Watch as turquoise, calm waters lap the shore, hike Islamorada’s tropical trails and join in on the seasonal celebrations to create holiday memories that last a lifetime.

Situated between the saltwater wilderness of the Everglades National Park and the deep blue waters of the Florida Straits, Islamorada is made up of six islands: Plantation Key, Windley Key, Upper Matecumbe Key, Lower Matecumbe Key and the offshore islands of Indian Key and Lignumvitae Key. Regardless of your location, the beauty of Islamorada transports you far from the real world.

Out-of-the-Ordinary

Book the family on a fishing adventure. The weather is perfect this time of year, and Islamorada’s not dubbed the Sport Fishing Capital of the World for nothing. If you prefer hiking, forge the nature trails at Long Key State Park or view an old quarry dug by the late Henry Flagler’s railroad workers inside Windley Key Fossil Reef Geological State Park.

For out-of-the-ordinary family enjoyment, stop at Robbie’s Marina on the main road and hand-feed one-metre-long hungry tarpon from the docks. Guard your fingers! Next, catch a dolphin, sea lion and parrot show at Theater of the Sea marine mammal park.

Party Like a Local 

To celebrate the Holiday Season, make your way to Founders Park for the 10th Annual Islamorada Chamber’s Huge Holiday Fest on December 5. Kids of all ages love the 10-metre tree, which blows magical snow from its branches. A 20-ton mountain of snow—Islamorada’s own famous Snow Mountain—is a favourite among mitten-clad munchkins. If you brought along your dog, take part in the Fido for the Santa Paws contest. Shop the Holiday Bazaar for special gifts and enjoy food and entertainment, as well as Santa, throughout the day. Come 7 p.m., the Holiday Fest Parade begins with the Coral Shores Hurricane Marching Band. The 16-hectare Founders Park also features an Olympic-sized pool, tennis and basketball courts and a dog park.

Keep in the spirit with a free, family-friendly, outdoor concert featuring traditional holiday music on December 20 at the ICE amphitheatre in Founders Park. Just take along some festive snacks, chairs and a blanket.

Around the islands, browse through the area’s burgeoning boutiques for unique holiday gifts you won’t find at home. And there’s no shortage of places to enjoy a family feast, headlined by fresh-from-the-dock seafood served at tiki-covered bars, dockside fish houses, gourmet beachfront cafés and secluded island bistros.

Travel Planner

Plan your holiday getaway to Islamorada with a visit to fla-keys.com/islamorada.