Should you invite your friends on vacation?

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.

Wish You Were Here?

vacation with friends — Female friends in discussion while sitting poolside at luxury suite of tropical resort at sunrise Thomas Barwick / Getty Images

In the previous section, we brought up some financial issues involved with co-vacationing. What are other questions you should consider before forming a vacation gang?

What kind of vacation is it? Will it be an adventurous one? A relaxing one? A drunken one? This will help determine the type of friends you invite, if any. If you're looking to have a week you'll never remember and your friend's a teetotaler, you might want to reconsider.
Do you play well with others? Can you make concessions, or will you be tempted to play the "You're on my vacation!" trump card if a group decision isn't going your way? Do you tend to dominate decision making? This might be a good thing if your friend is a go-with-the-flow type of person. On the flip side, are you a relaxed, easy-going person who's considering inviting your hard-charging, type-A friend?
Do you keep similar schedules? Is one an early riser, and the other a late-nighter?
If you have kids, do they/could they get along? If not, can you both laugh it off while breaking up the fight?

The most important aspect is simply making sure you and your friends are on the same page about the vacation -- its costs, its activities, and its expectations Decide beforehand what kind of expenditures are reasonable to expect, and how payment will proceed. One person can find the lodging (with the other's approval or help), but both parties should book separate rooms if possible. Build some "alone" time in, days when all parties can go their separate ways and do their own thing. Make plans for one nice "going out" meal or special activity, and discuss the possibility of going in together on common meal items for breakfasts and lunches -- bread, cereal, milk.

Accept that even though it's "your" vacation, once your friends agree to go, it's going to be just as much their vacation.

As long as you have clear communication about your wants, needs, schemes and peeves, taking your friends on vacation can be a great way to enhance both your vacation and your friendships.

Should you invite your friends on vacation?

Wish You Were Here?

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