Carlita Pitts of Rockville, MD on Life, Lessons & Legacy

We’re looking forward to introducing you to Carlita Pitts. Check out our conversation below.

Carlita, so good to connect and we’re excited to share your story and insights with our audience. There’s a ton to learn from your story, but let’s start with a warm up before we get into the heart of the interview. What do you think is misunderstood about your business? 
A common misconception is that my business is simply about promoting wine. While wine is certainly at the heart of it, the real focus is wine tourism—or enotourism—which is so much more than just sipping a glass. My work is about curating immersive experiences that connect people to place, culture, and community through wine.

Wine tourism is about discovering the story behind the bottle: visiting the vineyards, meeting the winemakers, enjoying elevated tasting experiences, hiking through the vines, indulging in wine-paired dinners, and knowing exactly where to dine, stay, and explore. It’s an intentional and elevated approach to travel that blends wine, food, hospitality, and local culture into a full-bodied experience.

I’m not just sharing what to drink—I’m guiding people on where to go, what to do, and how to savor every moment along the way.

Can you briefly introduce yourself and share what makes you or your brand unique?
I’m Carlita Pitts, the founder of DiVineLita, a wine tourism brand that curates elevated, culturally rich experiences for those who want to explore the world through wine. At its core, DiVineLita is about more than tastings—it’s about immersing travelers in the beauty of wine destinations through thoughtfully designed experiences that blend wine, culture, and connection.

From vineyard hikes and intimate wine-paired dinners to discovering hidden gems and boutique stays, I create experiences that tell a story—where to sip, stay, dine, and indulge with intention. What sets DiVineLita apart is its focus on inclusivity, aesthetics, and meaningful curation. I highlight underrepresented voices and off-the-beaten-path destinations to ensure wine travel feels both welcoming and aspirational.

Right now, I’m planning a curated holiday wine weekend in Charlottesville and co-hosting a wine club event with Shayla Varnado, founder of Black Girls Wine, in collaboration with Oenoverse—an initiative based at Blenheim Vineyards that’s dedicated to making the Virginia wine industry more inclusive and accessible. I’m also expanding DiVineLita’s offerings to include domestic and international wine retreats, exclusive tastings, and unforgettable travel experiences for those who want to sip, savor, and explore—beautifully.

Appreciate your sharing that. Let’s talk about your life, growing up and some of topics and learnings around that. What was your earliest memory of feeling powerful?
One of my earliest memories of feeling powerful was in elementary school, when the Mayor of Columbus at the time, Greg Lashutka, visited our school—and I was chosen to introduce him. I remember being so nervous, practicing my speech over and over, and especially making sure I could pronounce his name just right. But then it hit me: I was chosen for a reason. If I wasn’t capable, they wouldn’t have picked me.

When the day finally came, I delivered my speech with confidence and clarity—I knocked it out of the park. Afterwards, the mayor even sent me a personal thank-you note, which my principal gave to me. That moment stayed with me. It wasn’t just about public speaking—it was the first time I truly believed in myself and recognized the power of my voice. It showed me that preparation, presence, and believing in your own ability can create lasting impact.

If you could say one kind thing to your younger self, what would it be?
“Trust your voice and your vision—you’re not meant to follow the path, you’re meant to create one.” I’d remind her that her love for storytelling, beauty, and creating meaningful experiences isn’t random—it’s purposeful. One day, those passions will become the foundation of something powerful. Keep showing up, even when the road feels unclear—because you’re building something that only you can bring into the world.

So a lot of these questions go deep, but if you are open to it, we’ve got a few more questions that we’d love to get your take on. What’s a cultural value you protect at all costs?
Authenticity—especially cultural authenticity—is a value I protect at all costs. Early in my career, I worked in a professional environment where people constantly made jokes about the way I spoke, the way I dressed, even the way I carried myself. It was subtle at times, but the message was clear: to succeed, I needed to assimilate. That experience left a lasting impact on me.

It taught me that dimming your light to fit in doesn’t serve anyone—not you, and not the people who need to see someone like you succeed. That’s why I show up fully as myself in everything I do, and why I center authenticity in my brand. Through DiVineLita, I create spaces where culture isn’t something to hide or downplay—it’s something to celebrate. I believe people should be able to experience wine, travel, and connection without feeling like they have to leave parts of themselves behind.

Before we go, we’d love to hear your thoughts on some longer-run, legacy type questions. What false labels are you still carrying?
That I’m too much—too sensitive, too ambitious, too expressive. And at the same time, not enough—not polished enough, not “professional” enough, not the “right kind” of woman to belong in certain spaces. Early in my career, I often felt like I had to edit myself—my voice, my style, even my cultural identity—to fit into environments that didn’t reflect or affirm who I was. I was made to feel like showing up fully as myself was somehow wrong.

Those false labels still linger at times, especially when I’m doing something bold or stepping into new rooms. But I’ve learned that trying to fit into spaces that weren’t built for you is exhausting—and unnecessary. Now I choose authenticity over assimilation. The very things I was once told to tone down are the same things that make my brand and my vision powerful. I’m still learning to shed those labels, but every time I show up as my full self, I reclaim a little more of my voice—and that’s what I hope to inspire in others, too.

Contact Info:

  • Instagram: @iamthelita

Image Credits
The photos are all my images

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