Winter in Islamorada offers more than just beautiful scenery. It is a season of world-class fishing, enchanting manatee encounters, and holiday traditions infused with island charm.
Seasonal Nature & Activities
Sailfish Season (November -April)
Winter marks the height of sailfish season in Islamorada, drawing anglers from around the world to pursue this fast and acrobatic species. Known for their spectacular leaps and fighting spirit, sailfish are the ultimate winter trophy offshore. While sailfish are the star of the season, anglers also enjoy excellent action with other prized gamefish such as king mackerel, wahoo, and blackfin tuna. Inshore and backcountry trips deliver just as much excitement, with redfish, snook, and spotted sea trout keeping rods bent all winter long.
Top Fishing Charter Options
If you are looking to get on the water, Islamorada offers some of the best charters in the Keys:
- Robbie’s of Islamorada provides a wide range of options including reef and wreck, backcountry, tarpon, and shark fishing with both private and shared charters available. Their captains bring deep local expertise to every trip.
- Live Action Charters specializes in inshore and backcountry excursions, perfect for anglers seeking a more personalized Keys fishing adventure.
Manatee Encounters
Cooler months bring Florida’s gentle giants into Islamorada’s marinas and canals as they seek warmer, shallow waters. Winter visitors often spot manatees in a few public places around town, including Tavernier Creek, the canal behind the Islamorada Library, and the Worldwide Sportsman/Bass Pro docks. Watching them surface and glide peacefully through the clear blue water is a highlight of the season.
Festive & Holiday Events
Holiday Fest at Founders Park
Friday, December 5, 2025 | 4:00–10:00 PM Location: Founders Park (MM 87) This festive signature event transforms the park into a tropical winter wonderland. Celebrate with a parade at 7:30 PM, the lighting of a 35-foot snowing holiday tree, a massive 30-ton Snow Mountain for sledding, artisan shopping at the Holiday Bazaar, Santa’s arrival by fire truck, and a fireworks finale over the water.
Holiday Boat Parades & Lighted Bike Parade
Decorated boats drift along Islamorada’s waterways, while the Lighted Bike Parade invites families and friends to ride through the village in holiday glow. Dates are typically announced in fall.
Festive Lights on the Water
Throughout December, waterfront homes and docks glow with tropical holiday décor including string lights, wreaths, palm wrapped bulbs, and lit up boats that create magical evening strolls.
Where to Stay in Islamorada
If you are looking for a luxury vacation rental in Islamorada, The Islands of Islamorada offers an unmatched experience. With spacious private villas, a beachfront setting, and upscale amenities, it is the ideal home base for a winter getaway. During the holidays, The Islands invites guests to create new traditions with a festive calendar of seasonal programming. Highlights include Christmas trees delivered to your villa, cookie decorating kits for families, and wellness activities designed for the season. Blending comfort with curated holiday touches, The Islands of Islamorada redefines what a luxury vacation rental in Islamorada can be. The Islands’ concierge can book your fishing guide trips and arrange all the details for your winter escape.
Escaping the cold weather, ask about rates for long-term stays to get your fill of the tropics. As The Islands of Islamorada serves as your home base to soak in the heat during the cold winter months.