It’s almost time to start thinking about going on holiday. Unless you’re me, in which case it’s always time to be thinking about going on holiday. More specifically I want to talk about how to plan a group holiday.

Our last couple of big overseas holidays have been group affairs. The first had 8 people for the whole trip. The next one had varying numbers as people came and went for different sections of the journey. In the end we had 9 at its peak.

Lots of people I spoke to thought that it was a daunting task. But to be honest, once you have more than 5 people, the principles remain the same. So, let’s have a look at how to structure and bring together a group holiday.

Define Your Holiday Goals

At the start you need to know what this holiday is going to be about. You also need to understand that people have different goals that they want from a holiday.

For example, I’m a classic Clark. W. Griswald (National Lampoons Vacation) character. I like to set myself a plan to see as much as possible while on holiday. I like to make sure I get full value out of it.

Other folks I know prefer a slower pace. Sleep in till 10 am, have a swim, a bit of lunch, then off to see an attraction in the afternoon and back to the pool.

There are no right or wrong answers here. Both are valid ways to enjoy a holiday for those people. The trick of course is when you have two groups with opposing opinions. How to get it all to mesh.

Personally, I like to have a mix during the holiday. Spend some time with relatives, sometime racing around different attractions, then finish with some laid-back beach time.

Without the beach time at the end, you can easily get home and feel like you need a holiday.

I normally start the process with a backyard barbeque. Give the folks an idea of what I’m thinking, get some input, and see who’s on board. Obviously it’s early days and I haven’t mentioned prices yet. But just test the waters to see if there’s a willingness to come along.

Put Together a Timeline

When I plan a big overseas holiday for a group, I start at least a year out. Quite often I’m a bit further out than that as well, to allow everyone to accrue enough leave time.

If we have school aged kids with us, then obviously we take full advantage of school holidays. But I also keep an eye out for seasonal events that are going on in the region that we may be able to catch.

Once I have a basic season sorted out then I fill in the gaps. So, for us planning a summer holiday in Europe, I generally look at 6 weeks starting in the last week of June.

This allows us to get plenty of warm weather and long days but avoids some of the truly hectic weeks in August. It helps that the West Australian school holidays generally start at the end of June as well.

I then make up block calendar from about a week before and a week after the holiday. It’s here that I can start looking at where each location will fit and how we can get around.

You can get a sense of how many days you will spend in each place, and how those line up with weekends, sailing times, bus and train timetables etc.

Use Bases

For bigger group holidays I try to look for bases. That is, find somewhere that you can spend 4-6 days minimum. You can then take day trips from here each day in the region. Logistically, this is much easier than packing the group up every couple of days.

It’s much easier to give yourself 5 or 6 bases, as there’s less accommodation to book as well. It’s also less opportunity for things to be left back in the last location.

This method is really important if you try to plan holidays in the Greek islands for example. Although there are regular ferries, they don’t go from every port, every day. So, check your timetable and shuffle the blocks around till they all fit neatly.

Make Sure All Members Are On Board

Okay, so this is just another excuse for a barbeque. Not that I really need an excuse.

Layout the basic timeline and make sure everyone is happy. There will inevitably be some people who want more time in one place and less in another. That’s normal. Look for a compromise that works for everyone.

Know Your Destination

Knowing what you want to see and do at each location is also important with the last two steps. We’re making sure that our goals are similar, but also making sure that we have enough time at each place to get done what we need to.

You need to make sure that everyone understands that you can’t do everything in a few days. Some things will get missed. The world is a big place and there’s lots to see and do.

The group needs to accept that they have to choose a few things that are really important to them. If they get to some of the other attractions, then that’s a bonus.

Create a Budget

This is where giving yourself enough time pays off. For example. It is currently December 2021, and I am looking to plan a holiday for June 2023. That sounds a lot, but it’s only 18 months away. Most of us in Australia get 4 weeks holiday per year, so we need 18 months to accrue 6 weeks leave.

But importantly, I can now check prices for accommodation for June/July 2022 and pencil those in. There may be some fluctuations in the lead up, but it shouldn’t be too far out. At least this way you are checking the prices at the right time of year, as prices can vary a lot based on the high and low tourist periods.

The same goes with flights, car hire and other transport options. This way I can put together a ball park figure, so there are less chances of surprise down the track.

How Much?

At this stage I tend to look for accommodation around $50AU($34US) per person per night. Obviously, we don’t stay at the Ritz for that money, but we do get basic hotels, motels and hostels. Generally, we get breakfast included, or at least the ability to make our own breakfast.

This kind of accommodation suits our style, as we tend to be up early and out exploring all day. We really just need a clean comfortable bed and a bathroom.

Spending money can vary a lot depending on your tastes. At the moment, we budget $100AU($78US) per person per day. Some days at the beach we hardly spend at all, whilst a day at Disneyland will triple that figure.

In the end, for us it averages out about right. Having breakfast included with your accommodation helps a lot here as well.

While these numbers are pretty close for us, we always carry a credit card as well for back up. This helps for unexpected costs, or the odd impulse buy.

Start the Booking Process

Depending on the location, I will often start the booking process 12 months out. Jersey, in the Channel Islands for example, can book out very quickly for the summer. If I find somewhere I like in the previous year’s search, then I will get in early.

Good quality, reasonably priced accommodation will always sell out first. If you leave it too late, then you pay more for a place that’s not quite as close to the action.

Flights can be tricky to sort. As a rule, flights become available to book 300 days before scheduled departure. But when do they go on sale? That’s the big question.

If you are planning to use Frequent flyer points, then 300 days is when you need to book. Most airlines only have a few seats available for using these points, and they get snapped up quickly.

There are generally a couple of sale periods each year, so get to know your local travel agent and try to get some inside information on how it works in your area.

The two main links I use are Booking.com and Skyscanner.com.

Find Transportation for Your Group

Transport can be tricky. If you’ve read my post about how to travel Europe, then you know that I use a combination of planes, trains and cars to get around.

It will also depend on your group. Do you have several people in the group who are confident drivers? If so, then a few small hire cars could give you a lot of flexibility. However, you will miss out on some of the banter.

By using a larger people mover, you get a great group atmosphere, but it becomes hard when two groups want to go in separate directions. You need to discuss this with your people.

Cars are definitely the hardest option to decide on. Planes, trains and buses are simply a matter selecting the number of passengers and away you go.

Use planes and trains to cover large distances quickly and comfortably, then resort to cars or local public transport at your destination.

Check out my post, “How to travel around Europe“.

Bonding Over Food

Get the group together regularly in the lead up to the holiday. I call them team meetings and they are usually at our house around the barbeque.

We do this about once a month. During the meeting I bring everyone up to speed on what has been booked, how much is owed, and what is still to be booked.

This way, everyone can keep track of their expenses and know what to expect.

It also a great opportunity for everyone to chat about the places we’re going and get the excitement up.

Putting It All Together

At the start of the booking process I buy enough of those cheap display folders for every member of the party.

As I book each item, I print out the booking and put it in the folder. I try to keep them in order so that it follows a logical progression through the holiday.

Travel insurance is always the first thing in the folder, followed by copies of the passports, flights and so on.

I make sure that I have a copy of everyone’s travel insurance. Just in case they were in a bad accident, at least I can get the process started for them.

Some of my group rely on the insurance that they get from their credit card. That’s fine. I just make sure that they get all relevant policy details and contact numbers to me before we fly.

Each member gets to hold onto their folder during the planning process, and they bring it to each team meeting so that I can add in the new bookings and information.

You will need to check everyone’s passport personally. I know it sounds crazy, but sometimes people are convinced that they have a couple of years left on it, when in fact, it’s about to expire. Check it yourself.

Buy The T-Shirts

Yep. I get team shirts made up for each family holiday. Just one shirt each. A nice dressy polo shirt with our emblem embroidered on it. In our case we call these our “Gone Batty” shirts. Our family crest has a black bat on it, and we’re possibly a bit mad, so this works for us.

We have a picture of Batty Coda from the 90’s movie Fern Gully on it, with the year of the trip.

It might sound a bit off, but we love it. We use this shirt as our travel shirt. So, when we’re going on planes and trains for example.

It makes it much easier to keep an eye on the team, and the local taxi drivers don’t hassle us, as they think we’re part of a tour group.

Conclusion

And that’s it, you’re ready to go. Give yourself enough time and work through it step by step.

A group holiday with family and friends can be a great bonding experience, and something that you will talk about, and laugh about for years to come.

Give it a try. Jump in and build some memories.

If you found this useful, then try these posts as well.

16 Tips to stay healthy while traveling.

How to travel the Greek Islands.

Budget family travel for beginners.

Stress-free traveling with kids.

Cheers and happy travels.