Key West’s holidays happen outdoors and mostly after dark: a parade down Duval, a parade of lit-up boats through the harbor, and three bars that each lower something at midnight on New Year’s Eve. Here are the December 2026 dates the organizers have posted, what is open on Christmas Day and New Year’s Day, and how to get home that night.
The month at a glance
| Date | What | Where | When |
|---|---|---|---|
| Wed 25 Nov | The Harbor Walk of Lights is lit, then on every night to New Year’s Eve | Historic Seaport | From 6 p.m. |
| Mon 30 Nov | City Christmas tree lighting | Bayview Park | 6 to 8 p.m. |
| Thu 3 – Sat 5 Dec | End of Prohibition celebration | Sloppy Joe’s, 201 Duval | |
| Fri 4 Dec | Holiday Village and the BeLighted Bike Ride | Coffee Butler Amphitheater, then Duval | 4 to 10 p.m. |
| Sat 5 Dec | Holiday parade | Truman Avenue, then Duval | 7 p.m. (city) or 6:30 (Seaport calendar) |
| Sun 6 Dec | City menorah lighting | Bayview Park | 5 to 7 p.m. |
| 7 – 27 Dec | Old Town Trolley’s holiday lights tour | From Mallory Square | 60 minutes |
| Fri 11 Dec | No Dry Tortugas ferry, a maintenance day | ||
| Fri 11 Dec | Custom House holiday concert and bazaar | 281 Front Street | 5 to 8 p.m. |
| Sat 12 Dec | Lighted Boat Parade | Historic Seaport | Music 6 p.m., parade 8 p.m. |
| Fri 25 Dec | Christmas Day: no city buses | ||
| Thu 31 Dec | Three New Year’s Eve drops | Duval Street and the Seaport | Midnight |
| Fri 1 Jan | New Year’s Day: no city buses |
The dates are the organizers’ own, and where the city has filed a notice for an event, the times in the table are the city’s. Key West Holiday Fest, the island-wide umbrella presented in part by the Lodging Association and the county’s tourism council, has not posted its 2026 calendar yet, and the Holiday Historic Inn Tour has no 2026 dates either; last year it ran on two December evenings, the 12th and the 19th.
The Lighted Boat Parade, Saturday 12 December
The 35th Schooner Wharf Bar Lighted Boat Parade sails into Key West Bight at 8 p.m. on Saturday 12 December, and the music on the Harbor Walk starts at 6 p.m. It costs nothing to watch. Viewing is all along the Harbor Walk of Lights at the Historic Seaport, and the judges’ stand is at Schooner Wharf Bar, 202 William Street. Come early and you see the decorated boats still at the dock.
The bar goes over the route with the captains on Thursday 10 December and hands out prizes to the top 12 boats on Monday 14 December. Last year nearly 30 boats took part, Santa among them on a lit-up Coast Guard Station Key West boat; entries over the years have run from a kayak with battery-powered lights to classic schooners.
The holiday parade, Saturday 5 December
The city’s own Hometown Holiday Parade is on Saturday 5 December. The city’s street-closure notice runs from 7 to 9 p.m.; the Historic Seaport’s holiday calendar says it starts at 6:30, so be on the curb by then. It sets off on Truman Avenue at White Street, turns onto Duval and comes down Duval to Eaton Street: floats, local marching bands, a lot of children and an appearance by Santa. Truman between White and Duval, and Duval between Truman and Eaton, are the route.
The night before, Friday 4 December, Wesley House’s Holiday Village is at the Coffee Butler Amphitheater at Truman Waterfront from 4 p.m., and the BeLighted Bike Ride, a parade of lit-up bicycles, rides from there along Southard, Whitehead, Front and Duval and back.
The lights
The Harbor Walk of Lights runs along the seawall at the Historic Seaport, past Greene, William and Margaret streets to the ferry terminal. It is lit on the evening of Wednesday 25 November, Thanksgiving Eve, from 6 p.m., with a Christmas tree built of fishing buoys at Greene and Elizabeth streets and another of lobster traps at the Margaret Street end, and it stays lit every night through New Year’s Eve. It is free, two blocks from Duval, and the boat parade passes along it.
The city lights its Christmas tree at Bayview Park on Monday 30 November, 6 to 8 p.m., and its menorah there on Sunday 6 December, 5 to 7 p.m.
For the houses, Old Town Trolley runs its Holiday Sights and Festive Nights tour from 7 to 27 December: an hour on the trolley past the island’s best-decorated houses, from Mallory Square, from $33.95 for adults and $22.95 for children 3 to 12, plus a 5% city fee. It takes 35 to a trolley, and the tickets are reservation-only and non-refundable, though you can reschedule up to 24 hours ahead.
New Year’s Eve: three drops at midnight
Key West does Times Square three times over, in three different bars, at the same moment.
The conch shell at Sloppy Joe’s
The 33rd Dropping of the Conch Shell at Sloppy Joe’s, 201 Duval Street on the corner of Greene, lowers a giant conch shell to the bar’s roof at midnight, with the show live from the roof from 10 p.m. The bar takes no reservations and charges no door fee; tables go to whoever sits down first, and inside you watch the drop on the bar’s screen. The shell was a local artist’s idea: Tobias McGregor brought it to the bar in 1993 so the whole street would count down together, and redesigned it in 2005.
The red high heel at the Bourbon St. Pub
At the Bourbon St. Pub and New Orleans House, 724 Duval Street, a drag queen rides a giant red high heel down from the balcony as midnight strikes, after a three-hour stage show on the street. It is the 29th, and the pub’s listing for the night runs from 8 p.m. to 1 a.m. The balcony above is the pub’s VIP party; the show itself is in the street.
Since last year the rider is chosen by a national contest, “If the Shoe Fits”. Its finals were set for 10 October 2026 outside the pub, and the pub still lists this year’s winner as to be announced. Sushi, the original queen, rode the shoe for 25 years, then Christopher Peterson and Randy Roberts; last year’s queen, the contest’s first, was Mulan Alexander of Dallas. Sushi now designs the winner’s costume.
This is the one closure the city has posted for the night. Its notice shuts the 700 block of Duval from 2 p.m., and runs to 2 a.m.
The pirate wench at Schooner Wharf
At Schooner Wharf Bar, 202 William Street in the Historic Seaport, the Lowering of the Pirate Wench at midnight is on the bar’s 2026 calendar, with three local and national acts from early in the day; its New Year’s Eve page still carries last year’s lineup. Last year the wench was the bar’s owner, Evalena Worthington, coming down the mast of the tall ship America 2.0 in front of the bar to cannon fire, with no cover charge.
Choosing one
By the OpenStreetMap foot router, Schooner Wharf is about 6 minutes’ walk from Sloppy Joe’s, and the Bourbon St. Pub about 12 minutes the other way, up Duval. All three land at midnight, so pick one and get there early. Last year a fourth joined them, a ticketed Gatsby gala at First Flight Island Restaurant & Brewery, 301 Whitehead Street, once Pan Am’s first ticket office, which “lands” a flight attendant in a replica plane at midnight; it has no 2026 date posted.
Getting home that night
Walk, and stay close enough to. All three drops are on Duval or at the Seaport, and Old Town’s hotels and guesthouses are a walk from both.
- The bus stops at 8 p.m. Key West Rides, the on-demand service that replaced the city’s routes on the island, runs from 6 a.m. to 8 p.m. every day, and no city bus runs at all on Christmas Day or New Year’s Day, or on Thanksgiving. The Duval Loop is suspended. Getting around without a car has the rest.
- Taxis are few and capped. Key West licenses 56 of them, and on New Year’s Eve the city code caps a ride at $3.50 a person per trip.
- If you drive in, park once. The Old Town garage at 301 Grinnell Street has 300 spaces, first come, first served, at $6 an hour or $48 a day plus tax, and allows overnight parking, though special event rates may apply, set by the city manager. Mallory Square’s 100 spaces are $7 an hour. The parking page has every lot.
Christmas Day and New Year’s Day: what is open
| Christmas Day, Fri 25 Dec | New Year’s Day, Fri 1 Jan | |
|---|---|---|
| Hemingway Home | Open, 9 a.m. to 5 p.m. | Open |
| Key West Lighthouse | Listed as open Monday to Sunday, 10 to 5 | Same |
| Fort Zachary Taylor | Open, 8 a.m. to sundown | Open |
| Dry Tortugas ferry | Sails; sold out as of 16 October | Sails; sold out as of 16 October |
| Old Town Trolley | Running | Running |
| Key West Garden Club | Closed | Closed |
| Eco-Discovery Center | Closed for roof repairs | Closed |
| City buses | No service | No service |
The Hemingway Home says it is open 365 days a year, and so is the state park at Fort Zach. The trolley runs 364 days, closing only on the last Saturday in October for Fantasy Fest. The Key West Art & Historical Society lists the lighthouse as open Monday to Sunday with no holiday closure; on Christmas morning, a call to 305-294-0012 settles it. The Garden Club at West Martello opens daily except Christmas and New Year’s Day. NOAA’s free Eco-Discovery Center is temporarily closed while NOAA works out the repairs its roof needs, with no reopening date.
The Dry Tortugas ferry’s one December day off is Friday 11 December, and its next is not until 19 January. Over the holidays the boat is full: on 16 October 2026 its own calendar had no seat left from 20 December to 4 January, and the Viator listing on the Dry Tortugas page had no date after 31 October. On those dates the way on is the standby sheet at the terminal, 100 Grinnell Street, from 6:30 a.m. on the morning, and nothing is guaranteed.
Ships in port
The piers are busy through Christmas. On the Pier B calendar, December 2026 has a ship every day except the 9th, 30th and 31st, most of them in from about 8 a.m. to 5 p.m. Two stay later over Christmas: the Margaritaville Islander from noon to 7 p.m. on Christmas Eve, and the Zuiderdam from 8 a.m. to 6 p.m. on Christmas Day. Pier B lists no ship at all from 30 December to 2 January.
The city’s Mallory T-Pier calendar is different. One of three ships, the American Pioneer, American Ranger or American Maverick, is tied up there on most December days, often for two nights at a time: from 23 to 27 December across Christmas, and from the morning of 30 December to 5 a.m. on 1 January. On those evenings a ship is at the square at sunset. The cruise-days page shows how to read both calendars.
December weather, water and sunset
December is mild and mostly dry: an average high of 78°F and low of 68, and 2.2 inches of rain in the month, on the National Weather Service’s 1991–2020 normals for Key West. New Year’s Day is a little cooler, January averaging 76 and 66.
The water is cooling toward its low for the year. NOAA’s Key West harbor station averaged 74°F across the Decembers of 2023 to 2025, and the last twelve days of the month averaged between 71 and 75. A winter evening on a boat is cooler than it feels ashore, so take a layer for the boat parade or a sunset sail.
Sunset is the earliest of the year, by the U.S. Naval Observatory’s tables: about 5:38 p.m. on 1 December, 5:46 on Christmas Day and 5:50 on New Year’s Eve. That puts Mallory Square before dinner, and leaves a long evening before midnight. Sunrise on New Year’s Day is at 7:11.
Where to stay
For New Year’s Eve, stay in Old Town. Booking.com’s Downtown Key West list is Old Town’s guesthouses, inns and hotels, a walk from Duval and the Seaport. Book it early. If it is a vacation rental, check the address against the city’s list of licensed properties before you pay; the where-to-stay page has the check and the other areas. Both lists are at the end of this page.
Sunset from the water
December is sailing season, and with the sun down at about 5:40, a sunset sail is over early in the evening, long before the drops. The sail below is $79 for about an hour and a half with the bar included, capped at 24 people, from the Hyatt Centric on Front Street, with free cancellation up to 24 hours before. Honest Eco’s dolphin search and sunset sail runs from mid-October to April, 15 October to 30 April in 2026–27, so it is in season too; the sunset sail page compares the three. January to March, the festival season and spring break, has its own page, and for the rest of the year the best-time page goes month by month.
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