Key West Guide

Local Events in Key West

Key West hosts some of the most vibrant and unique events in the Florida Keys throughout the year.

Fantasy Fest

The annual 10-day Fantasy Fest in October is Key West's signature event, drawing tens of thousands of visitors for a spectacular celebration of costumes, parades, street parties, and themed balls. The week culminates in the enormous Fantasy Fest Parade down Duval Street, filled with elaborate floats, costumed performers, and live music. It is a one-of-a-kind event that captures Key West's creative and uninhibited spirit.

Hemingway Days

Held each July in honor of Ernest Hemingway's birthday, Hemingway Days is a week-long celebration featuring the Hemingway Look-Alike Contest, a running of the bulls, a marlin tournament, a street fair, and literary events at the Hemingway Home and Museum. The festival draws fans of the legendary author from around the world and is one of Key West's most beloved traditions.

Key West Lobsterfest

Taking place in August during the Florida spiny lobster season, Key West Lobsterfest is a delicious celebration of the Keys' most famous seafood. The event features live music, food vendors serving fresh lobster dishes, a street fair, and the ceremonial first lobster dive. It is a highlight of the summer calendar for locals and visitors alike. Check this weekend's guide for what is happening now.

Red Ribbon Auction

An annual charity event supporting HIV/AIDS care and prevention in the Florida Keys. The Red Ribbon Auction features live and silent auctions, dinner, entertainment, and a strong sense of community purpose. It is one of the most important fundraising events in Key West and a testament to the island's caring community spirit.

Key West Art Walk

On the third Thursday of every month, the Key West Art Walk invites visitors and locals to explore the island's vibrant gallery scene. Participating galleries in Old Town open their doors for evening viewing, often with wine, live music, and the chance to meet local artists. It is a wonderful way to experience Key West's creative community.

Duval Street Festivals and Street Parties

Throughout the year, Duval Street plays host to a wide range of festivals and street parties, including the Key West Food and Wine Festival, Pride celebrations, Goombay Festival, and seasonal block parties. These events often feature live music stages, food vendors, art displays, and the electric energy that makes Key West famous.

Holiday Boat Parades

December in Key West means holiday boat parades. Festively decorated vessels cruise through the harbor while spectators gather at the waterfront to watch. The Key West Holiday Boat Parade is the main event, with boats adorned with lights, holiday decorations, and even costumed characters. A magical way to celebrate the season island-style.

Key West Pride

The annual Key West Pride celebration in June is one of the most vibrant LGBTQ+ events in the country. The week-long festival includes a parade down Duval Street, drag shows, pool parties, live entertainment, and community gatherings. Key West has long been a welcoming destination for the LGBTQ+ community, and Pride is a highlight of the social calendar. Contact Steve Conley for more about the Keys lifestyle.


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Contact Steve Conley for the latest updates on Keys events.

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Dates subject to change. Check the official Key West Chamber of Commerce calendar for the latest event information.

Conley Sales Group is a real estate Team affiliated with Compass. Compass Florida, LLC d/b/a Compass is a licensed real estate broker and abides by equal housing opportunity laws. All material presented herein is intended for informational purposes only. Equal Housing Opportunity.