I planned a trip overseas for the first time

Three weeks ago, I boarded a plane to England for my first holiday as an “adult”! I was crazy excited, but also pretty scared. This was the first trip I had ever planned on my own, and I had this sinking feeling that I had either forgotten to do something important or that something would go wrong. Luckily nothing horrible befell me, so I decided to sum up my experience planning an overseas holiday below.

When I started planning the trip, I thought it would be a breeze. I had been saving up for more than a year, and I’m pretty good at admin, so why would I worry? Turns out, there’s quite a bit more to planning a trip than just buying tickets and having some money saved up!

There’s so much admin

I knew there would be admin involved in planning my holiday, but I didn’t realise just how much. First, just finding dates to book flights was much harder than I anticipated. I had wanted to go during that wonderful period in April and May where South Africans are overwhelmed by long weekends and public holidays to minimise the number of leave days I’d need to request; but unfortunately my boyfriend wasn’t able to take leave during that time. We had been looking for specials and discounts on flights to the UK since last July, and eventually, we decided to stay up until midnight on Black Friday and see what deals we could find.

We were lucky enough to find semi-direct flights (with just one quick changeover in Joburg) for about R5 000 cheaper per person than they would have cost originally. I had wanted to confirm dates with my boss before booking anything, but the special was selling out quickly and I couldn’t really phone him awake at 1 am, so I took a deep breath and booked our dates. Because we’re both broke twenty-somethings, we were obviously looking to save as much money as possible, so after checking and rechecking departure dates, we eventually booked an overnight flight on a random Tuesday. With our tickets in the bag, I thought the hardest part was over.

How naive of me. The admin was actually just beginning.

Visas are a bitch

My boyfriend’s family were kind enough to invite us to visit them in Spain while we were in the UK, which meant that I would have to get both a UK visitor’s visa and a Schengen visa. No problem! Or so I thought. All in all, the two visas combined cost me almost R3 000, not to mention all the additional fees for scanning and uploading documents, random “unforeseen” extra costs, and of course the petrol to and from Cape Town, and the time I had to take off of work.

Fair warning: the whole process of applying for a visa is stressful from start to finish, so have all the documents they require (and any extras you can think of) ready, channel your inner Santa and go through the checklists at LEAST three times before you even think about booking your appointment. Otherwise, you might end up spending a few hundred bucks extra to upload documents last minute.

Once everything had been uploaded, all my necessary documents had been printed, and I’d taken a few hours off of work to drive to Cape Town, the worst part started — waiting to find out whether my application was approved. Eventually, after three weeks of stressing, I got the good news, bribed my boyfriend to pick up my passport so that I didn’t have to take more time off from work, and got to do it all over again. Fun.

So. Much. Admin.

The next bit of admin I severely underestimated was getting travel insurance from my medical aid. I thought I could just go on their website, download the form and be on my way, but it turned out to be a bit more difficult than that. At work, I was in the process of switching over from one medical aid plan to another, and we just kept running into problems. Eventually, we were told that the new medical aid had been activated, but when I tried downloading the form I couldn’t access it, as the plan change hadn’t officially been activated yet.

After a couple of hours on the phone with their helpline, I finally got someone to send me the form in an email and I was good to go. Until I got to the Spanish consulate and was told that the documents I had were the old version, which meant I had to pay a massive convenience fee to be able to send in the documents later that day.

How will I stay connected?

Did I even want to stay connected? Maybe a three-week break from my cellphone would do me good… It’s not like I’m that active on Instagram anyway.

Eventually, I decided I’d have to get a SIM card, if only to make sure I don’t get separated from my boyfriend or lost in a foreign country. But trying to figure out which provider to use and what the best deal will be was becoming an impossible task. I’m one of those people who like making lists and planning ahead, so I was getting very stressed about this whole cellphone situation, but I had decided to wait until I got to the airport, as trying to shop for a SIM online isn’t as easy as I had thought.

Last but not least, how will we spend the time?

As I mentioned earlier, I like planning and making lists. My boyfriend not so much. He’s happy to take it one day at a time and decide what he wants to do on the day, while my inner Amy from Brooklyn 99 reared her head, making me feel I as though I needed a laminated itinerary for every day so that I could see as many sights as possible and not miss a thing.

If you only have a few days in one of the most popular tourist cities in the world, it’s much easier to see everything you want to see if you map out your route beforehand, but try telling that to my boyfriend! He thinks I stress too much and work myself up over nothing, so I decided to try to take it easy and just go with the flow… you can see how that turned out here.

All in all, planning a trip as a semi-adult was much harder than I thought it would be, but it’s also kind of liberating! I was free to do what I wanted when I wanted, which is great but also kind of scary.

Are you planning your first trip alone? Maybe you’re a seasoned traveller and you have some advice for my next holiday — please let me know in the comments!

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