Squad deep: How to do group getaways

The reality of group holidays

Its almost time for Dezemba Boss and here come the conversations about going away with friends (its a little late to start thinking about this now but anyways), so allow me to share some of the little knowledge I have about this topic. One of the toughest things about planning a getaway with friends is finding people who share your vision. Without pointing out the obvious:

If you want to go in squad deep you need a winning squad!

Here is a reality check you need to face sooner or later – not all your friends will make good travel buddies. So basically, some people must just be left behind. This is not Friends Like These, if you saying the wrong things we are leaving you in your red chair. But how do you spot the red chair guy? Im so glad you asked…

  • The red chair always has an issue with the price but is not very helpful in finding anything cheaper. (It goes something like “no guys, my uncle’s brothers whoever has a place we can stay by blah blah”) – forget this person sorry.
  • They suddenly have all these relatives that require attention a couple of weeks/days before you need to go
  • Red chairs lead from the front in the beginning but as the plans go on they become a silent partner (“???”) 
  • This person doesn’t do trips outside of you either (so…nope its not personal – they just not the getaway type)

Not everyone is a red chair though, most people actually like the idea of going away but they may be low on cash or not the planning type. In such cases, you can work around it and make a plan for everyone to go – I mean that is what friends are for! Truth be told group holidays are some of the best ones, the memories last a lifetime.

However, here are a few tips on how to select your getaway squad:


  1. Don’t overlook your day 1s

My day 1 (Pointe Aux Piments, 2013)

I have sisters I would go to the moon with. Before anyone else – they are truly my day 1 squad. These people were there when visiting gogo was a holiday so doing a fancy trip with them now is all the more special. Take my advice, don’t overlook your family when planning a group trip.

This squad includes cousins and family friends (the ones your parents know). Here’s why this group is key: there are people back at home who care about the collective going away. If brokeness happens to you on holiday, or you get deported, thrown behind bars or accidently lose a member (which could very well happen to my cousins and I), the team at home will make a plan because they care about you all. Trust me, there’s nothing like a desperate situation to show you who your real friends are!

2. Good strangers make for good holidays

Good strangers make good holidays (Tofo, 2015)

Wooah! Don’t get me wrong, I don’t mean any random people (although this is pretty much what a Contiki is). I mean it in a ‘bring-a-friend-we-dont-know’ way. Everyone knows at least one other person. This works because its easier to convince one person to go with you than trying to take a whole group of your friends.

For example, Thandi invites Sindi, Sindi invites Lebo and Lebo brings Thato along and already you have a squad of 4… any squad bigger than 4 leaving at the same time is actually a miracle!


3. Don’t invite your friends with children (..first)

Friends with children know how to find a good deal and comfort is important to them, they are most likely to book cosy accomodation. Its not about you though (lol) they want a break without breaking the bank or their backs. They care about getting back to their kid in one piece. Secondly, they are not going to any remote places where they cannot call or Facetime their child. No wifi zones just won’t cut it with these friends.

Now that I have sugar coated it for you, welcome to the sad reality that your friend with a child will [probably] bail on you.

A child is an excuse that you cant get upset at unfortunately. In most cases, there is nothing wrong with your friend’s child but every parent has used their child as an excuse to bail even if they won’t admit it. *Disclaimer: this mostly applies to moms & please note that none of my friends were harmed in the making of this post… I hope.

4. Book first, recruit second 

birthday getaways
Birthday squad (Durban, 2016)

I did this for my birthday this year and it worked out perfectly but you must do this way in advance. Services like booking.com offer free cancellation if you don’t manage to get a squad together in time.

It is easier to find people who are willing to go if they don’t have to sit through the booking admin and the changing prices. Once the place is booked, you will know exactly how much money people need to contribute to the trip. If the red chair starts fumbling, you see it right here! This also means that you are not leaving your planning until the last minute when everything is fully booked.

5. Limit the squad

Two is a crowd... you can't sip with us
You can’t sip with us (Istanbul, 2015)

Last year, Katli and I went to Istanbul together – the easiest trip I’ve ever taken. She knew where she wanted to stay, I knew what I wanted to see and that was that.

Having less people go is less admin and you don’t have to deal with too many opinions nor shut down too many far-fetched suggestions. So the chances of you going are more likely.

If you can get the right squad together in time, these trips usually work out wonderfully! In fact, one of my all time favourite holidays was in Tofo Mozambique – I was the “friend-we-don’t-know.” We managed a whopping 14 or 15 people and it was a highlight of note! Good holidays are a foundation for good friendships so dont stress so much that you dont know who you going with and just go!

Good luck with planning your next holiday and don’t forget to invite me – good strangers make for good travel buddies… sometimes… Creep…lol


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