Key West Christmas events 2026: the full season

The 2026 holiday season in Key West, Florida runs from Wednesday, Nov. 25, when the Harbor Walk of Lights is switched on at the Historic Seaport, to New Year’s Eve, when three Old Town bars lower a conch shell, a red high heel and a pirate wench at midnight. When we checked the organisers’ own pages on Oct. 21, 2026, the big dates were posted. Below they are in order, with confirmed dates marked and every disagreement between sources named. Christmas in Key West is an independent planner published by LPE Realty LLC. We are not the City of Key West, Schooner Wharf, the Historic Seaport, the Lodging Association or any venue, and we sell no tickets.

• keywestchristmas.org lists "Wednesday, Nov. 25" (marked "Free"): "The Lighting of the 21st annual "Harbor Walk of Lights"" at the 2026 "Fishing Buoy Christmas Tree"; "Lights come on at 6:00pm", "holiday music starts at 5:00pm", at the "Greene and Elizabeth St. plaza." It says "Santa and Mrs Clause will be making a NICE list and passing out treats!" Key West "Bight" Before Christmas: keywestchristmas.org (Harbor Walk of Lights)
• Holiday Fest calendar: "Key West Holiday Fest, the southernmost city's annual joyous celebration of the season, kicked off on Thanksgiving Eve and continues through December." It quotes Jodi Weinhofer, President of the Lodging Association of the Florida Keys and Key West. Key West Inns (Lodging Association of the Florida Keys and Key West): Holiday Fest Calendar

The season in date order

Times are as the organiser lists them. “Confirmed” means the organiser, or the City on its own calendar, shows the 2026 date.

Date (2026)	Event	Time listed	Status
Wed. Nov. 25	Harbor Walk of Lights lighting (Fishing Buoy tree, then Lobster Trap tree)	6 PM and 7 PM	Confirmed
Nov. 25 to Dec. 31	Harbor Walk of Lights, nightly	Every evening	Confirmed (end date differs, see below)
Mon. Nov. 30	City Christmas tree lighting, Bayview Park	6 to 8 PM	Confirmed by the City
Thu. Dec. 3	Pet Pictures with Santa, Harbor Walk at William St.	6 to 8 PM	Confirmed
Dec. 3 to 5	End of Prohibition Celebration, Sloppy Joe’s	Not listed	Listed by Sloppy Joe’s
Fri. Dec. 4	Holiday Village and BeLighted Bike Ride, Coffee Butler Amphitheater	City 4 to 10 PM; Holiday Fest 5 to 9 PM	Not confirmed on the organiser’s page
Sat. Dec. 5	Hometown Holiday Parade	City 7 PM; keywestchristmas.org 6:30 PM	Confirmed (time differs)
Sun. Dec. 6	City Menorah Lighting, Bayview Park	5 to 7 PM	Confirmed by the City
Sun. Dec. 6	Schooner Wharf Tree Trimming Party and Toy Drive	From 6 PM	Confirmed
Dec. 7 to 27	Old Town Trolley holiday lights tours	Evenings	Confirmed by the operator
Dec. 8 to 27 (not Dec. 10 or 15)	Conch Tour Train holiday lights tours	6 to 8:30 PM departures	Confirmed by the operator
Fri. Dec. 11	Custom House Holiday Concert and Bazaar	5 to 8 PM	Confirmed
Fri. Dec. 11	Holiday Historic Inn Tours, Night 1	6 to 8 PM	Confirmed (inns and price not posted)
Sat. Dec. 12	Rudolph Red Nose 5K, Duval Street Pocket Park	8 AM to noon (closure window)	City notice, not the organiser
Sat. Dec. 12	35th Lighted Boat Parade	Music 6 PM, parade 8 PM	Confirmed
Fri. Dec. 18	Holiday Historic Inn Tours, Night 2	6 to 8 PM	Confirmed (inns and price not posted)
Sat. Dec. 19	Great Gingerbread Build, Truman Little White House	11 AM to 2 PM	Confirmed by the Truman Foundation
Sun. Dec. 20	Holiday Classic Car Show and Toy Drive, Harbor Walk at Greene St.	11 AM to 3 PM	Confirmed
Dec. 22 and 23	Holiday evening house tours, Truman Little White House	Dec. 22: 6 to 8 PM	Confirmed by the Truman Foundation
Dec. 29 and 30	OIRF Key West Home Tours	1 to 4 PM	Confirmed
Thu. Dec. 31	New Year’s Eve drops	Midnight	Three of four confirmed

The same list, with sources and the date we checked each one, prints below. To see what falls on a single night, use the checker on our December dates page.

Confirmed, and not yet posted

Four items on the season calendar were not confirmed by their own organiser when we checked on Oct. 21, 2026:

• Holiday Village and BeLighted Bike Ride (Dec. 4): the date is on the City’s street-closure notice and the Lodging Association’s Holiday Fest calendar, which names Wesley House Family Services as the host. We did not find it on a Wesley House page.
• Rudolph Red Nose 5K (Dec. 12): on a City street-closure notice; we did not find the organiser’s page.
• Waterfront Winter Wonderland: the Coffee Butler Amphitheater page describes an ice skating rink, rides and light displays “this December” but gives no year or dates. keywestchristmas.org marks it “2026 UPDATES COMING SOON!” and says it is closed Christmas Eve and Christmas Day.
• Key Lime wedge drop (Dec. 31): listed by keywestchristmas.org, not by Ocean Key Resort. See our New Year’s Eve page.

• The City of Key West calendar lists "Holiday Village & BeLighted Bike Ride – City Property Event Notice and Street Closure Notice" on "Friday, December 4, 2026", "4:00 PM – 10:00 PM", at "Coffee Butler Amphitheater", "21 East Quay Road": "There will be a rolling street closure along the parade route. Parade begins at the Amphitheater, to Southard, left on Whitehead, right on Front, right on Duval, right on United, right on Whitehead and returns to the Amphitheater." City of Key West: Calendar event notice
• The Coffee Butler Amphitheater ticketing page describes "Waterfront Winter Wonderland": "This December, the Coffee Butler Amphitheater at the Truman Waterfront Park will transition into a Key West Winter Wonderland" with "an ice skating rink, games, rides, attractions, music, light displays, and more." The page gives no year or dates. keywestchristmas.org lists it under "2026 UPDATES COMING SOON!" and says "Closed Christmas Eve and Christmas Day." Coffee Butler Amphitheater: Waterfront Winter Wonderland

Two more listings come from one source. The Holiday Fest calendar lists Nutcracker Key West at the Tennessee Williams Theatre, 5901 College Rd, Dec. 3 to 7, 2026, while keywestchristmas.org still says updates are coming. And keywestchristmas.org lists the MARC Christmas tree sale lot at 1401 Seminary Street, open until the trees run out or Christmas Eve; the Holiday Fest calendar gives Nov. 21 to Dec. 24, 2026.

• The Holiday Fest calendar lists "Nutcracker Key West" at the Tennessee Williams Theatre, 5901 College Rd, Dec. 3 to 7, 2026: "Some 200 local children and adults and 16 professional dancers from The Tallahassee Ballet join together". keywestchristmas.org marks it "2026 UPDATES COMING SOON!" Key West Inns (Lodging Association of the Florida Keys and Key West): Holiday Fest Calendar
• keywestchristmas.org: "MARC annual Christmas Tree Sale Lot", "More than 1500 trees travel from up North to Key West and are available until they run out or Christmas Eve, which ever comes first. 1401 Seminary Street." It is marked "2026 UPDATES COMING SOON!"; the Holiday Fest calendar lists Nov. 21 to Dec. 24, 2026. Key West "Bight" Before Christmas: keywestchristmas.org (Harbor Walk of Lights); Key West Inns (Lodging Association of the Florida Keys and Key West): Holiday Fest Calendar

• Start time differs: keywestchristmas.org says "Starts at 6:30pm"; the City notice and the Holiday Fest calendar list 7:00 PM. The Holiday Fest calendar says the parade "kicks off at Bayview Park and travels along Truman Ave. and Duval Street". Use the City's 7 PM and say the waterfront calendar lists 6:30. City of Key West: Calendar event notice; Key West "Bight" Before Christmas: keywestchristmas.org (Harbor Walk of Lights); Key West Inns (Lodging Association of the Florida Keys and Key West): Holiday Fest Calendar
• The Holiday Fest calendar lists "City of Key West Tree Lighting Ceremony at Bayview Park" on Nov. 29, 2026 at 6:00 pm "with a special appearance by Santa Claus!", while the City's own notice says Monday, Nov. 30, 2026, 6 to 8 PM. Use the City date. Key West Inns (Lodging Association of the Florida Keys and Key West): Holiday Fest Calendar
• The Holiday Fest calendar lists the Conch Train tours as "Dec. 8 and Dec. 11-23" and the Trolley tours as Dec. 8 to 23, departing "from Key West High School" (Conch) and Mallory Square (Trolley). The operators' own pages say Conch Train Dec. 8-9, 11-14 and 16-27, and Trolley Dec. 7-27, 2026. Use the operator pages. Conch Tour Train; Old Town Trolley; Key West Inns (Lodging Association of the Florida Keys and Key West): Holiday Fest Calendar
• The Holiday Fest calendar lists the Great Gingerbread Build as Dec. 19-20, 2026, 1:00 to 3:00 pm, while the Truman Foundation says Saturday, Dec. 19, 11:00am to 2:00pm. Use the Foundation's time. Key West Inns (Lodging Association of the Florida Keys and Key West): Holiday Fest Calendar

Hanukkah and the City menorah

Hebcal gives Chanukah 5787 as beginning at sundown on Friday, Dec. 4, 2026 and ending at nightfall on Saturday, Dec. 12, 2026. The City of Key West lists its annual Menorah Lighting Ceremony at Bayview Park on Sunday, Dec. 6, 2026, from 5 to 7 PM. That is the same park as the City tree lighting a week earlier. We did not find a 2026 listing for any other public menorah lighting in Key West.

• Hebcal: "Chanukah for Hebrew Year 5787 begins at sundown on Friday, 4 December 2026 and ends at nightfall on Saturday, 12 December 2026." Hebcal: Chanukah 2026
• The City of Key West calendar lists "The City's Annual Menorah Lighting Ceremony-City Property Event Notice" on "Sunday, December 6, 2026", "5:00 PM – 7:00 PM", at "Bayview Park". The Holiday Fest calendar lists the same ceremony 5:00 to 6:00 pm. City of Key West: Calendar event notice

Is anything open on Christmas Day?

Christmas Day 2026 is a Friday. Here is what the operators themselves publish:

• Hemingway Home and Museum: says it is “open daily, 365 days a year”.
• Fort Zachary Taylor Historic State Park: Florida State Parks gives 8 a.m. until sundown, 365 days a year.
• Sunset Celebration at Mallory Square: the operator calls it a nightly arts festival. Sunset on Dec. 25 is at 5:46 PM (U.S. Naval Observatory).
• City of Key West: all City facilities are closed Thursday, Dec. 24 and Friday, Dec. 25, and the City’s Key West Rides on-demand buses do not run on Christmas Day.

• Hemingway Home and Museum: "Museum is open daily, 365 days a year", "9:00am-5:00pm for walk-in visits", "Tours start every 15 minutes with the first tour starting at 9:15am". Adult "General Admission – $19"; "Children 5 and younger are FREE". Ernest Hemingway Home and Museum: Rates & Info
• Florida State Parks: Fort Zachary Taylor Historic State Park, "Hours 8 a.m. until sundown 365 days a year", "$6 per vehicle". "the park is the southernmost state park in the continental United States" and "boasts Key West's favorite beach, located at the southern end of the park, providing opportunities for picnicking, swimming, snorkeling, paddling and fishing." Florida State Parks: Fort Zachary Taylor Historic State Park
• The City of Key West calendar lists City office closures for Thanksgiving Day (Nov. 26, 2026), the day after (Nov. 27), "Christmas Extension" (Thursday, Dec. 24, 2026), Christmas Day (Friday, Dec. 25, 2026) and New Year's Day (Friday, Jan. 1, 2027), "All city facilities". City of Key West: Calendar event notice
• City of Key West: "Key West Rides On-Demand is an innovative form of transportation that will replace the North and South Lines". "This is a bus stop-to-bus stop service". Hours "Monday" to "Sunday 6 AM" to "8 PM", "(No service on Thanksgiving Day, Christmas Day, and New Year's Day)." Booking help: "305-809-3910". City of Key West: Key West Rides On-Demand Bus Service

For everything else, including the Truman Little White House, Audubon House, the Custom House and the Lighthouse, we do not give Christmas Day hours. Call ahead. Planning tips for the week are on our trip planner, and getting around without a bus that day is covered on our parking page.

Free things on the calendar

Organisers mark these 2026 events as free: the Harbor Walk lighting (Nov. 25), the Tree Trimming Party (Dec. 6), watching the boat parade from the Harbor Walk (Dec. 12), the Gingerbread Build (Dec. 19) and the Classic Car Show (Dec. 20). Pet Pictures with Santa is free to attend, and the photos are $25, cash or Cash App, for the Boys and Girls Club.

• keywestchristmas.org: "Thursday, December 3", "6:00pm" to "8:00pm", "21st Annual Pet Pictures with Santa", "At the 16' Nautical Christmas Tree on the Harbor Walk of Lights at William St." and "Pictures with Santa are $25 (Cash and Cash App accepted) to benefit our local Boys & Girls Club." Key West "Bight" Before Christmas: keywestchristmas.org (Harbor Walk of Lights)
• Schooner Wharf lists "Dec. 6 Rock Around Our Christmas Tree! Schooner Wharf Bar Tree Trimming Party 6:00 p.m." keywestchristmas.org lists the "Schooner Wharf Bar 2026 Tree Trimming Party and Toy Drive" on "Sunday, December 6", "Starting at 6:00PM", "FREE to Attend". Schooner Wharf Bar: Special Events (2026 Events); Key West "Bight" Before Christmas: keywestchristmas.org (Harbor Walk of Lights)
• keywestchristmas.org: "Sunday, December 20", "The Florida Keys Southernmost Car Club presents 2026 "Holiday Classic Car Show" & Toy Drive", "FREE", "11:00am" to "3:00pm", at the "Conch Republic Seafood Company parking lot" on the Harbor Walk of Lights at Greene St. Key West "Bight" Before Christmas: keywestchristmas.org (Harbor Walk of Lights)

Planning around the calendar

For the trip itself, see our December weather page, getting here, parking and beaches. Staying longer? Read living in Key West.

Questions people ask

Dates, rules and hours can change. The organisers have the final word: City of Key West: Visitors