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  • Key West Farmer’s Market

    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.

    FREE Family-Friendly Halloween Party at Truman Waterfront Farmers Market October 31 from 4pm to 7pm (the Market opens at 2pm) at the Truman Waterfront Park as part of the regular Thursday Farmers Market.

  • 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 Artisan Market

    Higgs Memorial Beach Park 1000 Atlantic Blvd., Key West

    Join the fun at the Key West Artisan Market on select Sundays! Discover local artisans showcasing colorful handmade crafts, unique jewelry, and delicious treats. Enjoy live music, tasty bites from local food vendors, and soak up the festive island vibes. It’s the perfect place to support creativity and find one-of-a-kind treasures!

    Free

  • Key West Farmer’s Market

    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.

    FREE Family-Friendly Halloween Party at Truman Waterfront Farmers Market October 31 from 4pm to 7pm (the Market opens at 2pm) at the Truman Waterfront Park as part of the regular Thursday Farmers Market.

  • 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.

  • Key West Farmer’s Market

    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.

    FREE Family-Friendly Halloween Party at Truman Waterfront Farmers Market October 31 from 4pm to 7pm (the Market opens at 2pm) at the Truman Waterfront Park as part of the regular Thursday Farmers Market.

  • Key West Farmer’s Market

    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.

    FREE Family-Friendly Halloween Party at Truman Waterfront Farmers Market October 31 from 4pm to 7pm (the Market opens at 2pm) at the Truman Waterfront Park as part of the regular Thursday Farmers Market.

  • Key West Farmer’s Market

    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.

    FREE Family-Friendly Halloween Party at Truman Waterfront Farmers Market October 31 from 4pm to 7pm (the Market opens at 2pm) at the Truman Waterfront Park as part of the regular Thursday Farmers Market.

  • Key West Farmer’s Market

    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.

    FREE Family-Friendly Halloween Party at Truman Waterfront Farmers Market October 31 from 4pm to 7pm (the Market opens at 2pm) at the Truman Waterfront Park as part of the regular Thursday Farmers Market.

  • The Southernmost Regatta

    The Southernmost Regatta event in Key West presents five days of exhilarating racing set against the stunning backdrop of the island's azure waters. Open to both One Design and ORC Racing/Cruising Keelboats, it provides a thrilling opportunity to compete on the open sea while immersing oneself in the vibrant island culture. As winter chills settle in elsewhere, participants can bask in the warmth of camaraderie, rekindling friendships amidst the excitement of competitive sailing.