The 5 Can’t-Miss Florida Events Happening in January 2026

Sam Truett
Jan 1
2 min read

If you think January is a time to stay inside and recover from the holidays, you are living in the wrong state.

In Florida, January is arguably the best month of the year. The humidity is gone, the mosquitoes are (mostly) dormant, and the event calendar is absolutely stacked. From a pirate invasion in Tampa to the world’s largest car auction in Kissimmee, here are the top 5 events you need to put on your calendar this month.

Classic cars lined up under a tent. A red car with its hood open is in focus. Other vintage cars and visitors are visible in the background.

1. Mecum Kissimmee 2026

Dates: January 6 – 18, 2026
Location: Osceola Heritage Park (Kissimmee)
The Vibe: High-octane history.
Why It’s Fascinating: This isn't just a car show; it is officially the world’s largest collector car auction. Even if you aren't bidding, it is a massive museum of automotive history that you can walk through. This year, they are auctioning over 4,000 vehicles, ranging from pristine 1960s muscle cars to rare Ferraris. It is loud, expensive, and incredible to watch.

People walk along a vibrant street lined with palm trees and colorful neon-lit buildings. Evening sky adds a lively atmosphere.

2. Art Deco Weekend

Dates: January 9 – 11, 2026
Location: Ocean Drive (Miami Beach)
The Vibe: 1920s glamour by the ocean.
Why It’s Fascinating: Most people walk past Miami’s pastel buildings without looking up. This festival changes that. It celebrates the unique architecture that put Miami Beach on the map. Expect guided walking tours, classic car shows, and a "Jazz Age" lawn party that feels like stepping onto a movie set. It is the best time to see South Beach’s history, not just its nightlife.

Crowded fairground at dusk with a lit Ferris wheel and carousel. Colorful lights and flags adorn the rides, creating a festive atmosphere.

3. The South Florida Fair

Dates: January 16 – February 1, 2026
Location: West Palm Beach
The Vibe: Classic Americana with a tropical twist.
Why It’s Fascinating: This is the first major fair of the year, often setting the trends for the "fried food" craziness you’ll see elsewhere later. Beyond the rides, check out the Yesteryear Village, a living history park inside the fairgrounds that preserves buildings from Florida’s early pioneer days.

Man holds girl with balloon on shoulders, facing manatee mascot at festival. Green tent in background with "Best of the Best" sign, sunny day.

4. The Florida Manatee Festival

Dates: January 17 – 18, 2026
Location: Downtown Crystal River
The Vibe: Small town charm + giant sea cows.
Why It’s Fascinating: You cannot have a "Fascinating Florida" January without manatees. As the Gulf temperatures drop, hundreds of manatees flock to the warm springs of Crystal River. This festival celebrates them with art, music, and—most importantly—boat tours that take you right out into the bay to see them in the wild.
https://www.gomanateefest.com

People in pirate costumes on stage, some raising arms. Audience in foreground celebrating. Palm trees in background. Festive atmosphere.

5. Gasparilla Pirate Festival

Dates: January 31, 2026
Location: Bayshore Boulevard (Tampa)
The Vibe: Mardi Gras, but with pirates and cannons.
Why It’s Fascinating: It is the third-largest parade in the United States. The "Ye Mystic Krewe of Gasparilla" sails a fully rigged pirate ship into downtown Tampa, demands the key to the city from the mayor, and then leads a massive parade down Bayshore Boulevard.
Note for Parents: The "Children’s Parade" (the alcohol-free version) happens a week earlier on January 24th.

Which one are you heading to? I’ll be at the Manatee Festival looking for the best spot to launch a kayak. Let me know in the comments where you are spending your January weekends!