How To Plan a Trip (That Actually Needs to Be Planned)

by Brenna Holeman

How to Plan a Trip

On the train through Switzerland (2006)

I’m currently planning a trip for about 10 days over the Christmas holiday. In my mind, I have a lot of time to plan this trip; in reality, I’m leaving in two weeks. I’m flying to Zurich, spending a day in Liechtenstein, taking the train to Innsbruck, then meeting my sister and her boyfriend in Vienna. From there, Zalie and I will go to Salzburg for a couple of days, and perhaps to Bratislava for a day trip. That’s four countries and six cities, three of which I’ve been to before (Zurich, Vienna, and Bratislava). But you know what they say – the shorter the trip, the longer the planning.

These past few days, I’ve thought a lot about trip-planning. I’ve flip-flopped between being totally nonchalant about it (“I’ve got loads of time! It always works out, no matter what!”) to totally stressed about it (“I’m flying to Zurich in two weeks and I have planned NOTHING! I need flights, hostels, hotels, trains, buses, AND I need to book a nice place for a Christmas dinner…”). This is actually quite unlike a lot of trips I’ve done, because it actually does require the booking of flights, hostels, hotels, trains, and buses – over the holiday season, there’s no way I’m leaving these things to chance. This isn’t like my recent trip to Berlin, where I booked the one hostel and the round trip flight from London a few days before, nor is it like my longer stints through Southeast Asia or South America, where I had nothing but a one-way ticket and an open mind. With a limited amount of time and with a fairly limited amount of money, I need to plan this. I need to plan this now.

So how am I doing it? How should you plan a trip that does, in fact, need to be planned?


Buses in Valletta, Malta

1. Look at a map. Yes, like a real map (OK, a Google image of one is fine, too). Even though my geography of Europe is pretty good – thanks, Sporcle – I still brought up a map of Austria and figured out what would be possible in 10 days, with only a couple nights in each location. In doing this, I realised that I’d have to fly in to Switzerland in order to see Liechtenstein. I then figured out that Zurich was the best place to fly into. I then saw that Innsbruck was about halfway between Zurich and Vienna. And so on. 

2. Constantly research distances and possible routes. The whole time I was looking at maps, I was Googling the distance between the cities. It takes only seconds to find out, for example, that Vaduz, Liechtenstein is 108 kilometres from Zurich. I then knew that it was possible to do a day trip there. I also search things like, “What is the easiest way to get from Zurich to Vaduz?” to immediately find out if I should be looking at trains, buses, flights, etc.

How to Plan a Trip 4

Flying to London, England

3. Once you’ve figured out where you want to go, research combinations of flights, train times, possible hotels, etc… but don’t book anything yet. Originally, I thought I would stay a night in Vaduz or another city in Liechtenstein. I then realised that I couldn’t really find anything within my budget online (I exclusively use Hostelworld and Hostelbookers to book hostels). It made more sense to fly into Zurich and book a hostel there for two nights, spending one of the days in Vaduz. Play around quite a bit with possible routes to find the one that is quickest, easiest, and cheapest.

4. Once you’ve realised you have accommodation and transportation options sorted, book the flights. As we all know, flight prices change all the time. As I was booking mine, the price on one flight jumped up £10, just like that. Again, research a lot; I’m a big fan of Expedia, and have often found flights on major airlines that are cheaper than the budget airlines through them. For this particular trip, I found that EasyJet had the cheapest flights and flew at the most optimal times for me, so I booked directly through them.

5. Next, book your domestic transportation such as trains, buses, etc. I always want to book my accommodation next, but figuring out which trains and buses are available to me and when will make a big difference on how I choose my hostels. If I book a hostel for the 22nd in Innsbruck, but then find out that I can’t get a train there, I’m screwed. Unfortunately, this will probably be the hardest part of the trip planning, as it can be extremely difficult to find websites that work. In the UK, I’ve used the Megabus website with success; for my European trip, I’m using Loco2. Some countries, such as Thailand, have frequent buses to popular destinations, so booking far in advance isn’t really a problem. For others, such as in most of Europe, reserving a seat ahead of time is crucial, even if you are on a Eurorail pass or something similar.

How to Plan a Trip 2

Flying to Rome, Italy

6. Now, book your accommodation. Sometimes I love this part, sometimes I hate this part. Vienna, for example, was very easy to book: I recognised the name of a hostel chain, knew it had a good reputation, read a few reviews, and booked. Zurich, on the other hand, required more time and research; there are very few hostel options in the city, and very few cheap options at all. After a few days of research online I decided to splurge and stay in a more expensive hotel – it just made sense in terms of location, security, and facilities provided. Make sure to weigh these options carefully, and consider what means more to you. If I read a dozen reviews of a hostel that claim it isn’t safe, as a solo traveller I’m going to opt for another place, even if that means spending a bit more. Sites like TripAdvisor are also extremely helpful to garner reviews and advice on places to stay.

7. Start researching things to do. This is the really fun part. I generally spend a bit of time online reading blogs and reviews on cities, and I’m also a big fan of guidebooks. Try to get a sense of the size of the place you’re visiting, and how much you could (and would want to) see in however long you’re staying. Typically, I like to have a few must-sees for each place, but I also leave some time completely open; if you plan too much, you may feel disappointed if you don’t accomplish it all. This also leaves room for spontaneity, as a lot of the best things I’ve done in a place were things I didn’t even know about until I arrived and a local person or other traveller clued me in to them.

How to Plan a Trip 3

 Vilnius, Lithuania

 8. Before your trip, make sure all the little details are taken care of, both for the journey itself and for the home you’re leaving behind for a few days/weeks/months. This includes packing, sorting out currency, making sure your passport is valid and you have any visas you might need, arranging a cat-sitter, etc. The sooner you do these things, the less stressed you’ll feel on the road!


 Madrid airport, Spain

Now… go and have an amazing holiday, knowing that you have everything under control!


You may want to check out these other related articles:

How to Plan For a Long (A Very Long) Trip

How to Pack For a Long (A Very Long) Trip

Taking Care of the Little Things Before a Trip

How to Save Money to Travel


How do you prepare for a trip like this, one that needs careful planning and organising?

*Please note, this was in no way a sponsored post. I genuinely use the companies listed above and don’t feel a need to be paid in order to share that information with you. 

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Alina December 6, 2013 - 4:41 pm

Great article, Brenna! I’ve been following your blog for quite some time, and I must say you’re my inspiration! Also, it’s nice to see a map of my city Vilnius in your photo 🙂

When I travel in Europe, I usually just pre-book hotel reservations (with a possibility to cancel without any additional fee – in case something doesn’t work out or I find a better option just before leaving). I do not buy train/bus tickets in advance either – if my flight is delayed/cancelled or something else happens and I don’t catch my train/bus, at least I don’t have to worry about the money I’ve paid for nothing. I’ve never had a problem in Europe with buying tickets for buses and trains on the spot. Maybe I was just lucky 🙂

In you case, though, I agree – Christmas season and all..
Anyway, good luck with your trip, I’m sure it will be splendid!

English is not my mother tongue, so apologies for any mistakes 🙂

Brenna Holeman December 6, 2013 - 5:50 pm

Thank you so much, Alina! That’s so sweet of you to say.

I wish that I could travel more spontaneously this time (I usually do) but, as mentioned, the holiday season means that things are booking up quickly. I’ve been fairly lucky in Europe before, too, but I don’t want to leave anything to chance when I have so little time to explore. As they say – the shorter the trip, the longer the planning!

Thanks again for your comment.

Zalie December 7, 2013 - 12:43 am

Great tips as always sister! You reminded me of some things I need to look into too 😉

Brenna Holeman December 7, 2013 - 12:37 pm

Thanks, Zalie! Now… which one of us is actually going to book that Christmas dinner??

Chelsea December 7, 2013 - 1:41 am

I’m right there with ya! I rarely ever plan a trip out (well, except for the occasional hotel). I find it so much less stressful to take it as it is and enjoy what comes to ya. Some of my most amazing memories came from random, spur of the moment, unplanned travel opportunities.

I must say I am SO envious! I have always wanted to visit Innsbruk. I look forward to reading about how it was. If you haven’t already been to Vienna you will love it! It’s one of my favorite cities.

There have been two incidents (one in Austria and the other in Paris) in which I was traveling during a holiday and we barely found a hotel (we didn’t plan ahead/book any hotels/hostels). Eventually we found an amazing hostel (I can’t remember the name of it) in Austria and in Paris we basically had to sell all our belongings for a hotel room it was that expensive.

I head off to Ireland in a few weeks! I noticed you were just there too. 🙂

Safe travels!

Brenna Holeman December 7, 2013 - 2:17 pm

Yes, I love spur-of-the-moment travel! I wish I could do it this time, but as your incidents prove, it’s not always possible. I’m excited for Innsbruck, too – and I’ve been to Vienna, but seven years ago. Can’t wait to see it again!

Have an amazing time in Ireland – I love that country! I was only in Dublin for a few days for a conference, but I need to go back and see more. I spent a lot of time in the countryside many years ago but I think it deserves a second visit…

Thanks for your comment!

expatkerri December 12, 2013 - 8:25 pm

Your photo from the airport in Madrid is amazing!! I love it!!

My tip for planning a trip is to go to Google Maps (I know) and click “images” and clicking around for photos that make you want to visit. I did this before my trip to China and that’s how I planned to visit Guilin (among other places).

I look forward to your photos from this trip 🙂

Brenna Holeman December 13, 2013 - 2:47 am

Thanks, Kerri! I took that in 2008, can you believe it…?

That’s a really good tip – I always do that, too. I’ve been Googling Innsbruck and Salzburg in the wintertime like crazy, as it gets me so excited to go.

I can’t wait to take photos on this trip, I wish you were coming with me!

Hitch-Hikers Handbook December 13, 2013 - 10:26 pm

Great article and lovely blog, Brenna! Thanks for connecting with us on Twitter! Keep up the great work and travel safe!

Brenna Holeman December 17, 2013 - 1:58 pm

Thank you very much!

Katie @ Domestiphobia January 16, 2014 - 9:03 pm

It sounds awful, but I actually needed this. So far in my life (and I’m 31! ha!), I’ve pretty much been the laziest traveler ever. I’m used to local trips in the U.S. where I can easily just wing it, and for anything else, I’ve always been with other people who cared more about the planning prospect. I was just happy to sit back and ride along. But now my little sister and I are planning a trip to Greece or Italy, and she’s worse at planning than I am. I think we’re in trouble. 😉 (But glad you posted this!)

Brenna Holeman January 16, 2014 - 11:22 pm

I’m pretty awful, too… but I’m glad that you found this article useful! I’m sure you’ll have an amazing trip…


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