We recently connected with Elle Caldwell and have shared our conversation below.

Elle, thanks for taking the time to share your stories with us today Did you always know you wanted to pursue a creative or artistic career? When did you first know?

I knew I wanted to pursue a creative path professionally during the height of COVID in 2020. Travel had always been a part of my life, but navigating the new challenges of traveling with children during a pandemic pushed me to look at it differently. After taking a trip to Disneyland with my 4-year-old daughter and my parents, I started sharing detailed itineraries and hosting Q&A sessions to help others plan their own trips.

Coming from a structured corporate finance background, stepping into the creator world felt completely different, but also completely necessary. What really confirmed this path for me was the overwhelming response I received. People flooded my inbox with questions about travel, especially those who didn’t feel represented in the traditional travel space.

As a Black, plus-size woman, I know how important it is to see yourself reflected in the experiences you want to have. That’s why, in 2024, I launched @travelwithhollywood as a dedicated space to build community, inspire adventure, and show women like me that travel can be both luxurious and accessible. Looking back, it feels like this was always where I was meant to be.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

My name is Elle Caldwell, and I’m the founder of @travelwithhollywood, a travel platform dedicated to helping plus-size Black women explore the world confidently, luxuriously, and affordably. My journey as a travel creator started in 2020 during the COVID-19 pandemic, but my love for travel goes back much further.

Before becoming a creator, I spent years in corporate finance, where structure and strategy were key parts of my work. When COVID hit, it completely reshaped the way we traveled, especially as parents. After a trip to Disneyland with my 4-year-old daughter and my parents, I started sharing detailed itineraries and answering travel-related questions on social media. What began as a hobby quickly turned into something much bigger when I realized how many people, particularly Black women, didn’t feel represented in the traditional travel space.

I created @travelwithhollywood in 2024 as a separate, dedicated space to build community and serve as a trusted resource for travel tips, itineraries, and inspiration. My focus is on helping plus-size Black women—many of whom are also moms—feel seen and supported as they plan their dream vacations. I know firsthand what it’s like to feel overlooked by the travel industry, so I’m intentional about showcasing destinations, activities, and accommodations that are welcoming, accessible, and size-inclusive.

Through @travelwithhollywood, I provide:
• Detailed Travel Guides & Itineraries – From city breaks to international getaways, I help take the guesswork out of planning.
• Budget-Friendly Travel Tips – I share how to enjoy luxury travel without breaking the bank, including hacks for flights, hotels, and excursions.
• Destination Spotlights & Reviews – Whether it’s family-friendly trips, solo adventures, or couple getaways, I offer honest insights to help my audience decide where to go next.
• Content for Moms on the Go – I highlight tips for traveling with kids, making vacations fun, stress-free, and memorable.
• Body-Positive Travel Advice – I focus on helping plus-size women feel comfortable and confident while traveling. From what to pack to how to handle excursions, I keep it real about what to expect.

What sets me apart is my focus on representation and relatability. I create content through the lens of a Black millennial mom who loves to travel but also understands the realities of budgeting, body image, and family logistics. My audience knows they can trust me to share practical advice, honest reviews, and tips that actually work.

One of the things I’m most proud of is the sense of community I’ve built. I’ve received countless messages from women who never thought luxury travel was for them until they saw my content. Whether it’s helping someone take their first solo trip or giving a mom the confidence to plan a vacation with her kids, I’m passionate about empowering women to create the experiences they deserve.

My main goal is to continue growing @travelwithhollywood as a space where travel feels possible, no matter your size, background, or budget. I want my audience to know that travel isn’t just about the destination—it’s about feeling seen, celebrated, and inspired along the way.

Looking back, are there any resources you wish you knew about earlier in your creative journey?

I wish I had tapped into networking groups and travel creator conferences way earlier in my journey. Connecting with like-minded creators who actually get the struggles and wins of this space has been a game changer. From learning how to pitch brands to swapping tips on editing tools, those connections make the process feel less overwhelming, especially as a mom juggling life and content creation. If you’re just starting out, don’t sleep on community. It’s not just about who you know; it’s about who’s willing to help you grow and building a support system.

Is there mission driving your creative journey?

My mission as a travel creator is simple—I want to show people who’ve felt like travel wasn’t for them that it absolutely is. As a plus-size Black woman, I know firsthand the doubts and fears that can creep in—whether it’s worrying about airplane seats or feeling out of place in certain spaces. I’m here to prove that we belong everywhere and that travel doesn’t have to be expensive, complicated, or intimidating.

Black women are stepping into the travel space like never before, and I’m here to cheer them on and push them to keep exploring. And let’s be real—traveling with kids can feel chaotic, but I’m living proof that it’s doable and so worth it. My goal is to help families create memories without breaking the bank or losing their minds. If I can do it, so can you!

Contact Info:

• Website: https://www.hollywoodluxurytravel.com
• Instagram: https://www.instagram.com/travelwithhollywood
• Facebook: https://www.facebook.com/travelwithhollywood
• Youtube: https://www.youtube.com/@TravelWithHollywood

Image Credits

N/A