The Ultimate Practical Travel Planning Guide: How to Plan a Trip?

Planning a vacation can be both the most exhilarating and the most daunting aspect of travelling. Sure, making a Pinterest board full of beautiful images is enjoyable, but when you start attempting to sort out the actual mechanics, you realise… oh god, this is SO MUCH WORK. Panic attacks ensue. Wow, I just described our wedding planning process as well. Is there anybody else?

However, preparing a vacation does not have to be a continual source of worry and stress! I’ve honed my vacation planning technique over the years and have it down to a science.

Maybe not a science, but more of a basic step-by-step blueprint. Breaking down each phase of travel preparation helps me cut through the complexity and approach things in a realistic, down-to-earth manner. It also makes me feel like the most organised person on the world, which is really beneficial to my ego.

At the conclusion of my planning process, I have a huge ol’ paper with all of the information I need for my trip, including where I’m staying and how to get there, as well as what to eat. I bring that paper with me and refer to it often during my journey. Then I return home and write it up as a blog article for you! It’s analogous to recycling in the digital era.

I’m going to teach you ALL of my trip planning secrets, and by the conclusion of this enormous book, you’ll be itching to plan a fantastic vacation.

By the way, I thoroughly tested the whole procedure on Jeremy. Most of our trips are now planned by him rather than me. I downloaded all of my vacation planning expertise into his lovely ginger brain during our year-long honeymoon, and he entirely took the responsibility off my shoulders, bless him. We both follow the procedure stated in this thread.

Buckle up, for this is a lengthy tutorial. You should bookmark it now so you can refer to it later.


It’s important to strike a balance when organising a vacation so that your days don’t seem unduly crammed. I honestly feel that every minute I spend searching things up at the hotel is a minute I don’t get to enjoy my trip!

In the same spirit, if we meticulously plan every single day of a vacation, we get worried when our travel plans break awry and our whole perfectly planned day – or week, or month – is wrecked.

As the kind of tourists that tend to attract disasters and travel failures, we’ve learned to always assume the worse. A well-planned journey requires both failure and flexibility. Here are some things I suggest not stressing about while planning a vacation!

Make no plans for each and every day.
Planning each day of your vacation might lead to disappointment: perhaps one day you wake up unable to participate in the activities you had planned, perhaps the weather changes, or perhaps you discover something else you’d want to do instead once you arrive.

Sometimes it’s inevitable, but wherever possible, make space for change.

Don’t plan every single meal.
When you travel, your hunger levels may be unexpected (we find ourselves feeling hungrier due to our increased activity levels), and waiting for the proper meal may result in hanger and dissatisfaction.

Instead, choose one or two restaurants for which you are prepared to travel out of your way, or make a list of possibilities. But don’t plan on attending all of them, and especially don’t plan out which ones you’ll go when!