5 Tips for a Planning a Group Holiday

As I shared in my recent post about celebrating my 25th Birthday in Lisbon, I went on a group holiday with 7 other people. As promised, I will be sharing with you some tips for planning a successful and enjoyable group trip with friends.

Now, I have specifically mentioned “with friends” because I feel like I’m not quite there yet when it comes to traveling with complete strangers. I am using the term “friend” quite loosely here but for the purpose of this post, a friend is someone with whom you know at least one other person in common and/or have met at least twice. Is that fair? I think it is. We can get into a conversation on how I feel about traveling with complete strangers in the comment section, but for now; here are my top 5 tips for a successful and enjoyable group trip.

Ready to take on the beach

1. Be Honest

Holidays can be very revealing of a person’s character and temperament. There is something about being away from your daily routine that brings out something else in all of us. As a result, it is always useful to be totally upfront in the beginning while planning the trip. Things like, are you a beach bum or a hiker? Do you prefer self catered or catered accommodation? etc. There are so many things that I can list but you get the gist. In my opinion you should never be afraid to state your preferences before going on a trip, in fact it will help inform you and others whether you are all a good fit and will enjoy each other’s company on the trip.

2. Set a Budget

As a rule of thumb, I would always be an advocate for setting a collective budget for the major things like flights/transport and accommodation. These are the basic necessities for any trip and should be agreeable to all. Especially as young people who are looking to stretch every penny, it is important for everyone to feel financially comfortable taking the trip.

While on the topic of finance, I found it important for bills to be settled as soon as possible while on the trip. Inevitably someone will pay for something on behalf of the group, and monies will be owed. Don’t wait till you’ve all gone your separate ways to start doing mathematics about who owes what, it can get VERY AWKWARD. If possible, keep a running tab of group payments and try to settle at the end of each day.

Selfies at Belem Tower

3. Be Flexible

Leading nicely on from tip 2 asking you to set a budget, it is also important to be flexible, as our faces differ so do our preferences and resources. This is particularly important if the group is from different stages in life and perhaps different tax brackets (not that it should matter), but try to make sure nobody is priced out or left out. Select options that meet most of the needs of the traveling party and try to ensure that the decisions not made by only one person.

Also make time to relax! Holidays can feel so short and you want to see all the sights, eat all the food and do all the things; but it’s no use coming back from a holiday tired. I personally go on holiday to relax, so make time to relax and bond as friends. We played a HILARIOUS game of articulate in Lisbon and I wonder if “Shaken Not Stirred” describing a movie character brings the same thoughts to everyone (let me know in the comments, VINDICATE ME!)

Chilling out 

4. It’s Okay to Split Up

Assuming everyone in the group is an adult, it is perfectly fine for the group to split up once in a while to enjoy activities of their choosing. Allow yourselves to be individuals even though you have come to a different city/country together, it is perfectly fine to want to experience things alone or without the whole group. This is particularly pertinent if there are couples in the group. I would however stress that if you are always going off on your own it begs the question, why did you come with the group?

Six ladies and a shadow

5. Share Your Memories

Holidays are meant to be fun, even more so when you do it with friends. The laughs, the jokes and all the banter. You want to capture those memories and share so that you have something to look back on. Take pictures, videos and share with each other. I love scrolling through my holiday pictures when I return to my routine, it brings me so much joy. Especially with the stage of life I am in now, friends move across town, across seas and some you don’t get to see again for years. So when you do get together, find ways to capture the memories so that you have something to look back on.

My favourite method of sharing pictures is iCloud Photosharing. This way everyone can see the pictures as well as add pictures (I believe). Other options are things like google drive, dropbox, etc. I’m sure there are many more, let us know what you use in the comment section.
Lastly, make sure you do it all again. Take time to travel with your friends it’s so worth it!

Have you been on a group trip before? Want to go on one? Let’s talk in the comments.

Until Next Time,



3 Comments Add yours

  1. Ore says:

    TAKE ME BACK!! Best group holiday, EVER.


  2. I think I am a tad scarred from grouo traveling tbvh.
    I might do it again, but not anytime soon.
    There was drama from the very first day and frankly, nah. Can’t deal with the conflicting wants and interests.

    But nice one that you could and maybe I’ll try again.



  3. It’s amazing that you could make a group trip that large happen
    I LOL’d at “monies will be owed” because I say that too and it is so true.

    Thanks for the tips, everything you said is honest and necessary.

    I love all your photos, I just might include Lisbon to my travel plans this year 🙂


Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s