How to Travel More Often

Travel seems daunting. That’s because it can be. There’s the philosophical ritual of packing questions. (What is essential to my survival?) Checking off the governmental and medical must-do’s only feeds anxiety. Budgeting can get downright existential. That’s the hardest part: trying to anticipate and calculate the emotional gain of an experience that’s yet to happen. And you end up wondering whether or not you should go in the first place.

Staycations, you muse, the 20 Expedia and Google Flights and Kayak tabs still aggregating in the background. They don’t sound so bad.

It doesn’t have to be so hard. All it takes is redefining what it is to travel. 

Stop overthinking.

It’s a tired metaphor, but travel and dating aren’t actually so different. Whether it’s another city or human being, both require a nosedive into the unfamiliar. Like the way they look, we can expect to know the temperature of someplace. We can Google, and through what other people or themselves have said, make an educated guess of their vibe and how to make the best of it. There’s only so much we can prepare for, but the fun is in not knowing—and finding out more about yourself in the process. Embrace that.

Know the kind of traveler you are, and be okay with it.

I confess: I can be real hotel potato. I love beach reads that sap my vocabulary. My joy is knowing that I have HBO, Showtime, and Starz on my television. Sometimes, the idea of eating a room service in a bathrobe sounds way more appealing than teetering/barhopping on cobblestones. So come winter, I’ll be opting for sun-drenched nothing over backpacking in Southeast Asia. My type A friends, evangelists of Google Destinations, think I’m both crazy and boring. But I don’t care: I’ll be having my version of fun. With so much travel-related content out there, it can be easy to feel pressured into measuring up to those jam-packed expectations. Create the itinerary that makes you excited, not full of dread.

A trip by any other name would smell as sweet.

Consider why you’re feeling the travel itch. Are you just burnt out from a project and need some self-care? Maybe HotelTonight and a little luck is all you need. Want some quality time with your girlfriends? A weekend up in someone’s cottage would have a lot less distractions than an all-inclusive (not to mention being a lot easier to coordinate). What makes travel worthwhile is not where you go, but who you’re with and what you’re doing.

Even if you’re the kind of person who finds joy in planning for the future, it’s important to remember that travel is all about the present—whether odd or magical, but always fleeting. Revel in the moment and you might just find it easier to spot those opportunities.

What’s your mental hack for ramping up those frequent flyer miles?