Taste of Island Life

Behind the scenes of a Key West community’s annual food festival 

September 26, 2025 | story and photos by Ashley Rodriguez

Kaylee Santopietro walks up to the pier at Truman Waterfront Park with a map and a mission. In the next 24 hours, this space will fill with tents, kitchen supplies, generators, porta potties, recycling bins and most importantly, thousands of people. As the event coordinator for a festival called Taste of Key West, Santopietro is laser-focused on the initial setup, which currently involves laying out bright orange duct tape on the concrete. She looks up from the sections she’s created. 

This restaurant goes here. The beer tent goes there. The wine tent goes here.

These careful calculations are just a taste of what the festival has in store, the first step for the 100-person crew that will bring the plans to life.

Nestled at the tail end of Florida’s island cities, in the southernmost point of the continental U.S., Key West is home to a tight-knit, bustling community that takes any chance to congregate in celebration. The town is known for its extravagant if not eccentric festivals, attracting locals and tourists alike. 

Taste of Key West is one of these events, held annually at a pier overlooking the western waters. This three-hour celebration of local flavors gives restaurants and prospective customers the chance to meet in one place, as guests weave between food, wine and beer stands serving samples to anyone with tasting tickets. 

Now, Taste of Key West has returned in spring for its 30th year, hosting over 4,000 guests. A smaller event team and members of a local nonprofit assemble most of the festival, with the help of over 100 volunteers.

Months beforehand, Santopietro sat at home sending emails, making calls and getting as many restaurants as possible on board. She expects to host some regulars, from several waterfront fine-dining restaurants to a hot dog stand. 

Less than a mile from the pier, volunteer coordinator Liz Love drives toward a repurposed church where volunteers have already lined up on the street. Love runs over, door keys in hand. 

Inside the church, colorful glass panes, tall ceilings and dark purple curtains form a stately backdrop for the group’s meeting, where volunteers will review the event details. Some of the seats fill with members of the community service group the Southernmost Coconut Castaways, beloved this year for their manning of the beer and wine tents.

Paul Duma, the Coconut Castaways’ membership director, anticipates pouring beers after working different corners of the event for over a decade. Sometimes that meant helping vendors get what they needed. Other times, he assumed the role of ambassador, eyes peeled for any person whipping their head around in confusion, ready to shake away their worries with a smile and an answer to their question. Having worked in restaurants all his life, he knows what to anticipate from event goers.

As the volunteers begin settling down, Love passes around a sign-in sheet while Nadene Grossman Orr, the festival’s director, plops a bag of demonstration items down on the stage. The stash features a wine glass, a beer pint and dark blue T-shirts with event branding.

“Let’s get this party started,” Grossman Orr says, before addressing the volunteers with a raised eyebrow.

“Remember,” she adds, “this is called taste of Key West.”

Laughter erupts from the crowd, which catches onto what Grossman Orr is implying. There’s a delicate balance between giving the attendees what they want and leaving just enough to be desired. Duma remembers when customers threw tickets at him for a full pour; he reminded them there are rules he must abide by. 

Grossman Orr brings out the glassware and points at the serving cutoff, just below the Taste of Key West logo — a cue to avoid completely inebriating the crowd.

Once they’re dismissed, most of the volunteers exit through the open arches where a cool breeze passes through. Some stay back to ask questions or make casual conversation. The Coconut Castaways stand in one corner.

“Hi Paul!” one woman says.

“Paul!” another one chimes.

Duma greets two volunteers warmly with a hug. The smiling faces are his reason for returning each year, he said. This reward comes before the event has even begun.  

A week before the event, Santopietro and the rest of the Taste of Key West team are on crunch time. Grossman Orr is working closely with a local news publication to create a comprehensive map for attendees. Santopietro locks in the last couple of restaurants, relaying the information to Grossman Orr.

A few days before the event, Scott Maurer, the executive chef at Hot Tin Roof Restaurant, meets with his team of chefs in the morning to begin preparation. The sample menu is savory and sweet: southern pickled shrimp tacos and double fudge bacon brownies. 

Before he joined the waterfront restaurant, Scott Maurer logged a long history of culinary endeavors, from the Culinary Institute of America in New York to multiple executive sous-chef positions across the country. His role at an Orlando hotel would introduce him to his wife, a pastry chef. The pair moved to Key West in 2015 to pursue job opportunities. Now Maurer’s wife, Charity Maurer, works with him at Hot Tin Roof.

In the early mornings preceding the festival, the team of chefs narrowly whiz past one another in their prep kitchen. The tight space buzzes with constant sound — pots brewing, pans sizzling, refrigerator doors opening and slamming and orders flying between Scott Maurer and his team. The preparation is no small feat: between 500 and 600 samples in total.

On the big day, Santopietro gets a head start. The event doesn’t start until 6 p.m., but by the afternoon, she’s greeting trucks, SUVs and sedans as they drive into the parking lot of Truman Waterfront Park. Any onlookers may be confused to see these cars on the sidewalks and grass if it weren’t for Santopietro playing traffic control, waving a sparkly gold binder to direct vendors and patrons.

“It’s going to be a good day,” Santopietro sings.

Scott Maurer and other restaurant staff unpack all the essentials, including their own branded tents, tables, signs and a couple coolers. He watches as a new addition emerges from the truck, a highly coveted item for an event like this: chairs.

The crew aims jokes and jabs at one another like a game of pingpong.

In the meantime, Charity Maurer carefully lays down decorative grass on the table. She fluffs the blades and takes them to another table to cut out flowers and place them within the grass.

Directly across from them, Duma arrives at the beer tent at 4:45 p.m. The group assigned to the tent loads beer cans onto ice. They separate cardboard boxes and beverages, attentive to a new initiative this year to recycle and reduce single-use plastics. Any spills on the cardboard material mean they will go straight to the waste bin.

Duma looks out to the body of water fewer than 20 feet away from him, thrilled about the added environmental consciousness. The thought of trash blowing straight into the ocean makes him shake his head.

Santopietro checks her smart watch. It’s finally showtime. 

“Beer drinkers are fun people,” Duma says.

Santopietro, meanwhile, is running around all corners of the festival to ensure everything is running smoothly. She makes a pit stop at the VIP tents, keeping an eye out for anyone trying to enter without their exclusive lanyards and purple wristbands. Then she exits, engulfed by a sea of thousands of people.

Emerging from the crowd, Briening takes her place, spotting a familiar friend working at the VIP tent. The worker and another of Briening’s friends immediately huddle together to catch up. 

“It’s a good place to reconnect with people,” Briening says. 

A few vendors down at Scott Maurer’s tent, he and his crew deliver tacos and brownies to the hungry crowd, which he says is visibly larger than previous years. Just before 7 p.m., the restaurant staff displays their last prepared set of tacos.

“Well, that was quick,” Scott Maurer says, studying the table in disbelief.

The event doesn’t end for another two hours, and there’s no sign of the crowd slowing down. The team will just have to make sure the bacon brownies are enough to satisfy passing attendees. 

Then, Charity Maurer brings a tray of brownies to the front table.

“This is it,” she says.

The restaurant’s food and beverage manager, Sarah Kelley, looks over, and her eyes widen.

“Shut up — are you serious?” Kelley asks.

Scott Maurer replies with a joke about how the crew should send out the charcuterie snacks they have in the cooler.

“We’ll do dynamic pricing. Five tickets. Six tickets,” he says. 

Kelley hands one lucky customer the last dessert.

Maurer checks his watch. The time reads 7:09 p.m.

Briening strolls around the pier in no rush to reach each vendor. She gets her hands on one of her favorite samples of the night, a lobster roll. 

As the sun finally sets, casting strokes of peach and tangerine through the sky, guests ease their way to the end of the pier to take photos.

Santopietro uses the time to check on the vendors, channeling updates to the event team and volunteers. 

The darkening sky welcomes another shift in the attendees. People move their feet and bop their heads, loosening up as music streams through the speakers of a nearby DJ booth. Estelle’s “American Boy” plays, and a man in line for a restaurant moves his head and sings along. 

Back at his tent, Scott Maurer and his crew sit on chairs and coolers, still reeling from how quickly the night and the samples left them. Maurer runs through questions and possible solutions in his mind, disappointed the restaurant’s plans had fallen short. 

Then a guest approaches the table.

“My kid really needs a water,” she says. “I’ve gone to a bunch of vendors.” 

Kelley rises from the cooler, letting the woman know they have a few bottles to spare. Scott Maurer lights up then, a quick flicker of amusement in his eyes. 

He furrows a brow before meeting the woman’s gaze. 

“Eight tickets. Dynamic pricing,” he jokes. 

At 9 p.m., the staff take down their tents, vendors pack their cars and the crowd gradually files out. Clean-up volunteers cruise around in golf carts, taking trash bags out, emptying recycling bins and conserving any of the used glasses that attendees left behind. 

Santopietro watches the last of the VIP guests leave the tent, thanking her for a wonderful event. She sighs with relief.

Briening steps off the pier. 

“I’m very full,” she thinks to herself. 

In previous years, Briening took a five-minute walk to the Green Parrot, a nearby bar. But this time, she heads to the bike racks. She cruises straight home, passing the dim green lights of the establishment where locals flock, drinking until it’s time for their next event.