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Six Things To Consider Before Traveling With Friends

by joeheg

“Let’s go somewhere together!”

Going on a vacation with friends. Sounds like fun, right? Even if it’s just a trip for you and your bestie, there are some things you need to consider before you start planning. While some of these might seem obvious, if you don’t settle them before the trip there might be some awkward moments ahead.

This isn’t even starting to consider the discussion about how everyone going on the trip is dealing with COVID-19. Pro-mask and anti-mask people should put off any trips until after all of the #coronacrapola is over with.

Here are six things you should decide before you start planning a trip with your friends:


person holding coins

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Get the money question out of the way early. While you might think you know how much money your friend will spend on a vacation, you’re not sure until you ask. If your friend is all Motel 6 and you’re Park Hyatt, someone isn’t going to be happy with the plans. If you’re good friends, then there’s bound to be a middle ground but getting that hammered out early will make it easier to agree on the rest of the plans.

Mobility/Health Issues

If you’re not best friends, you might not know if someone has a health issue that will impact their travel style. Maybe they can’t walk for a long period because of joint problems. Other people can’t sit for long stretches of time. What if someone has breathing problems?

There could also be invisible problems like chronic fatigue, anxiety and/or panic attacks that you might not know about. You don’t want to book a stay at a capsule hotel for someone who is claustrophobic.

Even if you’re good friends, these topics might not have come up before but it’s better to know about them in advance because any problems will affect everyone on the trip.

Dietary Restrictions/Meal Preferences

Tying into health issues would be dietary restrictions. Maybe your friend is a diabetic or is allergic to shellfish. You need to understand this going into the trip. You will have to adapt your preferences to accommodate your friend so it might be necessary to skip the Oyster Bar.

A more general issue would be meal preferences. Do you like to eat a big breakfast every morning but your friend likes a cup of coffee and a danish? Or maybe you need to eat several small meals throughout the day but your friend likes a three-course dinner every night. Someone’s going to have to give.

Morning Person/Night Owl

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Do you like to get up early and see the sunrise (If you do, what’s wrong with you?)  If you do and are in bed every night by 9PM but your friend is a night owl, there are going to be some major scheduling conflicts. It’s much easier if everyone has the same preferences but if that isn’t the case, you’ll need to decide whose schedule you’re going to follow and when.


If you’re going to a place with plenty of things to do, what do you want to see? Do you like museums, theater and to eat at nice restaurants? Maybe your friend wants to do some bike riding or go on a walking tour and is bored to death at museums.

There might be places you want to see but is it worth it to make your friend miserable for several hours? Maybe they’ll go along but you know they’re hating every second and now you’re not enjoying yourself, either. Why did we decide to go on a trip together?

adult art artistic artists

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These are things you only learn after traveling with friends.

Stay Together or Divide and Conquer

Here’s the biggest question. You went through all this trouble to plan a trip together. It would make sense that you’ll want to spend time with each other. However, it might be better, and more enjoyable for everyone, if you spend some time apart. You can sleep in, go check out that museum and then have some crab claws and your friend can wake up early to go on a hike and then find the place that makes the best sugar-free cheesecake as a treat. You’ll both enjoy your day and can spend the evening telling each other about your adventures while you both think your day was so much better than the one your friend had.

Final Thoughts

These are just a few of the things that can happen when you go on vacation with friends. It’s really rare that you’ll find someone who you just click with on all cylinders. None of these things should be deal-breakers, and if there are it might be better to reconsider if the trip was a good idea in the first place.

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This post first appeared on Your Mileage May Vary

1 comment

2btravel June 2, 2019 - 8:45 pm

From personal experience here are a few others:
1. Travel Style – are group tours OK or a never-ever? If you’re planning the trip on your own are you all ok with taking an organized day trip out of town that requires being at certain places on time or are you all go-with-the-flow people?

2. Bedding – some people don’t like to share a bed. If you’ve got an even number of people traveling that can usually be handled with two people in each room. But it’s often difficult to get rooms with three beds, even if one’s a rollaway. Having hotel status or the points to upgrade is great but it seems most suites are a king + sofa bed and if nobody wants to share it becomes an issue. I really wish more suites had king beds that could be split into twins AND still have room for a daybed or full-sized sleeper sofa. Something bigger than a rollaway at any rate.

3. Snoring – when traveling with your spouse you know whether or not they snore but it can be a rude awakening (literally!) for friends who aren’t used to sleeping in proximity to one another. Discuss how to handle before it happens.

The meal thing can be a real issue when you’ve got one person who’s a pickier eater than the others. It seems that we often end up letting that person select our restaurants because the others are more flexible.

A good list that certainly made me nod in agreement on many of the items.



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