An independent planner owned by LPE Realty LLC · (561) 652-6917
Key West, Florida · Thanksgiving to New Year's Day
Christmas in Key West runs from the Harbor Walk of Lights lighting on Wed. Nov. 25, 2026 to New Year's Eve on Duval Street. Schooner Wharf lists its 35th Lighted Boat Parade for Sat. Dec. 12 at 8 PM; the City's Hometown Holiday Parade is Sat. Dec. 5. This independent planner gives every date with its organiser's source.
What is on this date? Plan an evening
An independent planner owned by LPE Realty LLC (561) 652-6917
Christmas Eve sunset off Mallory Square, 2012 A film cut from 8 real photographs of Key West in December: the waterfront at sunset, Christmas lights in Old Town, Duval Street and the beach. Credits
Lighted Boat Parade 2026
Schooner Wharf Bar lists its 35th Lighted Boat Parade for Dec. 12, 2026 at 8 PM, with the judges' stand at Schooner Wharf. keywestchristmas.org adds music from 6 PM and says you can watch all along the Harbor Walk.
Source: Schooner Wharf Bar: Special Events (2026 Events), checked 2026-10-21. Source: Key West "Bight" Before Christmas: keywestchristmas.org (Harbor Walk of Lights), checked 2026-10-21.
35Days
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Coming up
Only events whose organiser or the City of Key West has posted a 2026 date, checked October 21, 2026. Each card adds to your calendar in one tap.
Thanksgiving Eve kickoff of the Harbor Walk of Lights: countdown and lighting of the Fishing Buoy Christmas Tree, then the original Lobster Trap Christmas Tree. Santa and Mrs. Claus hand out treats; the Cheryl Cates Toy Drive starts here.
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Free
Three blocks of holiday lights and nautical displays along the seawall past Greene, William and Margaret streets to the Key West ferry terminal.
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Free to walk
The City's annual tree lighting at Bayview Park. The Holiday Fest calendar lists it a day earlier (Nov. 29); the City's own notice says Nov. 30.
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Not published
Santa photos for pets and families at the Historic Seaport, hosted by The All Animal Clinic, to benefit the Boys & Girls Club.
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Free to attend; pictures with Santa $25 (cash and Cash App)
Decision tool · evening planner
Choose how long you have and what you enjoy. The planner picks sourced stops in Old Town, puts them in walking order from the Historic Seaport, and points you to a City lot if you are driving.
Or start from a ready-made plan:
Start on the lit Harbor Walk after dark, eat at the Seaport, finish at a bar on Greene Street.
Sunset at Mallory Square, a walk up Duval, then the Harbor Walk lights.
Three museums in daylight, the fort and its beach, then back to the Seaport after dark.
Stops come from our sourced list of Key West places (checked 2026-10-21). Distances are straight lines between OpenStreetMap coordinates, not walking routes, and time per stop is your chosen time split evenly. Holiday hours are published for only some places, so check each one before you go.
Back on the island every December? See what living in Key West involves.
The season in four nights
Key West's December has no single organiser. These four dates frame it, each from the group that runs it.
Nov. 25
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!"
Source: Key West "Bight" Before Christmas: keywestchristmas.org (Harbor Walk of Lights), checked 2026-10-21
Dec. 5
keywestchristmas.org: "Saturday, December 5", "2026 Key West City "Hometown Holiday Parade"", "Starts at 6:30pm", "Parade starts on Truman Ave. (at White St.) then proceeds to Duval St., then down Duval St. ending at Eaton St." and "Of course Santa will make a guest appearance!"
Source: Key West "Bight" Before Christmas: keywestchristmas.org (Harbor Walk of Lights), checked 2026-10-21
Dec. 12
keywestchristmas.org lists "35th Annual Key West Lighted Boat Parade 2026" on "Saturday, December 12" with "Music at 6:00, Parade starts at 8:00pm." The listing is headed "Schooner Wharf Bar & Galley and Absolute Vodka".
Source: Key West "Bight" Before Christmas: keywestchristmas.org (Harbor Walk of Lights), checked 2026-10-21
Dec. 31
Sloppy Joe's events page: "Thursday, December 31, 2026", "10:00 pm Sloppy Joe's 33rd Annual Dropping of the Conch Shell at midnight to ring in 2027!" "This year, the conch shell will drop for the 33rd time at the corner of Duval and Greene Street." "Customers inside the bar will be able to see the conch shell drop on Sloppy-Tron."
Source: Sloppy Joe's Bar: Events, checked 2026-10-21
On foot from the Seaport
From the Harbor Walk to the museums of Old Town. The evening planner above puts stops in walking order and tells you which City lot is closest.
Key West Bight
keywestchristmas.org says the Harbor Walk of Lights runs along the seawall past Greene, William and Margaret streets to the ferry terminal, and is lit every evening through New Year's Eve.
End of Wall Street
Home of the nightly Sunset Celebration. Its operator says it starts about an hour before sunset; mallorysquare.com says two. The Naval Observatory puts December 2026 sunsets between 5:38 and 5:50 PM.
281 Front Street
The 1891 building is now the Key West Museum of Art and History. The City lists its Holiday Concert and Bazaar for Friday, Dec. 11, 2026, 5 to 8 PM.
907 Whitehead Street
The museum says it is open daily, 365 days a year, 9 AM to 5 PM, with guided tours starting every 15 minutes.
Decision tool · beach matcher
December days in Key West are warm enough for the beach. Tell us what you need and we match you to the island's public beaches using what each operator publishes, and we flag anything they do not say.
| Beach | Restrooms | Showers | Free parking | Dogs | Wheelchair | Picnic | Playground | Snorkel | Food | Fishing | Lifeguards |
|---|---|---|---|---|---|---|---|---|---|---|---|
| Simonton Street BeachCity of Key West · 0.3 mi | Yes | Not published | No | Not published | Not published | Not published | Not published | Not published | Not published | Not published | Not published |
| South BeachCity of Key West · 1 mi | Not published | Not published | Not published | Not published | Not published | Not published | Not published | Not published | Not published | Not published | Not published |
| Dog BeachCity of Key West · 1 mi | Not published | Not published | Not published | Yes | Not published | Not published | Not published | Not published | Not published | Not published | Not published |
| Fort Zachary Taylor Historic State Park BeachFlorida State Parks · 1.2 mi | Yes | Yes | No | Not published | Yes | Not published | Not published | Yes | Yes | Yes | No |
| Clarence S. Higgs Memorial Beach (Higgs Beach)City of Key West · 1.2 mi | Yes | Yes | Not published | Not published | Not published | Yes | Yes | Not published | Yes | Not published | Not published |
| Rest Beach / C.B. Harvey ParkCity of Key West · 1.3 mi | Not published | Not published | Not published | Not published | Not published | Not published | Not published | Not published | Not published | Not published | Not published |
| Smathers BeachCity of Key West · 1.9 mi | Yes | Yes | No | Not published | Not published | Not published | Not published | Not published | Not published | Not published | Not published |
Check = the operator says yes. Dash = the operator says no. Question mark = the operator does not say; ask before you go. Miles are straight-line from the Historic Seaport.
Features, fees and hours come from each operator's own page (Florida State Parks for Fort Zachary Taylor, the City of Key West for the City beaches), checked 2026-10-21. The City calls Dog Beach its dog-friendly beach. Fort Zachary Taylor says it has no lifeguards; the City pages do not say either way. Distances are straight lines, not driving routes.
Want the beach in your own December, every year? See what living in Key West involves.
December at the water
NOAA's 1991 to 2020 normals give Key West an average December high of 77.7 F, and its water temperature guide lists 75.3 F for the month. Florida State Parks opens Fort Zachary Taylor, beach included, from 8 AM until sundown, 365 days a year.
Photo: Julian Lupyan, CC0 (cropped)
Eat and drink
Hours from each place's own website, checked October 21, 2026. Holiday hours change and parade nights are busy, so check before you go.
open-air bar and restaurant (Harbor Walk)
202 William Street, Key West, FL 33040
"An island institution since 1984" on the site of the old Singleton Shrimp factory, "At the foot of William Street on the Historic Harbor Walk." The Seaport lists it as pet friendly. Its own events list includes a tree trimming party and the Lighted Boat Parade (see research/events.json for dates).
Breakfast: "Breakfast served Mon. thru Thurs. 8:30 am – 11:00 am"; "Fri. & Sat. 8:00 am – 11:00 am & Sun 8 am till Noon." Bar hours not published on the home page.
Source: Schooner Wharf Bar (official site), checked 2026-10-21
seafood restaurant and raw bar (Historic Seaport)
231 Margaret Street, Key West, FL 33040
On the Seaport's dining list. The City runs a 19-space "Half Shell Raw Bar Parking Lot" at the same address (parking.json).
"Open Everyday" "11:00 am – 10:00 pm"; happy hour "7 Days a week 4:30 PM to 6:30 PM"
Source: Half Shell Raw Bar (official site), checked 2026-10-21
brewery and restaurant (Key West Bight)
201 William Street, Key West, FL 33040
Own site: "A Craft Brewery located at the Historic Key West Bight with a great beer selection, a full food menu." Hours not in the home page text; check before going.
Source: The Waterfront Brewery (official site), checked 2026-10-21
seafood restaurant (Historic Seaport)
631 Greene Street, Key West, FL 33040
On the Seaport's dining list.
"Open Daily at 11:30am"; listed Monday to Sunday "11:30am – 9:30pm"; "Closing times vary, so please call!"; "Daily Happy Hour from 4-7pm"
Source: Conch Republic Seafood Company (official site), checked 2026-10-21
casual seafood shack
801 Caroline Street, Key West, FL 33040
On the Seaport's dining list. Hours not in the official site's page text; check before going.
Source: B.O.'s Fish Wagon (official site), checked 2026-10-21
cafe (Historic Seaport)
205 Elizabeth Street, Key West, FL 33040
On the Seaport's dining list at 205 Elizabeth Street. Not the same as 'The Old Fisherman's Cafe' that OSM maps on Front Street.
"Open 7 days a week 7am – 5pm"
Source: Fisherman's Cafe (official site); Key West Historic Seaport: Food, checked 2026-10-21
historic bar and restaurant
201 Duval Street, Key West, FL 33040
"Est. 1933 | Corner of Duval & Greene Since 1937!" "Live music every day 10 a.m.- 2:00 a.m."
Bar: Mon. – Sat. 9:00 am – 4:00 am; Sunday 10:00 am – 4:00 am. Kitchen: Mon. – Sat. 10:00 am – 10:00 pm; Sunday 11:00 am – 10:00 pm.
Source: Sloppy Joe's Bar (official site), checked 2026-10-21
historic bar
428 Greene Street, Key West, FL 33040
Own site: the building at 428 Greene Street was built in 1851 as an ice house.
"Mon-Fri: 10:00am – 2:00am"; "Saturday: 10:00am – 2:00am"; "Sunday: 10:30am – 1:00am"
Source: Captain Tony's Saloon (official site), checked 2026-10-21
After the holidays
The Census Bureau's Vintage 2025 estimate puts Key West at 24,999 people on July 1, 2025. LPE Realty LLC, a licensed Florida brokerage, owns this planner and can talk you through buying or selling a home on the island.
Quick answers
Saturday, December 12, 2026. Schooner Wharf Bar lists its 35th annual parade at 8:00 p.m., and keywestchristmas.org lists music from 6:00 and the parade at 8:00pm. The City's event notice covers 7 to 10 PM at the Historic Seaport.
Saturday, December 5, 2026. The City of Key West lists it from 7:00 to 9:00 PM. keywestchristmas.org says it starts at 6:30pm, so arrive before 6:30 to be safe.
It is the holiday light display at the Key West Historic Seaport and Key West Bight Marina, part of the Key West "Bight" before Christmas celebration. 2026 is its 21st year, with a nautical theme honoring the waterfront's maritime history.
Source: Key West "Bight" Before Christmas: keywestchristmas.org (Harbor Walk of Lights)
Yes. The Conch Tour Train and Old Town Trolley both run a Holiday Sights and Festive Nights Tour in December 2026. Both are about an hour and need reservations.
Source: Conch Tour Train: Holiday Sights and Festive Nights Tour
Three venues list a midnight drop: the conch shell at Sloppy Joe's, the red high heel at Bourbon St. Pub, and the pirate wench lowered down the mast at Schooner Wharf Bar.
Source: Key West Inns (Lodging Association of the Florida Keys and Key West): Holiday Fest Calendar
NOAA's 1991-2020 normals for Key West International Airport give an average December high of 77.7 F, a low of 68.3 F, and 2.16 inches of rain.
Source: NOAA NCEI U.S. Climate Normals 1991-2020, station USW00012836 (Key West International Airport)
By air into Key West International Airport (EYW), which Monroe County owns and operates. By ferry on the Key West Express from Fort Myers Beach. Or by road on U.S. 1, the 113-mile Overseas Highway.
Source: Monroe County, FL: Airports
Journal
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After the holidays
This planner is owned by LPE Realty LLC, a licensed Florida real estate brokerage. If you keep coming back for the boat parade and the Harbor Walk lights, we can walk you through buying or selling a home in Key West: process, timing and costs, with no pressure.
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