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Solo Travel

Solo Travel for the Slightly Anxious

By Kelly McCoy · October 2025 · 8 min read

Solo Travel for the Slightly Anxious

Solo travel is sold as either 'transformative' or 'terrifying' and the truth is mostly 'pretty nice, occasionally great, occasionally awkward, much easier than you think.'

If you've been talking yourself out of a solo trip for years, here's the gentle truth: the version of the trip you're afraid of is mostly imaginary. The real version is more like 'eating a really good sandwich alone in a park while watching strangers and feeling weirdly powerful.'

Start with a destination that does the work for you. Lisbon, Copenhagen, Tokyo, Kyoto, Edinburgh, Vancouver, Sydney. Walkable, English-friendly (or polite-friendly), low-key, well-mapped. Save the deep Sahara for trip three.

Book the first two nights somewhere lovely. Splurge a little. A nice hotel or guesthouse with a real lobby is your anchor while you adjust. After two nights you can go cheaper and weirder if you want.

Eat dinner at the bar. Bartenders talk to solo diners. So do other solo diners. So do off-duty servers. This is the single best solo-travel hack. The 'table for one' fear evaporates the moment you sit at the bar.

Have one anchor activity per day. A walking tour, a cooking class, a museum, a long walk with a destination. Even one structured thing keeps the day from drifting into 'I have been alone in this room for 14 hours.'

Talk to people, but on your terms. Walking tours and group day trips are basically friend-vending machines. You don't have to keep in touch with anyone. You're allowed to enjoy two hours of company and never see them again.

Safety logistics: share your hotel address with someone at home. Use a money belt for valuables (genuinely, even in 'safe' cities). Trust the gut. The gut is correct more often than the brain.

Last thing: the first dinner alone is the hardest. After that it gets weirdly easy. By day four you'll be slightly insufferable about how much you love traveling alone. This is a normal phase. Welcome to it.

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