Our Story

Timing Is Everything

Some would say we were on two completely different paths.

Honestly, that’s true — at least in the beginning.

Before we became The Womacks, we were both working as production cast singers for Royal Caribbean. The funny thing is, even though we were working for the same company, we never actually worked together. It’s amazing to think that our paths may have crossed countless times without us even knowing it.

Timing has always played a major role in our story.

At the time, Derek was just two weeks away from starting rehearsals with another company when the phone call came: a takeout cast contract on Wonder of the Seas — which, upon completion, would become the largest cruise ship in the world. A takeout cast meant something special. No other cast had ever performed the shows before. Everything would be built from the ground up.

That opportunity was exciting because installing a show had always been a dream. Creating something from scratch felt like the kind of challenge worth chasing.

At almost the exact same time, Aili had already accepted a contract with another company as well. She was only about a month away from rehearsals when she received the same call from Royal Caribbean for Wonder of the Seas.

The motivation for both of us was surprisingly similar: the opportunity to help build something brand new, perform on one of the most groundbreaking ships in the world, and take a chance on something bigger.

So we both made the leap.

We boarded flights to France to join the ship.

And that’s where we met.

Our flights landed within minutes of each other.

Like we said…

timing played a big part in our story.

Building the Dream

As we got to know each other, we quickly realized how much we had in common — not just as performers, but as people.

We both came from musical families and understood how deeply music and performing could impact people’s lives. Entertainment wasn’t just a job to us; it was something personal. We both believed in the power of live performance to create connection, joy, healing, and unforgettable memories.

We also shared a common goal: becoming guest entertainers.

Before meeting Aili, Derek had already stepped into that world with a Stevie Wonder tribute show called A Night of Wonder. After finding representation and performing the show on stages around the world, things were beginning to gain momentum.

Then the pandemic changed everything.

Like so many performers, we found ourselves back home trying to navigate uncertainty while continuing to work on our craft. Derek returned to Florida. Aili returned to New York City. But even during that difficult season, the dream never disappeared.

So when we eventually decided we wanted to build something together, we made a plan.

The idea was simple in theory: take one final contract as production singers, save money, and spend every free moment building our own guest entertainer shows from the ground up.

That contract ended up lasting nearly ten months, which gave us time to truly pour ourselves into the creative process.

Together, we built everything: the song lists, scripts, vocal arrangements, orchestra charts, media, costumes, transitions, and even our signature a cappella section. Night after night, in between performances and rehearsals, we worked toward creating a show that genuinely felt like us.

Eventually, we had something we were proud of.

But there was one problem: time was running out.

Our contract was almost over, which meant we were about to lose access to the stage, orchestra, production team, and technical support that had helped bring our vision to life. If we were going to take the leap, it had to happen now. So we reached out to our colleagues onboard for help. And thankfully, they believed in us. A very special thank you goes to Tornado Tanya for giving us our shot.

We had one opportunity.

One performance.

One chance to put our show in front of a live audience.

And when that moment finally came, it felt electric.

Standing on that stage performing something we had built together from scratch was one of the most fulfilling experiences of our lives. We could feel the audience connecting with the music, the stories, and the energy we were trying so hard to create.

By the end of that show, we knew something important: we were on the right path.

Just the Beginning

After our contract ended, we decided to take some much-needed time off. Life at sea had become such a major part of our lives that, honestly, we didn’t even really have a place of our own back in the United States anymore. So after getting married, we decided to settle down in St. Augustine, Florida — a place we had spent a lot of time in over the years and completely fallen in love with. There was something special about the city, and for the first time in a long time, it felt like home.

But even then, we still weren’t officially guest entertainers.

All we had was our vision, our shows, and a belief that if we kept pushing forward, eventually the opportunity would come. So we started sending our materials everywhere we could: agencies, entertainment companies, cruise lines, industry contacts — anyone willing to watch. Some conversations felt promising. Others felt uncertain. But through all of it, we stayed committed to the process and to each other.

Then one day, we received a phone call.

Princess Cruise Lines had originally considered giving us an opportunity, but at the time there weren’t many available dates. However, another performer had suddenly cancelled, and they wanted to know if we could step in on short notice. Without hesitation, we said yes. We flew out to the ship, performed the show, and hoped for the best.

That performance changed everything.

After speaking with the entertainment team onboard, we learned that audiences had absolutely loved the show. Soon after, we started receiving future dates well in advance, and before long, our calendars began filling up. And the craziest part? This is only the beginning.

Over the past year, we’ve had the privilege of traveling to more than 30 countries, meeting incredible people from all over the world, and sharing music with audiences we never could have imagined reaching.

What continues to inspire us most are the stories people share after the shows.

Audience members have told us how certain songs reminded them of meaningful moments in their lives, loved ones they’ve lost, relationships they cherish, and memories they thought they had forgotten. Those conversations remind us why we do this.

Music connects people.

It always has.

And our mission is to continue finding the music that brings people together and sharing it in a way that feels honest, joyful, and unforgettable.

It is truly our joy and privilege to entertain you.

Welcome to our story.

Welcome to The Womacks.