Planning a vacation sounds fun... until the Google tabs multiply, your group chat spirals, and someone says, “Let’s just wing it.” Sound familiar?
Whether you are someone who loves the thrill of planning or secretly wishes someone else would just handle it, there’s no one-size-fits-all approach to getting a trip off the ground.
Some people thrive on spontaneity. Others won’t sleep until every museum ticket is pre-booked. Some dive headfirst into the dream destination, while others just want the when and where.
The truth is: how you approach vacation planning says a lot about you. Are you decisive and take-charge? A go-with-the-flow team player? A spreadsheet lover? A big-picture dreamer? All are valid. All are valuable.
This has been adapted from the Center For Leadership and Educational Equity, Compass Points: North, South, East, and West - An Exercise in Understanding Preferences in Group Work. The Illustrations were designed and drawn by my wonderful husband, Don Rahn.
Here’s the best part—once you understand your personal travel planning style, you can actually make the process more enjoyable, less stressful, and totally tailored to how you work best. As you identify the planning styles of those traveling with you, the DREAMING, DESIGNING, and DEPARTING process becomes a time for sharing, listening, collaborating and fun! Everyone is able to contribute in their own unique way.
So before your next getaway, let’s find out: Which type of travel planner are you?
Meet the four fabulous personalities that just might sound a little (or a lot) like you…
Let’s Go Louise
Are you the one in the group chat typing “Just book it!” while everyone else is still thinking? Do you have your eye on the goal and a calendar reminder set for 6 AM flight check-in?
You might be a Let’s Go Louise if:
You thrive on action and making decisions fast
You’re assertive, confident, and task-oriented
You love a good itinerary and don’t mind taking charge
Louise is our leader—decisive, goal-centered, and always ready to roll. If there’s a problem, Louise has already solved it, packed a snack, and scheduled the Uber.
Visionary Violet
Your head’s in the clouds—but in the best way. You dream big, you think outside the box, and you’re always cooking up the next creative travel idea.
You might be a Visionary Violet if:
You’re full of enthusiasm and spontaneity
You value flexibility and freedom
You get more excited about possibilities than reservations
Violet may not have booked the hotel yet—but she’s got a Pinterest board full of dreamy spots and a camera roll of screenshots that could inspire ten amazing trips.
Detailed Denny
If you're the one with the color-coded spreadsheet, multiple tabs open, and a backup plan for your backup plan—welcome to Team Denny.
You might be a Detailed Denny if:
You crave structure, logic, and precision
You’re focused, analytical, and organized to the core
You take pride in researching all the options
Denny finds joy in the planning itself—and usually ends up saving the day with that crucial piece of info no one else remembers.
Patient Peter
You’re all about the journey and the people on it. You take your time, listen carefully, and want everyone to feel included.
You might be a Patient Peter if:
You’re supportive, calm, and generous with your time
You don’t love confrontation and prefer going with the flow
You value the process more than the destination
Peter is the glue that holds the group together. While others are stressing over logistics, Peter is making sure everyone feels heard and no one gets left behind.
So, which one are you?
Or maybe you’re a mix! A little Violet sparkle with a Denny checklist? A Louise go-getter with Peter’s steady hand? No matter your style, knowing your strengths helps you plan (and enjoy) a vacation that feels just right for you—and your travel crew.
Because here’s the thing: every planner type has something essential to offer.
Louise helps the family depart—keeping things moving, on time, and confidently headed out the door.
Violet keeps the dreaming alive, inspiring fresh ideas and unexpected adventures you’ll be talking about for years.
Denny makes sure the design phase is rock solid—organized, thorough, and full of well-researched choices.
Peter ensures everyone feels included, heard, and cared for—making the entire process feel less like a task and more like a team effort.
In the Seldom A Dull Moment world, we believe planning a trip should be a family adventure in itself. When you honor the strengths of every style—whether you’re dreaming, designing, or departing—you set yourself up for a vacation that’s not just memorable, but meaningful.
Take the quiz to find out your travel planner type, then share your results and tag your travel buddies. Who’s your Louise? Who’s your Violet? And who’s in charge of snacks?
Let’s Dream, Design, and Depart—your way.
At Seldom A Dull Moment, we believe every vacation starts with a dream—and ends with a story worth telling. Let’s figure out how you plan, so your next trip is less stressful and more spectacular.
Ready to Dream, Design, and Depart? Let’s go.
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