One of the best times of the year to visit Key West is during the holiday season, especially from late November through the month of December. This quirky little island city at the southernmost edge of the continental United States turns festive without ever losing its flip-flop soul. Think palm trees wrapped in lights, warm breezes off the Atlantic Ocean and Gulf of Mexico, live music floating down Duval Street, and sunsets that feel like a daily gift.
If you’re planning a Key West vacation and wondering if December is the best month to go, the short answer is yes. The long answer? Let’s dive into the best things, best places, and most unique activities that make December such a great trip.
Holiday Lights, Palm Trees & Old Town Vibes ✨
By Thanksgiving, holiday lights and festive lights begin appearing across Old Town, the Historic Seaport, and around the island’s beautiful historic homes and historic inns. Palm trees glow, porches sparkle, and casual evening walks turn into full-blown sunset celebrations.
This is the perfect time of the year to wander with a cocktail, soak up the holiday spirit, and admire the creative light displays locals go all out for. Add a slice of key lime pie, and you’re officially doing December in Key West the right way.
Don’t miss:
- Decorated historic homes throughout Old Town
- The popular Holiday Historic Inn Tour
- Neighborhood strolls filled with Christmas carols and tropical cheer
Year Round Historic Walking tour (self guided)
Mallory Square & the Famous Sunset Celebration 🌅🎶
No matter the time of year, Mallory Square is one of the most iconic Key West attractions, but December adds a festive twist. During the day, you might spot Santa sightings, and as evening approaches, the square fills with performers, artists, and live music.
The nightly sunset celebration is one of the most beloved Key West experiences, and December’s mild Key West weather makes it especially enjoyable.
Lighted Boat Parade at the Historic Seaport 🚤✨
The annual Lighted Boat Parade is a true Florida Keys tradition and a favorite annual event for visitors and locals alike. Boats decked out in holiday lights cruise past the Historic Seaport, creating a glowing, floating parade that feels both festive and unmistakably island-style.
Arrive early, explore the shops, enjoy dinner, and settle in for one of the most memorable moments of the Christmas season.
Trolleys, Trains & Easy Island Exploring 🚋
One of the best ways to explore the island during the winter months is by hopping aboard the Conch Tour Train or a trolley. During December, themed rides often highlight decorated neighborhoods, local legends, and plenty of holiday spirit.
Prefer to explore on your own?
- Rent a golf cart
- Walk Old Town early in the morning or after sunset
- Plan a relaxed full day trip broken up by food, shade, and sightseeing
Water Sports & Outdoor Activities in December 🌊☀️
Yes, it’s December. And yes, water sports are still very much on the table.
Thanks to warm water temperatures (usually mid-70s) and generally sunny weather conditions, December is a fantastic time for:
- Snorkeling the coral reefs
- Dolphin watching
- Parasailing
- Kayaking
- Glass-bottom boat tours
If getting wet isn’t your thing, a sunset cruise is always a good plan and one of the most relaxing Key West experiences this time of year.
New Year’s Eve on Duval Street 🎉🥂
New Year’s Eve in Key West is legendary and nationally televised. Streets fill with music, parties pop up everywhere, and the energy is pure celebration.
Choose your countdown:
- Conch Shell Drop outside Sloppy Joe’s Bar in the heart of Old Town
- Pirate Wench Drop at the Historic Seaport
- Red Shoe Drop (yes, that one)
If you’re looking for a good time, this is one night you won’t forget.
December Weather: What to Expect 🌤️
December falls squarely in the dry season, making it part of high season and peak season in the Florida Keys.
Typical December conditions include:
- Average daytime highs in the low 80s
- Cooler evenings in the 60s
- Less humidity than the summer months
- Fewer afternoon thunderstorms
Hurricane season officially ends in November, though tropical storms are always possible. Overall, expect warm weather, plenty of sunny days, and comfortable evenings.
Getting to Key West ✈️🚗
The easiest way to arrive is by flying into Key West International Airport (also called Key West Airport). Once you’re here, a car isn’t necessary and parking can be limited.
Other easy options:
- Walk or bike Old Town
- Rent a golf cart
- Use taxis or shuttles
Driving down from Key Largo? Turn it into a scenic journey through the small islands of the Keys.
Bonus Day Trips & Iconic Stops 🗺️
If you’re staying longer, add these to your list:
- Dry Tortugas National Park for a once-in-a-lifetime boat trip
- Bahia Honda State Park for beaches and views
- Truman Little White House
- Key West Lighthouse
- Custom House Museum
- Exploring the Historic Seaport and Key West Marina
You can also book deep sea fishing, museum visits, and classic island tours to round out your stay.
Why December Is One of the Best Times to Visit Key West 🌴🎄
Between festive lights, outdoor activities, holiday concerts, live music, and that laid-back island vibe, December consistently ranks as one of the best months and the best time to experience Key West.
Whether you’re here for the Key West Holiday Parade, holiday cookies, Christmas carols, or ringing in the New Year with a conch shell drop, December delivers sunshine, celebration, and some of the most beautiful places in North America.
If you’re planning to visit Key West, December is always a good plan.
