You’ve made the decision to go. You’ve figured out why. Now comes the fun part: shaping the blob of potential in your hands into an actual trip.

Step One–The Decision

Step Two–The Reason

Step Three–The Itinerary

Step Four–The Budget

Step Five–The Booking

Step Six–The Pack

Step Seven–The Trip

The itinerary is my favorite part of planning. I love sitting down with my calendar and all my notes from my research on our destination and imagining where we’ll be and what we’ll be doing/seeing/eating on a given day. It fuels my excitement for an upcoming trip and helps motivate me to get me through those not-so-great days by knowing what’s just around the corner.

It’s not only an exercise in daydreaming though: having a good, solid itinerary roughed out–even if you end up not sticking to it, as is a likely scenario–will help down the line when it comes to having to figure out what your budget will look like and what sort of clothes/gear you’ll need to bring. This is especially true if you’re planning on booking group tours, if you’re an adventure junkie who might be looking at activities like long treks or camping, or if you just like to have a schedule.

It’s at this point that I like to create a document and/or spreadsheet using Google Drive for the itinerary. That way I can share it easily with Jeff and other people who want to know our itinerary, like our parents or other friends interested in a similar destination. It’s also nice to be able to access it from anywhere, add or delete information as necessary, and not have to worry about keeping track of loose sheets of paper. A normal Word document or Excel sheet shared via Dropbox or other cloud services works just as well. I also totally understand the draw of handwriting if that’s what works for you; just try to keep everything for one trip in the same place, like a dedicated notebook or folder.

It’s a Date

The first thing I do when I’m roughing out an itinerary is to open my calendar up to the general time we’ve decided to go and look at specific dates for departure and return. The more flexible you can be with your dates, the better, especially if you’ll be flying–try to avoid flying during times when business fliers will be active like Fridays and Sundays, since ticket prices tend to be most expensive then. I tend to stick to the middle of the week–Tuesday through Thursday–for my flights, but if you are leaving on the weekend, try to plan for during the day on Saturday. The same sort of logic applies to other mass transport like night buses or trains, but if you’re driving you’ll only really need to worry about rush hour.

For our upcoming trip Taiwan, I narrowed it down to two possible days each for departure and return, leaving the decision until when we actually decided to book our plane tickets later on down the line. To remind myself, I used pencil to write “Taiwan?” on each day in my calendar, and then typed in both dates into the Google document.

So Much to Do, So Much to See

Once I’ve narrowed down my dates, I count to see how many days I’ll have to enjoy my destination. I never count the dates scheduled for flights or heavy travel: I know that I’ll want whatever time is leftover on those days to recover from or prepare for the exertion of getting there. Some people might be perfectly fine dropping their bag off at their place of accommodation and heading out that first afternoon or night they get in, or squeezing in one last museum trip under the wire before dashing off to catch their return flight–but I am not that person. I don’t like to rush–rushing means forgotten passports, missed flights, ceiling-shattering stress levels, and a generally unhappy experience for everyone involved.

For single-destination trips (like a long weekend in Tokyo), I just make a bulleted list of stuff I want to do during that time in no particular order. If I’m feeling especially organized I’ll rank them in order of “I have to do this or I’ll LITERALLY DIE” to “meh, either way.” If there are things we’ve booked in advanced, like when we visited the Ghibli museum, I’ll list those first and in chronological order, followed by the other activities that aren’t set in stone yet.

For multiple destinations trips, like with Taiwan, I’ll group things based on when we change location. The first order of bullets will be the city names (Kaohsiung, Taipei), with the second order of bullets coming after that a list of possible things to do.

Multiple destinations also offer a tricky question: how much time will you spend where? It all depends on what you think you’ll want to do, which is why it pays to really understand your reasons for the trip right off the bat. For example, the only thing I want to do in Taichung is to drink bubble tea, so that’s going to be an afternoon stop over on the way from Kaohsiung to Taipei in the middle of our trip instead of a few days’ stay.

No matter single or multiple destination, I try to keep my list down to one to two activities per travel-free day. I’ve mentioned before how it’s easy to get overwhelmed by packing too much in to too little time, and I think that this is a good general rule to follow–at least for my travel style. Inevitably though, I start out listing down twice that much and then refining it as my planning progresses.

Keep It Fluid

As with everything, if it isn’t booked and paid for, it isn’t set in stone. At this point you haven’t booked anything yet, which means anything is possible. The rough draft of your itinerary at this stage is just a way of getting a clearer picture of the type of trip you’re getting yourself into. Besides, chances are that your actual trip will look very little like your original itinerary, especially if you don’t end up booking anything other than the flights.

So why make an itinerary at all if it’s just gonna change? Well, the most important reason is for budgeting purposes. By keeping track of everything I want to do during the trip, it’s easier for me to get an idea of how much I might be spending, how much I still need to save, and where I might need to cut some things if it makes the trip too expensive. It also helps me figure out what I’ll need to bring–do I really need my boots if the only “hiking” we’ll be doing is up the tallest hill outside of the city?

For me, though, it’s mostly about that gratifying feeling of fantasy becoming reality–the more detailed my itinerary gets as I add in dates and prices and other information, the more excited I get.

Your Turn!

What’s your itinerary looking like for your trip? Are you gonna be in one place the whole time, or several?