Winter in Islamorada is one of the most captivating seasons in the Florida Keys. Warm breezes, turquoise water, vibrant marine life, and festive moments create the perfect backdrop for a laid-back Florida Keys winter vacation. Whether you are drawn by world-class winter fishing, wildlife encounters, or seasonal events, Islamorada offers something special for every traveler.
Peak Fishing Season in Islamorada
Sailfish Season (November through April)
Winter is the pinnacle of sailfish season in Islamorada, attracting anglers from around the world. Sailfish are known for their striking speed and dramatic leaps, making them a top target throughout the cooler months. Offshore waters also deliver strong winter action for king mackerel, wahoo, and blackfin tuna.
Inshore and backcountry anglers enjoy steady bites from redfish, snook, and spotted sea trout. With such variety, winter is one of the best times of year to plan an Islamorada fishing trip.
Trusted Local Fishing Charters
Islamorada’s longtime captains and guides create exceptional days on the water. Two guest favorites include:
Robbie’s of Islamorada, offering reef, wreck, offshore, and backcountry trips with both private and shared charters.
Live Action Fishing Charters, specializing in personalized inshore and backcountry excursions for anglers of all experience levels.
Winter Wildlife: Manatee Viewing in the Florida Keys
Cool temperatures draw manatees into the Keys’ warmer canals and marinas, making winter one of the best seasons to spot these gentle animals. Popular areas include Tavernier Creek, the canal behind the Islamorada Library, and the docks at Worldwide Sportsman. Their slow, peaceful movements through the clear water provide a memorable winter wildlife experience.
Seasonal Festivities and Holiday Charm
Friday, December 5, 2025 | 4:00 to 10:00 PM
Location: Founders Park (MM 87)
Founders Park transforms each December with a festive parade, the lighting of a towering holiday tree, a 30-ton Snow Mountain, artisan shopping, Santa’s arrival, and fireworks over the water.
Saturday, December 13, 2025 | Boats Line Up 6:30 PM, Parade Begins 7:30 PM
Location: Blackwater Sound (MM 104)
Colorful, decorated boats fill the Key Largo waterways in this annual holiday parade.
Tropical Holiday Lights
Throughout December, waterfront homes, palm trees, and docks glow with coastal holiday lights, creating the perfect backdrop for an evening stroll.
Where to Stay: Winter at The Islands of Islamorada
Nestled among the turquoise waters and lush landscapes of Islamorada, The Islands of Islamorada offers a residential-style resort experience that combines privacy, comfort, and true Florida Keys tranquility. Guests can choose from spacious one-bedroom suites or expansive four-bedroom waterfront villas. Each villa includes a full kitchen and generous living space, creating the perfect home base for families, couples, and extended winter stays.
Imagine sipping coffee on your private terrace each morning while taking in endless ocean views. At The Islands, you can enjoy the warmth of a tropical holiday season without needing a passport.