Holiday Magic in Paradise: Your 2025 Guide to Key West’s Festive Events

This winter Key West is lighting up the island with holiday magic tropical style. December in paradise is filled with sparkling lights, waterfront celebrations, festive tours, and that unmistakable Key West charm that makes the season feel extra special.

Check out Krystal's 2025 guide highlights the must-see events that bring the island to life. Share it with friends, clients, and visitors looking to experience the joy of the holidays Key West style.

Key West Lighted Boat Parade

A Key West classic and one of the most anticipated holiday events of the year. Imagine a fleet of boats big, small, quirky and creative gliding across the historic Key West Harbor covered in twinkling lights and festive décor.

Grab a waterfront seat or hop aboard one of the participating vessels to enjoy the parade from the water. Expect holiday music, tropical vibes, and a whole lot of island cheer. This is one event your December calendar needs.

Best for: families, visitors, and anyone who loves a holiday celebration that glows on the water.

Holiday Historic Inn Tour

Key West’s charming inns and boutique hotels open their doors for a rare “behind-the-scenes” holiday experience. Each stop on the tour is decked out with unique seasonal decorations think tropical wreaths, gingerbread architecture, island-inspired Christmas trees, and historic homes wrapped in twinkling lights.

Local musicians often perform, and some inns offer light bites or festive drinks. Strolling from inn to inn on a cool December evening feels like stepping into a living holiday postcard.

Best for: history lovers, design enthusiasts, and anyone who wants a more intimate, old-town-meets-holiday experience.

Key West Holiday Village

Set in the heart of the island's holiday scene, the Key West Holiday Village brings festive fun for all ages. Expect artisan vendors, live performances, themed nights, and plenty of spots for that perfect holiday photo.

From tropical Santa visits to holiday markets and sweet treats, the Holiday Village captures the joyful spirit of island life. It’s a community favorite and a must-see for visitors wanting a taste of local holiday cheer.

Best for: families, shoppers, and guests looking to soak up holiday energy in a lively setting.

Why December in Key West Feels So Magical

There’s something special about celebrating the season in paradise. The weather is cool but breezy, palm trees sparkle with lights, the island slows down just enough, and locals embrace the holiday season with the easygoing warmth Key West is known for.

Whether you’re taking in the sunset at Mallory Square, exploring festive neighborhoods, or sipping something delicious on a porch wrapped in garland, the island just feels… magical.

Key West holidays aren’t just about events they’re about community, creativity, and celebrating in a place that feels like home.

If you’re planning holiday content, looking for things to do, or helping clients plan their trip, this guide is your go-to resource for everything festive in paradise.

And if you ever need personalized recommendations best viewing spots, local traditions, or hidden gems I’ve got you covered.