What To Do This Weekend in the Florida Keys

Labor Day weekend is one of the best times of the year to be in the Florida Keys. This guide covers what to do on Saturday, September 5, and Sunday, September 6, 2026, from a Saturday-morning 5K in Key West to Womenfest celebrations and sunset gatherings at Mallory Square and Robbie's of Islamorada. Whether you are visiting for the holiday or calling the Keys home, here is your plan for the weekend.

Saturday, September 5

Parrots & Margaritas 5K Run/Walk: Key West, 8:00 AM

Saturday kicks off with the Parrots & Margaritas 5K Run/Walk in Key West, starting at 8:00 AM at Kaya Island Eats, 618 Duval St. It is a fun, low-key 5K run/walk for every pace, a relaxed way to ease into the holiday weekend. The race is part of the 3rd Annual Just a Few Friends Festival, a Labor Day weekend celebration in Key West that honors the legacy of Jimmy Buffett, and runners and visitors can stick around after the race at Kaya Island Eats for live music, margaritas, and Trop-Rock festivities. Register for the Parrots & Margaritas 5K online, and confirm final details in the OurKeyWest weekend roundup before you go.

Womenfest Key West Continues Through Sunday

Womenfest Key West runs September 2 through September 6 under the theme "Lost Women in the Arts," and it is in its final stretch this weekend. One of the largest LGBTQ+ women's festivals in the country, Womenfest fills the island with live music, parties, arts events, and community gatherings through Sunday. Check the festival schedule and the Key West events calendar for what is on each day.

Saturday night brings Decades of Divas, the festival's '80s Prom: a themed party with photo booths and live DJs. It is a favorite excuse to dress up, dance, and relive the big-hair decade, and one of the standout nights of Womenfest's final weekend.

Sunday, September 6

Womenfest Final Day and Closing Celebration

Sunday, September 6, is the last day of Womenfest Key West. It is the final chance to catch the remaining programming and the festival's closing celebration, so save room in the day for it. The island stays lively from morning to night as the festival wraps up over the holiday weekend.

Sunday afternoon features the iconic Womenfest Tea Dance at La Te Da, 3434 Duval St, a classic Key West tradition and a relaxed way to close out the weekend with an afternoon of dancing and good company before the festival draws to an end.

A Day on the Water: Lobstering Along with Snorkeling

Regular spiny lobster season is open in the Florida Keys, running from August 6 through March 31. That means an early-September day on the water can include lobstering along with snorkeling, and many charters and rental outfitters pair the two on the same trip.

Before you get in the water, review the FWC lobster regulations and follow them on every dive. Lobsters must be larger than the minimum size, with a carapace that measures more than three inches, and each diver is limited to six per day. No take is allowed in protected no-take areas, egg-bearing lobsters must be released, and you need the proper gear, including a measuring gauge and a divers-down flag.

Sunset Celebrations at Mallory Square and Robbie's

Sunday evening closes the weekend the classic Keys way: with a sunset celebration. In Key West, Mallory Square gathers street performers, musicians, and a waterfront crowd to watch the sun drop into the Gulf of Mexico. Up in Islamorada, the Morada Sunset Celebration at Robbie's brings art vendors and live music with views over Florida Bay as the sky turns gold and pink. Both are favorite end-of-weekend traditions, and an easy way to squeeze in one more dose of island time.

If you are dining around sunset, both towns have an easy answer. In Key West, El Meson de Pepe at Mallory Square serves authentic Cuban cuisine with live salsa music as the sun goes down, just steps from the celebration itself. In Islamorada, Lorelei Restaurant & Cabana Bar is famous for sunset views and live music, right down the road from Robbie's on the bayside. Grab a table early, order something cold, and settle in for the show.

The Keys are at their best in good company and on the water. Whatever your pace this Labor Day weekend, there is room for it here, from a 5K start line in Key West to a sunset toast over Florida Bay. Have a great weekend, and if you are thinking about making the Keys more than a vacation, reach out any time.

Disclaimer: Event schedules and details may change. Confirm directly with event organizers before visiting.