How To Plan A Holiday You’ll Really Enjoy [9 Simple Steps]


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If you don’t plan your holiday properly, you could end up feeling very stressed, lose money, or miss out on things. Learn the 9 easy steps for how to plan a holiday today to avoid disappointment – and make the most of everything.

How To Plan A Holiday You'll Love [9 Simple Steps]

Ideally, going on holiday should be a fun experience that allows you to reset and recharge from the stressors of everyday life.

However, if you don’t plan effectively, you may quickly find yourself wanting a holiday after you get back, to recover from whatever happened.

And that’s not the aim at all!

So – where do you start when booking a holiday?, and what needs to be considered when it comes to travel planning?

It can be overwhelming to say the least, and there’s a lot of moving parts to consider.

But don’t worry, because here are some fantastic (and easy!) tips to help you plan your holiday for maximum enjoyment and minimal stress.

Do these things and you’ll be sipping a glass of (*insert your favourite holiday drink*) with your feet up on your perfect trip before you know it.

So, without further ado, let’s get started…

9 Things Needed For Stress Free Holiday Planning

#1 – Know The Rough Holiday Idea

By this I mean that every holiday usually starts with an idea of some sort:

  • Family holiday in the school summer holiday
  • A camping holiday with another family
  • Taking the in-laws away for a mid-week break in school holidays
  • Weekend away with the girls (or any group holiday)
  • City break with your partner

These are still all very open ended, with a LOT of decisions to make as your plan get’s more defined, but it’s a starting point that makes it easier to work everything else out.

I liken this to being at the top of a funnel. A funnel is wide at the top and tapers in to a very narrow end. Your plans right now are wide and vague (at the top of the funnel). As you work your way through the rest of the steps detailed below, you’ll slowing define things and get to the bottom of the funnel where your well planned holiday awaits!

#2 – Know Who’s Coming On Holiday

It may be obvious, but double check who you think will be coming with you.

This may include partner, children, parents, extended family, friends etc… – you just need to ensure everyone’s on the same page as to who is coming.

The reason this is the second step is because there’s nothing worse than getting further down the planning process only to find that the camping week with another family has now turned into camping with 3 families.

Not because that’s a bad thing in of itself, but because you may now not be able to accommodate everyone in the original site, and you now have to start again from scratch.

If that sort of extra stress and work load can be avoided. I’m in!

#3 – Know When You’re Going

When you know who’s coming, and have a rough idea of the holiday type you’re going on – then it’s time to plan exactly WHEN you’re going.

Yes, you will already know you want a week/weekend/fortnight etc… away – but now you need to know when works for everyone involved.

First thing first is to get everyones availability.

Think about:

  • Annual leave dates that can be taken from work
  • School holiday dates (sometime you can be really lucky and there’s an inset day attached that you can use to your advantage because going on a Thursday night instead of a Friday means you get an extra night away – or it’s cheaper to go Thursday to Thursday rather than Friday to Friday. These days can be missed all too easily – I’ve done it myself and got annoyed for doing so, so don’t make the same mistake I did!)
  • Will any time be needed before or after the holiday as well? (if you’re travelling far, then jet lag may mean you have to take a day off when you get back, to re-calibrate!, or you may have to fly back very late at night with the kids and so booking the holiday to come back the day before school starts again could be a disaster for everyone…).

When you have all this information you can more easily see what date(s) works for everyone.

IMPORTANT – A great tip that should definitely be taken into consideration is whether any extra people are needed in order for your holiday to be taken.

Are there people who aren’t going in your holiday that are needed for you to be able to go?

For instance – grandparents looking after the kids while you go away, a neighbour can feed the cat but is away for some of the holidays as well so you need to plan around them as well, or your favourite place for your dog to stay always has limited availability so you need to be sure they’ll get in.

If any of these aren’t possible, then that puts your holiday at just as much risk as if anyone going ON the holiday can’t make those dates.

#4 – Work Out Your Budget

A holiday is supposed to be a relaxing time, so the last thing you want to do is create financial stress for yourself by spending money you don’t have. 

Before you can start to really hone in on booking anything you should sit down with whoever will be paying any part of the holiday bill, and determine what your budget for the holiday will be.

Remember – you don’t have to have a hugely expensive holiday to make it fantastic.

That’s not the aim. The aim is to have a great time – whatever you end up doing…

  • Travel – if you’re going abroad, will you fly or take a ferry? If staying closer to home, will you drive, car-share, or get the train? Is car hire a good idea at any stage? What level of travel will you all want to take (economy vs. premium, for example).
  • Accommodation – Hotel, cottage, apartment, lodge, camping, Glamping etc…
  • Food – Self catered with lots of cooking yourself, eating out most of the time, half board, all inclusive etc…
  • Activities – Will anyone want to do something specific that costs anything? Maybe there’s a water park for the kids that needs to be factored in for a day or two, or your friends may be wanting to do a wine tasting session one afternoon – etc…
  • Anything you need to buy before you go (passport renewal, insurance, suncream and toiletries, clothes, specific kit for activities you’re doing while away…)

It’s so easy to forget something if you don’t plan for it up front – for instance – a taxi that’s needed to the airport should be budgeted for, not just the flight itself.

Also – it’s a good way to set everyones expectations for the type of holiday you’ll be looking at (especially important if you’re going away with people you haven’t before).

#5 – Choose Your Holiday Destination

Based on your budget, ideal preferences, and available dates, you can now go ahead and decide on the chosen destination you’d like to travel to.

When picking a destination, you should keep in mind things like the following:

  • Is the weather going to be right there for the time you’re available? You don’t want to go somewhere that’s too hot or not hot enough because you didn’t check beforehand.
  • Are there any areas that anyone doesn’t want to go to? Either through safety fears, or because they’ve already been there etc…
  • Is there anything going on in a destination that you either would love to see, or want to avoid? Maybe there’s a huge festival in the town over one weekend that you know means the prices are higher than usual, or there might be an event that you’d really like to line up your visit with so you get to see it.

When it comes to balancing destination and budget – you can often create a fantastic travel plan with varying levels of cost in the same place.

So, if you’ve got a specific destination in mind but think you may not have the budget for it, it’s worth seeing if there are any deals to be had, or if there’s a way you can go and do the holiday slightly differently.

It’s all about weighing up which parts are the most important to you as to what you can compromise on if needs must.

Check Your Documentation and ID

I can’t stress enough how important it is to ensure that all your travel documentation is in order before you travel – so if you have picked a location that needs ANY paperwork at all, you need to be aware of that and sort it asap.

  • Check your passport is in date and has the correct time remaining to be allowed to use
  • Do you need a Visa to enter any country? (funny story: I went to Florida for work and straight after was meeting my family in Paris for our family summer holidays. My flights took me via Canada, and although I had my American Visa all sorted for the work trip, I had no idea that I also needed a Canadian Visa to even be allowed to be in the airport for my connecting flight to France! Lesson very much learned – and it was all OK in the end as I managed to apply and get the Visa while waiting for the flight – phew!)


If you’re travelling somewhere that requires proof of vaccination status, you’ll need to either check you’ve got your vaccination records or get yourself vaccinated.

Ideally, you should check all time frames that your destination’s needs call for – before you book your holiday.

You don’t want to book and THEN realise that you won’t be getting something in time…

Handbag with holiday items in it including passport and sunglasses

#6 – Book The Big Stuff ASAP

Now it’s time to bring it all together and look to book the big parts of the holiday.

Any travel and accommodation should be first – because you won’t be going away if either of these aren’t booked!

Check out any deals that there might be available for the places and times you’re looking at (if you’ve got a couple of places in mind then price and availability will be the main deciders).

Think about booking through a travel agent as they can often find great deals or a package holiday that include things you may not have been able to get.

They will also have some great travel advice for the area you’re heading to – so you can find out some of the inside scoop!

And always look with an open mind because that’s usually when you come across some brilliant places to stay!

TIP – I highly recommend getting travel insurance. Unforeseen problems like cancelled flights, unexpected illness, or lost luggage can lead to surprise expenses. If you have insurance, you can relax knowing that even if something goes wrong, you won’t be completely out of pocket.

TIP – Once you have all of your travel documents such as booking confirmations and details of any accommodation, it’s a good idea to take photocopies and give them to someone you trust and keep in contact with, like a close friend or family member. This way, someone always knows where you are and can contact you if necessary.

#7 – Create An Itinerary

So – you’ve got the big stuff booked – Yay! You’re going away.

Now – what will you do while you’re away?

Again this may well depend on your budget, what’s in the area you’ve picked etc…. but now is the time to give it some thought.

I recommend grabbing a paper and pen and marking out a grid (calendar style) of the days of your holidays. If you need to – you can break each day up into sections (morning, afternoon, evening – for example).

Then get another sheet of paper and brainstorm everything you want to do while you’re away – things like:

  • Visit / Day trip
  • Walks
  • Kids activities
  • # times you may want to eat out
  • Going to the beach / swimming pool etc…
  • Shopping in local area
  • Relaxing

When you have both the grid AND the list of things to do – you can start to work out what goes where.

Doing it like this is great for a LOT of reasons:

  • You know when you need to book anything, so you can do this up front to save possible disappointment from last minute decisions.
  • Everyone can see up front the holiday that’s awaiting them – so expectations match reality.
  • You can research great places to eat before you go if you know you’ll be eating out. You can even book early to make sure you get in.
  • You can work out transport to and from places you want to visit – as this needs to be booked as well (maybe car hire is a good idea when you see how many places you’re going to be going, for example).

You’ll know pretty quickly if there’s an issue if you plan things up front, because you can walk through your holiday as you plan it out, and that will show up anything that could go wrong before it actually does…

For example – you realise you’re going to be rushing around too much trying to fit everything in, and that won’t work because you want to relax as well for some parts of the time away.

Or what if you’ve planned to go somewhere on a specific day but have found out that it’s closed that day for some reason. Better to know now and shuffle your plans around than go and not be able to get in.

Summer Quote - Summer Is A State Of Mind

#9 – Know What You Need To Take

Now that everything else is arranged, it’s time to think about what you’re going to need to take with you.


The best way to approach this process is to grab a paper and pen and write down everything you can think of that you may need:

  • Medications – these are vital that you take with you what you need so is always #1 on the list
  • Clothes suitable for climate and the activities you’ll be doing while away
  • Toiletries and Beauty products
  • Entertainment (books, magazines, films etc…)
  • Something to carry everything in (suitcase, bag, car boot etc…)

Alongside all your personal packing, there may well be things that you need to take, but that can be shared out between those who are going with you.

Maybe you’ll be self catering with another family and so need to take food and cleaning items – you can divide things up so that you don’t end up bringing double of things – as that’s a waste of time, energy, AND money!

Once you’ve got your packing list, you’re all planned and ready for packing nearer the actual holiday.

All that’s left now is to start to get excited for the adventures that await!

Related: 35 Crucial Tasks To Do Before You Go – Pre Holiday Checklist

How To Plan A Holiday You'll Love [9 Simple Steps]

Going on holiday should never be a source of stress, so before you go, it’s important to spend time planning to the best of your ability.

Once you’ve researched, budgeted, and chosen a destination, you’ll then book travel and accommodation and get all the necessary documents to go away.

All that then leaves is working out how you’ll be spending your time away and deciding what you’ll need to take with you.

If you follow all of this advice, you should be able to enjoy a lovely, relaxing time on the perfect holiday for you. After all – you planned it that way, right!

And when you’ve planned the perfect getaway, why not make your future self happy by setting up everything to be easier when you get back as well?

This article was written by Chrissy

Hi - I'm Chrissy... Having run my own business for 12 years as a Professional Organiser and Interior Designer, I know what works (and what doesn't!) when it comes to setting up a home that works both functionally and aesthetically. Now you can mostly find me in a coffee shop or at home, working full time on (which I setup back in 2011) sharing all my tips and ideas. My mission is to help you create a home that you love to live in every day...


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