The Notorious Challenges of Planning Group Trips and How to Overcome Them

In 1997, I was the tender age of 9 when Notorious B.I.G. released the album “Life After Death”. This classic work included the hit song, “Mo Money Mo Problems”. Twenty years later, this song still plays every time I plan a group trip.

The more people involved means more money, more opinions, and typically more problems. Speaking from experience (I’ve managed the logistics of trips ranging from 10 to 200 people, large groups trips can come with as much joy as it will come with headaches. Here are my top tips for you to keep in mind while planning your next group trip:

Speak Your Piece and Keep Your Peace

No matter the group size, communication plays a huge role in trip planning. Even if the whole group lives in the same city and sees each other often, there are a lot of details that need to be discussed before going on vacation.

Be as thorough as possible about deadlines for bookings, when money is due, visa information, travelling times, and anything else that is relevant for your trip.

You don’t have to send out a full PowerPoint – although I’ve have done it with no shame – but clearly explain all actionable items to people. Whether it is about transportation, dinner reservations or needed documents, thoroughly explain so your fellow travellers can be prepared. Although people will still ask the very things you explained, the amount of times you have to answer the same question will drastically decline.

Once you are abroad, people have everything they need, which means you can focus on the priority of your trip…having a great time!

If you aren’t familiar with the mobile application GroupMe, the virtual chat room is a great tool for trip planning. The app allows you to add an unlimited amount of people and acts almost like a text thread without taking up storage on your phone.

I start a chat for every trip so I can give all members real time updates and drop pertinent information. Utilising the built-in calendars for housing links, reservation info, itineraries and other information is helpful for all of us, as we can find the information we need quickly on the app.

What about your friends?
Even with a large group trip, finding time to explore with your friends is key. These men take an annual group brothers trip yearly to celebrate their friendship, bond, and success. One of the best parts of getting your friends from different places to visit a new country is making memories together (and of course taking really great pics)

Sometimes Your Words Just Hypnotise Me

With large group trips, it’s inevitable that you will send some type of email to the other travellers. The larger the group and the more details you need, the longer the email.

I hate to be the bearer of bad news, but if you are the person that sends emails that causes continuous scrolling, they probably aren’t getting read. With the average person taking less than five seconds to read an email, your paragraphs are lost between scrolling Instagram and discovering a new music playlist.

Yes, you do need to be as detailed as possible, but there are ways to do this and keep it short. If you answer when and where the event or activity is (including any important travel info such as cab directions, cost, shuttles, etc), why they signed up and what they are getting, you have the day covered.

I typically send out one initial email in depth then a reminder of action items closer to departure.

Where The Real Playas At?

There is always one traveller who wants to invite their bestie that lives on the other side of the country, their cousin who wants to take their first international trip or their colleague who they are silently crushing on.

I planned a trip to Colombia with 13 people, which rapidly grew to over 200, as a result of people inviting their friends, who invited their friends, and so on. That’s a lot of different (and potentially clashing) personalities, tones, and moods.

As most of us know, traveling with the wrong person or people can dampen your whole trip. Although not everyone has to do everything at one time, you will most likely have activities that include people you don’t really know.

Again, GroupMe helps me overcome this problem. It also allows people to get a sense of others and see who else is going on the trip. Yes, people will shoot their shot in other traveller’s DMs, but it is a great way for people to meet beforehand.

On a smaller group trip of 35 to Dubai, we met up for happy hour at a local bar so we could get a sense of each other before we took flight. We did similar for the Colombia trip, scheduling dinners and outings in Chicago, Washington D.C, New York and Atlanta.

Building the familiarity also led to friendships and bonds being built outside of the trip. We have since then taken other trips together and met up frequently.

With a dab of mud
If you can’t play in the mud with your friends, are they really your friends? Our trip to El Tomuto Volcano included wading around in a very buoyant volcano filled with mud. Of course we did it for the culture with the dab!

I Love the Dough

Collecting money from each traveller before a trip can be a hassle for a few reasons.

One, depending on how large your group is, how you collect money can pose issues. PayPal only allows you to withdraw $1000 (£770/€850) every 30 days. If you are paying for your accommodation, excursions or vehicle rental for the whole group, it’s not always plausible to pay out of your own pocket and collect the money later. Also, accepting too many forms of payment can be confusing and hard to keep track of.

I typically make people choose between Venmo or Quickpay. They are less stringent on the flow of money and have room for flexibility.

Additionally, getting people to hand over the funds can turn into a man hunt. Trips sound really good until it’s time to pay the organiser. If possible, try to set up payment schedules. Websites like HomeAway and VRBO allow people to pay a portion of the money on the the day of booking and the remaining balance at a later date (depending on your timetable and the house selected)!

In terms of receiving payments from travellers you don’t know, tell your friends that if they have invited a personal friend, brother, cousin, or parent, they are also responsible for ensuring that they pay you in a timely manner.

Speaking of money, please be mindful of everyone’s budget. A consultant from a large firm may make more than the second grade teacher. The great thing about travel planning is that you have options. I usually give people a low end, mid level, and high end choice for housing and activities. Nine times out of ten, we land in the middle.

I also put free and/or cheap activities, lunches or sites in the agenda, utilise Groupon and reach out to vendors directly for group discounting. I found an amazing deal for a spa day in Dubai for $24 (£18/€20) per person, just by simply emailing the company directly and asking if they had any specials that weren’t advertised.

Everyday we lit
Very diverse in their careers (entrepreneurship, marketing for Nike and sales), these men added different flavours of thought and diversity of personalities to the trip. Having people that view things differently help your trip come together from angles you may not even think of.

Everybody Got a Part to Play, Back to Yours

You will get bombarded with questions you have answered in detail, opinions, and negative responses. Unfortunately, these issues are just part of the role of organising the trip.

You don’t have to respond to everything as soon as someone asks. If you took the lead in planning, I understand that you want the trip to be the best trip anyone has ever been in their life.

But heavy is the head that wears the crown. Take a moment, maybe even two, but always take the time to breathe. You don’t have to do everything at once.

But Remember… The Sky is the Limit

In the midst of the stressful elements, the most important thing is to have as much fun leading up to it as possible. You can put as much or as little into your plan as you want to. Enjoy moments leading up to the trip like helping people shop and stalking Instagram for great places to take pictures.

On one occasion, we had a contest where we all threw a few dollars into a pot and the person that created the best trip hashtag won. Remind yourself that all the stress will be worth it. Live your best travel life.

*Ok ladies, now let’s get in formation*
This picture went viral over Instagram and even making its way to CNN World. A lot of us so happened to have black swimsuits on and it was the perfect topping to our 150 person boat.

What are the areas you struggle with when trying to plan a group trip with your friends? Comment below!


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Brittany Bullock is Chicago cool kid residing in Dallas. Brittany is a strategic consultant by day and faux serial traveler and socialite by night, helping people plan trips. You can follow her on Instagram, @thebrittanyb_ to see what she is up to or visit her website,, for more info.


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