We had the good fortune of connecting with Olivia Barr and we’ve shared our conversation below.

Hi Olivia, is there something you believe many others might not?
As an entrepreneur, I disagree with the idea that business owners need to be involved in every aspect of their business. From marketing to operations, that mindset is overwhelming—and honestly, not strategic. Why force yourself to touch everything when you don’t have the time or expertise?

I’m building my business with scalability in mind, and my motto is: Outsource where possible. Yes, it’s important to have a general understanding, but I firmly believe in hiring professionals who are experts in their fields. Take social media, for example—I only joined the major platforms within the last two years, and I’m no algorithm expert. So instead of struggling, I hired someone to create my reels. The results? Higher quality content and more engagement than I could produce on my own.

Outsourcing allows me to focus on the core of my business. Time is a limited resource, and as someone juggling entrepreneurship and life’s other responsibilities, I have to prioritize wisely.

Can you give our readers an introduction to your business? Maybe you can share a bit about what you do and what sets you apart from others?
My business was born from a love of culture, celebration, and connection. I run a travel concierge company based in the U.S. that specializes in curating unforgettable travel experiences centered around Caribbean events and festivals—think Crop Over in Barbados, CayMas in the Cayman Islands, and all the vibrant moments in between. I help first-time island visitors feel confident and excited about their journey by offering customized itineraries that include hotel accommodations, access to local events, ground transportation, and curated tours. Whether it’s a girls trip, a destination wedding, a birthday escape, or a mancation, I’m here to bring the vibes and take the stress out of travel planning.

What sets me apart? I don’t just book trips—I build cultural bridges. I’ve developed strong connections with local vendors, tourism boards, and bands across the Caribbean, and I use those relationships to give my clients access to authentic, insider experiences they won’t find on a generic travel site.

Getting here wasn’t easy. Starting out, I had to navigate how to position myself in a niche market, build trust without a long client list, and stay consistent even when bookings were slow. But I kept going because I believed in the vision—and my very first client (a close friend) reminded me that trust and relationship are the foundation of this business. I’ve also had the joy of seeing my daughter’s Caribbean heritage spark my own curiosity and passion. She’s been one of my greatest inspirations and the reason I leaned into the Caribbean with intention and purpose.

The biggest lesson I’ve learned? Consistency matters more than perfection. You don’t need all the answers to start—just enough courage to take the first step.

What I want the world to know is that my brand is about more than vacation—it’s about transformation. Through each trip, I aim to empower women (especially those aged 35–50 celebrating milestones), families, and groups to reconnect with joy, culture, and each other. My story is still unfolding, and I’m proud of how far I’ve come—this is only the beginning.

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
If my best friend came to visit for a week, I’d have a full itinerary ready to give them the luxe, local experience they didn’t even know they needed. Here’s how we’d do Dallas in style:

Day 1: Arrival & Soft Landing
Check-In: Hotel ZaZa or The Thompson Dallas — think boutique luxury with major Instagram appeal.

Welcome Dinner: YO Ranch Steakhouse — A true Texas welcome with mesquite-grilled steaks in a rustic-chic setting that screams Lone Star luxury.

Nightcap: The Henry Rooftop — Classy, cozy, and effortlessly cool with sweeping city views and a vibey, upscale crowd. Perfect for easing into Dallas with style.

Day 2: Culture & Cocktails
Brunch: First Watch — Light, bright, and delicious with fresh-squeezed juices and seasonal dishes.

Afternoon: Explore the Dallas Museum of Art, stroll through Klyde Warren Park, and don’t miss a visit to the African American Museum—a powerful and inspiring cultural stop.

Dinner: Kitchen + Kocktails by Kevin Kelley — Soul food meets high-end presentation, with a vibe that’s lively and luxurious.

After Hours: Catch live music at The Freeman Café in Deep Ellum—smooth tunes, good drinks, and a laid-back local crowd.

Day 3: Self-Care & Shopping
Morning: Spa day at Hiatus Spa + Retreat — It’s all about facials, massages, and next-level relaxation.

Afternoon: Shopping at NorthPark Center or Legacy West, plus a pop-in to The Plant Project and Indigo 1745—Black-owned gems that celebrate beauty, culture, and joy.

Dinner: Texas Spice at the Omni — Farm-to-table freshness and rustic Southern charm in a cozy-chic setting.

Day 4: Black Excellence & Local Flavor
Brunch: The Island Spot — Caribbean comfort food, island cocktails, and reggae vibes that transport you instantly.

Daytime: Explore Bishop Arts District for murals, indie coffee shops, and artisan finds. Then swing by Cedar Crest Golf Course for a scenic drive or relaxed round.

Dinner: Al Biernat’s — Iconic Dallas steakhouse with an upscale vibe and impeccable service.

Evening: Lounge at XOXO Dining Room & Garden — pink interiors, champagne walls, and a whole lot of glam.

Day 5: Wine & Wander
Day Trip: Head to Historic Grapevine for boutique shopping, wine tasting, and strolls down Main Street.

Winery Stop: Messina Hof Winery — Sip award-winning wines in a charming tasting room with Texas hospitality.

Dinner: Dakota’s Steakhouse — An underground dining experience with an elegant garden patio and a rich Dallas history.

Day 6: Turn Up & Toast
Brunch: Ebb & Flow – Plano — Lively, colorful, and perfect for a girls’ day out with shareable plates and stylish cocktails.

Afternoon: BBQ break at Hurtado Barbeque — It’s giving bold flavor, slow-smoked goodness, and Texas-sized satisfaction.

Evening: Vibes at Sandaga 813 — Live music, grown folks energy, and one of the best hidden gems for nightlife in the city.

Day 7: Departure Day – But Make It Chill
Brunch Send-Off: Yardbird Table & Bar — Southern classics like fried chicken, biscuits, and peach cobbler mimosas to seal the trip.

Last Stops:

Pan-African Connection — Cultural books, art, and Black-owned beauty.

Grab a taco from Fuel City Tacos for the road—it’s a rite of passage.

Shoutout is all about shouting out others who you feel deserve additional recognition and exposure. Who would you like to shoutout?
I want to dedicate this shoutout to my very first travel client—my dear friend, who has trusted me with her adventures time and time again. From obtaining her passport for our first trip to London, to jumping into the vibrant vibes of Crop Over and exploring CayMas with me last year, she’s been open, adventurous, and always ready to say yes to the experience. Her trust gave me the confidence to turn my passion into a business.

I also want to honor my daughter, whose Caribbean roots sparked something deep within me. Because of her, I was inspired to learn more about the region, embrace its rich culture, and build a business that helps others do the same. She unknowingly guided me toward a purpose I didn’t even realize was mine.

To both of you—thank you for being part of my why.

Website: https://www.caribbeanislandfestivals.com

Instagram: https://www.instagram.com/caribbeanislandfestivals/

Linkedin: https://www.linkedin.com/company/caribbeanislandfestivals/?viewAsMember=true

Facebook: https://www.facebook.com/profile.php?id=61564602747102

Youtube: https://www.youtube.com/@CaribbeanIslandFestivals

Image Credits
Burke Media (Cayman Islands)

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