Meet the Mastermind

Nadene Grossman Orr

President and CEO

Nadene Grossman Orr arrived in Key West in 1991 and quickly immersed herself in island life, building a foundation rooted in hospitality, connection, and community. What began as a love affair with the Florida Keys grew into a remarkable career defined by creativity, leadership, and an unwavering passion for elevating the guest experience.

In 2004, Nadene founded We’ve Got the Keys, transforming her deep local knowledge into one of the region’s premier event planning and destination management companies. Over the years, she and her team have produced hundreds of unforgettable corporate programs, incentive travel experiences, and large-scale citywide festivals. From custom-curated adventures to innovative event design, Nadene is known for crafting experiences that capture the heart of Key West while surprising and delighting guests from around the world.
Her leadership extends far beyond event production. Nadene has played a driving role in shaping Key West’s cultural landscape through her work with the Key West Songwriters Festival, the Key Lime Festival, A.H. Monroe’s signature community event Taste of Key West , and most notably, her role as Director of Fantasy Fest, one of the island’s most iconic and globally recognized festivals.
In 2024, her decades of service, mentorship, and community impact were recognized with the prestigious ATHENA Award from the Key West Chamber of Commerce—an honor celebrating outstanding women who excel in business leadership, uplift others, and inspire through example.
Nadene has also been honored to receive a Samuel’s House Women of Integrity Award. These accolades reflect what the community has long known: Nadene is a driving force whose passion, professionalism, and generosity make Key West a more vibrant place.
Today, Nadene continues to lead with heart, vision, and a deep commitment to her island community. She lives in Key West with her husband, Trevor, and their daughter, Meredith, embracing the local arts scene, spending time on the water, and celebrating the island she proudly calls home. For Nadene, every day truly is a great day to be in Key West.

Meet The Team

Event Director
Bio coming soon.

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Event Coordinator & Partnership Director
Born and raised in Baton Rouge, Louisiana, Kaylee Santopietro has always had a Florida girl's heart. That pull led her to Key West in January 2021, where she quickly fell in love with the island’s vibrant energy, close-knit community, and unmistakable spirit.
Kaylee joined We’ve Got the Keys in March 2021 and now serves as Event Coordinator and Partnership Director, playing an integral role in bringing the company’s signature festivals to life. From sponsorship development and marketing to logistics, permitting, and on-site production, she is deeply involved in every phase of each event. Her work supports five major festivals annually, managing hundreds of sponsors and helping generate significant funding that keeps these beloved events thriving.
What Kaylee loves most about her role is the people — reconnecting with familiar faces year after year and collaborating with the businesses, artists, and partners that make the Key West festival scene so special.
A true island girl at heart, Kaylee’s Key West story also includes a chance meeting at the Key West International Airport, where she met her now-husband. Today, she coordinates these grand island festivals remotely from Pennsylvania, blending big-picture vision with meticulous detail to keep the spirit of Key West alive—no matter the distance.

Admin Operations & Event Assistant
Jessica—affectionately known as J.R.—first arrived in Key West in 2017 as a traveling seasonal bartender, spending summers at the Lake of the Ozarks and winters on the island. Originally from Nebraska, she brings a strong background in promotions and event marketing, having served as a promotions manager for a local MMA organization and leading brand ambassador teams for large-scale events and liquor promotions.
With a foundation in art and a passion for creative expression, Key West ultimately drew J.R. back into the world of events as a full-time resident. She joined the We’ve Got the Keys team in 2023, where her exceptional attention to detail, ability to multitask, and creative problem-solving skills play an important role in festival production and execution.
Outside of work, J.R. is deeply connected to the Key West community. She hosts a weekly ice bath social at a local kava bar, is actively involved in the island’s wellness community, and enjoys costuming and creative design—bringing imagination and energy into everything she does.

Accounting & Event Manager
Bio coming soon.

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Keys Concierge Marketing Manager
Trevor grew up on the shores of Lake Michigan and jumped at the opportunity to live and work in a place where being on the water year-round did not include ice skates. He arrived in the keys in 1996 and has worked in Key West hospitality sales, marketing, and operations ever since.

He likes drinking Pina Coladas, and getting caught in the rain. He's not into yoga. But if you need someone to help promote your business . . . He's your Guy!
As the marketing and distribution manager with our concierge referral program, Trevor is literally the "driving force" at We've Got the Keys . . . Driving equipment and supplies to events . . . Driving marketing materials to hundreds of concierge locations throughout Key West . . . He's even been know to drive a Fantasy Fest parade float on occasion. Chances are, if you need something from We've Got the Keys, Trevor will be driving it to you!