Many new names were announced as winners in this year’s Best of Upper Keys awards ceremony on Nov. 11 at Whale Harbor Restaurants & Marina. The first-time awardees jumped out of their seats as the crowd of 180-plus erupted in cheers. It’s a moment they won’t forget for years to come. The second running of the premiere people’s choice awards welcomed 15 new categories to the list.
Photos by DOUG FINGER/Keys Weekly
First-time Winners
Ashley Arrabal – Best Volunteer
Capt. Slate’s Scuba Adventures – Best Dive Shop
Dillon’s Pub & Grill – Best Bar & Best Wings
Keys Pet Nanny – Best Business
Klara McGarry – Best Bartender
Koty James & The Keybillies – Best Musician/Band
LaRhonda “LaLa” Oloizia – Best Server
Pinfish Entertainment – Best New Business
SouthState Bank – Best Bank
Taylor Hale Studio & Gallery in Islamorada wins Best Art Gallery. 
The Upper Keys Weekly’s Best of Islamorada at Whale Harbor Saturday, November 11, 2023. Photo by Doug Finger 
The Upper Keys Weekly’s Best of Islamorada at Whale Harbor Saturday, November 11, 2023. Photo by Doug Finger 
The Upper Keys Weekly’s Best of Islamorada at Whale Harbor Saturday, November 11, 2023. Photo by Doug Finger 
The Upper Keys Weekly’s Best of Islamorada at Whale Harbor Saturday, November 11, 2023. Photo by Doug Finger 
Pinfish Entertainment in Tavernier won Best Place to Take the Kids and Best New Business. Owner Matt Struhs holds the plaque next to his wife, April. 
The Upper Keys Weekly’s Best of Islamorada at Whale Harbor Saturday, November 11, 2023. Photo by Doug Finger 
The Upper Keys Weekly’s Best of Islamorada at Whale Harbor Saturday, November 11, 2023. Photo by Doug Finger 
The Upper Keys Weekly’s Best of Islamorada at Whale Harbor Saturday, November 11, 2023. Photo by Doug Finger 
The Catch’s LaRonda “LaLa” Oloizia wins Best Server. 
The Upper Keys Weekly’s Best of Islamorada at Whale Harbor Saturday, November 11, 2023. Photo by Doug Finger 
The Upper Keys Weekly’s Best of Islamorada at Whale Harbor Saturday, November 11, 2023. Photo by Doug Finger 
Best Musician/Band went to Koty James & the Keybillies. 
The Upper Keys Weekly’s Best of Islamorada at Whale Harbor Saturday, November 11, 2023. Photo by Doug Finger 
Best Business went to Keys Pet Nanny and owner Sarah Taylor. She’s pictured with family. 
The Upper Keys Weekly’s Best of Islamorada at Whale Harbor Saturday, November 11, 2023. Photo by Doug Finger 
Tavernier’s Froggy’s Fitness takes the Best Place to Work Out plaque. 
The Upper Keys Weekly’s Best of Islamorada at Whale Harbor Saturday, November 11, 2023. Photo by Doug Finger 
The Upper Keys Weekly’s Best of Islamorada at Whale Harbor Saturday, November 11, 2023. Photo by Doug Finger 
Kit Carson Mobley, of Islamorada’s DirtyBoat Charters, takes Best Fishing Guide. Manuela Carrillo Mobley, sales director with Keys Weekly Newspapers and Overseas Media Group, is also pictured. 
Ashley Arrabal, Key Largo Rotary club president, pictured here with husband Bryan, comes away with Best Volunteer.
Winners in New Categories
Ziggie & Mad Dog’s – Best Steak
Capt. Kit Carson Mobley – Best Fishing Guide
Chef Michael’s – Best Seafood
Islander Girl Snorkel & Tours – Best Watersports
Froggy’s Fitness – Best Place to Workout
Keys Chocolates & Ice Cream – Best Dessert
LeBouef’s Marine – Best Marine Services
Miss Monroe Boutique – Best Clothing Store
Natalie Shea, Shen Health – Best Alternative Healthcare Provider
Puerto Vallarta Mexican Bar & Grill – Best Margarita
Pasta Pantaleo – Best Artist
Pinfish Entertainment – Best Place to Take the Kids
Regan Roth Insurance Agency – Best Insurance Agency
Shell World – Best Gift Boutique
The Hale Gallery – Best Art Gallery
