Published 4 min read
Key West Holiday Season 2026: Thanksgiving to New Year’s
Key West’s dated holiday events are mostly in Old Town, on Duval Street and at the Historic Seaport on Key West Bight. This page covers the events we could confirm on the City of Key West’s and Key West Historic Seaport’s pages, the Florida Keys visitor site and the organizers’ own pages, read on October 30, 2026. Where a 2026 detail is not published, we say so. Shortlist condos and homes on Key West rentals, then book on the property site. If you are choosing an area, see the Key West neighborhood guide.
Quick answer
The City of Key West Holiday Parade is Saturday, December 5, 2026, at 7 p.m., from Truman Avenue and White Street down Duval Street to Eaton Street. The 35th Lighted Boat Parade is Saturday, December 12, at Key West Bight. On New Year’s Eve, the Red Shoe Drop is at Bourbon St. Pub, 724 Duval, and the 33rd Conch Shell Drop is at Sloppy Joe’s, Duval and Greene.
The 2026 holiday calendar
- Thanksgiving: Thursday, November 26, 2026.
- Christmas Eve and Christmas Day: Thursday, December 24, and Friday, December 25, 2026.
- New Year’s Eve and New Year’s Day: Thursday, December 31, 2026, and Friday, January 1, 2027.
Many rentals set their own minimum stay for these nights, and it can differ from the rest of the season. Read the minimum for your exact dates on the booking site, not the general winter rule.
City Holiday Parade (December 5)
The City of Key West’s parade registration page lists Saturday, December 5, 2026, at 7 p.m. The Historic Seaport’s parade listing gives the route: it starts on Truman Avenue at White Street, turns onto Duval Street and ends at Eaton Street, and the listing says Santa appears. The seaport listing shows a 6:30 p.m. start, so plan to be on the route before 7. It is free.
Lighted Boat Parade (December 12)
The Historic Seaport’s boat parade page lists the 35th annual Lighted Boat Parade on Saturday, December 12, 2026, with the event running 6 to 11 p.m. The procession starts from Key West Bight by Schooner Wharf Bar, where the judges’ stand is, and continues along the harbor. Schooner Wharf’s special events page lists the parade at 8 p.m. and an awards ceremony on December 14.
- Tree trimming party: the same Schooner Wharf page lists a tree trimming party on Sunday, December 6, at 6 p.m.
- Harbor Walk lights: it also lists the Harbor Walk of Lights through the holidays, from November to January. No exact start date is given.
New Year’s Eve on Duval
- Red Shoe Drop: the Florida Keys visitor site’s Red Shoe Drop page lists Thursday, December 31, 2026, outside Bourbon St. Pub, 724 Duval Street. A giant red high heel carrying a drag queen is lowered from the balcony at midnight. The page suggests arriving early for a viewing spot.
- Conch Shell Drop: Sloppy Joe’s New Year’s Eve page lists its 33rd annual Conch Shell Drop at midnight at the corner of Duval and Greene Streets (201 Duval).
Duval Street is crowded on New Year’s Eve. If you are staying in Old Town, plan to walk. If you are farther out, check parking and taxi options before you book.
What to confirm before you pay
- The minimum stay and cancellation terms for your holiday nights.
- Whether the pool is heated in December, and whether there is an extra charge for it.
- Parking: Old Town spaces are limited. Ask how many cars the home allows.
- House rules and occupancy: Key West rental tips. For what to bring, see the winter packing list.
If one feature matters for a holiday stay, start with these Key West and Florida Keys pages; each lists only rentals whose own listing title or website mentions that feature: Key West and Florida Keys rentals with a pool (12), Oceanfront rentals in Key West and Florida Keys (11), Waterfront rentals in Key West and Florida Keys (10), Key West and Florida Keys condo rentals (15). Confirm the feature and the holiday minimum stay with the owner or manager in writing before you pay.
FAQ
When is the Key West Holiday Parade in 2026?
Saturday, December 5, 2026, at 7 p.m., per the City of Key West. It runs from Truman Avenue and White Street down Duval Street to Eaton Street.
When is the Key West Lighted Boat Parade?
Saturday, December 12, 2026, starting from Key West Bight at the Historic Seaport. Schooner Wharf lists the parade at 8 p.m.
Does BnB Search book the stay?
No. Compare on the hub, then finish on the site linked from the listing.
Start browsing stays
Sources
- City of Key West — Holiday Parade registration (December 5, 2026) (read October 30, 2026)
- Key West Historic Seaport — 2026 Hometown Holiday Parade (read October 30, 2026)
- Key West Historic Seaport — 35th Annual Lighted Boat Parade 2026 (read October 30, 2026)
- Schooner Wharf Bar — special events (read October 30, 2026)
- Florida Keys & Key West — New Year’s Eve Red Shoe Drop (read October 30, 2026)
- Sloppy Joe’s — 33rd Annual Conch Shell Drop (read October 30, 2026)
Related
Things to do · Winter packing · Rental tips · Neighborhood guide · New Year’s Eve beach rentals