My Satisfying Retirement : A Disappointing Vacation



A week or two ago I asked about your vacation plans for this coming summer and fall. Has Covid and its aftermath changed how and where you will go? Have the last few years of being pent-up made you ready to hop onto or into anything that moves…any excuse to get out of town?

As expected, the responses reflected folks’ mixed emotions about an important part of their life that is being approached with caution. Slowly, major trips are being rescheduled and fingers crossed by some, while others remain close to home or in the more protected confines of an RV.

With these travel possibilities ahead, one reminder must be voiced: all of us have probably experienced at least one vacation that didn’t live up to expectations. The planning, the anticipation, along with the money and time invested produced a flop. No matter how we sugar-coated the experience, that vacation was disappointing. Yes, even post-Covid, a getaway can get away from you.

Of course, some of the reasons can be purely bad luck: getting sick or being injured can happen. Something goes wrong at home or with family and the vacation must be ended quickly. But, in thinking about vacations my family and I have taken over the years, there are five factors that seem to conspire to lay waste to the best-laid plans. Being reminded of their potential to mess things up may help you avoid a vacation washout. 

Over or Under Scheduled

I am a planner. When my family and I take a vacation, the days are often plotted as carefully as a military campaign. If we are going to spend the money and take the time, by golly, we will not waste a minute, we will enjoy everything at double speed. Luckily, my wife and one of my daughters are fine with this. Our other offspring though does her best to suggest we take time off to smell those darn roses, sleep in, and leave time for simple pleasures. I will be the first to admit, that her approach has gained much appeal as I get older. Why should a vacation be a forced march?

When Betty and I took our first Alaskan cruise a few years ago (just before Covid was even a thing), I became aware of the joys of under-scheduling. Yes, a cruise ship offers all sorts of ways to separate you from your time and money. But, you can choose to skip most of it and simply enjoy the scenery passing by the windows, eat when you are hungry, and watch others rush from seminar to casino to sales pitch. 

Each of us feels most comfortable with one of these two models. Adopting the wrong approach can leave you frustrated.  

Unrealistic Expectations

You walk to the corner mailbox and back once a day. You stroll with the dog to the neighborhood park first thing every morning. Neither of these activities means you are ready to hike across England or tackle part of the Application Trail. Swimming a few laps in your pool doesn’t prepare you for an ocean dive to earn your scuba certificate.

A vacation with an ambitious goal can be tremendously satisfying, or quite a letdown. Trying different foods, and avoiding the top tourist destinations while seeking out where the locals go are laudable targets. Trying something physically beyond your capabilities, or forcing yourself to only eat local cuisine for a two-week stay in Sweden will probably lead to disappointment, if not injury or illness.

Knowing your limits and knowing what crosses the line from interesting to excessive is important.

Wrong place or wrong time

You don’t like cold weather yet you decide to go to Iceland in January because the airfares are cheap. Bugs and humidity drive you batty. Even so, you decide Miami in August would be a fun experience because the hotels are less expensive. 

Your oldest child just landed the lead in the school play, but you think it best to take the whole family on a camping trip to Yosemite. Your wife opened a new business that needs her full-time attention for several months. You are surprised when she balks at a week in New York City.

A vacation is a balancing act between time, needs, and location. While not everyone may be jumping with joy, everyone should be engaged enough to agree that the potential for fun exists.

Expecting it to be the same as home

I shudder when I hear a tourist complain about something by saying, “We do that differently at home.” My immediate thought is, well, stay home! What would be the point of going somewhere and having everything just like where you live? Isn’t the point of travel to see and experience differences? 

During our trips to Europe, I can’t count the number of times I heard travelers react poorly to everything, from the time restaurants open to the type of toilets that are available. A foreign country isn’t home. Even parts of this country have different customs and norms, even names. Don’t ask for a milkshake in Boston or a grinder in Amarillo. Different can be good.

Bad weather (really bad!)

We have spent 3 days stuck in a motel in Key West during a hurricane. We have almost been blown off the road during an RV trip through West Texas. Betty and I experienced six straight days of rain in Bermuda. We were caught in a blizzard near Yellowstone in late May.

Bad weather happens. It happens when you are spending time and money on a special trip. Mother Nature always wins. You can only change plans on the fly. Make the most of a bad situation, but realize you will have a great story to tell when you do get home (our daughters still remember the Key West “adventure” almost 30 years later). 

Bad weather also teaches us that no matter how much we like to be in control, that is usually just an illusion.

There is never a bad time to learn to exhibit more patience at things you cannot change. There is never a wrong time to learn to adjust your plans.

But, why do these learning moments have to happen on vacation?