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Vacationing With Friends: Avoid the Drama

I am picky to an annoying level, I am rather cheap but prefer quality over quantity, I have a strong distaste for chain restaurants (with the exception of Jimmy Johns which is home of the #14 and is like meat candy on a delicious baguette), I hate to be too hot, I love to sleep in and I often become “that girl” at brunch. There. I am not perfect.

girls night outThey say friends are the family you get to choose. So, you’d think a vacation with friends would be easier than a vacation with family.

NOPE.

I have gone on several friendcations.” Each one of them ended with a different frustration. For instance, a recent trip to Chicago sans children was delightful, but it was a lot of looking at each other saying, “What do you want to do?” I always hate having to entertain people.

This particular trip was children free. I wanted to live that up, but quickly found that I didn’t want to sit in a noisy bar with twenty-somethings. I wanted to have an adult dinner, catch a show at a comedy club, return to the hotel and make sheet angels in the king size bed, watch Craig Ferguson with a bottle of wine and then sleep in until 9 AM. My friends on the other hand, wanted to live it up in the Windy City, which was great, but they didn’t seem willing to part ways to do their own thing. This brings me to my first point…

A friendcation doesn’t mean you need to spend every second together.

I am such a foodie. Trying new and interesting things that I don’t have access to in Small Town U.S.A is a real treat to me. Caviar – sure! Goat – bring it on! Bone marrow – I’m brave, lets do it! My friends on the other hand like to stick with what they know, which is also fine. I wanted to try The Purple Pig, but I knew it wouldn’t be something our pals would enjoy. I’ll save it for another time. So, another tactic is…

Create a list of attractions/places/things you want to do. Share it with your friends and be willing to compromise!

Money. It tends to be the root of a lot of arguments. When we are hopping in and out of cabs or have road tolls to pay, we first create a Cash Stash where everyone chips in a specific amount. Then we use money from that stash to pay things we are splitting. If there is any cash left, we just divide it equally. We tried just alternating paying for cabs and tolls, but found some rides were more expensive than others. They repeatedly said it was no big deal, but it became a big deal later.

Create a cash stash or budget for shared expenses and have everyone contribute a set and equal amount.

Another regret I had when it came to my experiences with friendcations…not speaking my mind. Everyone has different opinions, feelings and preferences. Be understanding of that, but be willing to talk things out. I really wish I would have laid out an issue I had with my friends relying on me to entertain them. Perhaps they felt they needed to stick with me and whatever I was doing or maybe they were dying for a few minutes alone too!

Remember, this is everyone’s vacation and sometimes a gentle and honest discussion could make all parties happier.