Things to Do in February 2026 in Islamorada
February is one of the best months to be in Islamorada. The weather is mild, the water is active, and the calendar is full of events that feel distinctly “Keys”—from sailfish tournaments to art walks and waterfront markets. Whether you’re here to fish, explore, or simply enjoy island life at a slower pace, February delivers.
Even better? Staying at Kon Tiki Resort puts you right in the middle of it all—most events are either walkable or just a short drive from your waterfront cottage.
Sailfish Tournament Season Is in Full Swing
February is prime time for sailfishing in the Florida Keys, and Islamorada proudly hosts two major tournaments that draw anglers from all over.
Islamorada Bartenders Sailfish Open
📅 February 12–14, 2026
📍 Islamorada, FL
This popular tournament combines competitive fishing with a laid-back, social atmosphere. Expect strong sailfish action during the day and lively evenings around town. Even if you’re not fishing, it’s fun to watch the boats return to the docks and see the daily weigh-ins. Not in the industry? Support our local bartenders by stopping in during happy hour—our Islamorada Happy Hour Guide highlights the best spots to raise a glass.
Poor Girls Sailfish Tournament
📅 February 19–22, 2026
📍 Islamorada, FL
A longtime favorite in the Keys tournament lineup, the Poor Girls Sailfish Tournament brings together skilled teams and a great crowd. February’s consistent weather and active sailfish make this one of the best times to experience Islamorada’s fishing culture.
Staying bayside at Kon Tiki? Our complimentary dockage and central location make tournament days easy—whether you’re participating or spectating. If fishing isn’t your thing, there’s plenty more happening around town.
Morada Way Third Thursday Art Walk
📅 February 19, 2026
📍 Morada Way Arts & Cultural District
The Morada Way Art Walk is a monthly favorite—and in February, it’s especially enjoyable thanks to cooler evening temps. Local galleries open their doors, artists line the street, and food trucks and live music set the tone for a relaxed night out.
Best of all, Morada Way is within walking distance of Kon Tiki Resort, making it an easy, stress-free evening. No parking headaches, no driving—just stroll over and enjoy.
Gigantic Nautical Flea Market
📅 February 7–8, 2026
📍 Islamorada, FL (short drive from Kon Tiki Resort)
The Gigantic Nautical Flea Market is a must for boaters and ocean lovers. You’ll find marine gear, nautical décor, fishing equipment, artwork, and all kinds of coastal finds—new and used.
Even if you’re not shopping for boat gear, it’s a fun event to browse and soak up the local vibe. From Kon Tiki, it’s a quick drive, making it easy to stop by without committing a full day.
Not Into Events? There’s Still Plenty to Do
February is also a great month for everything else Islamorada does well:
- Explore the water and outdoors with our guide to the Best Outdoor Activities in Islamorada
- Spend a quiet afternoon beach hopping using our Best Beaches Near Islamorada
- Wind down with waterfront cocktails using our Islamorada Happy Hour Guide
- Or simply relax and enjoy why Islamorada makes the perfect home base for exploring the Florida Keys
Stay Central, Stay Local
February events in Islamorada are easy to enjoy when you’re staying in the right spot. Kon Tiki Resort offers bayside cottages, Old Florida charm, and a quiet atmosphere—while keeping you close to fishing tournaments, art walks, beaches, and restaurants.
Whether you’re planning around a specific event or just looking for the best time to visit, February checks all the boxes.