• Key West End of Prohibition Celebration

    Sloppy Joe's Bar 201 Duval Street, Key West, FL, United States

    Take a step back into old Key West and celebrate the end of Prohibition with five days of fun filled Prohibition-themed films, cocktails, history, live entertainment and a blowout party at Sloppy Joe's at the corner of Duval and Greene Streets.

  • Key West Farmer’s Market

    Truman Waterfront Pier Southard St, Key West, FL, United States

    Discover the vibrant flavors and local treasures at the Key West Farmer's Market, held every Thursday at the Truman Waterfront Pier. Browse an array of stalls brimming with freshly harvested produce, artisanal goods, and handmade crafts, all crafted with passion by local vendors. Immerse yourself in the lively atmosphere, where the scent of ripe fruits mingles with the sounds of live music, creating an unforgettable experience for visitors and locals alike.

  • Key West Farmer’s Market

    Truman Waterfront Pier Southard St, Key West, FL, United States

    Discover the vibrant flavors and local treasures at the Key West Farmer's Market, held every Thursday at the Truman Waterfront Pier. Browse an array of stalls brimming with freshly harvested produce, artisanal goods, and handmade crafts, all crafted with passion by local vendors. Immerse yourself in the lively atmosphere, where the scent of ripe fruits mingles with the sounds of live music, creating an unforgettable experience for visitors and locals alike.

  • 34th Annual Schooner Wharf Bar Lighted Boat Parade

    Schooner Wharf Bar 202 William Street, Key West, FL, United States

    Don't miss this magical nautical display of holiday lights on board every manner of watercraft in Key West Harbor. The judges stand is located at Schooner Wharf, 202 William St. Viewing is available from all along the Harbor Walk. The parade starts at 8 p.m.

  • Key West Farmer’s Market

    Truman Waterfront Pier Southard St, Key West, FL, United States

    Discover the vibrant flavors and local treasures at the Key West Farmer's Market, held every Thursday at the Truman Waterfront Pier. Browse an array of stalls brimming with freshly harvested produce, artisanal goods, and handmade crafts, all crafted with passion by local vendors. Immerse yourself in the lively atmosphere, where the scent of ripe fruits mingles with the sounds of live music, creating an unforgettable experience for visitors and locals alike.

  • The Florida Keys Southernmost Car Club – Holiday Classic Car Show & Toy Drive

    Conch Republic Seafood Company 631 Greene St, Key West, FL

    Come check out this festive event during your stay! Guests are encouraged to bring an unwrapped toy for the Monroe County Domestic Abuse Shelter. Classic cars from every era will be decked out for the holidays, hosted by the Florida Keys Southernmost Car Club in honor of founder Dick Moody. Non-member cars may even enter free with an unwrapped toy—making it a fun and meaningful outing for all.