The Awkward Questions Nobody Asks

Six small, faintly embarrassing problems of travelling alone over fifty, answered properly.

A few years ago I was standing in the middle of the departures hall at Gatwick with a rucksack on my back, a cabin case at my feet and a bladder making urgent representations to management, and I realised I had no idea what you are supposed to do. There is no sign. There is no procedure. There is nobody to hold your bag, because you are travelling alone, which is rather the point. I stood there weighing up the relative humiliation of each option for a good ninety seconds, which when you need the toilet is roughly a geological age.

Nobody asks that question out loud. Not on a forum, not in a Facebook group, and certainly not of a friend who travels a lot and has recently started using the word “nomad” about herself without irony. You do not ask, because asking makes you sound like a man who has never successfully left his own postcode. So you work it out on the spot, badly, and then never mention it again.

I have come round to thinking those are the only questions that really matter. The big ones get answered everywhere: visas, vaccinations, whether the tap water will do for you. What nobody writes about is the ordinary business of being a person on your own in an unfamiliar place. The toilet. The walk back to the hotel in the dark. The morning you wake up ill in a room where not one living soul knows your name. Those are the ones that sit in the back of your head at four in the morning, and past fifty they sit there rather more loudly than they used to, because you have reached an age where you are supposed to have the answers.

So here are six of them, answered properly. No bravado, no cheerful instruction to put yourself out there. Just what I actually do, and what I got wrong first.

What do you do with your luggage when you need the airport toilet?

The one that started all this. There are four workable answers depending on how much you are carrying and how much being stared at bothers you, and the option most people reach for first, the accessible cubicle, is the one to think hardest about. It also deals with the particular horror of a seventy litre rucksack and a cubicle door that opens inwards.

Read it here: What to Do With Your Luggage When You Need the Airport Toilet

What if I am simply too nervous to go?

This is not a pep talk, because pep talks have never once worked on me. The best thing I know for nerves is to make the first trip small enough to be boring: one night, your own country, a train you can get off at any point. The piece is about collecting evidence that you can do it, which is a very different exercise from trying to talk yourself into feeling brave.

Read it here: Nervous About Solo Travel Over 50? Start Closer to Home

What happens if I fall ill, alone, somewhere nobody knows me?

The question people are most frightened of and least willing to say out loud. What to do in the first hour, when a pharmacy is genuinely enough and when it absolutely is not, how to get seen by a doctor in a country whose health system you have never thought about, what your insurance actually covers, and the plain practical business of being unwell in a hotel room with nobody to fetch you anything.

Read it here: What to Do If You Get Ill While Travelling Alone Over 50

Is it safe to walk back to the hotel on my own after dark?

Usually yes, and the things that make it safer are duller than you would hope. Route choice, where the phone lives, and knowing the moment to take the taxi you had decided not to pay for. Past fifty you present differently on a dark street than you did at twenty five, better in some ways and worse in others, and it is worth knowing which is which rather than guessing.

Read it here: Walking Back Alone After Dark: Solo Travel Safety Over 50

Should I arrive somewhere new after dark?

The cheap flight always lands at half past eleven at night. This is about what that actually costs you once you add it up: the arrivals hall at midnight, the transfer you have not arranged, and the business of finding one particular door in a street you have never seen in daylight. Also the handful of occasions when paying for the earlier flight is the cheaper decision.

Read it here: Should You Arrive Somewhere New After Dark? Solo Travel Over 50

Would I be better off just booking a package?

An honest comparison rather than a sales pitch, because the answer is not always the one a travel blogger is supposed to give. What a package genuinely buys you, where the single supplement does its damage, and the three things that move the price more than anything else. Sometimes the package wins outright, and I say so.

Read it here: Package Holiday or Book It Yourself? Solo Travel Costs Over 50

Where to start, if you are right at the beginning

None of this is a course and there is no order to it. Read whichever one is currently keeping you awake and ignore the rest until it becomes relevant, which it will, usually at an airport, usually at the least convenient possible moment.

If you have not booked anything yet and the whole idea still feels faintly ridiculous, begin with Start Solo Travel, which is the shortest honest version of everything I know. If you would rather have it on paper to take with you, the free guides are here, and they cost nothing, because putting a price on them never sat right with me.

And if the question keeping you awake is not on this page, write and tell me. I would far rather spend a fortnight on the thing you are too embarrassed to ask than produce another list of packing tips that nobody needed.