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How to Make Trying a New Sport or Hobby on Vacation Actually Fun (and Not Totally Awkward)

  • January 26, 2026
  • Jules

There’s something about stepping outside your daily grind that makes new adventures—and new hobbies—way more appealing. Maybe you’re basking in tropical sun, backpacking through the Rockies, or just chilling at a country guest house with a listless afternoon ahead. Suddenly, you’re eyeing a stand-up paddleboard, a salsa class, or a pile of fly fishing gear and thinking… why not? If the little voice in your head is screaming “I’ll look ridiculous!” or “I have no clue what I’m doing!”—honestly, you’re in great company.

Here’s the real scoop on trying a new sport or hobby during your next getaway—with a few pro tips so you actually enjoy the ride (and maybe even surprise yourself).

Start With Curiosity, Not Pressure

No one expects you to nail the perfect backhand, catch a giant trout, or salsa like you’re auditioning for a music video. Treat your first try as play, not a performance. On vacation, everyone’s a newbie at something, and the best memories are usually the ones where you’re laughing, splashing, or missing the shot instead of racking up a score.

Let’s be real—most of us are used to being good at what we do in our daily lives. There’s real magic in letting yourself be a beginner again. Ask locals for recommendations, or scan the “Activities” board at your hotel or hostel for ideas you never would’ve thought of at home.

Do Your Homework—Just a Little

You don’t need to overthink things, but a quick Google or a chat with an instructor before you dive in can make things way less intimidating. Wondering if you need special shoes, a helmet, or that mystifying fly fishing gear? Ask! Rentals and “intro” classes are made for travelers like you. 

Go Easy on the Gear

Tempted to buy all the flashy equipment? Unless your new sport is love at first swing/paddle/cast, stick with rentals or borrow from the activity provider. This goes for everything—rackets, surfboards, mountain bikes. Instructors can help fit you with the right size or type, and if you turn out to be a natural, you’ll have a much better idea of what’s actually worth buying.

Buddy Up (Or Join a Class)

Taking on something new is a whole lot less awkward—and way more fun—with friends, family, or a bunch of other travelers. Sign up for a group lesson or invite your travel companion to be your partner-in-crime. Everyone will look at least a little bit silly, and no one cares.

Document Your Wins (and Fails)

Don’t shy away from photos or videos—even if you’re flailing. The big grins, flubbed casts, and accidental spins are the vacation stories you’ll tell for years. If you do manage a heroic moment, you’ll definitely want the bragging rights.

Stay Open—You Might Just Find a New Obsession

Some hobbies are forever “holiday only,” but you never know what’ll stick. That archery lesson, snorkeling trip, or afternoon spent learning paella might become your next go-to hobby… or at least your favorite “remember when” anecdote.

End on a High Note

Even if you only advance from “terrible” to “hey, not too bad,” celebrate it. Treat yourself to that ice cream, sunset drink, or big dinner with new friends.

New sports and hobbies are what vacation is all about—stepping out of routines and into unscripted fun. Go ahead, get a little out of your comfort zone. On vacation, nobody’s keeping score—except maybe your photo album.

Imahe: Unsplash – Robson Hatsukami-Morgan

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