Group Travel Checklist - Should I Travel With These People?

Here you are wondering to yourself if you should embark on a trip with 10 people to Thailand for a wedding or maybe to carnival in Rio. You aren’t comfortable traveling alone, but you’re also unsure about the weirdos you call your friends and their reliability.

I’ve made this checklist just for you! If the people/person you intend on traveling with (regardless of how many of them there is) can pass this checklist - you’re cleared for take off. Now I understand this check list won’t be perfect science, bullshit happens ALL the time on trips that you just can’t foresee. Also, I didn’t give this checklist an actual number of items to discuss, because I began writing it and just things kept popping into my head. I truly do believe this list will REALLY make you think about who you are going with and make your decision much more straightforward.



  • Does this person have a solid source of income?

    • Not here to insult those who may not be gainfully employed, not at all. But if this person is a ‘oh shit forgot my wallet’ type or someone who isn’t consistent with their actual bill payments, this ain’t the one. Drop them. If they can’t take their bills seriously, they sure as hell won’t take this trip seriously.

      • Special mention to those who are also cheap. There’s people who DO have a very good, steady job but won’t spend a cent on living it up a little on vacation. If you are the ‘YOLO IM ON VACAY’ type of spender, and the other person is frugal Freddy, this probably won’t work.


  • Does this person arrive on time for group outings?

    • I realize this will offend some of the people who are (undoubtedly) good people but just bad with time. Trust me, don’t travel with those either. The last thing you need is Tommy Toolate making the whole group miss an activity because he was hungover and you were all too nice and waited for him.

  • Is this person a scammer?

    • Don’t do it. You don’t want to find out at the gate that the credit card used to purchase their flight was owned by Henry Connor the 3rd but it’s Rachel Smith that’s somehow on the flight with you. You don’t want to get to your destination country and suddenly ALL those credit cards in hand have been cut off because the actual owner(s) of them caught on and now your travel partner has no funds.

  • Can you be near this person without feeling a murderous rage for an extended period of time?

    • I realize some folks travel with people out of availability, not necessarily because they WANT to travel with them. Folks are afraid of traveling alone and whatnot. You really have to think to yourself if this person is someone you will not want to kill. Traveling is already taxing on GOOD relationships. When there are delays, lost bags, you’ve been in transit for 40+ hrs etc. So now, think about the person(s) you chose to go at this with very carefully.

    • Also, to add to this one - when it comes to personalities make sure you’re choosing someone/a group of people who is/are either very much like you so you can do everything together OR is/are nothing like you but has/have a strong sense of independence. You definitely do not want someone who doesn’t have similar interests as you accompanying you to shit they don’t want to do and you have to listen to them complain whole time. You want someone who can be independent and feels comfortable going off to do their own thing as well.

  • How is this persons hygiene?

    • I know, I know - this not the most comfortable conversation to have with yourself nonetheless with another person. But seriously, do you want to travel with Tamara Toostink? Hygiene is a big deal in a travel partner because you do not want to be stuck next to someone who bathes twice a week in a hot-climate country for a 15-hr direct flight home. Also, in your hotel/AirBnB room this will be the most unpleasant of situations for someone who is a clean freak. Now, if both of you smelly I guess this might work out. But if you are someone who takes pride in washing your bushy parts regularly, I would REALLY advise against traveling with someone who avoids bathing like I avoid middle seats in an airplane.

  • Food. Food. Food.

    • Are you a squid in its own ink broth eater? Or maybe you like chicken fingers and fries only? You see how this could end up being an issue right? If you are someone who absolutely loves to eat anything and everything but your travel companion won’t step out of the foreign McDonald’s - this could cause a lot of shitty situations. I also mean, literally, shitty. Because if you are traveling with someone who has a very weak stomach or even might have a seafood allergy etc. Oh boy. Obviously this one isn’t a complete deal breaker, but you really should consider that you may not ever have a meal together in a seafood restaurant because they may have a severe allergy OR that you may be stuck bringing your yummy kebabs off the street into the local Pizza Hut to appease your travel buddy.

  • How is this person with cultures/people/places different than theirs?

    • This one falls perfectly after food, because a big part of experiencing other peoples culture is enjoying their food.

    • There’s no nice way to say this, but is your travel partner some country bumpkin that might embarrass you or a whole nationality/race when you get there? There’s always an A for effort to those people who are trying to get out and explore the world so that they can be exposed to different types of people, languages and cultures. However, are they ACTUALLY about that life? When I was at the Louvre in Abu Dhabi, my friend and I watched a pale European woman make fun of and pretend to make her eyes different to match a statue of Buddha. That’s frigging disgusting. Also, we watched countless women at the Mosque in Abu Dhabi be told over and over again to cover their hair. Is this really the kind of people you want to be with when you travel? I would personally die of second-hand-embarrassment being associated with someone who behaves like that.

  • Does this person have a substance abuse issue?

    • Another very uncomfortable conversation to have. This is no way meant to demean those who have drug or alcohol abuse issues, I hope all of you get help for those issues. However, big big HOWEVER, that doesn’t mean you should bring those people on trips with you while they’re still in full abuse mode. People who abuse alcohol at an all-inclusive resort might actually drink themselves into oblivion. Or imagine at carnival? All those all-inclusive fetes or playing mas in the hot sun with all that liquor on the road. Do you want to be with someone who will drink over their capacity and you’re now finding them almost getting run over by the big truck? Or they’re so sick, you have to now LEAVE playing mas (that you paid a lot of money for) to take them home and care for them? Fuck that. Moving on to drugs, I mean smoking a little bit of weed in Jamaica or Amsterdam won’t really cause you too much issue. When you get into places like Bali or shit, even maybe Vegas? Don’t be out with the person who will be doing lines of coke off the toilets in Vegas. Even worse, don’t be with the person who will do hardcore drugs in Bali and now they end up in jail for life because they had meth on them.

  • What is their relationship status?

    • Oooooh spicy time! Let’s talk about what you might have to consider when it comes to both SINGLE people and TAKEN people on vacation.

      • Single People: Honestly, is this person going to be Battry Betty on your trip? Obviously plenty single people travel just fine and don’t bring back their shenanigans to your hotel, but what if this person does? You go to a club and your travel buddy picked up some foreign girl and brought her back to your hotel, she crazy, now she has stolen your damn passport and your toiletries. I realize this is a little wild, but seriously. If the person you are traveling with is single, you probably should find out what (who?) they’re trying to get into while you’re vacationing. You might be single and just NOT want to participate in any shenanigans, while your travel partner thinks he’s running his own brothel.

      • Taken People: I’ve had worse experiences traveling with those who have a significant other, than those who are single. That’s just speaking for myself, but holy shit does that come with its own set of problems. Is the girl you’re traveling with going to argue with her man the ENTIRE GODDAMN TRIP? You leaving for Egypt for two weeks, right before you leave, her man pisses her off. Guess what that flight, the whole trip, all activities etc. gonna look like now for you? Now you’re stuck with Miserable Mindy for the whooooooooole trip just because she is CHOOSING to argue with a man who is six time zones away. There are plenty boyfriends and girlfriends who will intentionally start arguments with their s/o that is going on a trip without them, just to ensure they are miserable and therefore, do not cheat or DARE NOT have a good time without them present. (stupid, I know) But sadly, this WILL become your problem as the person on the trip with them. Be sure they’re in a stable relationship situation or just know how to ignore people a million time zones away while traveling.

  • Is this person FUN?

    • This one might seem kind of silly, but seriously, are you really going to have a good time with this person/group of people? It doesn’t matter how well prepared, smart, reliable etc. someone is - will you actually have a bomb ass time with them on this trip? There are some people who are super hype for a trip, have their money right and everything but then when you get to your location they are just lame and boring or want to stay in the hotel on Twitter or watching Netflix. Why the hell did you even come on the trip then? Booerns. There are vacations that are meant for relaxation, absolutely, but if you planned out a whole fun trip with someone and they might end up being homebody Harry the whole time, you really could have just gone alone.

(Special mention: People who will take good pictures of you for IG, definitely take with you. People who know how to swim if you don’t, definitely take with you. Nurses, always take nurses with you. Definitely don’t take vegans anywhere. People who know how to shut the fuck up, definitely take with you.)


Whatever you do - stick with your gut when it comes to anyone you will travel with. That’s really the most basic tip to give. I wrote a post before on How to Travel In a Group and Still Remain Friends, because even the best of friends can have problems while on road. All of these weird logistics and factors are also the reason I prefer to travel alone, although I am fortunate to have fun and reliable friends.

I really hope this either made you laugh, offended you or maybe even (by some miracle) helped you with some group trip you were contemplating. You can put in the comments below what are some of your red or green flags when choosing to travel with people!

  • Mirna