Stop Overplanning: How to Make Your Travels More Enjoyable
We’ve all been there. You touch down in a new city with an itinerary so tightly packed it looks more like a military operation than a holiday. Sunrise at the viewpoint. Breakfast at the most Instagrammed café in town. A three-hour walking tour before lunch. Two museums, a market, and a sunset cruise — all before dinner.
By day three, you’re running on caffeine, power bars, and pure stubbornness. Sure, you’ve seen everything, but have you actually experienced anything?
In the age of travel FOMO and “top 10 must-see” lists (and yes, I know we too are guilty of these!), it’s easy to treat a trip like a box-ticking exercise. But here’s the truth: slowing down, doing less, and letting go of the plan can make your travels infinitely more enjoyable — and often more memorable.
The Modern Travel Trap
Somewhere along the way, travel stopped being about simply going somewhere — and started feeling like a competition. Social media feeds drip-feed us endless lists of “must-sees” and “unmissables”, and before we’ve even booked the flight, our itinerary is bulging at the seams.
The logic seems harmless enough: “I’m here once, so I need to make the most of it.” But “making the most of it” often translates into a frantic rush from one attraction to the next, barely catching your breath, let alone a meaningful moment. You spend more time scanning Google Maps than soaking in the view. Meals get downgraded to quick snacks grabbed between activities, and those quiet, serendipitous encounters — the ones that stay with you for years — simply don’t fit into the schedule.
It’s the paradox of modern travel: the more we cram in, the less we truly experience. And the pressure isn’t just self-imposed — it’s fuelled by the fear of missing out and the belief that a “successful” trip is one that leaves you completely spent.
What Happens When You Overplan
At first, overplanning feels productive. You’ve got colour-coded maps, confirmation emails neatly stored in your inbox, and a schedule so precise it would impress an air traffic controller. You know exactly what you’re doing at 9:15 a.m. on Thursday — and that certainty feels like control.
But once you’re on the ground, reality has a way of pulling rank. Trains run late. That “quick” museum visit takes twice as long because you actually want to read the plaques. The weather turns. A long lunch stretches into an afternoon. And suddenly, your perfectly crafted timetable starts unravelling — leaving you stressed instead of savouring the moment.
Physically, the pace catches up with you fast. Early starts, long walks, and non-stop sightseeing chip away at your energy reserves. Add jet lag, climate differences, and constant navigation, and by day three you’re operating on autopilot. Your feet ache, your camera roll is full, but the memories are hazy because you never truly paused to enjoy them.
Mentally, overplanning keeps you locked in “what’s next” mode. Even while standing in front of something spectacular, your brain is running calculations: How long until the next tour starts? Will we have time to grab lunch? Are we cutting it too close? That constant forward focus robs you of the here and now.
And perhaps most damaging of all, a crammed itinerary leaves no oxygen for spontaneity. You pass a lively street market but can’t stop because you’re late for a guided tour. You skip that quiet little bookshop because it’s “not on the plan.” The best travel memories — the ones you retell years later — are rarely the ones you scheduled down to the minute.
Natural History Museum, London.
The Beauty of Doing Less
When you stop trying to see everything, you give yourself the space to truly experience something. A slower pace allows you to sink into a destination, rather than skim across the surface.
Doing less changes the way you notice things. Instead of rushing to the next landmark, you might linger in a local café, watching the ebb and flow of daily life. You hear the way people greet one another, you catch snippets of conversation, you notice the small details — the uneven cobblestones, the faded paint on a shutter, the way the late afternoon light hits a particular corner. These aren’t the things you find in a guidebook, but they’re the ones you remember.
It also gives your trip a rhythm that feels more human. Not every day has to be an action-packed adventure; some can be about rest, or about exploring just one part of a city in depth. That breathing space lets the experience settle in, instead of blending into a blur of activities.
There’s a practical benefit, too. A looser itinerary means you can pivot when something unexpected comes along — whether that’s a pop-up market you stumble across, a local festival you didn’t know about, or an invitation to join fellow travellers on a spur-of-the-moment hike. Without a rigid schedule, you have the freedom to say yes.
And more often than not, it’s those unscripted moments that become the highlights of a trip. The tiny restaurant you found by chance that served the best meal you’ve ever had. The conversation with a stranger that turned into a lifelong friendship. The sunset you watched from a random street because you happened to be there at the right time.
Doing less doesn’t mean doing nothing. It means leaving room for the trip to surprise you — and that’s when travel really starts to work its magic.
How to Build a Flexible Itinerary
Travelling without a plan might sound liberating, but in practice, most of us prefer at least some structure. The trick is to create a framework that gives your trip direction without locking you into a rigid timetable.
Start by identifying your “anchor” experiences — the non-negotiables you know you want to do. This could be visiting a particular museum, hiking a certain trail, or eating at a renowned restaurant. Spread these anchors across your itinerary so you’re not packing too much into consecutive days. This creates natural breathing space between your bigger activities.
Next, protect your unplanned time. Block out entire mornings, afternoons, or even full days with nothing scheduled. These blank spaces aren’t wasted — they’re your chance to follow your curiosity, explore a neighbourhood at your own pace, or simply take a long lunch without worrying about the clock.
Be realistic about how long things take. Travel times, queues, and the occasional wrong turn can eat into your day faster than you think. Build in buffers so you’re not constantly in a race against time.
Finally, think twice before pre-booking everything. Securing popular tours or key accommodations makes sense, but the more you lock in, the less flexibility you have to follow those in-the-moment opportunities — like a last-minute day trip, joining new friends for dinner, or catching a live band you just discovered.
By blending planned highlights with intentional gaps, you create a trip that’s both memorable and adaptable — one that leaves space for the unexpected without sacrificing the experiences you came for.
Vegueta (Old Town), Grand Canaria.
World Locals Tip
If you’re ready to swap a jam-packed schedule for a more rewarding pace, here are a few quick ways to keep your itinerary light and flexible:
Plan one major thing per day — give it the time and attention it deserves, and let the rest of the day unfold naturally.
Leave room for surprises — the best moments often aren’t on the list.
Build in buffer time — so delays, detours, and long lunches don’t throw you off.
Stay in one place longer — fewer check-ins and check-outs mean more time to actually enjoy where you are.
Don’t be afraid to skip something — if you’re exhausted or something better comes along, it’s okay to let go of a plan.
Travel isn’t a competition to see who can fit the most into the shortest amount of time. It’s about connection — with places, with people, and with yourself. When you give up the need to do it all, you make space for the kind of moments that can’t be scheduled: the laughter over a shared meal, the quiet beauty of an empty street at dawn, the unexpected friendship formed on a park bench.
A lighter itinerary doesn’t mean you’ll see less; it means you’ll see more of what actually matters. You’ll notice the details, feel the rhythm of a place, and return home with stories that aren’t just a list of attractions, but memories woven from experiences you truly lived.
So next time you’re planning a trip, resist the urge to overfill your days. Choose a few things you can’t wait to do, leave the rest open, and let the journey surprise you. After all, the best adventures rarely happen on a timetable.
