• Sunset Celebration at Mallory Square

    Sunset Celebration at Mallory Square

    The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […]

  • Sunset Celebration at Mallory Square

    Sunset Celebration at Mallory Square

    The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […]

  • Sunset Celebration at Mallory Square

    Sunset Celebration at Mallory Square

    The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […]

  • Key West Songwriters Festival

    Key West Songwriters Festival 512 Eaton St, Key West, FL, United States

    The Key West Songwriters Festival 2026 marks a major milestone as the 30th anniversary of the world’s largest festival of its kind. For five days, the island transforms into “Nashville by the Sea,” where the hidden faces behind your favorite radio hits take center stage to perform their songs and tell the stories of how […]

  • Sunset Celebration at Mallory Square

    Sunset Celebration at Mallory Square

    The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […]

  • Sunset Celebration at Mallory Square

    Sunset Celebration at Mallory Square

    The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […]

  • Sunset Celebration at Mallory Square

    Sunset Celebration at Mallory Square

    The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […]

  • First Friday Art Walk

    First Friday Art Walk
    First Fridays on Fleming Fleming Street, Key West, FL, United States

    The First Fridays on Fleming is the signature monthly art stroll for Old Town Key West, specifically highlighting the “boutique” galleries and studios along the 500 block of Fleming Street. It serves as the island’s version of a First Friday Art Walk, offering a sophisticated but relaxed alternative to the rowdier Duval Street scene. 2026 […]

  • Sunset Celebration at Mallory Square

    Sunset Celebration at Mallory Square

    The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […]

  • Islamorada Farmers Market

    Islamorada Farmers Market
    Florida Keys Farmers Market 81001 Overseas Hwy, Islamorada, FL, United States

    The Florida Keys Farmers Market (often referred to as the Islamorada Farmers Market) is a vibrant Sunday tradition in the Upper Keys. Known for its “oasis” atmosphere, it’s much more than a grocery stop—it’s a social hub featuring live music, colorful murals, and a lush garden setting that feels like a hidden park. Schedule & […]

  • Sunset Celebration at Mallory Square

    Sunset Celebration at Mallory Square

    The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […]

  • Sunset Celebration at Mallory Square

    Sunset Celebration at Mallory Square

    The Sunset Celebration at Mallory Square is the nightly heartbeat of Key West—a “multicultural circus” and arts festival that has been a mandatory island ritual since the late 1960s. Every single evening, locals and visitors gather at the water’s edge to toast the setting sun in a communal salute that is equal parts high-energy street […]