Updated for 2026

Every festival, every parade,
every excuse to party.

Key West has a national-caliber festival nearly every month. We track the ones worth flying for and tell you when to book your hotel months ahead.

Last updated August 2026Dates are compiled from each event's official page — tap an event to confirm on the source.

JANUARY3 events

Jan 21–25, 2026

Mile 0 Fest

Texas red-dirt + Americana songwriter festival at Truman Waterfront. 4 days, 40+ artists.

MusicParty

Jan 21–25, 2026

Key West Food & Wine Festival

5 days of tastings, dinners, and pairings across 30+ KW restaurants.

FoodRomance

Jan 18–23, 2026

Key West Race Week (Quantum)

Premier mid-winter regatta. Spectator-friendly from Mallory Square.

Fishing

APRIL1 event

Apr 17–26, 2026

Conch Republic Independence Celebration

10 days celebrating KW's 1982 'secession.' Battle of the Conch Republic, drag races, parades.

HistoryPartyFamily

MAY1 event

May 6–10, 2026

Key West Songwriters Festival

The largest songwriters festival in the world — 200 writers, 50 venues, mostly free.

MusicRomance

JUNE1 event

Jun 3–7, 2026

Key West Pride

5-day Pride celebration. Sea-to-Sea Rainbow Flag, street fair, drag, parade down Duval.

LGBTQ+Party

JULY2 events

Jul 29–30, 2026

Mini Lobster Season

Two-day sport lobster mini-season before commercial opens. KW restaurants run lobster specials.

FoodFishing

Jul 21–26, 2026

Hemingway Days

Papa Hemingway look-alike contest at Sloppy Joe's, marlin tournament, short story competition.

HistoryParty

AUGUST1 event

Aug 6–9, 2026

Key West Lobsterfest

Street fair, pool parties, the Lobster Boil — KW's biggest summer block party.

FoodParty

SEPTEMBER1 event

Sep 2–7, 2026

Womenfest Key West

Largest women's vacation week in the world. Pool parties, tea dances, charters.

LGBTQ+Party

OCTOBER3 events

Oct 14–17, 2026

World Sailfish Championship

Million-dollar sailfish tournament out of Stock Island.

Fishing

Oct 16–17, 2026

Goombay Festival (Bahama Village)

Bahama Village street party — junkanoo, conch fritters, calypso. Kicks off Fantasy Fest week.

HistoryFoodMusicFamily

Oct 16–25, 2026

Fantasy Fest

10 days, one theme, body paint everywhere. The Captain Morgan Parade is the climax. 21+ vibes.

PartyLGBTQ+

NOVEMBER1 event

Nov 4–8, 2026

Key West World Championship Offshore Powerboat Races

200mph powerboats lap the Truman Waterfront. Free spectator viewing all week.

FamilyParty

DECEMBER3 events

Dec 12, 2026

Key West Lighted Boat Parade

Schooner Wharf boat parade — 40+ decorated boats. Watch from Historic Seaport.

FamilyRomance