The Travel Gamble: When Good Trips Go Bad

Someone I know, who is travel-averse, is fond of saying that taking a trip is a gamble. And it is – just like getting married or accepting a job offer or, indeed, getting out of bed in the morning.  Like life itself, there are no 100% guarantees. If you’ve had the foresight to purchase insurance, you might get reimbursed for the money you spent, but you can never get back your time, and that’s the most precious thing of all. 

I cruise a lot, so I’ll focus here mostly on that mode of travel, but what I’m going to say is also applicable to flying to Hawaii for a week to stay in a fancy resort, backpacking through Europe and sleeping in hostels, or taking a road trip through the backwoods of your own U.S. state. And while I’m writing with traveling for pleasure in mind, some of this also applies to traveling for business.

Attitude is everything

In the real estate business, the mantra is “location, location, location.” When you’re traveling, whether for pleasure or work or something in between, it’s all about “attitude, attitude, attitude.”


Adopt an attitude of gratitude. Wherever you are in the world, your attitude determines your outlook and frames your experience.  Some people manage to be miserable in a penthouse suite with a butler waiting on them hand and foot, because the bar was out of their favorite wine. Others stay in a tiny closet-sized windowless room but somehow have fun even when it rains every day and the ship loses power and the plumbing stops working and they’re stranded at sea for days.

Several years ago, I met a group of ladies who were on the infamous Carnival Triumph “poop ship” cruise back in 2013. I listened in fascination to their “war stories” and how they “just pretended we were on a camping trip in the middle of the ocean” and made the best of a situation that had others suing for compensation for “mental injury.”

Here’s the thing: Having bad things happen on your trip doesn’t mean you have to have a bad time. Sounds contradictory, I know.  But while you can’t control the weather, the policies and practices of big corporate travel providers, or the fellow human beings you encounter along the way, the good news is that you can control how you react to those events and people. And you can have a good time in spite of them all.

NOTE: I am obviously not talking here about a trip where your plane crashes or your ship sinks or your hotel burns down and sends you to the hospital. I’m talking about the million and one little things that I see people list in their trip reviews that culminate in “It was the most horrible week I’ve ever spent and no one should ever cruise on/fly with/ stay at this cruise line/airline/hotel ever again.”

small stuff

Manage your expectations

Sometimes it seems as if some of the folks who get the very best top-of-the-line treatment on a cruise or at a hotel are the ones who complain the loudest about small negatives.  world-1301744_960_720That always prompts the less privileged to comment about #firstworldproblems. Of course, in truth, the problems of all of us who are blessed to be able to travel frequently for pleasure – in any level of accommodations – are first world problems, because that’s the world we live in.

But when you think about it, it makes sense that those who are most blessed are sometimes the most irked by the “small stuff.” When you pay more  for a higher grade of experience, you set your expectations differently. What we have to remember is that a higher price may get us a larger/nicer room and more amenities, but it doesn’t buy us immunity from the human, mechanical, and natural blunders and unexpected events that can disrupt our best-laid plans.

The key to happiness, then (and not just on a trip but in all of life) is to manage your expectations. Hope for the best; prepare for the worst. 

Good trips go bad for a myriad of reasons. Lack of planning is a common one, but even if you spend two years mapping out your routes and researching your destinations and comparing costs and considering the pros and cons of various airlines, hotels, ships, train companies, restaurants, and other options, things can still go awry. That’s the “gambling” part. Crossing out Plan A and writing Plan B on a blackboard.

Always have a backup plan. Many people plan extensively for their trips and everything they want to do, but it’s all a part of Plan A. They fail to have a Plan B; they don’t even consider what they’ll do if some or all of their primary plans don’t work out the way they’ve imagined them in their dreams. In fact, overplanning every single little detail is one of the worst culprits when it comes to creating unrealistic expectations.

If you’re OCD like me, you are going to make detailed plans. But if you want to have a great time, you’ll keep those plans flexible. A downpour on the day you were going to take a helicopter ride to the top of the mountain doesn’t have to be a disaster.  In fact, it can end up being an adventure (I know – been there, done that).

How to even the odds

We said traveling is always a gamble, but not all gambles have the same chances of success or failure.  When you bet on the 30-to-1 horse who’s never finished in the money before, he might come in first but your likelihood of winning (albeit with a lower payoff) is greater if you bet on the 1/5 four-time champion.

horse racing

There are ways to increase your odds of “winning” at the travel game, too.  Buying travel insurance will help protect you from a financial standpoint if things go wrong, but discounting those types of disasters (having to cancel the trip, lost baggage, delays, and other reimbursable events), you can also take steps to make it more likely that you’ll enjoy yourself by avoiding the minor annoyances – especially if you’re someone who doesn’t like unexpected surprises.

Note that none of these measures will guarantee that something out of ordinary won’t happen to throw a wrench into the works of your well-oiled preparations, but they can help you avoid the “expected unexpected” things that, for some people, can detract from the experience. 

First, don’t be first. If you want an experience as close to glitch-free as possible, don’t book the maiden voyage of a ship, or its first few sailings out of a new home port, or be one of the first to visit a new port of call (especially something like a private island that’s just opened).

only a testIn the software world, we call such people “beta testers” or “early adopters” and those of us who opt to try out brand new versions of operating systems or applications know that we’re bound to hit some snags and discover some bugs.  In fact, part of the fun of being on the cutting edge is getting to provide feedback on what works well and what doesn’t and how the product can be improved.

Sometimes beta software won’t have all of the planned features functional yet, and the same is true with a brand new ship, island, hotel or resort.  New amenities will be added as time goes on, policies will be adjusted, and things will be different a few months later. Those of us who got there first and got to experience the rough edges can take comfort in the fact that we helped make it better, and enjoy watching the changes take place.  But if you’re going to insist on everything being finished and perfected, don’t be a first-timer.

EDIT: This blog post is a prime example of what you get in the beginning vs. what you get if you come later to the party. The original version that I published had some typos and a couple of formatting errors. I came back to fix them, read through the whole thing again, saw some places where I could add more, throw in a graphic, or polish the language a little. The current version is, in my opinion, better.

Second, do be flexible. Keep things in perspective. It’s a vacation. Relax and enjoy your time off work and away from your daily routine – yes, even if some things aren’t perfect. Learn to change your attitude and your focus.focus

Whenever I see a review that begins with “Everything went wrong” or “I didn’t like anything about this ship” or “all the crew members/other passengers were rude and unfriendly” I know right then that I’m not going to give this reviewer much credibility.

Pilots say “any landing you can walk away from is a good one.”  My philosophy is also that any cruise you don’t have to swim away from is a good one, at least in some ways.

ship in storm

I’ve had some not-so-great cruises, where a combination of factors made me wish at the worst moments that I’d stayed home. But even on my rock bottom dead last least favorite one, there were some absolutely wonderful moments and experiences. I met some great people and I learned some things, even if one of those things was that I didn’t want to cruise on that ship ever again.

The trick is to focus on the good things instead of the bad ones. Negativity is a learned behavior that becomes a habit. But so is positive thinking! You can train yourself to notice all the things that go right and the friendly people you encounter, and put the plans that fall apart and the obnoxious folks who cross your path on the back burner of your mind.

Here’s an example from a friend of mine: “On my first ever and only cruise holiday, we found ourselves chasing an out-of-season hurricane; and several people were queasy or sick, including my husband. While this ruined a couple of activities (including a long-awaited chocoholics buffet that I did not have the heart to attend without him), we did get to enjoy super brisk morning walks on deck in the gusty winds that made us feel we were having a genuine seafaring experience. This may sound trivial, but it’s about trying to ‘turn a frown upside down’ in whatever way you can.”

Do your homework. Before you book a particular cruise or resort, read everything you can about it. Find out whether the activities, ambiance, food, and rules are a good fit for what you want out of a vacation. homework With the plethora of information available on the Internet today, there’s no excuse for not knowing that the cruise line you booked doesn’t allow you to bring your own alcohol on board or the experience you booked doesn’t include anytime dining or the cabin you selected is right above the nightclub.

Read both the travel provider’s “official” literature and the customer reviews with a small grain of salt, though. The cruise line or hotel web site will naturally highlight the best and make their ships or resorts sound like a floating or land-based paradise. Reviews will be all over the chart — for any particular venue you’ll find people who loved it and people who hated it.  Even two people next door to each other on the same ship or in the same hotel at the same time can have drastically different opinions.

Coming up: I’m working on a blog post on “how to read reviews without drowning in conflicting information,” so stay tuned for that. 

Be prepared. Whether you were ever a scout or not, it’s a good motto for travelers.

Here’s a case in point: when my checked bag was lost on the flight that was taking us to 20th anniversary vows renewal cruise, I learned the importance of packing enough clothes in a carry-on to get by in case it ended up being all I had. Now I make sure that carry-on duffel includes a pair of shorts, a pair of jeans, a skirt, and a couple of tops that can be worn with any of the foregoing. Also a pair of sandals that can be worn with casual clothes or to dinner with the skirt and top (I always wear my bulkiest walking shoes to board) and underwear (which they don’t usually sell on the ship).

Brighten someone else’s day.  However badly your cruise might be going, there is probably somebody else on board whose problems are worse. When you encounter somebody who’s grumpy or abrupt, give him/her the benefit of the doubt.

Sure, there are some folks who are just obnoxious and you can run into them anywhere – on a ship, at a hotel, at the grocery store back home; it’s best to just steer clear of them.  But often those who seem negative are just dealing with their own unfortunate circumstances.smiles

Many people on cruise ships have chronic physical conditions or even terminal illnesses. Some are there to try to recover from a painful loss of a loved one or a marital breakup or a business failure or to escape a bad family situation. The possibilities are endless. A smile and kind word from you might just make a difference in how they feel at the moment or even for the rest of the day. It never hurts to give it a try.

How to complain effectively

Does all this talk about being positive and focusing on the good parts mean you shouldn’t complain if a travel provider doesn’t provide what you reasonably expected? Of course not.  But there is a difference between random ranting and lodging an effective complaint that has a chance of a) getting you some compensation or b) making real, positive changes in the experience for everyone in the future.complaint

I don’t know how many times I’ve gotten “special treatment” – not because I’m special, or know people in high places, or bribed someone, but simply because I complained nicely.  Most of the time, the people to whom we take our grievances aren’t the ones who caused the problem; they’re simply charged with the task of cleaning up the mess.  The more you make an effort to sympathize with their position and establish rapport, the more likely your issue will go to the head of the “doing something about it” line.

An example: we were once on a flight that connected in Orlando with its final destination in Miami. There was a mechanical problem, the last leg was delayed for several hours, and when we finally got to MIA, one of our bags was missing. We weren’t the only ones. The line at the desk was long and mostly angry. The two ladies working it were under seige. People were yelling, a few even threatening. When it was my turn, I smiled and spoke softly: “I certainly wouldn’t want your job. I really admire you for not running off screaming into the night right now.”

She smiled back, the tension in her face relaxed just a little, and although she wasn’t able to magically make my bag appear (it had been left in Orlando), she called me several times at our hotel that night and the next morning to update me on the status, and managed to get my bag to the ship before we set sail. I’m not sure that would have happened if I’d ranted and raved at her the way some other passengers were doing.

Complaining is an art, not a science. The first rule of complaining effectively is: be assertive, not aggressive. Be reasonable, not emotional. Speak slowly and softly. Be understanding of the other person’s situation; he/she is doing a job, not intentionally trying to destroy your day. Don’t whine; don’t play the victim. Enlist the other person as a partner in a mission to set things right, not as an opponent who loses if you win.

Complain to the right people. Determine who has the authority and capability to solve your problem and don’t waste time with functionaries who can’t.  And before you voice your complaint, know what it is that you want.

Prioritize – don’t hit the person with a long litany of large and small gripes.  Decide what’s important and see if you can get those addressed.  Then, when it comes to the small stuff, let it go.

Manage your disappointment

Sometimes it seems as if the universe is out to interfere with your plans and make sure you don’t realize your dreams. A couple of years ago, I booked flights to St. Thomas and a a week in a beautiful condo for my husband and myself to celebrate our anniversary.  A little over two months before it was to happen, hurricanes Irma and Maria came along and wiped out the resort and much of the island.

I then scrambled to reschedule everything at a Seven Mile Beach resort on Grand Cayman. The night before we were to leave, when I went to check us in for the flight, I found out that he had forgotten to renew his passport and it was expired so he couldn’t fly. Travel insurance doesn’t cover “forgetfulness.”

Was I disappointed? Of course. I’d been looking forward to the trip for almost a year. But there was nothing I could do about it at that late date. So we made the best of it, found some local things to do, enjoyed the time off at home, and learned from the experience (I now have his passport expiration in my calendar six months before the date with urgent reminders).

Every unfortunate incident that we go through is an opportunity to learn something and to grow as a person. I could have gotten mad at him; I could have gotten mad at mother nature (he could have flown to St. Thomas without a passport since it’s a U.S. territory). I could have sat home and pouted because I didn’t get the trip I had put so much time into arranging and that we had put so much money into. But what good would that have done?  We had a nice anniversary, albeit not the one I had envisioned.

Any time you have to depend on some other person or company or force of nature (and when you travel, that is always the case), you risk being let down.  People forget, airlines cancel flights, cruise ships miss ports, islands get devastated.  But you don’t have to let your (understandable) disappointment make things worse.

When life hands you lemons, make lemonade. If you don’t like lemonade, trade them in for pineapples and make piña coladas. 

pina colada no bg


Following these tips might not result in a perfect, flawless cruise or other trip. But it will be a happier one if you adjust your attitude, manage your expectation, and when it’s warranted, make your complain in the right way.  So go ahead – roll the dice and take a gamble on travel.  The payoff is worth it.

And may the odds be ever in your favor.


About debshinder

Technology analyst and author, specializing in enterprise security. Author of or contributor to over 25 books, including "Scene of the Cybercrime." Fourteen-year Microsoft MVP, married to Microsoft FTE Tom Shinder, and proud mom of two wonderful grown-up human children and three amazing Japanese Chin pups. In my spare time, I love to travel - especially on cruise ships - and write about my grand adventures.
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