I’ve done a fair amount of travelling alone and I’ve been bad at it in most of the ways it’s possible to be bad at it.
None of these mistakes ruined a trip. They just made things harder, more expensive or less enjoyable than they needed to be, which is worse in a way, because you don’t notice at the time.
Here they are, roughly in the order I made them.
1. Packing for a Person Who Doesn’t Exist
The first time I went away alone I packed for someone with a much more interesting life than mine. Nice shirt for the nice dinner. Trainers and boots and sandals. A book I was definitely going to read.
I wore about 40 percent of it and carried the rest up several flights of stairs in a building with no lift.
The rule I use now: lay out what you think you need, then remove a third. You can buy anything you’ve forgotten, and every country sells socks.
Carry-on only if you possibly can. It changes your relationship with airports, trains and stairs entirely.
2. Booking the Whole Thing in Advance
I once had eleven days planned to the hour, six cities, every train and hotel booked before I left.
Then I found a town I loved on day three and couldn’t stay, because I had a non-refundable room 200 miles away. That’s a genuinely miserable feeling.
Now I book the first two nights and the flight home. Everything in between gets decided a day or two ahead.
The exception is peak season in popular places, where you do need to book. But even then, book fewer nights in more places than you think.
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3. Trying to Fill Every Day
This is the big one. Alone, with nobody to negotiate with, it’s very easy to build a schedule with no gaps in it.
Three museums, a walking tour, a viewpoint at sunset. Then you’re exhausted by day four and stop enjoying any of it.
Now I plan one thing a day. One. Everything else is optional, and the empty afternoons are consistently the bits I remember.
Sitting in a square for two hours watching a city work is a legitimate activity, not a wasted afternoon.
4. Staying in Hotels When I Wanted Company
Hotels are the loneliest accommodation there is. You check in, nobody talks to you, and you’re in a room on your own with a television.
If you actively want quiet, that’s perfect. If you’d like to meet someone, it’s the worst possible choice and I made it repeatedly while wondering why I felt isolated.
Hostels with private rooms are the answer a lot of people don’t know about. Your own room and door, plus a common area and a bar downstairs. Best of both, and cheaper.
Guesthouses and small B&Bs where the owner talks to you also work well.
5. Not Eating Properly
I spent a whole trip in Spain eating supermarket bread and cheese in my room because sitting alone in a restaurant felt awkward.
That’s a genuinely bad way to experience a country whose entire culture happens around a table.
What fixed it: eat at the bar rather than a table. Eat lunch as the main meal, when dining rooms are full of people alone. And bring nothing to hide behind, because looking at your phone makes you feel more conspicuous, not less.
Nobody is looking at you. This turns out to be true almost everywhere.
6. Carrying Everything in One Place
I had my card, my backup card, my cash and my passport in one bag. When that bag went missing for four hours in Naples I understood what a poor plan that was.
Now: one card and some cash on me, the rest in the accommodation. Photos of my passport and documents in cloud storage. A backup card from a different bank.
Alone, there’s nobody to lend you money or spot you a room. Redundancy matters more than it does with a friend.
7. Ignoring the First Evening
The first night alone somewhere new is the hardest part of any solo trip, and I used to arrive late, eat nothing and go to bed feeling like I’d made a mistake.
Arrive in daylight if you can. Walk the neighbourhood for an hour so it becomes familiar. Eat somewhere, anywhere, rather than skipping it.
That one evening sets the tone for the whole trip. Get it right and the rest is easy.
8. Not Telling Anyone Where I Was
For a long time I’d just go, and check in with people when I felt like it.
It’s not really about danger, though that’s part of it. It’s that a rough plan shared with one person at home costs you nothing and means somebody would notice.
Share your location with one person. Send them your accommodation. Message when you move city. It takes thirty seconds.
9. Comparing My Trip to Other People’s
Scrolling other travellers’ photos while sitting in a mediocre room in a city I hadn’t warmed to is a special kind of self-inflicted misery.
Some days alone are flat. You’re tired, the weather’s bad, the museum was shut. That’s not a failure of the trip, it’s just a Tuesday.
Solo travel gets sold as a permanent revelation. Mostly it’s ordinary life somewhere else, with occasional extraordinary bits, and that’s plenty 🙂
10. Not Going Sooner
The mistake I’d actually undo. I waited years for someone to be free, for the right time, for enough money.
The first trip was four days, ninety minutes from home, and it was terrifying for about six hours and then completely fine.
Start small and close. You don’t need to fly to the other side of the world to find out whether you like your own company.
Common Questions
What is the biggest mistake solo travellers make? Over-scheduling. Alone there’s nobody to slow you down, and exhaustion arrives faster than you expect.
How much should I book in advance? The flight and the first two nights. Beyond that, book a day or two ahead unless it’s peak season somewhere popular.
Are hostels worth it if I want my own room? Very. A private room in a hostel gets you a door plus a common area, and it’s usually cheaper than a hotel.
How do I stop feeling awkward eating alone? Sit at the bar, eat your main meal at lunch, and leave your phone in your pocket.
Where should I go for a first solo trip? Somewhere close, somewhere you speak the language or English works, and somewhere you can walk. Four days is plenty.
