How I Plan a Disney Day When I’m Not Working as a Travel Planner
by Jenna Caron
Some days, I slip out of “Disney travel planner Jenna mode” and into “I’m just here for the vibes and a dole whip” mode. It’s a subtle shift. One moment I’m mentally planning optimized Lightning Lane stacks and the next I’m debating which park bench has the superior people-watching potential.
When I’m not working, my Disney day becomes far more organic. I still rope drop with a competitive sparkle in my eye. I still wake up early to make the most of the lower crowds (plus I am a morning person), sip something iced, and wander toward whatever attraction feels right. I love these low pressure days! Even better, lets just pin trade and don't ride anything LOL!
I adore this version of Disney because it reminds me why I fell in love with it in the first place. When you strip away the strategies and hacks, you’re left with something simple: a place designed for joy. And it turns out joy thrives when you’re not trying too hard to chase it.
So, how do I plan these “off the clock” days? First, I set one tiny intention. Maybe I want to ride my favorite underrated attraction, or maybe I want to sit in Hollywood Studios and pin trade to finish my latest set. Giving myself a soft goal turns the whole day into a treasure hunt rather than a checklist.
Next, I wander. I follow music drifting from somewhere unexpected. I let myself sit way longer than usual in pavilions or gardens or quiet little corners that never get enough love. This is how I rediscover details I rush past when I’m in “help my clients win the day” mode.
And my favorite part is that everything feels like a bonus. If the lines are long, who cares? I’m not on a schedule. If I stumble across a cavalcade, I treat it like the universe tossing me confetti. If I end up sitting on the hub grass with cold brew and no further plan, that’s perfection.
Don’t get me wrong: I adore planning. My canva docs are basically a personality trait. But giving myself permission to be a guest, not an expert, refreshes my love for these parks. It lets me reconnect with the version of myself who fell for the magic before she ever started teaching it.
So here’s my gentle push for you: every so often, give yourself a “no rules Disney day.” Let curiosity make your choices. Allow delight to interrupt your plans. And remember, the magic doesn’t always live in optimization. Sometimes it’s found in wandering without a map.
