Should You Plan Every Aspect of Your Trip (Or Should You Wing It?)

One of the hardest aspects of planning a trip is knowing how much to actually plan. Do you want every hour of every day accounted for, leaving no room for spontaneity? Or do you wing it completely, with the risk of missing out on something you really wanted to do. There’s no easy answer – that’s why I’m writing a post about it!

Trip Length

An easy way to decide how much to plan in advance is looking at the length of your trip. If you’ve only got a week or two and want to make the most of your time, you’ll probably need to do a fair amount of planning and booking. This is especially true for activities that might end up selling out in advance. If you only have a week or two and aren’t planning to see much (more of a relaxing trip) you won’t need to organise too much in advance. You’ll want to book your hotel and that’s about it – everything else in that situation (food, most activities, transport) can be booked on the go.

If you have a longer trip, say a month in a country, you’ll have a lot more flexibility. You might still want to book some things in advance (an internal flight / train / bus or an important tour) but I wouldn’t be booking every hotel etc in advance. The main reason for this is that once you’re in a country you’ll find out about places you hadn’t planned on going to, or you might meet some friends and want to join them.

Covid Planning — One aspect you definitely need to plan for is Covid — do your research about what the destination you’re going to requires — it changes a lot so keep up to date with it.

Saving Money

One very tempting reason to plan and book most aspects of your trip in advance is the possibility of saving money. Booking websites often have good discounts or claim that tours / hotels are about to sell out, giving us customers lots of motivation to book.

I found this when trying to plan our (covid cancelled) trip to Europe. I love to wing it (while booking the occasional hotel / transport in advance) but while searching buses in Europe I saw some awesome deals. It’s annoying to have to book a bus months in advance, but the sometimes the savings are too good to turn down.

I also found that it was good to book some trains in India in advance. The sleeping cars often sell out on popular routes, and you don’t want to do a 24-hour train journey in India in the cheap seats. So – booking in advance can definitely save you money, but you’re sacrificing some freedom in doing so.

Holidays VS Travelling

If you’re travelling for months at a time, slowly moving from city to city, you won’t need to book much in advance. It can still be good to book hotels though, especially in big cities and especially if you’re arriving at inconvenient hours. Apart from that, it can be good to jump on a good transport deal from time to time, but part of the joy of long trips is the freedom, so the less planning the better!

A holiday is quite different. It’s usually only for a week or two and you’re usually escaping the strain of a 9-5. It’s natural to want to micro-manage these kinds of trips, as it can be quite stressful to wing it. I’d still advise you to leave some wiggle room though – some of the best holiday moments are the spontaneous ones. Of course some people never plan any aspect of their holidays — it could be something to look into if you’re looking for an adventurous holiday.