Should you invite your friends on vacation?

Will they still be friends when the snowball fight blows over -- and the vacation ends?
Will they still be friends when the snowball fight blows over -- and the vacation ends?
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When you were a kid, you (or, rather, your parents) may have extended an invitation for a pal to tag along on a family summer vacation. Nothing seemed more exciting than spending an entire week -- an entire week! -- with your best bud. Sometimes, however, the novelty wore off after a few days. The nonstop contact took the fun out of the trip, and possibly your friendship. By trip's end, you may have been more than ready to part ways. But then there were other trips, where your friend's company on vacation was a good thing from start to finish. And, returning home, those friendships were even stronger for it.

The risks and rewards of vacationing with friends are pretty similar as an adult -- the company you keep could make the vacation one you'll fondly remember always, or ruin the trip and maybe the relationship.

There are some important things to consider before you invite a friend on vacation, and we'll go ahead and talk about the most unpleasant one: money. Whether you think so or not before the trip, money is going to be an issue.

Here are some money-related questions to factor into your decision:

  • Are your friends on the same financial level as you? Financial discomfort may arise if one party has a lot more spending money than the other, especially when it comes to lodging decisions (two stars or four stars?), dining decisions (will you be buying groceries while they eat lobster in restaurants all week long?) and other activities ("Let's charter a fishing boat!").
  • Check-snatchers or check-hagglers? Are you good enough friends where one can cover a check and the other can make up for it on the next check, or settle up at some later point? Nothing is more tiresome or frustrating than haggling over every single dinner check or on-the-run expense that pops up.
  • Do you have similar spending attitudes? Even if you earn the same amount of money, one party may be more inclined to pinch pennies while the other prefers to figuratively make it rain hundred-dollar bills.
  • Who will be paying for what and how? Would one party be responsible for booking hotel rooms while the other secures tickets to various attractions or shows?

So should you invite your friends on vacation? We'll find out right after we discuss a few more things you should consider.