
A room packed with dignitaries and community members watched as winners jumped out of their seats to grab their plaques during the fourth annual Best of Upper Keys at Playa Largo Resort on Nov. 14.
From restaurants and local businesses to community icons and nonprofit organizations, the premier people’s choice awards celebrated all the Upper Keys has to offer to guests and residents.
More than 250 attendees spent the evening cheering winners while laughing at the roasts and jokes offered by the hosts, the Keys Weekly’s Jason Koler and Britt Myers.
Square Grouper Islamorada came away the biggest winner in this year’s Best of Upper Keys. The restaurant run by Lynn and Joe Bell secured Best Lunch for the third time and Best Overall Restaurant for the fourth straight year, as well as Best Dessert for the second year in a row. Above the restaurant, Sunset Lounge won a brand-new category in Best Raw Bar.
Florida Keys Brewing Co. in Islamorada came away with three wins, including Best Live Music for the fourth-straight year, Best Bar for the second time and Best Beer Selection. C&C Wood Fired Eats in Key Largo took home Best Happy Hour and Best Pizza for the fourth year in a row. Islamorada’s M.E.A.T. Eatery & Taproom took Best Burger for the fourth time. Robbie’s Hungry Tarpon Restaurant took Best Bloody Mary for the fourth straight year.
In the community category, the Upper Keys Rotary Club’s annual Gigantic Nautical Market won Best Festival/Event. Plantation Key Colony secured a four-peat for Best Neighborhood, as did Reef the fox for Best Local Celebrity and Monroe County Commissioner Holly Raschein for Best Elected Official. Best Educator went to Key Largo School’s Pam Caputo.
Additional categories resulted in new winners in this year’s Best of Upper Keys. City Hall Cafe in Islamorada came away with Best Wine Selection, while Lazy Days in Islamorada won Best Cook Your Catch. The host of the event, Playa Largo Resort, won Best Resort/Hotel. And Islander Resort in Islamorada hoisted the Best Wedding Venue plaque.
As for business, CBT Construction won Best General Contractor for the fourth straight year. Other four-peats include Island Hammock Pet Hospital in Key Largo for Best Veterinary Hospital; Tim Matthews Tree & Landscaping for Best Landscape Company; Hershoff, Lupino & Yagel for Best Law Firm; and DePaula Jewelers for Best Jewelry Store.




A complete list of the winners is at keysweekly.com or on page 5.
From Sept. 18 to Oct. 5, residents and readers from the Florida Keys and beyond nominated all their favorites in the food and drink, community and business divisions by visiting keysweekly.com. The top vote-getters in each of the 86 categories moved on to the finalist stage, as people logged in for 13 days to make their picks. More than 235,000 votes were cast during the finalist round from Oct. 16 to Nov. 2.
The fourth annual Best of Upper Keys was made possible thanks to the host sponsor Playa Largo Resort, which provided the venue, food and drinks for guests. Event sponsors include HNO Productions, First Horizon Bank, Baptist Health South Florida, Ocean Sotheby’s International Realty, H&R Block Key Largo, Going Aire and Overseas Media Group.
Proceeds from the event support the Florida Keys Children’s Shelter, which serves multiple youth groups throughout the island chain. The shelter in the Upper Keys is located in Tavernier. Ben Kemmer, children’s shelter CEO, said it’s the shelter’s 40th anniversary. Over that span, the shelter has served more than 20,000 kids.
“The Best of Upper Keys is a wonderful community celebration, and it’s awesome to see everyone recognized for their dedication and hard work,” Kemmer said. “We’re thankful for all the support this event provides to the shelter. Every bit helps us keep doing what we do for the kids in our community.”
Stay tuned for what’s in store for the fifth annual Best of Upper Keys.


















