Rebel Travel: 6 Rules I Break Every Time I Leave Home

Leave the map. Take the magic.

May 05, 2025

Who needs blue skies when you’ve got main character energy?

I’ve been on the road a lot lately—and there’s more to come this summer (hello, Italian Dolomites!). All this movement has me thinking about what actually makes a trip feel great for me.

Not just fun. Not just efficient. But meaningful. Alive. Mine.

Because I used to treat everything from backpacking to urban getaways like a checklist in a trench coat—book the perfect hotel, hit every landmark, come home with photos and foot pain.

But somewhere between a national park pit toilet and a mountain thunderstorm, I realized: I don’t want to perform travel. I want to experience it.

So these days, I travel on Rebel Time.

Here are six rules I break on purpose—and why you might want to, too.

1. I Don’t Try to See It All

The pressure to see “everything” is a trap. I’d rather get to know one quirky corner of a neighborhood than rush through all the top 10 crowded must-sees with a blister and a bad attitude.

Sometimes the best moment of a trip is sitting on a bench, drinking bad coffee, and people-watching like it’s my job.

2. I Talk to Strangers

Not just “Where’s the bathroom?” Small talk. Deep talk. Grocery store cashiers, park rangers, the 85-year-old woman sweeping her stoop. Locals are the keepers of the real stories—and every trip is richer when I ask more questions than I answer.

3. I Don’t Save the Best for Last

If there’s a cold plunge lake on Day One, I’m diving in. If the trailhead café has homemade chocolate croissants at 10am, I’m ordering one—with coffee and zero regrets. I’ve learned not to wait for the “perfect moment”—it’s already here.

4. I Eat Dessert First (Sometimes Literally)

Rigid meal schedules? No thanks. Sometimes breakfast is gelato. Sometimes lunch is bread, cheese, and a bottle of wine on a hotel bed. The joy of travel is delighting in the unexpected—and food should be part of the rebellion.

5. I Let Myself Get Lost

Some of my favorite travel moments happened because I took the wrong turn on purpose. Maps are helpful. Serendipity is better.

6. I Take Fewer Photos (But Better Notes)

I still snap the occasional sunset, but now I write down what I felt. The smell of the honeysuckle. The ache in my feet. The sound of someone laughing in a language I didn’t understand.

Photos are souvenirs. Stories are souvenirs you actually use.

Here’s what I’ve learned: the best trips aren’t the ones where everything goes to plan. They’re the ones where you show up fully—open, curious, imperfect, alive.

So go ahead. Break a few rules. Make up new ones. And if someone gives you a weird look for ordering wine with your pancakes?

Just wink. You’re on Rebel Time now.

Question for you: What’s a travel rule you love to break—or one you secretly wish you could? Drop it in the comments. Let’s build our own anti-itinerary: