Henry Menendez of HNO Productions can’t help but laugh during the opening introductions.

Sixty-five coveted plaques were presented to the upper island chain’s finest businesses, nonprofits and people during the Nov. 11 Best of Upper Keys awards ceremony at Whale Harbor & Restaurants in Islamorada. 

In its second year, the Best of the Upper Keys raised $26,350 — up from $19,050 in 2022 — between ticket sales, sponsors and raffles. Funds will support the Florida Keys Children’s Shelter’s mission in aiding runaway youth and counseling families in times of need. 

Square Grouper Islamorada and Dillon’s Pub & Grill in Tavernier led the way for most awards, with three each. Lynn and Joe Bell, the mother-son team who own and manage Square Grouper, were handed plaques for Best Lunch, Best Place to Take a Date and Best Overall Restaurant. Dillon’s received Best Bar and Best Wings, and the restaurant’s Klara McGarry took Best Bartender.

A new bowling, ax throwing and arcade destination in Tavernier made a splash at the awards. Pinfish Entertainment and owner Matt Struhs took home Best New Business and Best Place to Take the Kids. The Best of Upper Keys also saw a number of back-to-back winners, including Monroe County Mayor Holly Merrill Raschein for Best Elected Official, Reef the fox for Best Celebrity, Key Largo School’s Tiffany Zepeda for Best Educator and Dr. Stan Zuba for Best Doctor. 

Event emcees Jason Koler and Britt Myers dished out the zingers, the roasts and the jokes in between the award presentations. The evening also recognized veterans in the crowd as the event fell on Veterans Day.  

In September, thousands of people from the Keys and beyond nominated their favorites in the food and drink, business and community divisions by visiting The top three vote-getters in the 65 categories moved on to the finalist stage, as people logged in daily for roughly two weeks to make their picks. The Best of the Upper Keys is run similarly to the Key West Bubbas People’s Choice Awards, which began in 2014, and the Best of Marathon, which began in 2008.

Involvement in this year’s Best of Upper Keys increased from the year before, with a total of 217,170 voters cast.

The second annual Best of Upper Keys was made possible thanks to the support from event sponsor Whale Harbor Restaurants & Marina. Not only did they serve up delectable appetizers, but they also offered staff support and a premier venue overlooking the ocean. 

Event sponsors included First Horizon Bank, Baptist Health Mariners Hospital, Dr. Michelle, audiologist, Going Aire, HNO Productions, Overseas Media Group and Artisan Group Builders.

Alvin Bentley, Florida Keys Children’s Shelter chief financial officer, said proceeds from the event will support programming. The shelter serves multiple youth groups throughout the Upper Keys and the rest of Monroe County. 

“All those dollars are going directly to the programming and the employees who are making a difference in these kids’ lives,” Bentley said. “These kids have to have a support system in place, and that support system are the employees who we have at our organization.”

Stay tuned for next year’s Best of Upper Keys.

Jim McCarthy is one of the many Western New Yorkers who escaped the snow and frigid temperatures for warm living by the water. A former crime & court reporter and city editor for two Western New York newspapers, Jim has been honing his craft since he graduated from St. Bonaventure University in 2014. In his 4-plus years in the Keys, Jim has enjoyed connecting with the community. “One of my college professors would always preach to be curious,” he said. “Behind every person is a story that’s unique to them, and one worth telling. As writers, we are the ones who paint the pictures in the readers minds of the emotions, the struggles and the triumphs.” Jim is past president of the Key Largo Sunset Rotary Club, which is composed of energetic members who serve the community’s youth and older populations. Jim is a sports fanatic who loves to watch football, hockey, mixed martial arts and golf. He also enjoys time with family and his new baby boy, Lucas, who arrived Oct. 4, 2022.