Confessions of an Overplanner: How I Prepare for an International Trip
If you've ever packed your suitcase the night before an international flight and somehow made it to your destination with everything you needed, I genuinely admire you.
I am not that person.
I'm a planner by nature, and when it comes to international travel, I probably put more thought into the process than most people. Even before I became a travel advisor, I was the person creating detailed trip booklets and handing them out to my fellow travelers. Maps, reservation details, packing lists, daily itineraries—you name it, I probably color-coded it.
Some people might call it overthinking (or other more…colorful terms). I prefer to think of it as setting myself up for a smoother, less stressful adventure.
As I write this, I'm preparing for a winter trip to Norway—a destination I've been to before but have been longing to return to. While every destination requires a slightly different approach, my preparation process is pretty consistent no matter where I'm headed.
One thing I always want to be transparent about is that I'm still building my own collection of passport stamps. Although I'm a travel advisor, I haven't spent decades traveling the globe full-time. In fact, a lot of clients who come to me have actually been to more places than I have! Instead, I've spent years putting my natural planning and organizational skills to work—researching destinations, designing personalized itineraries, learning from experienced travelers, and helping clients create vacations that fit their travel style. Every trip I take becomes another opportunity to learn something new and bring that knowledge back to the people who trust me to plan theirs.
Here's what my planning process looks like.
Step 1: Research Beyond the "Top 10 Things to Do"
I love seeing iconic things.
I don’t love getting there too late for the shuttles, after the line is closed, or planning for 60F temperatures when it’s actually 85F.
I want to know:
What is the weather actually like?
What time does the sun rise and set?
Are restaurants open late?
What local customs should I know?
How easy is public transportation?
Are there hidden gems locals recommend?
For Norway, that has meant researching winter road conditions, daylight hours, and the best opportunities to experience the Northern Lights.
When I create itineraries for my clients, I include this information for each trip. I make sure you always have a packing list of appropriate clothes for the weather, tips on local customs and manners, currency and exchange information, and a list of other things to do if I want to change my plans once I get there.
Step 2: Make Sure My Documents Are Ready
Long before I start packing, I check:
Passport expiration date
Entry requirements
Travel insurance
Flight confirmations
Hotel reservations
Transportation plans
I also keep digital copies of important documents stored securely in case I ever need them. I keep them in a locked folder on my phone to keep it secure.
Step 3: Build a Flexible Itinerary
I love having a plan—but I don't schedule every minute.
I usually identify a few "must-do" experiences, then leave room for spontaneous discoveries. Some of my favorite travel memories have happened because I allowed myself the flexibility to wander.
For me personally, I intentionally book about 10% of my trip as “Free Days” on my schedule. That means this will be a day that I have open to explore things that I may have seen and wanted to do when I got there or just relax and soak in the sights. I will usually put a couple suggestions of restaurants, places to go or things to do, but I don’t create reservations or put anything in until I’m at my destination.
This worked out well for me one year when I did a snowmobiling excursion early in my trip and loved it so much, I wanted to do it again and had a day open to book it.
Step 4: Think About Packing Early
Packing isn't just about fitting everything into a suitcase.
For Norway in winter, I'm thinking layers, waterproof boots, gloves, camera gear, charging cables, medications, and all the little things that make cold-weather travel more comfortable. For summer trips, sunscreen, hats, and cool clothes that I feel comfortable in are key.
Starting early also helps me realize if I'm missing something before it's too late to order it.
Again, this is something that I create for my clients when they book with me; a personalized spreadsheet of everything you need to pack that you can check off as you go.
Step 5: Prepare My Phone
Before I leave, I download:
Offline maps
Airline apps
Hotel information
Translation tools
Important reservation confirmations
Local public transportation apps
I also make sure I have a plan for staying connected, whether that's an international phone plan or an eSIM.
If you book through me, I’ll let you know the best way to get around in the local transit routes - or book any private transfers if you want even less stress.
Step 6: Expect Something to Go Wrong
This might sound pessimistic, but I actually find it reassuring.
Flights get delayed.
Weather changes.
Plans shift.
Instead of assuming everything will go perfectly, I try to build flexibility into my itinerary and remember that sometimes the unexpected moments become the stories we tell for years afterward.
The last time I went to Norway, I had a very tight connection in Oslo that I knew might be a concern. Sure enough, my inbound flight was delayed, I had to collect and recheck my luggage, clear customs, and somehow make my next flight. Running through the Oslo airport in snow boots and parka at 3am was…..an experience. On the other hand, it’s something my friends and I laugh and reminisce about now.
The Best Part Is Still Ahead
There are three separate parts of any trip we take (especially the ones that mean a lot to us).
Planning the trip.
Experiencing the trip.
Reliving it afterwards through photos, shared stories, and a lifetime of memories.
Planning is one of my favorite parts of traveling because it builds anticipation. Every article I read, every map I study, and every reservation I make brings the adventure one step closer.
As I continue preparing for Norway this winter, I'm sure I'll learn a few new lessons along the way—and I'll be excited to share them here.
After all, travel isn't about being a perfect traveler. It's about staying curious, being prepared, and embracing whatever adventure comes next. And you need someone to help you along the way, you know who to call.
Yours in flight,
Tianna
