How I Plan My Short Backpacking Trips

One of the most daunting things about backpacking is planning the trip itself. There is a lot to do and, if you don’t know where to start it can become quite daunting.

Since the pandemic arrived at just the wrong moment, I had to cancel my first multi-country backpacking trip, however I think that it is the shorter trips that really need planning.

My current style of backpacking is short 3-5 day trips in one or two cities. This means you have to be pretty on the ball if you want to squeeze everything in.

*I don’t tend to fit all of my bucket list items in one trip, especially if I intend to visit again, so if you know it will be your only time in the country it may be worth taking 1-2 weeks to explore instead*

Here is how I plan my short backpacking trips:

Decide Where You Want To Go

The first big task is to decide where in the world you want to go.

There are 3 main avenues that I go down when choosing this:

It’s somewhere I’ve wanted to go for a while

I feel as though this is the main reason for most people’s travel and so I will open with it.

The easiest way to decide on where to go is if there has been somewhere on the top of your bucket list for a while that you really can’t wait to explore. This is the main reason I went to Portugal.

Instagram / Pinterest / Blog Posts / Vlogs

A great way of finding inspiration for where to go on holiday is to scour the feeds of travel bloggers / vloggers or friends and family who love to travel. Whether it is finding a great scenic photo on instagram, spotting a fascinating itinerary on Pinterest or just reading a blog post that makes you desperately want to see the place for yourself.

I have found many destinations that I desperately want to visit through these methods. Two that spring to mind are Cuba, which was brought to my attention by this vlog by DamonAndJo, and Colombia, a country I fell in love with by watching these videos by Backpacking Bananas.

There are destinations out there that you may never consider until you have them brought to your attention by others so this is a method I highly recommend.


This one may seem a bit strange however a lot of the trips that I have gone on have been spurred on by Skyscanner.

When you are looking to book your trip, there is an option to search everywhere and the site will give you a list of countries in order of what is the cheapest.

Screenshot of app I use to plan my short backpacking trips
A screenshot of the Skyscanner website

This is how I booked my first solo backpacking trip to Warsaw and has been very helpful when I have been looking for inspiration.

Check For Important Information

Once you know where you want to go it is important to check for any vital information that you have to know before you leave.

In the UK, my main source for this is the website which has all of the up to date information on entry requirements (VISAs etc.), safety, terrorism and health.

It is also important to ensure that you are up to date on any necessary travel vaccinations. I recommend taking a look at the NaTHNaC website to ensure that you know what, if anything, you will need to get before leaving.

Pick A Time To Travel

Deciding what time of year to travel can be stressful, especially if it is the only holiday you are going on that year or your trip is going to span several weeks / months.

There are a few things that I consider when looking at when I want to go on holiday:

Is there a limit to when you can travel?

This is, of course, the big one.

As someone who works part time and is also a student, I have a very limited amount of time in the year in which I can travel. Naturally, if I know I have holiday time off during a break from university then that is the time that I am looking to travel.

In this situation I am more likely to decide where I am going based on the time I can go than vice versa.

What season will it be where you are going and is it considered a good time to travel?

Whilst it isn’t the case for every country, some places that you may want to visit have recommended times to travel there based on the seasons. Rainy and Dry seasons, the hot and cold – in order to have the most comfortable and enjoyable trip it is worth considering.

Whilst I have been planning my future trip to South America, I have had to plan my route based on when it is advised to visit that country. This map by Scarlet Scribs is a really helpful starting point.

When is the cheapest time to travel?

A really great way to find a time to visit if you are not limited by time off or seasons is to use the Skyscanner cheapest month feature.

A screenshot of the Skyscanner website

This allows you to search for the absolute cheapest flight to a country, saving you a little bit of money that you can put towards your trip in other ways. If you have no limit on when you can go, this is a great way to decide.

Look Into Transport Options

Once I know when and where I want to travel, the fun part starts: spending money and booking my short backpacking trip.

The first port of call is to book my transport to the country I am visiting. If I know that I am only visiting once city (it is a short trip or a trip that has a set start and end point) then I will book a return trip but it is definitely worth just booking one way if you want to be spontaneous.

If you want to see how it goes and take a one way flight, make sure that you double check that entry to the country doesn’t require a return flight. If it does, use the Skyscanner website to search everywhere for the date of return and you can book the cheapest flight.

Since I am in the UK, flights tend to be my main mode of travel out of the country, however I am a fan of taking more eco friendly transport wherever possible. Trains, buses and boats are options depending on where you live and how far you want to travel and they are definitely worth considering.

All the best plane views have sunsets or sunrises

I personally like to arrive in a country as early in the morning as possible and leave as late as I can, so I often have to pay extra for this, however I enjoy being able to have a bit of extra time in the day to settle in and find my footing.

Pick Accommodation

One of the most important things to consider when planning a backpacking trip is where you are going to stay. In my experience, a good hostel or hotel can really make or break a trip and can leave you with a lasting impression of a country.

I use the apps hostelworld, airbnb and to find places to stay and think that scouring reviews is a really helpful way to ensure you will like the hostel or hotel you choose.

Find out more about the apps I when I travel here.

When I plan my short backpacking trips, having a social atmosphere is very important to me, as I will not be around long enough to slowly build up friendships with people.

Hostelworld is very helpful with this as it not only ensures that people leaving reviews have actually stayed there, but also gives a handy overview of the rankings for atmosphere as well as location, security and staff. This helps give a quick overview of whether or not I will like a place so that I can look into it in more depth.

Screenshot of reviews I use to help plan my short backpacking trips
The Hostelworld reviews for one of my favourite hostels: Oki Doki Old Town Hostel Warsaw

Another great way that I find hostels to stay at when I plan my short backpacking trips is to make a note on google maps whenever I see a blogger or vlogger recommend a hostel that seems it may suit me.

This is something that I do regardless of whether I have immediate plans to visit somewhere and I gradually have built up a collection of places that I would like to visit, stay at or eat at from looking at blogs and vlogs.

It has been very helpful when on the road and is a resource I would recommend to anyone.

Book Activities and Events

For me, the thing that really makes a backpacking trip special is the activities I take part in whilst I’m there. A big part of how I plan my short backpacking trips is deciding what I want to do in the countries I am visiting.

As mentioned previously, I like to place a star in google maps for the places that I want to visit and eat at, which helps me immensely when deciding which activities I want to participate in on my trip. I tend to like to have at least a few ideas for places to visit when leaving so that, if I am struggling to meet people, or feeling a bit lost, there is something exciting I can do.

Picture of my google maps for Ecuador.

This step depends a bit on how you are backpacking, but for short trips I like to book any must do activities or events in advance of heading out.

I did this on my Amsterdam trip for my visit to A’dam Tower as I knew it was something I wanted to do at sunset and so wanted to have booked ready. I also like to book a free walking tour on the first day I arrive to help myself get a feel for the city.

If you know where you are going to be, I highly suggest booking something you are 100% sure you want to do as it will relieve a bit of stress.

There is one exception to this however. If you are travelling solo and intend to meet people whilst backpacking, it may be worth waiting to book things in case people you meet want to come with you or invite you to do something more exciting on that day.

I hope this was a helpful insight into how I plan my short backpacking trips. Let me know if you have any questions and I will be happy to answer them.

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