The 20th Annual Florida Keys Seafood Festival in 2026 is a milestone celebration of the island’s rich commercial fishing heritage. Unlike many tourist events, this is a true “local” feast—the food is caught, cleaned, prepared, and served by Florida Keys fishermen and their families. Festival Dates: February 14 – February 15, 2026 The festival is […]
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 […]
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 & […]
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 […]
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 […]
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 […]
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 […]
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 […]
The Morada Way Art Walk is the premier cultural event of the Upper Keys, turning the heart of Islamorada into a lively, open-air gallery and street festival. Held in the Morada Way Arts & Cultural District (Mile Marker 81.5), this “Third Thursday” tradition brings together local artists, musicians, and culinary talent for an evening that […]
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 […]
The Upper Keys Rotary Gigantic Nautical Market (affectionately known as the “Gigantic Nautical Flea Market”) is the largest outdoor nautical show of its kind in the Florida Keys. Held at the expansive Founders Park, this two-day event is a massive “boat show with a beach,” attracting over 20,000 visitors who come to hunt for bargains, […]
The Old Island Days Art Festival (now officially renamed the Key West Art & Craft Festival) celebrates its 61st anniversary in 2026. This prestigious, juried outdoor show is a cornerstone of the island’s winter season, transforming the waterfront into a sprawling gallery for some of the country’s finest artists and craftspeople. Festival Dates: February 21 […]