Mallory Square Sunset Celebration or a Sunset Sail

The Sunset Celebration on Mallory Square is free. It runs every night of the year, weather permitting, on the waterfront plaza and dock at the west end of Old Town, starting about two hours before sunset and ending soon after it. The Key West Cultural Preservation Society, a non-profit, has run it since 1984: street performers, musicians, artists and food stalls, and a crowd that turns to the water as the sun goes down. The performers are not paid by anyone; they live on what you put in the hat.

To watch the same sunset from the water instead, the sunset sails leave the Historic Seaport, a few minutes’ walk east of the square, and sail out past it.

See the sunset sail

Start times by month

The Preservation Society publishes the times its performers set up. Arrive at the start for a spot on the seawall, or about an hour later, when the crowd and the acts are in full swing.

Start times from the Key West Cultural Preservation Society’s visitor page, checked October 2026; sunset at Mallory Square from the U.S. Naval Observatory. The Society’s page lists both 5:30 and 5:45 pm for April; check a specific date with the Society.

What you see from the square

Mallory Square looks west and north across the harbor to Sunset Key and Wisteria Island. From the summer months into mid-August the sun goes down toward Sunset Key; in winter it sets farther left, over open water. The sunset times guide has the direction month by month. In front of the square the harbor fills with boats at sunset: several of the sails on this site list Mallory Square and its Sunset Celebration as one of the sights they pass.

When a sail is the better evening

The square is the right answer if you want the street show and do not want to spend anything. A sail is the better evening if you want the sunset itself over open water, away from the crowd, with a drink in your hand and somewhere to sit. Sebago’s two-hour sail leaves the Historic Seaport, less than ten minutes’ walk east of the square, sails out past it and positions the catamaran for the sunset, with an open bar, hors d’oeuvres and live music. It is from $70 an adult on Viator (checked October 2026) and from $70 on GetYourGuide (checked October 2026):

Doing both

The celebration and a sail run at the same hour, so on any one night it is mostly one or the other. In winter, when the celebration starts at 3:45 pm, you can catch the first acts and still check in at 4:00 for a 4:30 pm sail on the Seaport side; in summer, with the square starting at 6:15 pm and the sails leaving at 6:30 pm, it is one or the other. Another option is the square on your first night and a sail on the next.

Getting there and parking

Mallory Square is a block from the north end of Duval Street, beside Opal Key Resort and the Key West Museum of Art and History. The City of Key West’s Old Town garage at 301 Grinnell Street charges $6 an hour and $48 a day plus tax, and its Key West Bight lot on Caroline Street $6 an hour (checked October 2026). The departure points guide has the walk to each sail’s check-in.