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I have never been very good at travelling according to a plan. Sometimes I land somewhere and don’t really know where I’ll be the next day. Sometimes I see a picture, hear a story, meet someone, and just decide that’s where I want to go next. I quite like that uncertainty, actually. There’s something enjoyable about not knowing exactly what the next few days are going to look like.

I’m conscious, writing this, that being able to travel this loosely is a fairly privileged position to be in, and not something everyone has the time, money or freedom to do. I don’t take that for granted. What I’m really writing about here isn’t the travel itself, it’s more a way of approaching a day, wherever you happen to be, that I think holds up even on a much smaller trip.

I remember landing in Krabi once without much of an agenda. Somewhere along the way I saw a picture of a place that looked beautiful, so I changed direction and headed for Koh Samui instead. There wasn’t really more to the decision than that, if I’m honest. I liked the picture, so I went. It sounds slightly irresponsible when I put it that way, and maybe it is, but some of my favourite travel experiences have started with decisions that weren’t particularly well thought through. You see something interesting, you follow it, and before you know it you’re somewhere you hadn’t planned to be.

Something similar happened, in a much luckier way than I probably deserved, during the 2018 World Cup. I’d decided I wanted to watch the matches from the quarter-finals onwards somewhere other than a hotel room, so I just followed the fixtures, ending up in whichever country had a team playing, watching from the main squares alongside the local supporters. It sounds grander than it was. Most of it was just standing in a crowd with a phone battery running low. It took me through Croatia, Belgium, Italy and France, and while I always knew roughly where I had to be for the next match, I had no real idea what I’d be doing in between. That was most of the fun of it, honestly, not the countries themselves so much as not knowing what the in-between days would look like.

I’ve done much the same thing closer to home too. Driven to Ooty simply to make it there in time for breakfast. Started early for Goa because I wanted to catch the sunset. Neither of those makes a huge amount of sense if you stop and think about it, there are far easier ways to have breakfast than driving all the way to Ooty, and Goa will still have another sunset tomorrow. But sometimes you just want to go, and the destination isn’t really the point. Sometimes you go because you want a particular sunset, or breakfast in a particular place, or just because a road looks like it needs driving.

The same thing happens abroad, and this is probably where it shows up the most. Some of my best days in cities like Istanbul and Budapest were days with no plan at all, just moving from one bar to the next, asking people I’d met where their favourite spot was. Instead of pulling up a list of the best bars in the city, I’d rather just ask someone who actually lives there. Where do you go? It’s a simple question, but it tends to take you somewhere you’d never have found on your own. Sometimes the person comes along. Sometimes they hand you another recommendation, and someone at that next bar hands you a third. One place leads to another, and the evening quietly turns into the itinerary. You’re not working through a list of attractions at that point, you’re just letting the people you happen to meet show you a small slice of their city.

I remember meeting a musician at a bar on one of these evenings and getting pulled into a long conversation I hadn’t planned on. I wasn’t out looking for some meaningful local experience that night. I’d just gone out for a drink. But that’s usually the kind of thing I end up remembering. You can travel a few thousand kilometres to stand in front of a famous landmark and still find that your strongest memory from the whole trip is a conversation with a stranger at a bar.

There have been a few other trips shaped the same way, not because I set out looking for stories to tell, but because that’s just how the days tended to go once I stopped scheduling them. A boat to Venice I hadn’t specifically planned to take. A ferry to another island near Mykonos because it seemed like the thing to do that afternoon. Walking into a market because it looked interesting from the street. None of it needed to be on an itinerary to justify itself, and none of it was particularly remarkable at the time either, it just added up to a nice way of spending a day.

I like walking around cities without knowing exactly where I’m going, sometimes for hours at a stretch. I’ll find a small restaurant, notice some graffiti, sit at a bar on a street corner, or just watch people finishing their evenings. Cities at night especially, when things quiet down and you start seeing a different version of the place. When you have somewhere specific to be, you tend to notice only what’s between you and that destination. When you don’t have anywhere particular to go, everything around you becomes a reason to keep walking. A shop you’d normally walk straight past suddenly looks worth stepping into. A restaurant catches your eye because it’s full of locals rather than tourists. You hear music somewhere down the street and go find it. And sometimes, in the middle of all that, you meet someone. That’s probably the thing I like most about travelling without an itinerary. There’s room left over for people.

We’ve all become quite good at planning holidays these days. Hotels researched, restaurants shortlisted, reviews read, entire days mapped out almost to the hour. There’s nothing wrong with that, to be fair, some trips genuinely need it. Travelling with children, working with limited time, having somewhere important to be, an itinerary makes life considerably easier in those situations. But I think we sometimes plan so thoroughly that there’s very little room left for discovery. If you already know where you’ll be at ten in the morning, where you’re having lunch, which museum comes after, and what time you have to leave, what happens on the day you actually find somewhere you love? You leave anyway, because the next thing is already booked.

I’ve never been particularly drawn to bucket-list travel either. If I’m in Paris and don’t get around to the Eiffel Tower, I don’t walk away feeling like I failed to experience the city properly. Maybe I’ll see it next time. Maybe I won’t. I might find a restaurant I like instead, wander into a bookshop, spend an hour in a gallery I’d never heard of, or just sit somewhere and watch people go by. The Eiffel Tower isn’t going anywhere. Neither, presumably, am I, at least not for a while.

For me, travel has always been as much about simply being somewhere as it is about seeing something specific. I don’t need to come home with a photograph of every landmark on the list. Often I’m perfectly happy just existing in a city for a few days and letting the day decide itself.

Part of this probably has something to do with how much of my working life has gone the other way entirely. I started out in a law firm, moved into investment banking, and later into retail, and across all three, planning, preparation, analysis, knowing exactly what comes next, has been most of the job. Businesses need plans. Teams need direction. Projects have deadlines that don’t move just because you’d rather they did. Important decisions can’t really be left to chance, not in that world. Maybe that’s exactly why the opposite feels so good on holiday. There’s something genuinely refreshing about waking up with no fixed idea of what the day will look like. Deciding where to eat because you’re hungry right then, not because you booked a table three weeks ago. Staying somewhere longer because you like it, leaving because you don’t, changing direction entirely because something caught your eye on the way to somewhere else. Taking a ferry simply because there happened to be a ferry. Driving to Ooty for breakfast, or Goa for a sunset, or asking a stranger where they actually drink and then going there yourself. None of it amounts to any great act of adventure, and I’d rather it not come across that way. They’re small, fairly ordinary decisions, most of them, the kind anyone can make on a weekend two hours from home just as easily as somewhere further away. That might be exactly why they’re enjoyable, and probably why they’re worth writing about at all.

I sometimes wonder what it actually is that makes me travel this way. Some of it might be a small dopamine hit, the little rush of deciding something on the spot and following it through. Some of it might be plain escapism, a temporary way of stepping outside the routines and responsibilities that fill up the rest of the year. Or maybe it’s simpler than either of those, just the pleasure of being in the moment without needing to know what the next street looks like, or where the next drink will happen, or who you might run into before the night’s over. I don’t think there has to be a deeper explanation than that. Sometimes you just go with the flow because it feels better than the alternative.

We spend a fair amount of our lives trying to control what happens next, the next meeting, the next quarter, the next target, sometimes even the next holiday. Even our free time gets organised around what we’re supposed to accomplish with it. Travelling without a plan gives me a break from that particular habit, though it isn’t the same as being careless about it. I still book flights and hotels when I need to. I still check ferry timings. Getting lost in an unfamiliar city is a lot more fun when you’ve got enough cash on you and a charged phone in your pocket. It mostly just means leaving some space open, for a wrong turn, a recommendation, a conversation, a market you didn’t know was there, a sunset that was never on the itinerary to begin with.

When everything is planned, you already know what you’re going to see. When you leave part of the day open, you get to see things you’d never have known to look for in the first place. A plan tells you where you’re going. Travelling without one tends to make you notice where you actually are.

Looking back, most of my favourite travel memories aren’t the places I deliberately set out to see. They’re the places I stumbled into, the people I ended up talking to, the roads I took because they looked interesting, the bar someone recommended, the market I wandered into by accident, the sunset I happened to catch without planning for it. Maybe that’s the actual pleasure in all of this, not needing to know what comes next, just being somewhere, staying curious, and seeing what happens. The best journeys, I’ve come to think, are usually the ones where you leave a little room for the journey to still surprise you.

Related reading: If this resonated, you might also like Why Do Indians Behave Differently Abroad? Thoughts on Travel Etiquette.