Keys to a Successful Vacation with Friends
Make this year’s trip the best one yet
Vacations are great in your 20s. Getting a crew together for a week of non-work activities is enough to get even the biggest workaholics excited.
It seems easy: text your friend group, see who’s interested, pick a destination, and you’re good to go right?
Wrong. A friend's vacation can be rewarding if done well. If executed poorly, fights can break out, and the foundation of a solid friendship can start to fracture.
As new grads enter the working world, their priorities start to change. Party animals suddenly are waking up at 6 am on the weekends. The fast-food junkies go on diets, or the big spenders start saving for a house or car.
All of these changes make it more difficult to plan a trip. The days of getting a hotel room in Miami and hitting the bars are over, it’s time for a new type of vacation.
Crucial components:
1. Pick the right friends
You may want all of your friends to be involved, but it can be a recipe for disaster. Some friends just don’t jive when they’re together 24 hours a day.
You know the saying “some people shouldn’t be roommates?” Well, some people shouldn’t travel together either. That person who doesn’t help around the house isn’t going to change their habits overnight for a vacation.
If you’re a neat freak, travel with other tidy people; a sloppy person will stress you out. If you’re messy, go slob it up with some of your carefree friends. You won’t want a neat freak killing your vibe all week.
2. Know your group dynamic
To pick the right friends for vacation, you need to know the group dynamic. You should know who’s messy, who’s the type A personality, and what everyone likes to do.
If someone has a bad ankle, they won’t do well on a hiking trip. If one of your friends is afraid of heights, it’s probably not a good idea to go rock climbing.
It’s best to avoid scenarios where you put someone way outside their comfort zone- this is a vacation, not boot camp.
3. Be clear about finances
It’s likely that your friends have different levels of income. The 5-star hotel may be spectacular, but if your software engineer friend plans everything, it may stretch a music teacher’s budget too thin.
A $1000 bill for a big group dinner won’t sit well with everyone, and stressful financial situations can begin to drive a wedge between friends.
4. Be flexible
Your trip will not be perfect.
That pre-storm gust of wind always seems to strike right as you unfold the beach chair. When that happens, you have to find a new plan before the rain soaks your beach towel.
Your response to unforeseen circumstances will make or break the trip. A surprise change in plans is a nice way to try something that wouldn’t normally be on your list.
Lost luggage? Buy that Hawaiian shirt in the airport and rock it all week long — and buy a toothbrush too.
A rainstorm on beach day? Go check out the local museum. Maybe even break out a board game.
You’re on vacation. Not every moment needs to be on the itinerary.
4. Communicate
I cannot stress this enough. Communication is by far the most important part of a drama-free trip. Any of the rules above rules can be broken without issue if good communication is involved.
A messy friend who says “Hey I don’t do a good job of cleaning throughout the week. I’ll try but I will definitely help clean everything on our way out” is a much better travel companion than the unexpected slob.
If one friend is ballin’ on a budget, it’s helpful if they clearly communicate their goals.
Extra credit: the more explicit the better. If you have a budget, be direct. Saying “I have a $500 budget for this trip. I may need to sit out for the fancy meal” is a lot more helpful than “I want to limit my expenses this week”. One person’s idea of low budget items may be expensive for someone else.
If one friend wants to relax all week, they should make their voice heard so the group doesn’t decide on a rigorous hike every day.
Get planning!
Vacationing with friends can be extremely rewarding. Some of my best trips ever have been with close friends. For your next getaway, talk to each other, and some time to plan so everyone has a good time.
There’s nothing worse than feeling like you need a vacation from your vacation.
