Key West Pride

Key West Pride is a multi-day celebration organized by the Key West Business Guild in early June. It includes a street fair on Duval Street, pool parties, drag shows and sunset sails. The week ends with a parade down Duval Street that carries a segment of the city's Sea-to-Sea rainbow flag.

Key West Pride is produced by the Key West Business Guild, a 501(c)(6) nonprofit formed in 1978 to encourage summer tourism and support the island's gay community. It describes itself as the country's first LGBTQ+ destination marketing organization and now counts more than 475 member businesses. The guild runs the Gay Key West Visitor Center at 808 Duval Street and also produces Tropical Heat, Key West Womenfest and the Headdress Ball.

The 2026 theme was Color the Island, built around identity, self-expression and creativity. The run-up to Pride Week included the Key West Pride Follies at the Key West Theater, a variety show of local singers, dancers and other acts, and Real Men Do Drag, a fundraiser by the Key West Mile Markers at Aqua Nightclub that the group says has raised more than $1.5 million for local charities since 2017.

Pride Week itself has opened with a guild membership luncheon, a GOLD party at Island House benefiting the local nonprofit Womankind, and a 21-and-over kickoff party at The Key West Cooking Show in the Shops of Mallory Square, with a local DJ, vendors, food and drinks included in the ticket.

Pride events celebrate LGBTQ+ people and mark the Stonewall uprising of June 1969. Most combine a parade or march with a festival of performers, community groups, vendors and food.

Key West Pride has included parade, street fair, pool parties, drag shows and sunset sails.

The organizer has not announced dates for 2027 yet. In 2026 it was held June 3-7, 2026. It usually falls early June, five days ending on a Sunday.