How to Plan a Trip With Friends

How to Plan a Trip With Friends
How to Plan a Trip With Friends

A reader of WONDERMENTARY recently asked how I planned my trips. Girl, you’ve come to the right person, because I’ve certainly had my fair share of planning trips with friends by now.

Chicago – Selfies & Sculptures at Millennium Park

This can be a tricky business, as everyone has different ideas on what they want to do, but there may not be enough time to do it all! So what’s the key to successfully planning a trip with multiple people? Communication and organization. Below, I will share some of my favorite tools that have helped us stay on top of our travel-planning game!

California – Our Roadside Pit Stops Along Highway 1

Enter my favorite tool, the one thing that I cannot live without when planning a trip: Google Drive.

Google Drive’s collection of collaborative tools makes trip-planning so easy. Here’s the process that I usually go through (and am currently going through, as I’m off to Portland next week!)

Create an itinerary using Google Docs

Google Doc example itinerary
This was my itinerary for Austin, for example.

This does not have to be a strict, hour-by-hour schedule. Create an itinerary that will serve as an outline for the trip, adding ideas of what you’d like to do for each day. The best part about Google docs is its collaborative abilities – click the “share” button and you can adjust you want to share with and their editing capabilities.

Google Doc sharing options

Plot all attractions, housing, and restaurants on Google Maps

Did you know that you can create and save individual maps in Google maps? TBH, I find secret joy from plotting out all my possible destinations and seeing where they are relative to each other (anyone else out there feel this way?).

That time when I plotted every single city I’d hit on my Grand Tour of Europe

This is immensely helpful when trying to figure out the best way to hit up as many places as possible in my limited time.

Paris – On a Mission at the Louvre. I went to SO MANY places in Paris that day…in the end I was pooped but oh so satisfied!

So how to create a map?

  1. Go to
  2. Click “Create a New Map”
  3. Go crazy! Customize symbols, create a bunch of layers, add driving directions, see how long it’d take you to swim across the Pacific Ocean…

Typically, for a single destination, I create a layer for “Things to Do,” “Places to Eat,” and “Where I’m Staying.” Gotta keep organized!

Split expenses with your friends using Splitwise

This app helps you keep track of how much money you owe each other. So, say, I paid $100 for dinner for 4 people. Then another friend paid $60 for gas, also for 4 people. We’d each enter our payment into Splitwise. Now, that friend who paid for gas would only owe me $10 instead of $25 because he/she paid my $15 portion of gas. Don’t want to do the math? Let Splitwise do it for you!

Orlando – Step Into Diagon Alley At the Wizarding World of Harry Potter

Create a budget using Google Sheets

This is an area that I could use more work on…? I typically start making a budget, feel overwhelmed/discouraged by the unknown costs, then give up. But this is a necessary skill and I will try harder to budget for my upcoming trip to Greece using Sheets. So if you’re awesome at personal finance, drop a sister some tips!

Austin – How to Spend a 3-Day Weekend in Austin

Now that I’ve armed you with my best tools and tips, go plan a trip with some buddies!

Have you ever planned a trip with friends? What worked? Didn’t work? Please share in the comments below!

Thanks for reading – and bon voyage!

  • Nikki Kumar

    Thank you Jessica, this helps a lot 😀

    • Glad to hear it 🙂 Where are you going?

      • Nikki Kumar

        Not anywhere just yet, but wanted to know for future reference. I want to explore downtown Dallas and all it has to offer during senior year!