If you're a South African passport holder, even if you don't actually need a holiday before assembling the documentation required for a trip to Europe, you certainly will need one after.

The last time I was in Europe I went to France, and that one-country visit required a fair amount of visa-obtaining preparation. At the time, I found it a bit of a nuisance. How I long for those days now.

This time around, I needed another Schengen visa, in addition to a Cypriot one because Cyprus was on my itinerary as well and is not yet a Schengen state.

During an incredulous phone call with the travel agent, during which she elaborated on the many ways European ministries are making it more strict for certain tourists to gain access, I wondered how exactly non-European, American and Australian passport holders have unstructured vacations in Europe, or indeed go backpacking?

The plan was to meet an American friend in Berlin (he simply had to book a cheap flight and then stick his visa-less passport and some cash from the ATM in his pocket. In other words, I was probably not going to be talking to him by the time I arrived). We were then to go by train to Prague and Vienna, but not decide in advance in which order nor for how long in each place. That's tricky, though, because to obtain a Schengen visa, one has to show that each night of accommodation is paid for in full.

So, with the requisite three months' bank statements and supporting letter from my account manager; ticket, accommodation and travel insurance paid for; photographs taken in a "biometric" way (and checking the list of requirements for how the photos must look alone can easily consume a full morning); and, in my case, a letter from my accountant detailing my self-employed status, not to mention some blood pressure meds, I was good to go on the German front. Cyprus, however, does not let you have your way with her that easily.

I was heading to Cyprus for a friend's wedding. I planned on staying at the parental home of another friend, who was also going to the wedding. To have the dubious pleasure of my company at his house guest, he was expected to submit copies of his Cypriot passport, write a letter of invitation as well as fill out a separate "Assumption of Responsibility" form, which in turn had to be certified by the mayor in his Cyprus district. He also had to apply for a bank guarantee in Cyprus and, furthermore, have that stamped by immigration there.

Once he and I managed to assemble this package in Cape Town, where we both live, by which time our friend and his now wife would probably be celebrating their third anniversary, I then had to have it couriered to Pretoria and await the possibility of being summonsed there for an interview. While I had no choice but to dispense with everything else on my agenda for the week to become a full-time aspirant Mediterranean island visa holder, it was possibly a little unreasonable to expect my friend to do the same.

And just when I thought the stack of documents bound for Pretoria couldn't get any thicker, I was advised by a consulate official to "strengthen my application" by making an affidavit to indicate that I had not applied for a Cypriot visa before.

So, unless I become the lucky recipient of an EU passport at some point or the island becomes a Schengen state, I strongly suspect that this will be my first and last time in Cyprus. In language the locals would understand, Opa, let's go!

• Herman is the author of Perfect Weekend: 52 South African newsmakers describe their downtime.