How to Easily Plan a Killer Trip

The other day I was walking through the travel section at the Boulder bookstore and found myself overwhelmed. I was thumbing through a Hawaii travel guide hoping to get some tips for our trip in August, but instead I found myself drowning in all the options and restaurants and hikes and do’s and don’ts and ahh!! I snapped the book shut and put it back on the shelf.

See, I’ve never been much of a planner. The whole thing where people have strict itineraries for their trips and actually follow them… That’s not for me. I don’t enjoy the planning before the trip or the rigid schedule during it, but even I know that trips don’t just come together with no planning at all.

In this post, I want to share how I take a minimal approach to planning, but still maximize time while I am on the trip. Let’s jump right in!


The Big 3

The first 3 things I plan for every trip are: how I am getting there, where I am staying, and how I am getting around once I get there.

For most trips this looks like flights, an AirBNB, and a rental car, but not always. Sometimes I drive out to visit a friend and am staying with them. Other times I’m flying to my destination, staying in a hotel downtown, and taking public transportation the whole time.

Whatever it may be, if I have those 3 things booked, I feel good about the trip.

Tools I use: Skyscanner, AirBNB app, Expedia or

Narrow it Down

Once I have all of the logistical things booked, I start honing in on things I want to do during each day. Usually I have a pretty good idea of what the destination is like – If I didn’t, I wouldn’t have booked the tri. So I start putting together a small list of “musts”!

Note: For most trips, it’s a mental list. Unless I am taking a long, international trip, no pen and paper (or google doc, I should say) planning really happens. When I am narrowing it down, I am usually just getting a general idea of what I want the trip to be like and a few big things that I really want to do while I’m there.

When it comes to finding out unique things to do or restaurants to visit and working them into your trip, there are few tools I’ve used that help with the process!


Oh Pinterest, a traveler’s favorite site. When I get tired of working, I head over to Pinterest. I’ll search for things to do for any of my upcoming trips or scroll through and add more places to my bucket list.

I keep 2 travel boards: one for trips I dream of going on and one for future trips that I have booked. If in my nightly Pinterest searches I find a particularly helpful article for an upcoming trip, I’ll save it to my “upcoming travel” board, so I can reference it later.

Restaurants on Yelp!

If I am not feeling it on Pinterest, I’ll head over to yelp! I love randomly searching on Yelp for restaurants in my own city or for places to visit on my trips. Yelp is amazing for all kinds of reviews, but it’s best at food related searches. I love trying to find cute coffee shops to work in, the classics in each city, or specialty shops that are really good at their thing.

Google My Maps

Once you have a general idea of things you want to do, you can put them all on the map with Google My Maps. This tool is handy for trips that demand more of a plan than just flights, AirBNB, and a hotel.

Basically, it’s a tool from google where you, the user, can create maps and drop multiple pins on them.

For example, here’s a map from a past trip I took to San Diego. My friends and I had several places we wanted to see, with only a few days in California, so we made the map in order to easily tell what we should do on each day.

Pro tip: My friend, Jessica, and I keep a shared map of restaurants we want to try in the St. Louis area. This way if we are ever downtown together at meal time, we can just pull up the map and go to the closest restaurant! We even got fancy and added layers for coffee shops, lunch spots, and dinner restaurants. .

Booking Timeline

You might be wondering when all of this is happening in relation to the trip.

First things first, I don’t consider any details or really even acknowledge that the trip is happening until I have my flights, AirBNB, and a rental car booked. So that’s the start of planning for me.

From there, it depends on the trip. Sometimes, that’s all I need to feel comfortable and I figure out the rest once I get there. Other times, I need a little bit more of a plan.

If I need more of a plan, the first thing I try to take care of are things that might sell out. For example, when Jess and I go to Hawaii, we are going to a luau. We aren’t concerned with our daily schedule yet, but we booked those tickets as soon as we could so they didn’t sell out.

Once I have that done, the planning gets really sporadic for me. If I’m feeling like researching things for a trip, I will. If I don’t, I don’t worry about it. I really only care about having a plan for the day by the night before. Other than that, it’s free game!

And that’s all I do! I think one of the reasons people don’t travel more is because it feels overwhelming, so it’s not fun! My hope is that by sharing my trip planning process, traveling feels a little easier. Thanks for reading, y’all!

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