The Most Ill-Advised Travel Scenarios

Travel regrets, I’ve had a few. But then, haven’t we all? Anyone who has ever felt compelled to strike out on their own or agreed – perhaps drunkenly, certainly prematurely – to take a voyage with someone they didn’t know well will no doubt have cherished travel horror stories of their own.

With a solid decade of independent travel to draw on – and with a few particular stinkers borrowed from friends – I’ve compiled a list of the Most Ill-Advised Travel Scenarios to avoid at all costs.

Rekindling Romance far from Home

Anybody else had the experience of a boyfriend moving away – say, thousands of miles across the country – then inviting you to visit and, conveniently, not being there when you arrive? Or when you make your own way to the hotel? All while being unreachable on all modes of communication?

Being stood up is bad. Being stood up on vacation is the worst.

Though we’d decided not to pursue an actual long-distance relationship, his (perhaps drunken) invitation to his new city seemed like a great idea – even up to the point when I booked my flights. A previous business trip-turned-reunion had sown the seed, and there was nothing to suggest a purpose-built visit would be anything less than fantastic.

However, upon arrival at San Francisco International Airport, he was nowhere to be seen. Nor did he ever turn up at the hotel he’d booked, leaving me to worry that something untoward had happened to him in his capacity as an undercover agent (something I fully appreciate sounds like the delusional invention of a trashy romance reader, but even I’m not sceptical enough to believe someone who wasn’t a federal agent could check his gun at airport security or travel with the president… and now you can see why I thought it was worth flying 2,400 miles to see him.)

Anyway. It later transpired something work-related had come up, or so he said. It didn’t matter. By that point, I’d already hit the town like a woman scorned and found plenty of friendly locals to fill the gap. I didn’t leave my heart in San Francisco, but I did leave behind any naive notions about guys who adopt multiple identities for a living.

The Foreign Trip with a New Boyfriend

I don’t really need to say any more about this, do I? Even a dirty weekend with a new beau is bound to be fraught with tension, anxiety, unfulfilled expectations and worse. Add on jetlag and a different country and a break-up is almost inevitable.

I’d planned to visit my brother, who was living in London, just as I had a couple of years before. So when my shiny new boyfriend invited himself along, I thought it would be a laugh. I should have known my brother would hate him intensely, but I didn’t expect the boyfriend – who had never been to the UK – to contradict any first-hand knowledge I had, to refuse to put away his stupid guidebook and to generally live up to every stereotype of the ugly American abroad.

Within hours we were barely speaking and had he kept his Lonely Planet guide so firmly glued to his face that he dropped from the Tube platform, who was I to interfere?

Nor could I conjure up any sympathy when he fell afoul of the Irish speed police in the Economy hire car I’d sorted out – though it probably didn’t help that I laughed at the €60 fine he had to pay on the spot.

Needless to say, we were finished before the wheels left the runway at Heathrow.

The Foreign Trip with a New Friend

I haven’t had first-hand experience of this particular scenario, but I have it on good authority that even when you remove the sex and romantic expectations, you’re essentially dealing with the same catastrophe as mentioned above. If you don’t know someone well, you should never, ever, under any circumstances travel with them. Especially to another country. My best friend travelled to the Mediterranean with a university friend who invited her to visit her family. Even if the accusations of casual racism, snobbery and general rudeness were exaggerated, it sounded like the trip from Hellas.

Another friend had the audacity to combine the two worst travel no-nos, visiting an ex-boyfriend in a foreign country. She came back so shell-shocked she’s never been able to touch schnitzel again.

The Consolation Prize Trip

When I was at university, a group of friends decided to take a roadtrip to New Orleans for Mardi Gras. I loved the idea of seeing New Orleans, having read enough gothic literature set in the city to send my heart aflutter, but was I drawn to the annual festival of bared boobs and vomitous gutters? Not even a little.

Still, when one of the trio dropped out, having already chipped in for the hotel and gas, I decided to exploit the cheap ticket and attempt to avoid the revelry.

But trying to ignore Mardi Gras is like throwing yourself in the bayou slathered in bacon and expecting the alligators to turn up their snouts in disgust. We parked the car and in seconds flat I was holding a hurricane (a particular New Orleans beverage renown for its immediate, destructive powers) and having beads hurled at my head. I did at least maintain my dignity and my clothing, but my refusal to shake what my mama gave me to balconies of baying boob hounds didn’t endear me to my pals. They’d signed up for a like-minded travel companion and I was the reluctant consolation prize, which made for rather an awkward drive home.

The Casual Roadtrip

Now this is a tricky one. My happiest travel memories are of a spur-of-the-moment, seat-of-our-pants road trip across Canada to New England with a dear friend. There was no agenda, no pressure, actually no plan whatsoever. We just fueled up and pointed east, stopping wherever the fancy took us. We may have barely escaped detention by Canadian Border Police. We may have sipped mysterious mountain brew with scary locals, might have attended an Octoberfest in deepest Ontario where a mariachi band played oompah music, and it’s possible we stayed in Vermont’s dampest, moldiest, most charmless motel room. But it was the Best. Trip. Ever.

Conversely, I’ve roadtripped with close friends whose spending habits, interests and ideas of what constituted an acceptable way to refuse an invitation from swingers did not meet my own. We’ve maintained the friendships (with each other, not with the swingers), but the road trip can make or break weaker bonds. Approach with caution.