Vacation Planning the Trello Way

We have an exciting time coming up. I’ll provide details at the end of the post, but I have several virtual appearances coming up. Combine that with the fact that it’s been a stressful year, and we are looking to take a break. This meant that my wife and I brought up our preferred vacation management tool: Trello. However, Trello is also an Atlassian tool, so why not share how we leverage the platform to plan our vacations?

Vacation planning right now brings up the obvious concern. As much as people would like it not to be, COVID is still out there. We are both vaccinated, which lessens the concern, but figuring out what to do was still tricky. This is where our new toys came in.

Just the two of us kayaking should limit our exposure, making this much-needed vacation possible for us.  

So let’s go over what Trello is and show you how we use Trello to manage trips so that everything can go as smoothly as possible.

What is Trello?

Trello is another of Atlassian’s project management tools. Some have called it “Jira Lite” before, but I think this does a disservice to both it and Jira. So instead, I like to think of it as Project Management for those who don’t need as much structure as Jira provides. At its most basic level, it’s an agile board where you can place cards into pre-defined columns. What does this allow? Quite a bit!

For our own safety’s sake, I won’t be sharing details on where we are thinking of going or when we are leaving. As such, I’ll be showing you the board we set up for our vacation last year, how we planned it all out in Trello, and how we leveraged different platform features to help us sort, organize, and understand what we have going on.


The first step is to figure out where we are going. After that, we set up a board on Trello for that. Last year we decided on Savannah, GA, and several of its outlying Islands.

Then, we got to get the basics in place. First, you will need a place to stay. We knew we wanted to divide our time between the Golden Isles and Savannah proper, so we arranged the week so we’d stay a few nights at one location, then the other. We record the details about each hotel, including pictures, rates, addresses, etc. We had several hotels up for each area during the early stages, and as each option was eliminated, we would archive its card. This helped us keep track of the options and finally settle in on a hotel!

Then, we have to eat. Fortunately, there are no shortages of places to eat in that area, so we put all the options we were looking at for each location, and once we had a list, it was pretty smooth sailing. Just pick a restaurant near where we were that day, and enjoy!

Finally, we needed to look at things to do. Again, we put in all the options we were interested in on the list, and as we committed to different options, we would lock it in by adding a label and date to it. Anything that failed to make the cut was archived off the board. 

During the entire process, we would keep track of different items by labels. For example, red options were time-locked, so they had to be done at a specific time or date. A Blue tag was for lodging, and Yellow items were tours we had signed up for. We used purple for attractions, and green items were things we could slot in wherever we had free time to kill. 


Our last step was to look at all the options we had agreed on – including the time-boxed cards and put everything on a general itinerary so we know what we’d like to do each day.  

What made this useful is we could attach anything to a card. Addresses, links, dates, checklists. It made it easy to have all the information we would need in one location throughout the entire trip.


Did you think I was done? No – we still have to pack for the trip! I have always been a VERY forgetful person. So, you have to pack things, and forgetting something is either money you have to spend or an extra stop once you get there. What to do?

Well, Packing lists! Last year, I made this packing list for a work trip (pre-COVID), but I have updated it and re-used it several times since. The idea is essential. You start with a list of things to pack on the left-most column. Every other column is a place it can go. Then, as you pack things, you move that item’s card from the “To be packed” column to wherever you packed it. 

You can also use labels to show how critical each item is. Something you cannot live without? Mark it in red. Something nice to have, but you can live without it for a few days? Green tag! 

The most fantastic feature with this is that you have a list of everything you have packed once you are done. These lists make going through a hotel to make sure you haven’t forgotten anything straightforward. Is everything on your list accounted for? Good? Then let’s go!

Of course, resetting this every time can be a pain, right? Well, no! Trello supports some pretty robust automation. For example, I made a “Reset” button on the board that moves all items in the “packed” columns back to “To be packed.” That way, I can return the board to its pre-packed state quickly and easily. Ready for my next adventure!

So, what do you think? Can you see yourself using some of these tools? Have you made anything similar in Jira? Let me know!

We have several events coming up over the next couple of weeks.

First, I have been asked by Everyone Games to join a Table Top RPG “One Shot” Streaming on Oct. 1 to help raise funds for organizations seeking to make gaming more accessible for people with disabilities. Specifically, I will be playing “The Jewel of Rezeedah,” a new module created by friend-of-the-blog Ben (@BMtheDM) on Twitch at 7 PM to 10 PM Eastern. You can find out more details about the schedule and how to donate here: 

Then, just a few days later on Oct. 5, I am speaking at JiraCon ’21 in partnership with Trundl. I’ve been getting the final details put together for the talk, and I think I have plenty of great information on how you can future-proof your Atlassian Career. Combine that with the fact that every other speaker is a veritable “Who’s who” in the Atlassian Community; this is a can’t miss event. So, if you have not signed up yet, get your tickets before it’s too late at

But that’s all I have this week. If you enjoyed this week’s article, please share this with your colleagues and friends on social media. You can find all my Social links on Linktree. You can also sign up below to get new articles delivered directly to your inbox. That is the fastest way to get notified about new events! But until next time, my name is Rodney, asking, “Have you updated your Trello board today?”


1 Comment

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.