Day 90: The Vacay With Friends, Do it at Your Own Risk

Vacationing with your friends can be fun, but does that mean it’s a good idea? These chums you enjoy for a few hours at dinner, or a cookout, or at a party with lots of other people may not mean you’ll want to hang for days on end. There is also the additional question of vacation styles. Some people prefer structured vacations with a set itinerary and others like me, prefer to wing it and take things as they come. Mix different vacay styles and too much togetherness and you might come home with one less friend. We tried vacationing with another couple once before and it was not great, now we’re looking at potentially doing it again. Stupid or optimistic?

When the husband and I vacation, and we have travelled quite a bit all over the world, we get along really well. Neither of us are huge into major tourist attractions, so beyond the major museums and a few mandatory tourist stops we like to just stumble about, going from one meal to the next and drink to drink. For us, it’s more about the local color and we’re not great at following a structured plan. We also enjoy opportunities to be social and each vacation there comes a time when we kind of wish we had friends with us. It looks fun when you see all those photos of groups at the ocean or skiing together. We’re fun, we want to be in a social group.

Then again, other people can be annoying and what if they want to get up at 7am so they don’t miss anything and hurry, hurry, hurry we need to make it here by then or there by now. It could be a catastrophic mistake if you vacation with the wrong types of friends. I am not what you’d call an easy-going person, but when I’m travelling I am anything but structured. Last Summer we went to Vegas with another couple and it was not what I would call successful. We stayed off the strip at the place they chose, we tried to work around their schedule, and yet they did not do a single thing to work with us. We barely saw them actually, which made us wonder what the hell the point was in vacationing together and when we did see them, they managed to muck up anything we wanted to do. It made us wonder why we should adjust our plans if they weren’t going to make an effort?

So now we’re considering Cancun over New Year’s with another couple. We could end up hating them, we could end up best friends, we could just get really drunk and not care. The problem for me, is that if you’re doling out upwards of 6K for a vacation you want it to be good, because if it sucks, you’re still out the money and the vacation time in addition to the possible lost friendship. In a big group none of this probably matters because there are enough of you that at any given time someone will be up for whatever, but when it’s just two couples shit can go wrong. Then again, it’s Cancun, it’s the husband and me, how bad could it really get with those two pluses going for us?