The Realities of Large Group Travel

Keeley Dority , Missouri, USA

Keeley Dority graduated in 2017 with a magazine journalism degree from the University of Missouri. She has been published in local newspapers, magazines and national blogs. She currently works for the Missouri Press Association as a media coordinator and is a freelance writer.

3 April 2018

The curated pictures of a large group of friends at the beach, on a boat, or at some national landmark can seem endearing. It’s easy to look and think, “wow, how careless and fun.” Just like a lot of social media, there is often a behind the scenes reality composed of chaos and bad attitudes. As an experienced group traveler, Keeley has some practical tips for us on how to enjoy group vacations and not let petty arguments get in the way.

How simple is it for everyone in that group of twelve to pose for the shot? How many shots did it take for everyone to agree on one image? After pondering the situation, the truth reveals something more like a nightmare.

Yet, traveling with a large group is possible. There’s a reason people keep doing it. The question is, how do you make it through a long weekend or even double digit days without hating your crew? The key is to prepare like you would for any other trip. You don’t want to go into the event thinking that because there are more people, there is less worry about. It’s usual quite the opposite.

How many tries does it take to get the photo right?

Keeley with friends in Italy


First, it’s important to think about who you’re traveling with. What is your relationship with these people before this adventure? If you’re acquaintances, you can’t expect them to know your habits or expectations for the trip without clear communications. If you’re going with a group of longtime friends, you can’t forget that people change, and if you haven’t vacationed in a few years, it might not be the same. Think about these personality traits before you jump into itinerary planning. Talk through major topics such as sobriety and eating restrictions. You don’t want things to be uncomfortable before they even begin.



After you’ve figured out the structure of your travel group, think about what you’re expecting out of the trip. For example, when I travel with my group of girlfriends, I always map out my own agenda. There will be things you want to do that others don’t.  So, you either should plan for time to explore by yourself, or accept that you might make another trip later. For me, I usually arrive the night before the rest of my group. It gives me time to get settled, eat at a restaurant of my choice or do some shopping. Arriving at the same time as everyone else can be overwhelming. You often hit the ground running without having time to feel comfortable in your environment.

“Don’t feel like you’re being selfish, if you’re spending time and money to travel, you deserve to see and do what you want. You just should do it in a way that’s not going to interfere with the rest of the trip.”

Having this alone time at the beginning can also allow you to be more open during the rest of the vacation. If you already feel satisfied with your time, you won’t be disappointed when your group decides to alter plans, or cancel an activity. You have that reassurance that you didn’t miss out. Don’t feel like you’re being selfish, if you’re spending time and money to travel, you deserve to see and do what you want. You just should do it in a way that’s not going to interfere with the rest of the trip. This can also be reversed, book an extra day at the end of the trip. If you’re having a party-style vacation, you might need a day to relax before heading home.

It’s all about managing your expectations.

Keeley and her friends in Nashville, USA.


No matter how well you know your travel group, do not let the topic of finances be left until the end. The one thing that can truly derail a nice vacation is the awkwardness of unpaid bills. This might come as an end of the night tab that nobody wants to cover. Once again, you must practice preparation and communication. My travel group uses the same money transferring app, and isn’t afraid to request money from an Uber ride or late night delivery order. We also make large financial purchases before the trip.

If you’re planning on doing certain activities, why not book them in advance? Everyone can pay on their own terms and you’re likely going to get a better rate than the day off. Plus, who wants to be the person that had to miss out because it’s day five and the cash flow is low? Keep this in mind when you’re traveling internationally as well. For example, many small, family restaurants in Europe will not split checks. Either take turns with a card, or always have cash. For my group of eight, we found that carrying an array of Euro’s was easier than dealing with international charge cards.

At the end of the day, everyone is going to travel different and that applies to large groups as well. It’s important to remember that traveling with friends and family enhances the experience.  But, the perfect vacation is not going to happen on its own. Really think about the people you choose to travel with. The most important thing isn’t that they have the same priorities or expectations as you, but that there is mutual respect in the group for everyone’s travel styles. Being honest about how you feel only makes your group stronger, and by the end of the trip, those group pictures feel like second nature. Traveling, whether it’s out of town or out of the country, is all about enjoyment, so plan and prepare, but don’t forget to just have fun!

Want new articles before they get published?
Subscribe to our Awesome Newsletter.

Have you seen these?

5 ways technology can influence your travels

Technological advances in recent decades have been incredible. Back in the 90s, when bulky laptops were a prized possession of the privileged, few could have dreamed we’d be carrying multi-function computerised devices around in our pockets today. The arrival of the...

read more

5 tips for road trips in Europe

One of the best things about Europe is that it is all fairly close together – making it perfect for a road trip. With so many countries to explore, hopping in a car (or campervan) will ensure you can see as much of this stunning continent as possible. However, a road...

read more

Skiing in Mzaar Kfardebian Lebanon

Skiing in Lebanon - the unexpected side of the Mediterranean 13 MARCH, 2018 Anastasia Pashkovetskaya Sitting on the coast of the Mediterranean and known more for its complicated past than its charming mountain villages, Lebanon is not most people's choice for a ski...

read more

Pin It on Pinterest

Share This