5 Questions: Catching Up With Townie Tourist

Jenny DeWitt

Founder of Townie Tourist


Ah, man. I’m so honored and thrilled to introduce you to Jenny DeWitt, often known as the Townie Tourist. If you have the chance to get five minutes with her, you’ll quickly learn that she loves to laugh. She’s bold. She’s free. She’s just Jenny!

Jenny is cut from the rare cloth of people that are from Orlando and choose to remain in Orlando. After years of traveling the world, she decided to plant herself just one mile away from the very hospital that she was born in. How cool? She stays busy with running her two businesses: Rebranded Media, which offers social media, content, and web design services and Townie Tourist, a go-to site for Orlandoans and travelers alike to learn the about the amazing people, places, and experiences in Central Florida that many often miss.



Where do you get your favorite cup of coffee? Easy Luck Coffee & Bodega, Downtown CREDO , and Lineage Roasting

What book are you currently reading? “The Coaching Habit: Say Less, Ask More, and Change the Way You Lead Forever” by Michael Bungay Stanier

What is a Townie Tourist? It means being a tourist in my own town, while creating a deeper connection with my community by exploring the where I live.

What or who has been your most interesting and fun Townie Tourist episode? I have more 300 episodes now, so it's pretty tough to choose just one. Of the Saturday morning shows, I really like the ones where I get to experience some bit of culture or history that I haven’t seen before.

Recently, I did a tour at the Museum of Arts and Science in Daytona and learned all about the giant sloths that lived here. I also really loved Green Gables in Melbourne. I had never been to Melbourne and I was met by the house's historic preservationist and his wife who dressed up in period clothes for the show. And I really loved collaborating with the Urbanist. He inspired me to start doing live videos. We did a tour of Grand Central Station in NYC. It was a Townie-style tour with lots of art and history.

What are your top three tips for locals when exploring Orlando? 1. Go a little bit outside your comfort zone and break routine: order something you wouldn't normally, hit up an event where you're pretty sure you won't know anyone, try a new restaurant, and take a back road or byway. We're supposed to feel awkward in new situations. Embrace it and see what happens.  

2. There are great resources like Pulptown, Bungalower, and Orlando Weekly that list hundreds of events for every budget. Each week, pick two. Make sure one is arts related. Within a month, you'll feel like a Townie Tourist, too.

3. Take a "lunch meeting" at a museum. Use that time to dive into science or art, relive a little bit of history, and tap into your creativity. It's a great way to gain perspective and feel connected.


Stay connected with Jenny on Instagram and be sure to sign up for her newsletter! Every Wednesday you’ll get three Townie Tourist tips. Shop her Swans Heart sticker here!

Be Bold,


P.S. One fun fact about Jenny and I is that we don’t drink alcohol! If you’re looking to cut back or find amazing drinks without the buzz, check out her zero-proof drink list here.