Welcome to the most wonderful time of the year—Florida Keys style. While the rest of the country is digging out of snowbanks, we’re out here deciding whether to wear our “fancy” flip-flops to the boat parade.
December is when the Keys truly shine. The humidity is a distant memory, the “Harbor Walk of Lights” is glowing, and the calendar is packed with events that make this island chain feel like the smallest, most festive town on Earth.
If you’re lucky enough to be here this month, here is your local’s blueprint for December 2025.
1. The Big Parades: Land and Sea
We don’t just do one parade; we do them on the street and on the water.
- Key West Hometown Holiday Parade (Dec 6): At 7:00 PM, the parade rolls down Truman Ave and Duval Street. Expect marching bands, local schools, and the most tropical Santa you’ve ever seen.
- Local Tip: Grab a spot on Truman Ave near the start of the route—it’s usually a little less chaotic than the Duval stretch.
- 34th Annual Schooner Wharf Lighted Boat Parade (Dec 13): At 8:00 PM, everything from dinghies to massive schooners will circle the Historic Seaport, decked out in thousands of LED lights.
- Local Tip: The festivities start at 6:00 PM. If you want a seat at Schooner Wharf Bar, you better get there by mid-afternoon.
2. Upper Keys Magic: Key Largo Boat Parade (Dec 13)
If you’re further north on the same night as the Key West parade, the Key Largo Boat Parade is the place to be. Starting at 7:30 PM on Blackwater Sound (MM 103-104), this is the 40th anniversary of one of the Upper Keys’ favorite traditions.
- The Theme: This year’s theme is “The Grinch in the Keys,” so expect plenty of neon green and Whoville-inspired nautical setups.
- The Best Viewing Spots: * Jimmy Johnson’s Big Chill: The official host and arguably the best seat in the house for food and drinks while you watch.
- Sundowners: This is where the awards ceremony happens at 9:30 PM, so the energy here is always high.
- Caribbean Club: For a more classic, “Old Keys” dive-bar vibe while the boats cruise by.
- Mote’s Coral Nursery (at Reefhouse Resort): They are hosting a special watch party ($5 entry) that includes a tour of their land-based coral nursery before the boats start.
- The Finale: Stick around after the last boat—the night wraps up with a huge fireworks display over the water.
3. The “Snow” in Islamorada: Holiday Fest (Dec 5)
Head to Founders Park on Friday, Dec 5 (4:00 PM – 10:00 PM).
- This is where you’ll find the 35-foot tall snow mountain. Yes, real snow in the Keys.
- There’s a parade at 7:30 PM, the lighting of a 35-foot tree, and enough holiday spirit to make you forget you’re standing next to a palm tree.
4. Holiday Lights & Local Shopping
- Conch Tour Train Holiday Lights Tours: Running nightly (Dec 8 and 11-23). It’s the easiest way to see the best-decorated houses in Old Town with a cup of cider in hand.
- Key West Artisan Market (Dec 14, 21, 28): Held at Indigenous Park. These December editions are perfect for finding hand-poured candles and Keys-inspired art for last-minute gifts.
5. New Year’s Eve: Choose Your “Drop”
On December 31st, pick your favorite Key West icon to watch “drop” at midnight:
- The Red Shoe Drop: Sushi in her giant red high heel at Bourbon St. Pub.
- The Conch Shell: The classic countdown at Sloppy Joe’s.
- The Pirate Wench: Dropping from the mast at Schooner Wharf Bar.
- The Key Lime Wedge: Dropping into a margarita at Ocean Key Resort.
The December “Local” Flavor
If you’re looking for a break from the holiday music, Stone Crab season is in full swing. Stop by Keys Fisheries in Marathon or The Fish House in Islamorada. Grab a bag of large claws, some mustard sauce, and find a quiet spot on the shore to enjoy the winter breeze.
