vacationing with friends

*This is Part Five of my Tri-umphant Friendship series where I explore what friendship means to me and others. Read Part One, Part Two, Part Three and Part Four.* 

You really don’t know someone until you’ve spent a week crammed into a tiny room with them. Things may be all fun and games when you see them normally, particularly if you mainly see each other for social events and celebrations. But things get real very quickly when you’re spending 24/7 together. You’ll learn each other’s habits with cleanliness, hygiene, sleep routines etc.

Luckily the majority of the trips I’ve taken with my friends have all gone pretty smoothly. Most of my inner circle I’ve been friends with for 15+ years so there really isn’t much more to know. At the same time, there have been hot mess trips where post-trip I literally speak to them never again. Now that I’m much more mature (hopefully) I know that the secret to any successful vacation with friends is lot of planning, and that’s where you can catch the majority of red flags for any drama that might come up. Trust me.

Schedule ahead of time. I can’t emphasize this enough. Even if you and your friends are all “chill people,” you’ll be glad that there’s at least an idea of what could be on the itinerary everyday. Do yourselves a huge favor and look up fun activities, research Yelp and travel guides for restaurant picks, and scope out the best bars ahead of time. By having at least a minimal amount of structure on this trip, you’ll take the stress out of having to come up with game plans on the spot and make sure that everyone in the group is on board.

Be open to change. While it’s important to make an itinerary, keep in mind you’re on vacation. So it should be a tentative schedule where nothing is set in stone. If you’re taking an Uber to your hotel, make sure to ask your driver for recommendations for restaurants and hotspots. Same thing when you’re checking into your hotel. Unless someone in the group has had their heart set on eating at a particular place or doing something specific, try to be as spontaneous as possible. The whole point of making a schedule is to take the stress out of figuring out what to do and where to eat, not for anyone to be a dictator if things don’t go exactly according to plan.

Keep social media to a minimum. Please don’t be that person slowing the group down because you need so many extra solo pictures. The general rule of thumb when it comes to social media posts is one per day, even if you’re on vacation. If you’re at a historical monument you get two. Trust me, no one cares about your photos for more than one photo per day (probably even less). Besides, if you’re traveling with friends, you should already be with the people who matter most. Try to be in the moment and have fun. You won’t regret it.

Start an iCloud Photo Sharing album (or Dropbox) for the trip. This works particularly well if you have one person who’s a photo enthusiast. This way you can save time by only using one camera for group photos, only one person needs to take photos of monuments, and you can save data/memory by sharing through a data cloud. Plus on top of that you will save so much time by not having to borrow other people’s phones, comb through their albums, and send yourself a 100 photos at the end of every night.

Make sure everyone is on the same page (spending wise). Having a diverse group of friends can be rewarding and challenging at the same time. Regardless of their current financial situations it’s important to gauge everyone’s comfort levels when it comes to the amount of expenses they’re willing to incur on a trip. Let’s take me for example, I love a bargain but at the same time if I’m on a vacation, I’m willing to throw down extra money in order to be comfortable. My days of cramming into a tiny room with ten other people are over. But not everyone feels the same way. It may be an uncomfortable topic but make sure to get some guidelines out of the way so that there won’t be any awkwardness while you’re on the trip. Before you even buy a plane ticket make sure that everyone is clear on the amount this trip will cost. If you think people might be embarrassed to discuss it in a group email, make sure to reach out to those you suspect might be on a budget individually to make sure that they’re comfortable with the expenses for the trip. Being upfront ahead of time will save everyone involved a lot of headaches in the long run

Have downtime. Even if this is just a weekend trip with your best friends, scheduling an hour of me time is essential for balance. Someone may want to take a nap, do some reading, catch up on some work, or you may even be having such a good time catching up, you guys end up sticking together. But the point is to have options in case some people in the group just want a minute for themselves.

Most importantly, try to have fun. You’re on vacation with your best friends. Act like it. As long as you keep things in perspective and try to make the most of things in a positive way, everything else will fall into place. Whether the food is bad, you’re in a tiny room or even if it’s raining, as long as you’re having fun, that’s all that you’ll remember from the trip.

Vacationing with friends

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