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Jun 27, 2023

Hilton Head Is Still Fun: A Podcast for Locals by Locals

Barry Kaufman

Photography By

Hydrangea Bloomington
A podcast for locals, by locals: with Caitlin Lee & Heather Rath

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We’ve all reached that point in our journey as Hilton Head Island locals at one time or another. We gaze over at the boogey board in the utility yard and realize that it hasn’t moved since the Bush administration. We find that the “brand-new” bike path by our house is now several years old, and we still have no idea where it goes. That amazing new restaurant is celebrating its anniversary and we haven’t been in to taste that appetizer everyone’s been raving about.

“You get in a rut. You do the same three things over and over again,” said Caitlin Lee, whose consultancy with Caitlin Does Local puts her in just about every orbit on the island. “A lot of time after working at home for 12 hours, I’ll ask myself what am I going to do? Put a show on Netflix or get on my bike and go watch the sunset somewhere?”

Her good friend Heather Rath, whose own firm, Heather Rath Consulting, puts her in the same tier of islanders that everyone knows somehow, shared her sentiment at one point. Until the two good friends combined their summer bucket list last year, compiling all the things they wanted to do on the island but never seem to get around to.


Heather Rath and Caitlin Lee record episode five of their new podcast, Hilton Head Is Still Fun.

“We did a bucket list in 2022, and then never did anything on it,” Rath said. 

But their efforts weren’t in vain. The seeds of that idea—actually getting out and enjoying the life that we sometimes take for granted here—took a year to germinate before sprouting this year as a new podcast, “Hilton Head Island is (Still) Fun.”

“The whole podcast is rooted in that bucket list, just highlighting all the things we love about the island and all the things we want to experience,” Rath said.

A freewheeling conversation between two old friends who, between the two of them, have nearly 40 combined summers of island life, the podcast distills the Hilton Head experience into bite-sized pieces easy to take in over a morning bike ride. The topics run the gamut—one focuses on our parks, one on celebrities the duo have encountered in their years here—but the topic itself is rarely the focus for long. One recent episode touched on the Savannah Bananas before thanking Reddit for helping Lee pick out a new fridge.

“These conversations are literally what we would talk about if you were sitting next to us at the Sandbar,” Rath said.

She’s not wrong. Even interviewing the two of them for a magazine story is an exercise in keeping up with the conversation. Their longstanding friendship manifesting in an easygoing chemistry, the two will bounce points off one another, spark sudden digressions into other topics, flow between subjects before you even realize the conversation has shifted, and weave between stories so smoothly at times you find yourself listening to two of them simultaneously.

For those of us who know them both (which is, statistically, most of us), it’s like sitting down for a conversation with friends. And for those who don’t, it’s an introduction to two essential islanders that they should. The chemistry is what keeps the show going, but its roots are what give it a heart.

The bucket list from which it was born has fueled many of the episodes so far, with the two of them enjoying helicopter rides, boat tours and other island experiences that they may have otherwise missed. So far, they’ve learned something:

“If you’re not having fun, it’s probably your fault,” Lee said.

The podcast not only documents their own journey of rediscovering the sense of wonder that brought them here, but it gives them an outlet for spotlighting everything on Hilton Head Island that makes living here so special.

“Caitlin and I are not opposed to a little negativity,” Rath said. (“We complain with the best of them,” Lee interjected.) “But we felt this podcast would be a great way to highlight the things we love. It’s cool that visitors are listening, but this is really for the locals.”

Every episode is about inspiration, about pushing yourself out of your rut, but really the subtext of it all is simple: It’s a love letter to the island.

“And the people are what make Hilton Head so fun,” Lee said. “If we didn’t have so many people who care so much about our community, we wouldn’t be having these conversations.”

On the subject of people, the question, “What guest would you want on the podcast, living or dead?” sparks another classic Lee/Rath idea volley. Everyone from the late John Curry and Charlie Simmons to island icons like Thomas Barnwell and Gregg Russell get name dropped in a flurry of conversation that is engaging as it is … well, fun.

And the sheer enthusiasm of their conversation tells you one important fact about the Hilton Head Island is (Still) Fun podcast: They are just getting started.

“More is more. There’s always room to talk about more people, and we’re never going to run out of content,” Lee said.

“And there are always going to be things that come up; there’s always something new worth highlighting,” Rath said. “We could do this entire podcast about stories people have about Shag’s. I’m being serious.”

That, of course, leads Rath to share a story about Shag’s, which dovetails into Lee’s stories about Hinchey’s in its Coligny days, then to myriad stories of bars gone by. As they speak, the easy chemistry between the two of them effortlessly creates a fascinating chronicle of the island they both love so much.

If you’re stuck in a rut, give it a listen. Even if you’re not, tune in to hear two treasured locals sharing their love of the island we all call home. Look for Hilton Head Island is (Still) Fun wherever you listen to podcasts. 

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