7 Tips to Plan a Holiday When You Absolutely Hate Planning

AD – This is a collaborative post. All thoughts and opinions are my own.

I love to plan most things in my life. I’m very reliable, good at managing my time and organising plans with friends. But when it comes to planning holidays, I am notoriously terrible.

I just never take the time to actually sit down and plan out where I’ll stay and what I’ll do. The whole thing gives me anxiety, so I don’t do it. But that doesn’t have to be the case.

In this blog post, I’ve put together a guide to planning a holiday when you absolutely hate planning. How can you beat the anxiety and get out to see the world? Let’s take a look.

7 tips to plan a holiday when you hate planning

If, like me, you absolutely hate planning holidays, this blog post is for you! I’ve put together 5 helpful tips to reduce stress and actually enjoying planning your next trip.

1. Dedicate time to planning

If you struggle to plan, it could be because you just don’t give yourself time to do it. Dedicate time to plan out your trip and think through everything you’ll need.

Split your planning into little chunks, such as booking a hotel, planning your itinerary and sorting out flights. This will help you feel less overwhelmed by the task of organising your trip.

Looking for more? Check out my guide to save money on travel in 2025.

2. Make it as easy as possible for yourself

If you don’t like to plan holidays, make it as easy as possible to organise your travels. Book a holiday with someone who loves to plan or look for simple, stress-free holiday destinations.

You could browse all-inclusive holidays or go somewhere nearby for a staycation. This will help to reduce anxiety and planning time.

3. Give yourself a deadline

Me and my boyfriend always put off booking holidays. We come up with excuses like not wanting to spend money or not knowing where we want to go.

So, we give ourselves a deadline. This pushes us to sit down and actually book a trip, rather than constantly putting it off.

It doesn’t always work, but it’s a good way to start thinking about what you want to do and when. Once you’ve met your deadline, you can just sit back and relax.

4. Tap into what you need

Before you plan your holiday, think about exactly what you need. Do you want to relax? What is your budget? Do you want to visit a new culture? Use your answers as a starting point.

If you feel anxious about planning a holiday, why is that? Take time to think about your triggers to reduce anxiety and really tap into what you can do.

For example, if it’s the planning itself, do it with someone else. If it’s spending money, choose more affordable options. If it’s the idea of flying, travel within the UK or your home country.

5. Use an online tool

Digital tools are there to help us! Use a tool like ChatGPT to help you plan out your holiday this year. You could ask it to plan a basic itinerary for you, or look into the best hotels in the area.

You can even use a holiday planning tool to help you plan your trip, organise your hotel or flight reservations, and get personalised support.

As always, it’s important to check over any information you receive from AI. However, if you just want to bounce ideas or sort out your thoughts, AI can be a good tool.

6. Ask for help

If you hate planning trips abroad, don’t be afraid to ask for help. Speak to someone who loves to travel. They can give you handy tips and even hotel recommendations for your holiday.

If you’re heading out on a big holiday, such as your honeymoon, speak to a travel agent. It might cost a little more, but they can plan everything for you, including your flights and hotel.

7. Be flexible

I think one of the reasons I find it hard to plan a holiday is that I’m not the most flexible person. Holidays are full of problems, whether it’s a tourist attraction being closed or a flight being cancelled. This can bring up a lot of anxiety.

If you’re like me, take time to accept that you may need to be flexible. You may not be able to tick off everything you want to do. You may have to change flights or come up with a new itinerary on the fly – and that’s okay.

Plan out a basic idea of what you want to do and when, but don’t be afraid to add a bit of flexibility to your plans, too. Let’s see if I can take my own advice this year!

Do you have any travel planning tips? What is your best tip for anxious travellers? How do you plan a holiday when you hate planning?

Let me know all your thoughts in the comments below 🙂

Happy reading x