• 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 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
  • Sheriff’s Animal Farm Open House

    Monroe County Sheriff's Office Animal Farm 5501 College Rd, Key West, FL, United States

    Celebrate Christmas at the Monroe County Sheriff's Animal Farm from 1 to 3 p.m. This will be the only open house during the month of December. Visit with the animals and participate in joyful holiday-themed activities. Gifts of fresh produce and other items, as well as cash gifts for the animals, are greatly appreciated!

    Gifts of fresh produce
  • Key West Songwriters Festival

    The Key West Songwriters Festival is the world’s largest of its kind and a career-launching event for country talent. It has helped kickstart the careers of stars like Kacey Musgraves, Florida Georgia Line, Jake Owen, and Maren Morris. Now in its 29th year, the festival attracts music lovers to Key West for five days and nights of live music and storytelling from both established and up-and-coming songwriters.

    Varies
  • 34th Annual Schooner Wharf Minimal Regatta

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

    Delicious food, island-style drinks, live music, and a FREE raffle set the stage for an unforgettable day on the Harborwalk. The real show? Homemade boats built from minimal materials (two sheets of plywood, a roll of duct tape, and some fasteners) racing — and often sinking — in spectacular fashion!

    Want to join the madness? Enter your vessel for a shot at awesome prizes and bragging rights. Whether you're building a boat or just here to soak up the fun, it's a day full of creativity, comedy, and community.

  • Sunset Celebration at Mallory Square

    Mallory Square 420 Wall St, Key West, FL, United States

    Join locals and visitors each evening for Key West’s iconic Sunset Celebration — now with extra flair! From June 1 to June 20, enjoy nightly live music, street performers, artists, and food vendors, all leading up to the Summer Solstice on June 20.

    Celebrate summer’s arrival with island vibes, stunning sunsets, and unforgettable entertainment on the water. Don’t miss it!

  • Key West Pride 2025

    Celebrate Pride the Key West way — tropical, vibrant, and unapologetically free. This year’s theme, “Still Rising,” honors the LGBTQ+ community’s powerful history, resilience, and continued fight for equality. Whether you’re a first-time visitor or a returning friend of the island, Pride in Key West is a celebration like no other.

  • Key Lime Festival

    Savor the tangy sweetness of the Florida Keys at the Key West Key Lime Festival, a mouthwatering celebration of the iconic citrus. Indulge in endless variations of this zesty fruit, from traditional pies to creative concoctions, crafted by local bakers and chefs. Dive into the festivities with pie-eating contests, rum tastings, and culinary demonstrations, all against the picturesque backdrop of Key West's tropical paradise.

  • 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.

  • 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.

  • Hemingway Days: Caribbean Street Fair

    Duval Street

    On this exciting day, Duval Street transforms into a vibrant marketplace where artisans and food vendors showcase their creative masterpieces. The event celebrates local Caribbean culture with immersive street performances, live music, and dynamic art displays that pay tribute to Ernest Hemingway’s enduring legacy. Guests can look forward to a unique cultural experience that blends history, art, and the lively spirit of the Caribbean—all in one spectacular day.