The Top Ten Challenges of Travelling as a Group

There is no doubt about the fact that travelling as a group can be a challenge. From having to rely on someone else to bring the tickets to managing communication between an excited clamour of holidaymakers, all sorts of issues come to light when we have to organise a large team.


But what are the biggest challenges faced when you book a group holiday. We spoke to a focus group of youngsters aged between 21 – 29 and found out the biggest hurdles to their group tripping.


Here’s our rundown of the top ten:

10. Ending up with ‘organised fun’ rather than spontaneity

Rounding off our list at number 10 is a challenge that probably doesn’t worry everybody but can have a huge effect on some people’s enjoyment of a trip.


As 28 year old Emily said ‘if you are trying too hard to organise a big group, the whole trip can end up a little too structured. Maybe not for everyone but for me, I prefer the freedom to do as I feel when I’m on a break. Too many other people can restrict that freedom.’


  1. Organising different add-ons to the holiday

Connecting transport, extra hotel beds, hire cars, insurance, extra luggage, equipment hire …. the add-ons list goes on and on. And everyone wants a sliiiightly different selection. Managing those logistics as well as the budget and payment schedule for every member of the group is certainly up there with the big guns when it comes to group holiday challenges.


  1. Different preferences for activities/accommodation/destination etc

People have different preferences. The more people you bring together, the greater the variety of difference. The greater the variety of difference, the greater the challenge to manage those differences and find a suitable compromise.


  1. People joining at different times

It’s very rare that a group is fully formed at the stage at which you decide that a group holiday is maybe something you want to do.


As 22 year old Tim says ‘there are always people who say they’re keen and then drop out because of money or timing issues. You can usually find a replacement but the final group has always gone through a few changes before you get there.’


Managing dropouts and the incorporation of newbies is always a challenge. Often you have to fast track a payment or reshuffle room allocation or seating arrangements. Extra work and hassle means that people joining at different times is definitely one of our top ten challenges.


  1. Falling out with others on the trip

It’s not just kids who squabble. Everyone can get irritated and, in the close knit community of a group holiday where hopes are high and expectations even higher, those irritances can be exacerbated and lead to some of the worst squabbles imaginable. And managing the fallout of an argument with someone you are spending your holiday with is a real challenge. It’s in at number 4.


  1. Getting everyone to agree on a date.

As we reported in our ‘focus on snowsports’ blog a few weeks ago, 45 year old Bill, told us that  the biggest challenge of organising a group trip for him and his family was finding a date that everyone could make.

‘Dates and timing are always the biggest hurdle with a group this size. There are so many other commitments to consider which is why you need to do the organising so far in advance.’

And this is a sentiment reflected in the views of the rest of our focus group. With busy work schedules, conflicting timetables and varying priorities, finding a date that everyone can do is easily one of the biggest challenges of organising a group trip. It’s in at number ….

  1. Organising payment

Paying for a group usually falls to one member who is then responsible for collecting everyone’s individual payments to make sure that they’re not then out of pocket. Here’s how Kelly, a 25 year old masters student put it:


‘One person having to make a payment for everyone can be challenging, either because they have to pay with their own money and wait for others to pay them back or if they’re waiting for everyone to pay them before they make the booking, prices might go up …. it’s just a bit frustrating…’

  1. Getting everyone to where they need to be

The difficulty of managing logistics is always proportionate to the size of the group you’re trying to manage. The more people there are, the more likely it is that someone might forget a passport or travel insurance or just their common sense.


As 25 year old Amy says, ‘most people feel safer when they’re travelling in a group and, especially if they haven’t been responsible for organising, they’re far more relaxed about things than if they had the responsibility for sorting them out’. It’s when the onus is on someone else to organise things that people pay less attention to travel information or times of flights or connections etc.


Getting important information across to all members of the group and making sure everything goes to plan is, therefore one of the biggest challenges faced by a group leader.

  1. Different budgets

Often a holiday or trip away from home is often seen as an escape from normality, a much needed break and something to make the most of. But when ‘making the most’ of a trip is constrained by the available budget and where members of the group have different budgets, that’s when a challenge arises. Those folks we spoke to have voted this in as number 2 on the list of group holiday challenges…

  1. Communicating with the group

Taking the top spot is this old chestnut. How do you speak to multiple people at once!? We’re getting there with group threads and chat apps but issues around important information getting lost amongst mindless nattering and the collation of all the discussions that happen in different applications are still pretty prevalent.

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