December in Key West marks the shift from hurricane season to our peak dry season. It’s the time of year when “winter” means sunny days in the 70s and the humidity finally breaks. The island leans into a tropical holiday aesthetic: you’ll find palm trees wrapped in lights, historic inns decked out in garland, and a calendar full of parades and boat processions. Whether you’re escaping the snow or looking to ring in 2026 with a conch shell drop, this guide covers the practical advice and local events you need to plan your December trip.

Why Visit Key West in December?

For many, December is the ultimate weather sweet spot. The humidity drops significantly, and temperatures average in the mid-70s. It is distinct from the quiet fall months; the island’s energy picks up as visitors arrive for the holidays. You get traditional Christmas elements – caroling, tree lightings, and eggnog – blended with our island style. Stone crab season is in full swing, the water is clear, and the sunset celebrations at Mallory Square are consistently spectacular.

Key West December Events and Festivals in 2025

Harbor Walk of Lights & Key West “Holiday Fest”

When:
- Lighting & display: The Harbor Walk of Lights at the Historic Seaport runs from November 26 through December 31, 2025.
- Holiday Fest program: The broader “Key West Holiday Fest” series runs December 1–24, 2025, bundling many of the events below.
Where: The Historic Seaport’s Harbor Walk of Lights along the Key West Bight.

Expect light displays, nautically themed decorations, and nightly waterfront ambiance anchored by the big harbor Christmas tree and lit up boats along the docks.

Holiday Village & BeLighted Bike Ride

When: Friday, December 5, 2025, 5–9 p.m.
Where: Coffee Butler Amphitheater at Truman Waterfront Park.

This family-friendly evening features a holiday market, kids’ activities, and the BeLighted Bike Ride, where participants decorate their bikes with lights and cruise through Truman Waterfront.

Key West Hometown Holiday Parade (Key West Holiday Parade)

When: Saturday, December 6, 2025, 7–10 p.m.
Route: Typically along Truman Avenue and Duval Street, lined with floats, bands, and local groups.

It’s one of the island’s biggest traditional parades, with locals and visitors staking out spots well before start time.

Eaton Street Christmas Stroll

When: Sunday, December 7, 2025, 3:30–7:00 p.m.
Where: Along Eaton Street in Old Town.

This afternoon event pairs live music, open houses, and holiday décor at galleries, historic churches, and cultural spots along Eaton Street.

Conch Train Holiday Lights Tour & Holiday Lights Trolley Tours

When:
- December 8, 2025, and nightly December 11–23, 2025, with departures about every 30 minutes between 6:00 and 8:30 p.m.
Where: Old Town pickup locations for the Conch Tour Train and Old Town Trolley.

The decorated Conch Train and holiday trolleys take guests on nighttime tours to see the best residential and commercial light displays around Key West.

Holiday Historic Inn Tour

When: Friday, December 12 & Friday, December 19, 2025, 6–8 p.m.
Where: Rotating historic inns and guesthouses across Old Town.

Each evening features a different set of properties, decorated for the holidays and open for walk-throughs with light bites and drinks.

Holiday Concert & Bazaar – Custom House Museum

When: Friday, December 12, 2025 (evening).
Where: Key West Museum of Art & History at the Custom House.

The Custom House lawn hosts a holiday concert plus a bazaar with local artisans, perfect for picking up gifts in between live performances.

Schooner Wharf Bar Lighted Boat Parade

When: Saturday, December 13, 2025
- Entertainment and festivities from early evening; parade scheduled around 8:00 p.m.
Where: Key West Historic Seaport and Harbor Walk, centered at Schooner Wharf Bar.

Boats decked out in lights, music, and decorations parade through the historic seaport—one of Key West’s signature December events.

Rudolph Red Nose 5K Run

When: Saturday, December 13, 2025, 8:00 a.m.
Where: Higgs Beach area.

A festive 5K where many runners dress in holiday gear—think reindeer antlers and red noses.

Stock Island Lighted Boat Parade

When: Monday, December 8, 2025 (evening)
Where: Waters off Stock Island, often near The Perry Hotel & Marina.

This separate boat parade gives you another chance to see illuminated vessels, this time around Key West’s working-waterfront neighbor.

Key West Triathlon

When: Sunday, December 14, 2025, first waves around 5:30 a.m.
Where: Higgs Beach and surrounding roads.

A USAT-sanctioned triathlon with swim, bike, and run courses along the Atlantic shoreline—expect early-morning road closures and plenty of athletes in town.

Key West Artisan Market – Holiday “Shop Local” Editions

When: Sundays December 14, 21, and 28, 2025, roughly 10 a.m.–2 p.m.
Where: Indigenous Park / Higgs Beach area.

A weekly open-air market with local makers, food vendors, and live music, with December editions leaning into holiday gifts.

Florida Keys Southernmost Car Club Holiday Classic Car Show & Toy Drive

When: Sunday, December 21, 2025, 11 a.m.–3 p.m.
Where: Parking lot at Conch Republic Seafood Company on the Historic Seaport.

A classic car show combined with a toy drive benefiting local kids.

Running of the Elves 5K & Holiday Jingle Bell Mile

When: Saturday, December 20, 2025, evening (approx. 6–9 p.m.)
Where: Courses in Old Town (details via local running clubs/event organizers).

Costumed runners take over Old Town for a festive 5K and themed mile race.

Christmas Eve & Christmas Day on Duval

When: December 24–25, 2025
Where: Duval Street and surrounding Old Town.

Many Duval Street restaurants and bars host Christmas Eve dinners, and “Christmas Day on Duval” turns the street into a daytime promenade with open bars, restaurants, and holiday crowds.

New Year’s Eve 2025 in Key West

When: Wednesday, December 31, 2025
Where: Multiple locations around Old Town.

Key West’s New Year’s Eve traditions include several different “drops,” all happening the night of December 31, 2025:

Conch Shell Drop at Sloppy Joe’s on Duval.
Red Shoe Drop with a drag performer descending from the balcony of the Bourbon Street Pub.
Pirate Wench Drop at Schooner Wharf Bar on the Historic Seaport.

Each features live music, crowds, and a midnight countdown.

Best December Activities in Key West in 2025

Water Adventures and Excursions

The water cools down in December (averaging 72-74°F), which changes the marine life dynamics. The visibility on the reef is often excellent, and this is prime time for sailfish and wahoo fishing.

Scuba Diving: Don a wetsuit (a 3mm long suit is standard for this time of year) and explore the Vandenberg wreck or the reefs. The cooler water often brings in larger pelagic species.
Sunset Sails: December sunsets are vivid. Booking a “Wind & Wine” cruise or a classic schooner sail allows you to watch for the green flash without the intense summer humidity.
Eco-Tours: Winter is a great time to spot manatees in the backcountry. Kayak tours through the mangroves offer a break from the holiday hustle on Duval Street.

Local operators we recommend include Captain Hook’s Dive Key West (that’s us!) and Sebago Watersports.

Eco-Tourism and Nature Exploration

December is fantastic for birdwatching as migratory species make their way south. Visit Fort Zachary Taylor State Park to hike the nature trails and spot warblers and painted buntings. The Key West Tropical Forest & Botanical Garden is also lush this time of year, offering a quiet respite.

Active Exploration

With the humidity gone, you won’t melt while exercising. Rent a bike and cruise the Florida Keys Overseas Heritage Trail. If you’re visiting with family, the Conch Tour Train and Old Town Trolley offer special “Holiday Lights Tours” in the evenings, taking you past the most decorated homes on the island.

Best Restaurants and Local Flavors

December is peak seafood season. Stone crab claws are the must-try delicacy, available at almost every seafood joint in town.

Fisherman’s Cafe for a casual, authentic conch ceviche.
Eaton Street Seafood Market for fresh-caught stone crab and lobster tails you can take back to your rental.
Latitudes or Hot Tin Roof for an upscale holiday dinner with ocean views (Book these weeks in advance for December dates—they fill up fast).

Culture and History

The Key West Art & Historical Society often hosts holiday markets at the Custom House Museum. Visit the Ernest Hemingway Home and Museum to see the grounds decorated for the season. For art lovers, the “Coast is Clear” Music & Arts Festival (typically early December) focuses on local storytelling and Americana music. Check out the Holiday Historic Inn Tours (usually two Friday evenings in December) to peek inside some of the island’s private inns.

Practical Tips for Visiting Key West in December 2025

Where to Stay: December is high season, especially the week between Christmas and New Year’s. Book your accommodations early. If you want a quieter experience, look for a rental in the Truman Annex or a B&B in the Meadows neighborhood.
Getting Around: Traffic gets heavy during the holidays. Stick to walking, biking, or the free Duval Loop bus. Rideshares are available but expect surge pricing on NYE.
Packing Guide: While days are warm, nights dip into the 60s (and occasionally high 50s if a cold front pushes through). Bring a light jacket or sweater for evenings and boat trips. It feels colder than you think when you’re on the water.
Weather and Safety: It’s the dry season, but the wind can pick up. If you plan on boating or diving, keep an eye on the marine forecast.

Frequently Asked Questions (FAQs)

Is it cold in Key West in December?

You can expect highs in the mid-70s and lows in the upper 60s. It’s perfect t-shirt weather during the day, though most people want a light layer for sunset sails or late-night walks.

Can you swim in Key West in December?

Yes. The water temperature hovers around 72°F-74°F. It’s refreshing for a swim, though divers generally appreciate a wetsuit for longer submerged times.

Is Key West crowded in December?

Yes, it is a popular time to visit. The first two weeks of December are generally quieter than the week between Christmas and New Year’s, which is one of the busiest weeks of the year.

Are shops and restaurants open on Christmas Day?

Key West is a hospitality town. Most restaurants, bars, and activity providers remain open on Christmas Day and New Year’s Day, often with special holiday menus.

Plan Your Trip

December in Key West offers a blend of holiday tradition and tropical relaxation. Whether you’re cheering at the Lighted Boat Parade or watching the last sunset of 2025 from Mallory Square, the festive spirit is contagious.

If you want to make the most of the clear water and comfortable winter conditions, anchor your plans around Captain Hook’s Dive Key West, conveniently located at 1708 N. Roosevelt Blvd. Our full-service Key West dive shop offers everything from guided reef and wreck dives (including trips to the famous Vandenberg) to dive certification courses and refresher training for rusty divers. W’re here to help you build a December getaway that pairs festive island energy with unforgettable time underwater.

Things to Do in December in Key West