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Planning in Advance Beats Regrets in the Moment

You head out on a vacation and after a few days you are miserable. You are not enjoying the trip and you and your travel companion start to verbally snipe at each other. What is the reason your vacation is not living up to your expectations?

Recently I wrote that there are many things that you can control that will allow you to avoid some potential vacation pitfalls. Today I will talk about planning and no, I do not mean sitting around swilling back drinks and kicking around holiday wish lists. I am speaking specifically about planning out your activities while taking into account a number of factors.

Thinking About Your Goal

I am not advocating approaching your vacation like you would a strategic planning session at work, but I believe that employing a little of the same evaluation process can actually work to your advantage. When that evening of dinner and drinks turns into a vacation planning session because you all spontaneously decided a road trip would be a great thing, don’t be afraid to engage a little logic and sprinkle it with a few selfish wishes.

No matter what anyone says, there is always a goal when planning a vacation. Even if it is as simple as “I want to relax and think of nothing” or “We want to escape the cold”. Spending time being a couch potato or enjoying a warmer climate, are goals. With either of those two goals, you are immediately ruling out the super busy, packed trip and definitely crossing off that northern photo session with the polar bears.

When planning a trip, decide and talk about your goals because conflicting goals are warning signs. Do you want to stay in your comfort zone or push your limits with new experiences? Is your vacation designed to have you cross destinations off your “must visit” list or spend time with friends and/or family? To arrive at your goal, ask yourself what you hope you will have achieved at the end of the vacation. I look back at some of the goals I set on previous vacations and they varied depending on work schedule and destination. Goals such as:

  • See the following sites (I listed the places or things I wanted to see).

  • Veg (translate this to 'relax and not think about work').

  • See as much of the country as possible (always a goal in countries I don't think I will be visiting again).

  • Visit with family.

  • See a play (not much of a goal that year but it was one of those vacations where I simply said I did not care what we did or saw as long as I got to see a play).

  • Try para sailing and spend time on the beach without getting burnt.

If you and your travel companion have goals that are polar opposites, then you are headed for trouble or in need of major concessions up front.

What Do You Want to Do?

Do you want to relax or see something specific? Is there a place or sight you have always wanted to see? Plan your vacation to suit your needs and yes you can be a little selfish. Don’t do things you do not want to do just because others are doing it and want you to go along. If you have always wanted to see the Sistine Chapel, don't go to Rome and miss out on seeing the Sistine Chapel because your travel companion(s) want to shop.

Wait you say, there are plenty of times you HAVE to do things you don't want to do? I am going to hold up my hand against your protests and cite two deviations from the “Do what you want” planning.

First there will be times when you may go on a vacation that you really do not want to take because of family circumstances. I hear from a number of parents who tell me their ideal vacation is not a water or theme park but because of the children, they go to these places. I get it, but in that case I say loop back to your goal. If your goal is to spend time with the family and ensure your children enjoy themselves, then what you want to do morphs from a “me” vacation to an “us” holiday and you are indeed doing what you want – pleasing the family. You are simply not going on your preferred holiday.

The second deviation is if you are involved in compromise vacation planning. When we were first married my husband and I disagreed on the perfect vacation so we alternated; one year we did what he wanted and the next year we did what I wanted (budget permitting of course). So during years when it was my husband’s choice, I was taken to see all the famous battle sites of the American civil war and we visited every fort on the American/Canadian border. When it was my turn to choose, my husband found himself taking anti-malaria medication and heading to points further afield. Now years later, I might plan a vacation around famous North American battle sites while he has me floating down the Amazon.

What is the Budget?

Basic rule, if you cannot afford a travel vacation, you probably should not be taking it. If you are taking a vacation you have been pressured into by friends/family and cannot afford, your resentment will be magnified and little things on the trip will balloon into big things. I will be writing more on budgeting in my next blog.


A friend told me she dumped her long term boyfriend because they always did things that he liked doing and according to her, they never did anything she liked. Vacations were spent on fishing trips. Perhaps the demise of their relationship was inevitable when she tossed his tackle box and fishing gear into the lake while on one of those trips. Prior to allowing her resentment to take over, they should have talked through vacation options such as alternating yearly vacation choices. Don’t resent your holiday if you did not speak up and be prepared to compromise.

Are there Other Factors?

Family situations (such as what you will do if the unexpected, such as a death, occurs while on vacation). People are split on this issue. Some will say that if a death in the family occurs they will finish out the vacation while other say they would return home immediately regardless of the loss of money.

Ill health or physical limitations also factor into a great vacation. If you are not up to an activity or your travel companion is not up to an activity, talk it over beforehand. Don’t become testy on day three of a cycling tour through Europe because you lack the physical capabilities to meet the demands.

Eating adaptability. Surprisingly enough, the ability to try or adapt to different foods often leads to conflict among travelers. This includes food sensitivities, limited pallets and the dreaded picky eater.

Don’t engage in activities that are frowned upon or illegal in different countries. You adapt to the rules of the country you are visiting because they do not have to adapt to your rules and norms. This will also be the topic of another blog so I will not go into detail here.

As evidenced by these common sense tips, certain problems that crop up on a vacation can be avoided by simple planning in advance. Always control what you can before you opt to take that holiday. Safe and happy traveling.

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