As the calendar has flipped to the final month of the year, the Upper Keys community holiday events kick into high gear (look no further than the picture packages in this week’s paper). From a tree lighting to a boat parade and winter wonderlands for the kids, Keys Weekly is proud to be your guide for this holiday season in town. Check out our listing of events below. And if we missed any, we want to know.

From left, Marines Mgy.Sgt. Gomez and Lcpl. Charles during the Florida Keys Toys for Tots Poker Run in 2020. CHARLOTTE TWINE/Keys Weekly

Florida Keys Toys for Tots Poker Run

When: Saturday, Dec. 11 at 9 a.m.

Where: Begins at the Florida Boy Bar & Grill at MM 68.5, bayside in Layton at 9 a.m. Police escort leaves at 10:45 a.m. en route to the second stop at Tuna’s Restaurant Patio, MM 80.5, oceanside, at 11:15 a.m. Final stop is at the Ocean View Pub at MM 84.5, bayside, Islamorada at noon. 

Details: A fun-filled day for a great cause, some 75 motorcycles will ride together over scenic bridges with a full police escort. Top five poker hands will select from high-valued prizes donated by local sponsors. Raffle tickets are also available. Registration is recommended. Advance registration is available by calling Ken “Sarge” Keidel at 305-951-0841. Every year the U.S. Marine Corps collects toys for children each year through the Toys for Tots program. More information at Florida Keys Poker Run & Motorcycle Parade on Facebook. 

Kids Night Out

When: Saturday, Dec. 11 from 5 to 9:30 p.m. 

Where: Founders Park, Islamorada

Details: Parents can enjoy a night out while their children enjoy holiday crafts, games, contests and more during the evening. Activities include dodgeball, movies, build-your-own ice cream sundae, crafts and chances to win prizes. Dinner and snacks will be provided. $20 per child and a $15 sibling discount. Be sure to bring sneakers and a refillable water bottle. Pre-registration is required by calling David Nero at 305-853-1685. 

Key Largo Boat Parade

When: Saturday, Dec. 11 at 7:30 p.m. Boats begin lining up an hour before. 

Where: Blackwater Sound in Key Largo. Great viewing spots include Big Chill, Sundowners, Key Largo Marriott and Caribbean Club.

Details: Put on by the Key Largo Sunset Rotary Club, this year’s boat theme is “Naughty-cal and Nice.” Boats will light the night as they parade near the shores of the Key Largo bayside waters. There’s no fee to enter the boat parade. Prizes are available, and each boat participating in the parade will get a ditty bag. More information at

MarrVelous Pet Rescue’s Pawliday Celebration & Grand Opening 

When: Sunday, Dec. 12 from 11 a.m. to 3 p.m.

Where: 68 Silver Springs Dr., Key Largo

Details: MarrVelous Pet Rescues has a home. Join them for an open house and grand opening at MM 101, bayside. Lots of fun and activities, including dog training and pack walk from noon to 1 p.m. Meet the adoptables and get a photo with Santa Paws. 

Santa Claus & Carolers Come To Town

When: Sunday, Dec. 12 from 5:30 p.m. to 9:20 p.m.

Where: Streets of Islamorada

Details: The Islamorada Firefighters Benevolent Association and Islamorada Fire Rescue will guide Santa Claus, Mrs. Claus and carolers through the roads and streets of Islamorada for residents to see. Santa and friends will begin the journey at the Islamorada Mobil on Lower Matecumbe at 5:30 p.m. They’ll end on Bee Street around 9:19 p.m. A full schedule of arrival times can be found on Islamorada Fire Rescue Department’s Facebook.

The ‘Santa Claus and His Carolers Are Coming to Town!’ event makes its way through Founders Park on Dec. 13, 2020. DOUG FINGER/Keys Weekly
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.