How to plan a trip you’ll actually enjoy

If you’re anything like us, the cold and dark days have got you planning your next escape: whether that’s a beach holiday with friends, a cute couples city break, or a trip away with the whole family.

The thought of trip admin (think, sourcing the cheapest flights and the perfect Airbnb) might fill you with excitement. But if instead you feel a creeping dread at the prospect of it all - that overwhelming feeling that, if you don’t do it, *nothing* will get done - you’re not alone. And it might be down to the fact that you’re all too used to planning trips for others to enjoy.

Taking on others’ needs ahead of your own is exhausting and worse, it might mean that you end up going on a trip that’s missing the elements you’re really craving. Maybe it’s because you want to make sure everyone has a great time, or because you just want someone to commit to going on the holiday (and so you take on all the boring bits). It might also be because it’s simply what you’re used to doing in everyday life already.

So, after speaking to our friends at Canopy & Stars, we wanted to pull together this guide on how to prioritise your own needs when it comes to planning a trip, so that we’re all going on holidays we actually enjoy in 2023. We hope you find it useful!

Ask yourself what you want from the holiday.

First things first: irrespective of who you’re going away with, ask yourself one key question: what do *I* want from my next holiday?

If you usually love a city break, but the work stress has you desperate to soak up some sun, make sure you advocate for a destination that hits your warm-weather requirements. Equally, if you know you get bored lounging on a beach all day, make sure the coastal towns you’re looking at have enough sights to keep you entertained during afternoon strolls.

Compromise is pretty much always necessary, but not getting your basic requirements met by a holiday is not.

Make people aware that you don’t *actually* love planning.

Gently reminding your friends, family or partner that you don’t actually *want* to be responsible for planning every aspect of the trip is a great place to start. Whilst it might seem like common sense that spamming the group chat to make sure everyone buys their tickets is not actually how you want to spend your weekend, the chances are they simply don’t realise how stressful you’re finding it. This is especially true if you're known in the group as the “planner” - or if scrolling through dream Airbnb destinations is basically your hobby in winter.

Your trip buddies will be super understanding and want to help out with making decisions (and if they’re not, you probably don’t want to go away with them anyway).

Delegate, delegate, delegate.

This really is key to planning a trip you’ll enjoy.

Unless you’re planning a surprise weekend away (a very tricky task to execute in itself) it’s definitely not on you to plan every aspect of the trip, and doing so just takes away the enjoyment.

If you feel any guilt or like you’re offloading chores onto others (which you shouldn’t feel anyway, but that’s a discussion for another day!),it’s crucial to remember that delegating really can be fun, especially if you play to everyone’s strengths.

If your partner’s a foodie, chances are they’ll love trawling through indie sites to find the best spots to eat. The same goes for your friend who loves nightlife the most. And it’s *especially* important not to be responsible for planning an activity you won’t even be taking part in (think, a day out at the golf course).

And it’s the same for you too - if your one holiday goal is to eat the best ice cream *ever*, make sure you know which spot you want to drag everyone to one day and make it happen.

Remind yourself that nothing is make or break!

When feeling stressed with holiday planning, it can be all too easy to focus on insignificant things (something we’re *definitely* guilty of). But even if something feels like the single most important thing in the *world* at that moment, the trip won’t be ruined if the restaurant you want to go to doesn’t serve the exact octopus dish that your dad loves (trust us).

Taking on too much responsibility for planning the trip means that you inevitably take on far too much of the guilt when something goes wrong. And let’s face it, something probably will go wrong - and that’s okay! We can’t plan for every eventuality, and if the trip is ruined because everyone gets food poisoning, that’s no one’s fault! Everything becomes a memory in its own way.

Don’t put pressure on yourself for it to be the ‘best holiday ever’.

We should never feel the burden of making sure everyone has the best time ever, but that applies to ourselves too. Our problems don’t magically disappear when we go on holiday, but there are often high expectations placed on us to return as a new person or feel entirely reset.

But holidays *are* an incredible opportunity to try out new things, eat some delicious food, swim in the warm sea, read more books, see awesome sights, and spend quality time with loved ones. And that really is enough! All that matters is that you’re getting something that you want from it.