Key West in December is warm, dry and festive: average highs are about 78°F, lows about 68°F, and the month typically sees only around 2 inches of rain. The big events are the Schooner Wharf Bar Lighted Boat Parade on Saturday, December 12, 2026, holiday lights along the Historic Seaport, and the city’s famous New Year’s Eve drops on Duval Street. The week from Christmas through New Year’s is one of the busiest of the year, so book lodging, dinners and boat trips early.
December is the start of high season in the Florida Keys. For the bigger picture, see the Florida Keys travel guide; for what to do once you arrive, start with the first-timer’s list of things to do in Key West.
Key West in December at a glance
- Weather: highs around 78°F, lows around 68°F, about 2.2 inches of rain over roughly six rainy days.
- Crowds: moderate in early December, very heavy from about December 20 through January 1.
- Signature event: Schooner Wharf Bar Lighted Boat Parade, Saturday, December 12, 2026, parade at about 8pm.
- Theater: “It’s a Wonderful Life: A Live Radio Play” at the Waterfront Playhouse, December 2 to 17.
- New Year’s Eve: the Red Shoe Drop, the conch shell drop and the pirate wench drop, all in Old Town.
- Book early: Christmas and New Year’s lodging, holiday dinners, Dry Tortugas ferries and sunset sails.
What is the weather like in Key West in December?
December weather in Key West is mild and mostly sunny, with average highs near 78°F and lows near 68°F. Humidity drops from its summer levels, and rain usually comes in short showers rather than all-day storms. Hurricane season ends November 30, so December trips carry little storm risk.
The one thing to watch is cold fronts. A few times a month, a front can bring a day or two of north wind, cooler nights in the low 60s and choppy water. That is when snorkel trips and Dry Tortugas ferries are most likely to be rescheduled, so leave a flexible day in your plans if a boat trip is important to you. Pack shorts and swimsuits, plus a light jacket or sweater for evenings on the water.
Is December a good time to visit Key West?
Yes. December is one of the best months to visit Key West for weather, and the holiday decorations on Old Town’s porches and the harbor add to it. The trade-off is price and crowds in the last ten days of the month.
| Window | Crowds | Prices | Why go |
|---|---|---|---|
| December 1 to 19 | Moderate | High season, but easier to find rooms | Lighted boat parade, holiday lights, theater, easier dinner reservations |
| December 20 to 26 | Heavy | Peak, with minimum stays | Christmas on the island, family trips |
| December 27 to January 1 | Heaviest | Peak, with the strictest minimums | New Year’s Eve drops and parties on Duval Street |
If you have flexibility, the first two weekends of December are the sweet spot: you get the boat parade, the lights and warm weather without holiday-week rates.
What holiday events happen in Key West in December?
The main holiday events in Key West are the lighted boat parade, the lights and decorations at the Historic Seaport, a hometown holiday parade, historic inn tours and holiday theater. Dates below are confirmed for 2026 where noted; others follow a long-running yearly pattern and should be checked closer to your trip.
Schooner Wharf Bar Lighted Boat Parade (December 12, 2026)
The Schooner Wharf Bar Lighted Boat Parade is Key West’s signature holiday event. Decorated boats circle the Key West Bight and harbor after dark, and it is free to watch. Dockside festivities start around 6pm and the parade begins around 8pm on Saturday, December 12, 2026. The best viewing is along the Harbor Walk between Schooner Wharf Bar and Turtle Kraals; arrive by 7pm for a spot at the rail. Strong wind or rain usually pushes the parade to the next night, so check Schooner Wharf Bar’s website on the day.
Harbor Walk of Lights
Each year the Key West Historic Seaport strings lights and holiday displays along the Harbor Walk, typically from the week of Thanksgiving through December 31. It is free, it is lit nightly and it makes an easy after-dinner walk from the restaurants at the Key West Bight.
Hometown Holiday Parade and historic inn tours
Key West’s hometown holiday parade traditionally runs on an early-December Saturday evening along Truman Avenue and Duval Street, with local floats and community groups. On two Friday evenings in December, the holiday historic inn tours open decorated guesthouses in Old Town for self-guided visits with treats along the way. Confirm 2026 dates with local event calendars before you go.
Holiday theater and the arts
The Waterfront Playhouse at Mallory Square stages “It’s a Wonderful Life: A Live Radio Play” from December 2 to 17, 2026, a good pairing with sunset next door. Tickets are on the Waterfront Playhouse website. The Studios of Key West on Eaton Street keeps its galleries free and open Tuesday through Saturday, 10am to 4pm, and hosts concerts and events through the season.
Sunset at Mallory Square
The nightly Sunset Celebration at Mallory Square runs all December, with street performers, artists and food carts. Sunset comes early this time of year, a little before 6pm, so plan dinner reservations for after the show rather than before.
What is Christmas like in Key West?
Christmas in Key West is low-key and warm: decorated conch cottages, lit palm trees, boat parades and dinners outdoors. Most restaurants and bars stay open, but many fill their Christmas Eve and Christmas Day books weeks in advance, and some attractions keep shorter hours. The Key West Butterfly and Nature Conservatory, for example, closes at 2pm on Christmas Eve and Christmas Day, and the Key West Art Center on Front Street closes on Christmas.
A few ideas for Christmas week:
- Take a holiday lights tour by trolley or tram, which typically run in the weeks before Christmas.
- Book a Christmas Eve or Christmas Day sunset sail from the Historic Seaport.
- Spend Christmas morning at Fort Zachary Taylor Historic State Park, which is open every day of the year from 8am to sundown.
- Reserve a holiday dinner at an Old Town restaurant well ahead, and have a backup plan for walk-in Cuban food.
What happens in Key West on New Year’s Eve?
Key West on New Year’s Eve is one big street party centered on Duval Street, with several of the city’s own midnight “drops” instead of a ball. The traditional drops, as listed by the Florida Keys tourism council, are:
- The Red Shoe Drop at Bourbon Street Pub, 724 Duval Street, where drag performer Mulan Alexander is lowered in a giant red high heel.
- The conch shell drop at Sloppy Joe’s Bar, 201 Duval Street, where a giant conch shell descends to the roof.
- The pirate wench drop at Schooner Wharf Bar, 202 William Street at the Historic Seaport, where a “wench” is lowered from the mast of a tall ship.
Lower Duval and the 700 block get extremely crowded by 10pm. If you want a view of a drop, stake out a spot early, or book a guesthouse in Old Town within walking distance so you do not have to drive or find a ride at 1am. For a calmer night, watch the last sunset of the year at Mallory Square and have a late dinner away from Duval.
What should you book early for Key West in December?
Book your room first. Old Town guesthouses and inns often require three- to five-night minimums over Christmas and New Year’s and fill months ahead. After that, lock in the things with limited seats:
- Lodging: book by September or October for the holiday weeks; early December is easier.
- Holiday dinners: reserve Christmas Eve, Christmas Day and New Year’s Eve dinners as soon as restaurants open their books.
- Dry Tortugas: the Yankee Freedom ferry carries a limited number of passengers per day and sells out in holiday weeks.
- Sunset sails and snorkel trips: book a few weeks ahead and pick a day early in your stay so you have a weather backup.
- Theater tickets: the Waterfront Playhouse is small, and holiday shows sell out.
- A January add-on: the Key West Food & Wine Festival runs January 27 to 31, 2027. All events are ticketed, 21 and older, and sold in advance.
What else is happening in the Florida Keys in December?
If you are driving down, the Upper Keys have their own holiday calendar. In Islamorada, the Morada Way Third Thursday Art Walk falls on December 17, 2026, from 6pm to 9pm, with open galleries, live music and food. Several other Keys communities, including Key Largo and Stock Island, have held their own lighted boat parades in December in recent years. The Florida Keys area page lists businesses up and down the chain, and the Florida Keys road trip guide maps the best stops on the drive. For local Key West listings, see the Key West area page.
FAQ
Is it warm enough to swim in Key West in December?
Usually, yes. Air temperatures typically reach the high 70s, and many visitors swim and snorkel all month. The water is cooler than in summer, and after a cold front it can feel brisk, so pick warm, calm days for long snorkel trips.
When is the Key West lighted boat parade in 2026?
The Schooner Wharf Bar Lighted Boat Parade is Saturday, December 12, 2026. Festivities start around 6pm and the parade begins around 8pm at the Key West Bight. Bad weather can move it to the following night.
Is Key West crowded at Christmas?
Yes. The week between Christmas and New Year’s is one of the busiest of the year in Key West, with full hotels and long waits at popular restaurants. Early December is noticeably calmer and often cheaper.
What is the Red Shoe Drop?
The Red Shoe Drop is Key West’s best-known New Year’s Eve tradition. At Bourbon Street Pub on Duval Street, drag performer Mulan Alexander is lowered in an oversized red high heel at midnight. It draws a large crowd, so arrive well before 11pm for a view.
How far ahead should you book a hotel in Key West for New Year’s Eve?
Book three to six months ahead for the best choice, especially for Old Town guesthouses within walking distance of Duval Street. Expect multi-night minimum stays and nonrefundable deposits for the holiday week.