Girls Trips

Want to test a friendship? Travel with the person.

I feel like there’s no in between when it comes to travelling with friends. The trip is either out of this world amazing, or you’ll board the plane back home with the friendship hanging on by a thin thread. As the old Caribbean adage goes: ‘see me and come live with me are two different things’.

Travel comes with a lot of potential headaches. From planning the trip, to getting to the destination and then spending a considerable amount of time with people in a foreign land – there are a host of things that can go wrong.

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Personally, I haven’t had any group travel nightmares but I’ve heard a couple. I’ve reflected on the trips I’ve taken with friends over the years and I think there are some key things that everyone should consider before planning a lah hay with friends.

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Can you deal with flakiness?

It is a truth universally acknowledged that when planning a trip, not everyone who said they’ll come will show up. And this is fine. Life happens and many times people just can’t commit to a trip they initially signed on to. On the other hand, there are flaky people who, for different reasons, won’t say no but never show.

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No shade, because I’m quite flaky, but this can be a real headache. Very often accommodation and travel package deals are very reliant on a particular number of people. Changes in the number of people travelling, often result in more money being spent in the long run and hotel rooms and travel packages having to be cancelled or re-booked countless times. This is annoying, especially if it’s a large group of people. I suppose a big part of this is knowing your friends, knowing who you can count on to commit (save life happening) and also mentally preparing for the flakiness from the get go. Note well that the flakiness can extend well into the trip so another thing to consider:

Can you coexist with these beings for a considerable amount of time?

Yes you’ll are friends – you may work with each other every day or have known each other since primary school – but can you coexist with this person for a considerable amount of time, in potentially intimate settings, without going crazy? There’s an infinite list of things that can go wrong while travelling – delays, cancelled flights, cramped hotel rooms, lost passports – and not everyone is cut out to deal with them.

Can you deal with an incessant complainer, whiner or overly fussy person?

Is your friend a complainer, whiner or overly fussy person?

Are you a complainer, whiner or overly fussy person?

Know what you’re signing up for and what you can deal with, before you purchase those tickets. Another consideration which should be a conversation would be:

Does everyone have the same expectations of the trip?

Some people travel to eat, some travel to sleep and others are bent on having a complete cultural experience. One of the points of any other type of group travel is to not just board the plane together, but to spend time enjoying the destination together. It’s therefore important to speak about those expectations before you buy those tickets.

Yes you all want to go to Mexico, but if you want to spend your week sipping margaritas by the pool, but your friends want to spend the days exploring the city, then you’ll are planning two completely different trips. It may work out fine at the end, but it can also result in someone’s face looking like this at the end of the trip:

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Another way to avoid that is to think about this:

Are you willing to compromise or try new things?

One of the great things about group travel is that almost everyone has different interests.  With more people researching different things to do in a particular place, you often end up doing things you may not have thought of doing before. It’s an opportunity to try something you may have not explored before.

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Earlier this year when I went to Barbados, two of us really wanted to go snorkeling while the other wasn’t on it but she took a chance, did it and loved it. Of course the end result isn’t always positive but group travel can often force you out of your comfort zone.

In some cases though, you may feel inclined to skip on something you really want to do to stay with the group. While this may sometimes be a necessary compromise, are you cool potentially doing things alone?

Yes you want to experience the country with your friends and you may also be very open to compromising on things you want to do to stay with the group, but if the rest of the group doesn’t want to go to the museum, are you okay going alone? It may be a good idea to not always let the group dictate your pace.

Know that there’s safety in numbers -especially if its nighttime or you’re trodding the unbeaten path – but don’t be afraid to leave the group for a half day to do a tour you wanted to do or to sleep in and relax. As I said before, people travel for different reasons so be open to splitting up and doing you during the trip. What’s important here is communicating with the group beforehand so everyone is on the same page.

I’ve gained countless memories travelling with groups of friends. Aside from group travel being cheaper you’re spending time in an exciting place with a group of people you’re fond of – it’s a win win.

Just remember that because so much can go wrong, things can get ugly quickly while travelling with friends so it may be a good idea to consider a couple things before booking those tickets. Have you travelled with friends before? Anything else you think someone should consider before planning group travel?

Let me know in the comments below 🙂



Note well that these considerations extend well beyond ‘Girls Trips’ and are applicable to any type of group travel.




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