Okay, so I’ve been planning this HUGE multi-country trip through Europe and Southeast Asia. Figuring out the best way to string all these places together was giving me a major headache. I mean, seriously, juggling flights, trains, visas, and figuring out what to actually do in each place? Forget about it!

So, I started like anyone else would: Google. I searched for, like, “best itinerary builder multi-country,” and a bunch of stuff popped up. Most of them were just travel agency websites trying to sell me pre-packaged tours, which is NOT what I wanted. I wanted full control, baby!
My Experiment Begins
I decided to just dive in and try a few different tools. My process was very scientific (not really):
- First up, spreadsheets. Yeah, good old Google Sheets. I figured I could just make columns for dates, cities, activities, transportation, costs, etc. It got messy, fast. It’s good for budgeting, I guess, but not so great for visualizing the flow of the trip.
- Then I tried some dedicated travel apps. One promised to be “AI-powered” and build an itinerary for me. I told the application where I want to go, when I want to go, and the budget * sounded cool, but the results were super generic. It suggested, like, the Eiffel Tower in Paris. No kidding! It felt like it was just pulling random top-10 lists from the internet.
- I even messed around with some mind-mapping tools. The idea was to visually connect different places and ideas. It was kind of fun, but ultimately not very practical for the nitty-gritty details.
The Turning Point and Finally Realized
I nearly gave up and start drawing it on my notebook. I just opened the new blank paper, and writing down my start day and end day on the top of the paper. And I started to write every city with possible dates I planned to go between them.
And I found out this is the best way to plan my route! Finally, I listed the cities, dates, and possible transportation ways between each place, and I drew the routes, lines, and arrows on the paper to make it more clearly!
After that, I just use a very simple online document editor, starting to write down the details of the places I am going to visit, copying and pasting some information from travel blogs. And I add some notes about Visa information, or some tips that remind me to buy tickets in advance.

Everything becomes clear and I know clearly when, where, and how I am gonna make my fantastic multiple-country vacation!