Key West’s wildly creative Nadene Grossman Orr holds the keys to something many can’t unlock — an insider’s knowledge of all things Florida Keys, her own success, and some of the Keys’ craziest, most outlandish and popular events.
“We’ve got connections,” said Grossman Orr, Key West’s event planner extraordinaire.
As president and chief executive officer of her 21-year-old company, We’ve Got the Keys, she possesses a lyrically melodious — and persuasive — voice.
With some of my team that make that magic happen at the Key West Songwriters Festival including Michael Blades, J.R. Henggeler, Jennifer Levering, Nadene Grossman Orr, Kade Mortenson, Kaylee Santopietro, Jordan Upchurch, Liz Love, Nick Doll.
(photo courtesy of Nadine Grossman Orr)
Grossman Orr produces the annual Key West Songwriters Festival, which is now in its 29th year and runs April 30 to May 4. The popular festival boasts nearly 250 performers on more than 50 stages throughout the southernmost island city in the continental United States.
The Key West Songwriters Festival, launched in 1995, is known today as the world’s largest festival of its kind. And it’s become a launchpad for emerging country artists and a showcase for top country music talent.
This year’s artists include Nate Smith, Chase Matthew, LOCASH, Jeffrey Steele, James Slater, Raul Malo, Rebecca Lynn Howard and a multitude of award-winning and emerging talent.
“It’s a rite of passage… a stepping stone for artists,” Grossman Orr said. “We had Luke Combs here in 2016, a year before he hit it big. We’ve had amazing artists such as Kasey Musgraves, Chris Stapleton, Maren Morris, Morgan Wallen, and Lee Brice. The artists have as much fun as the fans do at the festival.”
Grossman Orr helped water the fledgling seeds of the Key West Songwriters Festival’s development with founders Charlie Bauer and Drew Reid, the locally well-known owner and musician, respectively, at Hog’s Breath Saloon.
While working as both a Hog’s Breath cocktail server and a Hilton hotel concierge, she convinced Hilton’s local management to accommodate a few songwriters in exchange for a sunset performance on a waterfront pier.
“This allowed us to grow the festival and invite more performing songwriters,” she recalled. “From the inaugural events, we continued to partner with more hotels and venues each year. I’m just a creative thinker. The stars aligned.”
The Key West Songwriters Festival has proved to be so popular that current owner Rams Head Presents in 2022 franchised the Annapolis Songwriters Festival, modeled after the Key West fest, in Annapolis, Maryland. Sponsor BMI, representing more than 1.4 million songwriters, composers and publishers, selects featured talent.
My event director, Liz Love, me, and Kirby Myers at La Concha’s 99th celebration and grand opening event.
(photo courtesy of Nadine Grossman Orr)
We’ve Got the Keys organizes the fest’s events and schedules. “It’s logistical, like a giant puzzle, and my most challenging event,” said Grossman Orr.
Grossman Orr also produces and organizes other popular island-wide happenings including the Key Lime Festival, held July 2-6, over the July 4th weekend; Fantasy Fest, this year themed “Bedtime Stories & Magical Monsters” and slated Oct. 17-26; and a Taste of Key West, scheduled March 23, 2026, at Truman Waterfront Park.
Grossman Orr, known for creating lively outrageous events, said her favorite personal Fantasy Fest memories include showcasing many of Key West’s local personalities as grand marshal for the Fantasy Fest Parade and in the 10-day event’s Masquerade March, known as “the locals’ parade.” She especially enjoys seeing Fantasy Fest’s creative floats and parade groups delight scores of spectators.
We’ve Got the Keys, formed in 2004, also organizes and plans incentive travel programs, celebrations and events for groups, typically ranging from 25 to 400 participants.
“Our average size group is 50 to 80,” Grossman Orr said. “I love working with people and making memories of Key West experiences that will last their lifetimes.”
Grossman Orr first arrived in Key West in 1991, “fresh out of college” and just a week prior to Fantasy Fest, with a major in art and sociology from SUNY Geneseo. The native of South Setauket on Long Island, New York, came to manage the High Tide Gallery in the 800 block of Duval Street.
During the 1990s, she also worked in sales and crewed at Sebago Watersports Key West, was a cocktail server and a resort concierge. She has fond early memories of local icons Jimmy Buffett and Richard Hatch, the Blue Heaven restaurateur, and famed treasure hunter Mel Fisher.
“It was a pretty amazing time,” she recalled. “There were lots of Key West personalities who strolled the dock.”
In 2003, she reigned as Fantasy Fest Queen during the event’s milestone 25th anniversary, utilizing her local contacts as a concierge to raise the most amount of funds for AIDS Help Inc. (now A.H. Monroe, supporting individuals affected by HIV and AIDS).
My Family – My husband, Trevor, daughter, Meredith, and me.
(photo courtesy of Nadine Grossman Orr)
In Key West, Grossman Orr’s husband Trevor also works with We’ve Got the Keys, overseeing marketing programs with concierges. Daughter Meredith, 10, enjoys singing and acting with Bravo Theatre Camp, a five-week summer program culminating with a full-scale musical production.
“Key West is just a magical place,” said Grossman Orr, about her adopted hometown of 34 years.
Her motto: “Dream it. Do it.”
Where she dines: Origami Sushi Bar and Square Grouper Key West
Where she explores: Throughout the Florida Keys and in Michigan
How she relaxes: “I work too much … but with family and friends, at the beach, lake or anywhere near the water!”