How to PIBE in Key West🌴

A laid-back family guide to vacationing the PIBE way

We’re packing our bags and heading to Key West this summer—and naturally, we’re doing it the only way we know how: by Playing It By Ear. Or as we like to say… we’re about to PIBE.

If you're planning a family trip to this sunny slice of the Florida Keys, here's how to embrace the island spirit and truly PIBE your way through Key West.

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☀️ Step One: Don’t Overplan—Just Be Open

Key West is a vibe, not an itinerary. Sure, it’s helpful to know where the beach is (spoiler: it’s everywhere), but the best moments come when you leave space for the unexpected.

Wake up without an alarm. Let the kids pick where to eat. Wander down side streets and see where they take you. That’s PIBE energy.

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🌴 Where to Stay: Keep It Chill

Look for a spot close to Old Town, where you can walk or bike to all the action. Whether it’s a breezy cottage, a family-friendly resort, or a colorful Airbnb with a hammock, pick a place that feels like vacation the second you arrive.

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🚲 Move Like a Local

No rental cars needed—rent bikes, hop in a golf cart, or just cruise on foot. We recommend biking the island for an easy, laid-back way to explore. You'll pass pastel houses, chickens in the street, and maybe even find the best frozen Key lime pie you've ever had.

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🐠 Go-With-the-Flow Activities

When you’re PIBE-ing, skip the hour-by-hour plans and just choose what sounds good in the moment. Here are a few family-friendly favorites:

• Snorkeling at Fort Zachary Taylor State Park

• Sunset sailing with snacks and live music

• Conch Train Tour (kids love it and it’s secretly fun for adults too)

• Higgs Beach for laid-back sun, sand, and a little splash

Pro tip: Ask a local what they’d do today. You'll probably find a gem.

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🥥 Snack Often, Worry Less

In Key West, snack time is all the time. Here’s what to look for:

• Key Lime Pie on a stick 🍋

• Fresh coconut water from a street vendor

• Anything with conch (fritters, chowder, salad—you name it)

• Mango smoothies or fish tacos from a food truck

Let the kids eat ice cream before dinner. Let the grownups sip rum punch before noon. It's called vacation.

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👕 Dress Code: Vacation Mode

You’re gonna want light, breezy gear that can handle beach days and bike rides. For us, that means:

• Linen or cotton everything

• Sandals (or just go barefoot)

• Big sunnies

• And of course, our PIBE x Richardson Trucker Hat in navy – a must for salty hair and sunny days

Check out the full PIBE shop to gear up before you go!

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📸 Family PIBE Moments to Remember

Here are some of our favorite unplanned moments from Key West:

• Street chickens crossing in front of your bike

• Watching the sunset at Mallory Square (with street performers and snacks!)

• Nighttime ice cream in flip-flops

• Impromptu beach games at Smathers Beach

These are the core memories—because that’s what happens when you PIBE.

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🏝️ Final Word: Let the Island Lead

Key West isn’t just a place—it’s a state of mind. When you’re here, the best thing you can do is let go, lean in, and live easy. That’s what we mean when we say Play It By Ear.

So if you’re heading to Key West this summer, we’ll see you out there—hats on, plans off. Let’s PIBE in paradise.