What To Do This Weekend in the Florida Keys: September 11-13, 2026

This weekend in the Florida Keys is all about the water. The Swim for Alligator Lighthouse brings its 8-mile course through Islamorada, and Pennekamp Paddle Day, the America's 250 Red, White and Blue Paddle Parade, turns John Pennekamp into a red, white, and blue celebration. The Sunday farmers market, sandbar time, snorkeling, fishing, and sunset at Robbie's or Mallory Square cover the rest. There is no shortage of things to do this weekend in the Florida Keys.

Friday, September 11

Swim for Alligator Lighthouse: Check-In Day

Friday is check-in day for the Swim for Alligator Lighthouse. Athlete check-in and packet pickup runs from 10 a.m. to 7 p.m., with kayak check-in and drop-off during the same window. A pool practice session is available from 7:30 to 10 a.m. at the Ron Levy Aquatic Center at Founders Park for a $5 swimmer fee. All swimmers and kayakers must attend one of the mandatory safety meetings scheduled for 1 p.m., 3 p.m., or 6 p.m.

Even if you are not swimming, Friday night is a great night to settle in and watch the sun go down from a bayside table. In Islamorada, the Morada Sunset Celebration at Robbie's brings art vendors, live music, and the tarpon feed along the dock. It is a relaxed start for a weekend that rewards being on the water.

Saturday, September 12

The Swim for Alligator Lighthouse: Staggered Saturday Starts

Saturday morning belongs to the swim. The Swim for Alligator Lighthouse starts from the beach near Amara Cay Resort in Islamorada on the 8-mile out-and-back course to the iconic Alligator Reef Lighthouse. Staging opens at 5:45 a.m., and the official schedule staggers the start:

• 7:45 a.m., solo swimmers
• 7:52 a.m., two-person teams
• 7:54 a.m., three-person teams
• 8:00 a.m., four-person teams

Solo swimmers each pair with a support kayaker, and relays of two, three, or four cover the same course. Spectators get a front-row view of the start, and the race supports Friends of the Pool and local college scholarships.

Pennekamp Paddle Day: America's 250 Red, White and Blue Paddle Parade

On Saturday, September 12, from 11 a.m. to 4 p.m., John Pennekamp Coral Reef State Park in Key Largo hosts Pennekamp Paddle Day: America's 250 Red, White and Blue Paddle Parade, with free admission. The event features a Red, White and Blue paddle parade, along with glass-bottom boat experiences, live entertainment, food and other activities. Pennekamp sits at Mile Marker 102.5 in Key Largo and protects the only living coral reef in the continental United States.

Science Saturdays: Marine Ecology at REEF

On Saturday, September 12 at 11 a.m., head to REEF in Key Largo for Science Saturdays: Marine Ecology, focused on the remarkable marine ecosystems of the Florida Keys. It is a great fit for visitors interested in snorkeling, diving, and marine life.

Son del Mundo Hispanic Heritage Event

September 12-13 · Islamorada. Head to Islamorada for Son del Mundo, a weekend celebration of Hispanic heritage featuring culture, food, creativity and community. It is another option for visitors who want to experience more of the Keys beyond the water.

Boondocks Open-Air Market

On Saturday, September 12, from 9 a.m. to 2 p.m., the Boondocks Open-Air Market in the Lower Keys draws a crowd at Ramrod Key, Mile Marker 27.5. It is a good option for visitors staying in the Lower Keys.

When the paddling winds down, head back toward Islamorada for sandbar time. The Islamorada sandbar draws a friendly flotilla of boats, paddleboards, and swimmers. Then sunset picks a front row: Robbie's over Florida Bay, or Mallory Square in Key West.

Sunday, September 13

Islamorada Farmers Market

Sunday starts slow at the Islamorada Farmers Market, every Sunday from 10 a.m. to 3 p.m. at Mile Marker 81, where local growers bring fresh produce, tropical fruit, key lime products, honey, and handcrafts.

The rest of the Keys ride the same weekly rhythm. The San Pablo Church Market in Marathon opens Fridays, and the Key West market at Truman Waterfront runs Thursdays. Market hours and vendor lineups shift with the seasons, so confirm locally before you set out.

Turtle Hospital, Snorkeling, and Fishing in Marathon and Beyond

Head south to Marathon for a visit to the Turtle Hospital, the working sea turtle rescue center. Guided tours run daily, taking visitors through the rescue and rehabilitation areas. If you would rather stay on the water, Robbie's tarpon feeds and kayak rentals keep Sunday going without moving the car.

Fishing charters out of Key Largo, Islamorada, and Marathon are an excellent bet for tarpon on the flats or deeper ledges offshore, and snorkeling trips to the reef are in full swing. Weather conditions can change quickly in September, so check the latest marine and weather forecast before booking or heading out on the water.

For the sunset, settle in at Robbie's over Florida Bay or Mallory Square in Key West as the sky turns gold and pink.

Best Things to Do If You Don't Want to Attend an Event

If you are in the Keys for the water and the lifestyle rather than the event calendar, there is plenty to do this weekend without a ticket or registration.

• Snorkeling: the only living coral reef in the continental United States lies just offshore, and reef trips run daily from Key Largo, Islamorada, and Marathon.
• Fishing: tarpon on the flats and deeper ledges offshore are on the menu, whether you book a charter or head out on the water yourself.
• Kayaking and paddleboarding: calm bayside water and mangrove shorelines make rentals at places like Robbie's a relaxed way to spend an afternoon.
• Sandbars: the Islamorada sandbar draws a friendly flotilla of boats, paddleboards, and swimmers.
• State parks: John Pennekamp Coral Reef State Park protects the reef and offers glass-bottom boat experiences alongside its Saturday paddle parade.
• Wildlife: the Turtle Hospital in Marathon opens its working sea turtle rescue center with daily guided tours, and Robbie's tarpon feed brings the big fish right to the dock.
• Sunset: Robbie's over Florida Bay or Mallory Square in Key West are the classic front rows.

Travel Tips for This Weekend

September in the Florida Keys is still hot and humid, and the current forecast calls for a mix of clouds, showers and thunderstorms through the weekend. Weather conditions can change quickly in September, so check the latest marine and weather forecast before you head out, and confirm with your tour operator that your trip is running.

• Stay hydrated: with the heat and humidity, keep water with you through the day and reapply sunscreen often.
• Use reef-safe practices: wear reef-safe sunscreen and follow local rules at the reef and sanctuary areas.
• Book activities ahead: tours, charters, and rentals confirm schedules, so check status before you set out.
• Check the weather before boating: conditions can change quickly in September, so review the latest marine forecast before any trip on the water.
• Allow extra driving time: traffic through the Keys can slow you down more than you expect, especially on the Overseas Highway.

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