana, where we stopped and skinny dipped alone in a fresh water pool with a waterfall. THAT was epic…and free.

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