Key West Holidays & New Year’s Eve 2026
Prices & schedules checked October 18, 2026
A Key West December means lights on boats rather than snow on roofs. Here’s what’s confirmed for the 2026 season, with official links.
Schooner Wharf Lighted Boat Parade — Saturday, December 12, 2026
- The 34th annual parade sails into Key West Bight and harbor at 8:00 p.m. on December 12, 2026.
- The organizer says decorated motor and sailing vessels take part, and children can catch candy and beads thrown from the boats.
- Watch from the docks around Key West Bight (the historic seaport).
Holiday lights by tour train
The Conch Tour Train runs a seasonal Holiday Sights and Festive Nights Tour: a one-hour tour of the island’s most elaborately decorated houses, buildings and neighborhoods, with caroling and holiday-lights glasses. Dates and prices are on the operator’s site.
History weekends at Fort Zachary Taylor
Florida State Parks lists reenactor weekends at Fort Zachary Taylor Historic State Park on November 21–22 and December 19–20, 2026, 10 a.m. – 2 p.m. The park says local reenactors conduct historic demonstrations on the third weekend of each month.
New Year’s Eve: two drops on Duval
| Event | Where | What the organizer says |
|---|---|---|
| 33rd Annual Conch Shell Drop | Sloppy Joe’s, corner of Duval and Greene Streets | A giant man-made conch shell descends at midnight on December 31; a tradition since 1993 |
| Red Shoe Drop 2026–2027 | Bourbon St. Pub | Event listed December 31, 2026 from 8:00 p.m. to 1:00 a.m. |
Duval Street gets very crowded on New Year’s Eve. Book lodging early and plan to walk; see where to stay.
Sunset on the water this season
A December sunset sail is a popular way to celebrate. See our sunset and snorkel guide for options.
We may earn a commission when you book through our links, at no extra cost to you. Details
Viator prices change often, so we don’t quote them: the Viator buttons open the live listing, where you’ll see today’s price, times and cancellation terms. Facts on this page come from the operators’ own sites.
Sources
- Schooner Wharf Bar — 2026 Lighted Boat Parade (date, time, Key West Bight)
- Conch Tour Train — Holiday Sights and Festive Nights Tour
- Florida State Parks — Fort Zachary Taylor (reenactor weekends, hours, fees)
- Sloppy Joe’s — 33rd Annual New Year’s Eve Conch Shell Drop
- Bourbon St. Pub — Red Shoe Drop for New Year’s Eve 2026–2027