Trip Planning 101

Updated: Jan 8, 2019

New to traveling or trying to figure out a systematic and efficient way to travel? Here's how I do it and what has really worked for me!


These examples were taken from my Chicago trip, which I planned and went with @betweenballoons in the summer of 2018.


Even before I have booked my flights, I'm researching different places to eat and visit. There are a lot of resources online to figure out where to go and what to eat. Instagram is handy, just search up the place you want to visit and look for what's popular. Yelp and a simple Google search is helpful for domestic travels. Asia has Open Rice, which is their Yelp equivalent. Youtube also has a lot of travel and local vloggers that can help. Of course, these are all suggestions and just what's most known. You know yourself best and what you enjoy during vacation. A lot of plans also shift when I arrive to my destination and hear from locals about what they like or what has changed recently.


1. Map it out

As I'm going through this "research" phase, I will create a Google Maps and start bookmarking everything I have a slight interest in. The idea is to cast a wide net and just poke around for anything remotely attractive. It also helps you get to know the city on paper, you can see where everything centralizes around and visualize how to best navigate. I use these points to decide where I'm going to stay too.

There is a satisfaction in color coding everything

2. Itinerary

Here comes my inner type A. From my experience, it's most worth my time if I have a fairly flushed out plan going into the trip, and I always allow myself flexibility. If I don't get to something, it's totally fine. It's just an easier way for my mind to organize where I'm going and what I'm doing.

So based on the map from Step 1, I start thinking about the days and grouping restaurants and sites together. It just falls into a natural pattern of which direction I'll be headed to on that day.

This is especially helpful if you're going with a group with people arriving on different days and people prioritizing things differently. People know ahead of time where everyone will be and what they want to opt out of and be a part of. It makes traveling in a group much easier because you don't feel the need to follow so tightly with each other. (Or maybe that's just the introvert in me who doesn't want to be with people all the time and always trying to sneak moments away for myself.)

For all the visual learners out there

3. Book restaurant

This next one is so important. Getting dinner reservations is such a crucial part because the restaurants that I'm traveling for usually have a competitive reservation queue. Some times I'll already have restaurants booked before I even have a place to stay #priorities So even though this is listed as Step 3, it definitely goes back and forth with the itinerary. Most things in my schedule, like sightseeing and casual eats, are flexible but these are concrete. Even if it's domestic travels, I try to plan about two months in advanced to ensure I get reservations properly. (I'm sooooo spontaneous, I know).

Be mindful of the time zone tickets are released in

From here on out it's just adjusting the plans and continuing to research what I like. I hope you found these steps helpful and can use it on your own travels. If you have any questions, feel free to contact me or shoot me a message on Instagram.