Daily Inspiration: Meet Denita Simmons

Today we’d like to introduce you to Denita Simmons.

Hi Denita, it’s an honor to have you on the platform. Thanks for taking the time to share your story with us – to start maybe you can share some of your backstory with our readers?
Tailor Fit Travel was born in June 2018 from my passion for creating memorable experiences that bring families and loved ones closer together. I’ve always believed that travel isn’t just about going somewhere — it’s about connection, celebration, and making moments that last.

I entered the travel industry after years of being the “go-to planner” among friends and family. I loved organizing vacations, group trips, and special occasions, and I realized I could turn that passion into a business that helps others enjoy stress-free, personalized travel.

As Tailor Fit Travel grew, I began focusing on the areas where I saw the biggest joy and impact: family vacations, destination weddings, and guided group travel. These are the trips that create lifelong memories, and with the right support, they can be seamless instead of stressful.

Today, Tailor Fit Travel is dedicated to providing elevated travel experiences with hands-on planning, expert guidance, and genuine care. I help clients feel confident from the moment they start dreaming about their trip until they arrive back home — with their hearts full and their memories overflowing.

And as we continue to grow, my mission remains the same: to design travel that fits your vision, your milestones, and your unique version of luxury.

Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
Like any meaningful journey, it hasn’t been completely smooth — but every challenge has shaped the business into what it is today.

One of the biggest hurdles was the impact of COVID-19 in 2020. The entire world shut down, travel came to a standstill, and overnight, our industry had to navigate constant changes, cancellations, and uncertainty. It required patience, creativity, and resilience to continue supporting clients while also planning for a future where travel would return.

But the beauty of this industry is that travel always finds its way back. As the world reopened, Tailor Fit Travel bounced back stronger than before. Families were eager to reconnect, couples were ready to celebrate love again, and groups were excited to make up for lost time. That renewed enthusiasm fueled our growth and reminded us why we do what we do.

Today, we are continuing to thrive — smarter, more adaptable, and even more appreciative of every journey we get to help create.

Thanks – so what else should our readers know about your work and what you’re currently focused on?
Tailor Fit Travel is all about designing elevated, stress-free travel experiences that feel personal and intentional. I specialize in family vacations, destination weddings, and guided group travel — the types of trips that bring people together for milestones, memories, and meaningful moments.

What I’m known for is a hands-on, concierge-style planning approach. I don’t just book a trip — I learn what matters most to my clients, their travel style, and the vibe they want for their experience. From choosing the right resort or cruise to coordinating special touches and detailed logistics, I make sure everything is customized to fit their vision.

I’m most proud of the joy I see in my clients when everything comes together seamlessly — those messages and photos of families bonding, couples saying “I do” in paradise, or groups celebrating life together without the stress of organizing. Knowing I played a role in making those memories possible… that’s what fuels me.

What sets Tailor Fit Travel apart is the heart behind the service. I treat every trip with the same care and dedication I’d give my own — pairing expert guidance with genuine support every step of the way. For me, it’s not just about the destination — it’s about creating unforgettable experiences, one perfectly planned trip at a time.

What makes you happy?
What makes me happiest is seeing people I love enjoy life — whether it’s my family laughing together, my daughter experiencing something new, or even my dog getting excited for a walk. Those little everyday moments remind me why I do what I do.

Travel also makes me happy because it allows people to step away from routine, reconnect, and create the kind of memories my own family treasures. Helping others experience that joy is incredibly fulfilling. There’s nothing better than knowing I played a part in bringing someone happiness, adventure, or a special moment they’ll cherish forever.

At the end of the day, connection, love, and shared experiences are what fill my cup — and that’s exactly what Tailor Fit Travel is built to create.

Contact Info:

• Website: https://tailorfittravel.com/
• Instagram: https://www.instagram.com/tailorfittravelllc?igsh=MWxzcWw4cDZ3YWlmaw==
• Facebook: https://www.facebook.com/share/17TAE4KNBy/?mibextid=wwXIfr