Confidence

Your First Solo Trip at 60 Is Right on Time

The question usually arrives dressed up as something practical. Is it safe? Will I be lonely? What if something goes wrong? But underneath most of those is a quieter one: have I left it too late?

You haven't. You're better placed now than you were at thirty.

Why sixty is a good age to start, not a late one

Consider what a first solo trip actually asks of you. It asks you to make decisions calmly when a plan falls through. To read a situation and judge whether it's fine or genuinely off. To be comfortable in your own company for a stretch of hours. To handle money, logistics, and the odd bit of officialdom without panicking. To ask for help when you need it and to know when you don't.

There are practical advantages too. If you're past full-time work or have flexible arrangements, you can travel outside school holidays and weekends: cheaper, quieter, and far less frantic. You likely know your own tastes by now, which means you won't waste days on things you were told you should see and secretly don't care about. A better room is worth the money.

Three things people worry about

Safety. Most of staying safe is ordinary judgment, and you have decades of it. Choose destinations with good infrastructure for your first trip. Book the first two nights' accommodation before you fly so you land with somewhere to go. Keep a copy of your documents separate from the originals. Trust the instinct that says not this street, not this taxi. That instinct is one of your best assets, and you've spent years sharpening it.

Loneliness. This is worth separating into two things. Solitude, being alone, is often the point, and many women find they're better at it than they feared. Loneliness (the ache of it) is real but usually intermittent, and it tends to hit at predictable moments: the evening meal, a beautiful view with no one to turn to. You can plan around those. A guided walking tour on the first morning gives you your bearings and, often, a few faces to nod to later. Dinner at the bar rather than a table for two feels easier for many. A book you're genuinely enjoying makes eating alone a pleasure rather than a performance.

Health and the body. A sensible worry, and one you address with logistics, not by staying home. Travel insurance that covers your actual medical history, not a version you'd prefer. Medication in your hand luggage with a copy of the prescription. A realistic pace: one major thing a day, not five. Ground-floor rooms or lifts if stairs are a factor.

The practical shape of a first trip

Keep it modest and let it succeed. A long weekend or a week is plenty to prove the thing to yourself. Pick a city that's easy to reach and easy to move around in on foot or by simple public transport, somewhere the stakes of a wrong turning are low.

Build one anchor into each day: a lunch you've decided on, a museum, a particular square you want to sit in. The anchor gives the day a spine, and the hours around it can drift as they like. Resist the urge to fill every slot. The unplanned hour where you sit with a coffee and watch a place go about its business is often the one you remember.

Book accommodation that's central and well-reviewed by other solo travelers rather than the cheapest option on the edge of town: the money you save rarely justifies the walk back alone at night or the isolation. Tell one person at home your rough plan and check in with them once a day, not as surveillance but as a simple thread of safety.

And allow the first day to be slightly uncomfortable. It nearly always is. The unease of arriving somewhere unknown, on your own, is not a sign you've made a mistake. It's just the feeling of doing something new, and it passes, usually by the second morning.

If you're weighing where to start, the city guides are written for a first week like this, and the free starter guide walks you through planning a first solo week from the first decision to the front door.

If this is the nudge you needed, the free starter guide is the next step.

Free starter guide & The Letter. You'll start with “Your First Trip Alone.” By signing up you agree to receive The Letter, the Table for One email newsletter from Table for One Press. Unsubscribe anytime. Privacy.