How to Plan a Travel Itinerary (Without Turning Your Holiday Into a Military Operation)

I don’t know about you, but whenever I book a trip, I go through the same cycle: excitement → panic → endless Googling. Flights and hotels are the easy bit. The harder question is, what am I actually going to do once I get there? That’s when the dreaded “itinerary” comes into play.

Now, some people love planning every second — colour-coded spreadsheets, alarms set for sightseeing slots, even pre-booked lunch breaks (yes, I know someone who does this). Others just rock up and hope for the best. I’ve tried both, and honestly, the sweet spot is somewhere in between. Enough structure so you don’t waste half the trip arguing about whether to see a museum or grab a beer… but with enough freedom that you can stumble into those brilliant, unexpected moments.

So, how do you put together a travel itinerary without going mad? Here’s what I’ve learned (the hard way).

Start With the Fun Stuff

Forget timetables for a sec. Just dream a little. I usually start by scribbling a list of everything that sounds good — famous landmarks, local food, quirky spots I’ve seen on TikTok, that bakery my mate swore was “life-changing.” Don’t filter yet. Half of it might not make the cut, but it’s easier to whittle down than to sit there staring at a blank page.

Side note: always ask someone who’s been before. Friends love to give recommendations, and half the time they’ll mention little gems you’d never find on Google.

Maps Are Your Best Mate

Here’s the mistake I made in Rome: one day I planned to see the Colosseum, then nip over to the Vatican, and later “just pop” to the Spanish Steps. Google Maps quickly revealed this was insane. Everything looks close on paper until you’re melting in 30-degree heat with dodgy sandals.

Plot your must-dos on a map. Then group things together by area. You’ll save time, energy, and arguments.

Don’t Be Too Greedy With Time

I once tried to do six attractions in a single day in Paris. Spoiler: we managed two, and ended up knackered, hangry, and slightly murderous. The truth is, between queues, transport, food stops, and the occasional wrong turn, you can’t do it all.

A good rule is one big thing per day — like a tour, a museum, or a big hike — plus one or two smaller things if you’ve got the energy. The rest of the time, just wander. Honestly, wandering is often the best bit.

Factor in the “Boring” Stuff

Nobody likes to admit it, but travel isn’t just sightseeing. You’ve got airport transfers, hotel check-ins, food breaks, naps (yes, naps are sacred on holiday). If you don’t allow for them, your whole plan collapses.

And please, for the love of snacks, factor in meals. Nothing ruins a holiday like hanger. I now write “lunch?” in my itinerary just as a reminder to stop before I get snappy.

Leave Room for Spontaneity

The best travel moments are rarely the ones you plan. Like the random street festival we stumbled across in Barcelona, or the jazz band in a tiny New Orleans bar we ducked into to avoid the rain. If I’d had a rigid plan, we’d have missed those.

So I always leave space — a free morning, an unscheduled evening. If nothing pops up, fine, you can always go back to the list. But often, those gaps end up being the highlight.

Keep It Varied

It’s tempting to lump similar things together, but honestly, three museum days in a row is exhausting. I try to alternate: sightseeing, then something relaxed. Outdoors, then indoors. Food-focused one day, cultural the next. It keeps the trip from blending into one long blur.

Get Everyone Involved

If you’re travelling with mates, partners, or family, don’t hog the planning. Otherwise, you end up being the tour guide (and the person who gets blamed when it rains). Everyone should pick one “must-do” thing. That way the trip feels fair, and you don’t spend half the time in sulky silence.

Tech Helps (But Print a Backup)

Apps are brilliant. Google Maps for pins, TripIt for bookings, even Notes on your phone works. But batteries die, Wi-Fi drops, and data roaming costs a fortune if you forget to switch it off. I learned this the hard way in Amsterdam when my phone died and I couldn’t find the blooming hotel.

Now, I print one scrappy sheet with the essentials: hotel address, check-in times, a couple of key bookings. Old-school, but fool-proof.

A Real-Life Example

When I went to Lisbon, my first draft itinerary was chaos: all the viewpoints, all the trams, all the castles. On paper, brilliant. In reality, impossible. So I slimmed it down:

Day one: explore the old town, eat custard tarts, early night.
Day two: tram ride, castle, wander along the waterfront.
Day three: day trip to Sintra.
Day four: brunch, market, flight home.

And it worked. Enough structure to hit the highlights, but plenty of space for random discoveries (like the rooftop bar we found because we got lost).

Final Thoughts: How to Plan a Travel Itinerary

At the end of the day, a travel itinerary isn’t about squeezing in every single thing TripAdvisor says is “unmissable.” It’s about making your trip smoother, with just enough planning that you don’t waste time bickering, but not so much that you feel like you’re on a school timetable.

So jot down your dream list, group it sensibly, be realistic, and — this is key — leave wiggle room. Because the truth is, some of the best holiday memories aren’t planned at all.

And if all else fails, just make sure you know where your hotel is, where to get food, and how to get home. The rest tends to fall into place.