Plans, Panics, and Passport Stamps: How to Travel Like You Sort of Know What You’re Doing

There’s something almost poetic about boarding a flight with a passport in one hand and dreams of adventure in the other. Whether it’s a spontaneous weekend jaunt to the Cotswolds or a two-week dive into the rich cultures of Southeast Asia, a well-crafted travel itinerary is your behind-the-scenes MVP. It’s the difference between wandering aimlessly and wandering intentionally. And trust me, after years on the road, I’ve learned a thing or two about striking that perfect balance between structure and serendipity.

So, whether you’re plotting a swift city break or an international journey, here’s my take on how to craft an itinerary that’s flexible, fulfilling, and fabulously efficient.

Start with Purpose, Not Just Places. Before diving into Google Maps or Pinterest boards, ask yourself: What do I want from this trip? Are you chasing relaxation, culture, adventure, cuisine, or a bit of everything?

For short trips, especially weekend getaways, it’s crucial to have a clear focus. You won’t have time to “do it all”—and you shouldn’t try. For longer international escapes, define a theme or feeling you want the trip to evoke. This will anchor your plans and keep you from cramming your days with activities that look good on Instagram but don’t feed your soul.

Mind Your Time Zones and Transit Realities. This sounds basic, but you’d be surprised how many travellers overlook the impact of transit time. For international trips, factor in jet lag recovery, visa queues, and airport transfers. A 7-day holiday can quickly become a 5-day holiday if you don’t build in those travel buffers.

For short trips, avoid overambitious travel distances. If you’ve only got 48 hours, don’t waste half of it on trains, buses, or traffic jams. Choose destinations that are logistically kind—think direct flights, convenient public transport, or compact walkable cities.

Build Around Anchors, Not Every Hour. Your itinerary isn’t a military schedule. You don’t need to know what you’ll be doing at 11:42 AM on Day 3. Instead, build around anchors—those 1-2 major activities or experiences that define each day.

In London, for instance, your anchor might be a matinee at the Globe Theatre. In Kyoto, it could be a sunrise visit to Fushimi Inari. Plan those must-dos, then let the rest of the day breathe. This gives you flexibility for spontaneous detours (and trust me, those often become the best bits).

Think in Clusters, Not Chaos. Especially when abroad, geography is your best friend. Use map clustering to group your activities by location. No one wants to zig-zag across Paris five times in one day because they forgot the Eiffel Tower and Musée d'Orsay are on the same side of the river.

Apps like Google Maps or Sygic Travel are brilliant for this. Drop your pins, then look for natural neighbourhood groupings—Old Towns, museum quarters, foodie streets. Less transit = more enjoyment.

Mix the Majestic with the Mundane. Yes, you’ll want to see the Colosseum in Rome. But don’t forget to leave room for the everyday joys—the morning café that becomes your ritual, the small talk with a local shopkeeper, the sunset you catch by accident because you took a wrong turn.

Great itineraries blend highlights with hidden gems. I like to plan for about 60% structure and leave the remaining 40% for serendipity. Trust your instincts, and don’t be afraid to veer off course.

Prioritise Your Energy, Not Just Your Bucket List. Here’s something I’ve learned the hard way: burnout isn’t reserved for office life. Travel fatigue is real. Just because your itinerary can fit five museums and three markets in one day doesn’t mean it should.

When planning, consider your natural rhythms. Are you a morning explorer or a night owl? Do you thrive on constant movement or need moments of stillness? Design your days to suit you, not someone else’s blog post or TikTok reel.

Tech That Travels Well. A few of my favourite itinerary tools:

Google My Maps – Great for creating customised maps.
TripIt – Automatically pulls confirmation emails and builds a neat itinerary.
Rome2Rio – Brilliant for working out how to get from A to B around the globe.
Notion or Evernote – If you’re a planner like me, these are perfect for trip journals, packing lists, and day-to-day ideas.

Old-school tip? Always keep a printed version of your itinerary and accommodation details. Tech fails; paper doesn’t.

Always, Always Leave Room for Magic. If I could give you just one piece of advice: Don’t plan your way out of the very thing you travelled for—freedom.

Some of my favourite memories have come from the unscripted moments: dancing with strangers at a Lisbon street festival, being invited to a family dinner in Morocco, or discovering an unmarked hiking trail in New Zealand.

Your itinerary should guide you, not chain you. Leave the cracks wide enough for magic to sneak in.

Travel itineraries aren’t about ticking boxes—they’re about telling a story. And every good story needs rhythm, surprises, and a bit of heart. So whether you’re off for 72 hours or three weeks, let your plans serve the moment—not the other way round.

Because in the end, it’s not the perfect plan you’ll remember—it’s how the place made you feel.

Now go write your next adventure.