What To Do This Weekend in the Florida Keys | July 24-26

Things to do this weekend in the Florida Keys are shaped by one of the biggest annual celebrations in the Lower Keys: the 45th annual Hemingway Days festival in Key West, running July 22-26. But even if you are staying in the Upper and Middle Keys, this weekend delivers classic summer Keys experiences from world-class snorkeling and flats fishing to waterfront sunset dining and relaxed island exploration. Late July brings warm water temperatures in the mid-80s, calm morning seas, and long daylight hours perfect for outdoor activities. For the latest event listings, the Florida Keys tourism events calendar is a reliable source for up-to-date details.

Friday, July 24

Morning: Get on the Water Early

Friday morning is the best time to beat the weekend crowds. John Pennekamp Coral Reef State Park at Mile Marker 102.5 in Key Largo opens early, and the morning snorkel tours depart before the water gets busy. The coral reef formations are at their clearest in the morning light, and you can expect to see tropical fish, rays, and sea turtles. The park also rents kayaks and paddleboards for exploring the mangrove trails through Blackwater Sound.

In Islamorada, flats fishing guides launch from Robbie's Marina at Mile Marker 77.5. The backcountry on the Gulf side of Upper Matecumbe Key and Lower Matecumbe Key holds bonefish, permit, and tarpon during July. If you prefer to stay dry, the tarpon feeding at Robbie's dock is a free attraction that draws a crowd every morning. For more on what this area offers, see our Islamorada community guide.

Afternoon: Hemingway Days Begins in Key West

While Key West is a two-hour drive from Islamorada, the Hemingway Days festivities make this weekend worth the trip for many visitors. Friday afternoon events include the Hemingway 5K Sunset Run and Paddleboard Race, the Caribbean Street Fair on Duval Street benefiting Literacy Volunteers of America, and the Running of the Bulls parade with wooden bulls and costumed participants. The Key West Marlin Tournament continues through Sunday with more than $50,000 in prizes.

If you are staying in the Upper Keys, the Friday afternoon is a good time to explore the Morada Way Arts District in Islamorada. Galleries, boutiques, and the Florida Keys Brewing Company tap room are within walking distance of each other. The Islamorada Marketplace on 90, located along the Overseas Highway, hosts local vendors on Friday afternoons with artisan goods, tropical plants, and Keys-made products.

Evening: Sunset and Seafood

Friday night calls for waterfront dining at sunset. In Islamorada, Marker 88 on the bayside offers one of the best sunset views in the Keys, with an outdoor deck facing west over Florida Bay. Lazy Days Restaurant at the Marina is another strong choice with a more casual atmosphere and canal views. Both restaurants draw crowds on summer weekends, so reservations are recommended.

In Key Largo, Snook's Bayside Restaurant and Grand Marina at Mile Marker 100 offers dockside sunset dining. In Key West, the Papa's Pilar Cocktail Classic is a Friday evening highlight of Hemingway Days, with craft cocktails and live music. Check the official Hemingway Days schedule for exact times and locations of Friday evening events.

Saturday, July 25

Morning: Beach Time and Snorkeling

Saturday morning is prime beach time. Anne's Beach on Lower Matecumbe Key at Mile Marker 73.5 in Islamorada is a local favorite with shallow, calm water and a scenic boardwalk. Get there early to secure a spot under the shaded picnic tables. The July sun is intense by mid-morning, so bring plenty of water, sunscreen, and a wide-brimmed hat.

In Marathon, Sombrero Beach offers natural white sand, clear water, and a playground, making it one of the best swimming beaches in the Middle Keys. The water temperature is comfortable for swimming through the afternoon. For more on Marathon's beaches and neighborhoods, our Marathon community guide covers the area in detail.

For snorkeling, John Pennekamp Coral Reef State Park remains the premier choice in the Upper Keys. The Christ of the Abyss statue underwater is a popular destination for snorkel and dive tours. The park's coral reef formations are home to an abundance of tropical marine life, and water clarity in late July is typically excellent.

Afternoon: On the Water or On the Town

Saturday afternoon offers a range of options. Paddleboarding through the mangrove tunnels at Curry Hammock State Park near Marathon is a peaceful way to spend a hot afternoon. In Islamorada, the Morada Way Arts District is worth an afternoon of gallery hopping and boutique shopping. The Florida Keys Brewing Company tap room is a popular stop for a cold craft beer in a dog-friendly outdoor setting.

For anglers, afternoon reef fishing for yellowtail snapper and mangrove snapper is productive throughout July. Charter boats offer half-day trips that return in time for dinner. If you are traveling with dogs, Rowell's Waterfront Park in Key Largo has a designated dog swimming area at the end of County Road 905. For a full list of pet-friendly spots, check out our guide to dog-friendly beaches and parks in the Keys.

Evening: The Main Event in Key West

Saturday night is the highlight of Hemingway Days. The final round of Sloppy Joe's 45th Annual Hemingway Look-Alike Contest begins at 6:30 PM, where the winner is crowned "Papa 2026." This event draws national attention and fills Sloppy Joe's on Duval Street to capacity. If you are attending, arrive early.

For those staying in the Upper and Middle Keys, the Sunset Grille and Raw Bar at the Faro Blanco Resort in Marathon offers live music on weekend evenings, with a pool, tiki bar, and waterfront deck. In Islamorada, the Florida Keys Brewing Company tap room is a relaxed spot for a Saturday night out, within walking distance of several restaurants.

Sunday, July 26

Morning: Papa Birthday Bash and Brunch

Sunday morning in Key West kicks off with the Papa Birthday Bash from 9:00 AM to 1:00 PM, celebrating what would have been Ernest Hemingway's 127th birthday. The Key West Marlin Tournament concludes Sunday with the awards ceremony. These events mark the final day of Hemingway Days, and crowds are lighter in the morning than on Saturday.

In the Upper Keys, Sunday is a slower pace. Grab coffee and walk the waterfront in Key Largo, or enjoy brunch at the Key Largo Conch House with its outdoor garden setting. In Islamorada, the Morada Way area is quiet on Sunday mornings, making it a good time for a relaxed walk through the galleries before they open.

Midday: One Last Adventure

Use Sunday morning for one more Keys adventure. Kayaking the mangroves in Key Largo, fishing the flats in Islamorada, or visiting the Dolphin Research Center at Mile Marker 59 in Marathon are all solid options. The Dolphin Research Center offers dolphin encounters and educational programs that work well for visitors of all ages.

If you are looking for a relaxed end to the weekend, Anne's Beach in Islamorada or Founders Park for a quiet afternoon by the water are excellent choices. Founders Park also has a one-acre fenced dog park with agility equipment, making it a good option for travelers with dogs who need a run before the drive home.

Planning Your Weekend

Late July in the Keys means temperatures in the upper 80s to low 90s with high humidity. Pack water, sunscreen, a wide-brimmed hat, and mosquito repellent for evening activities near the mangroves. Check the National Weather Service Miami forecast before heading out, especially for afternoon thunderstorm potential.

Sunday afternoon traffic on the Overseas Highway (US-1) builds as weekend visitors head back to the mainland. If you are driving north from Key West after Hemingway Days, plan to leave by early afternoon or wait until after 6 PM to avoid the heaviest traffic. US-1 is the only road in and out of the Keys, and summer weekend traffic can add significant time to the drive.

For a deeper look at what each Keys community offers, check out our guides to Islamorada, Key Largo, Tavernier, and Marathon. Each one covers the neighborhoods, restaurants, and lifestyle that make these communities unique. And if a weekend in the Keys makes you think about a permanent move, I would love to help. As a local agent with over 30 years of experience, I know every waterfront, every neighborhood, and every opportunity in the island chain. Check out our buying guide to get started, or reach out to me directly.