What To Do This Weekend in the Florida Keys | August 7-9

Things to do this weekend in the Florida Keys are shaped by the biggest seafood celebration of the summer: the 28th annual Key West Lobsterfest, running August 5-9, 2026, which coincides with the opening of the regular spiny lobster season on Thursday August 6. This weekend marks the first full weekend of open-water lobster diving, and the Keys are buzzing with activity from Key Largo to Key West. For the latest event listings, the Florida Keys tourism events calendar is a reliable source for up-to-date details.

Key West Lobsterfest 2026: The Weekend's Headliner

The 28th annual Key West Lobsterfest spans five days from Wednesday August 5 through Sunday August 9, with the biggest celebrations happening Friday through Sunday. This festival marks the official start of the regular spiny lobster season (which opened August 6) and features a Lobster Boil on Duval Street, a massive street fair with live music, local vendors, and island-wide parties throughout Key West. The regular season runs through March 31, 2027, so this weekend is the first chance for divers and snorkelers to head offshore and target lobsters on the reef.

For visitors who choose to stay in the Upper and Middle Keys, the regular season opening means excellent lobster diving opportunities closer to home. The patch reefs off Islamorada and Marathon hold healthy lobster populations, and local dive shops and charter operators are running full schedules this weekend. For everything you need to know about rules, bag limits, and licensing, check out our complete guide to Florida Keys Lobster Season 2026.

Friday, August 7

Morning: First Full Day of Regular Season Lobster Diving

Friday morning is the first full day of the regular spiny lobster season, and the reefs are ready. John Pennekamp Coral Reef State Park at Mile Marker 102.5 in Key Largo opens early, and snorkel tours are running full schedules to the coral reef formations. For the best reef sites and dive operators, check out our diving and snorkeling guide. The morning light provides the clearest water conditions for spotting lobsters among the coral heads. The park also rents kayaks and paddleboards for exploring the mangrove trails through Blackwater Sound.

In Islamorada, several dive operators are running trips to the patch reefs off Upper Matecumbe Key and Lower Matecumbe Key. The reef formations in the Islamorada Sanctuary Preservation Area hold spiny lobster during the summer months, and water temperatures in the mid-80s make for comfortable diving without a wetsuit. For more on what this area offers, see our Islamorada community guide.

Afternoon: Key West Lobsterfest and Duval Street Fair

The Key West Lobsterfest street fair kicks into high gear on Friday afternoon along Duval Street and at Truman Waterfront Park. The five-day celebration features live music, local artisans, seafood vendors, and of course plenty of fresh Key West lobster prepared in every style imaginable. The Lobster Boil is a highlight, with massive pots of spiny lobster, corn on the cob, and red potatoes served family-style.

If you are staying in the Upper Keys, Friday afternoon is a great 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 Open Air Market at Boondocks (Mile Marker 27.5) on Saturday from 9:00 AM to 2:00 PM features local vendors and island creativity, worth the drive for a unique shopping experience.

Evening: Sunset and Fresh Catch Dining

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 Lobsterfest continues into the evening with live music and street performances. The Summer Studio Series at the Tennessee Williams Theatre on Friday night features their Performance & Dance Social #5 starting at 7:30 PM, an engaging evening of live performance art.

Saturday, August 8

Morning: Beach Time and Open Air Market

Saturday morning is prime time for a beach visit before the day heats up. 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 August 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.

The Open Air Market at Boondocks (Mile Marker 27.5) runs Saturday from 9:00 AM to 2:00 PM. This market features local artisans, handmade crafts, tropical plants, and Keys-made products. It is a great stop on the way to or from Key West Lobsterfest.

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 lobster divers, Saturday afternoon is prime time for a second day on the water. The patch reefs off Marathon and Big Pine Key are productive lobster grounds, and the calm summer seas make for excellent conditions. If you are staying in the Middle Keys, check with local dive shops in Marathon for guided trips and equipment rentals. For a full list of pet-friendly spots in the area, check out our guide to dog-friendly beaches and parks in the Keys.

Evening: Lobsterfest Main Event and Live Music

Saturday night is the peak of Key West Lobsterfest, with the biggest crowds, the best live music, and the most elaborate seafood offerings. The Duval Street Fair continues through the evening with street performers, artists, and vendors. The Lobster Boil runs all day and into the night, and several Duval Street bars are hosting special events and live bands.

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. For a truly special evening, Burdines Waterfront at Mile Marker 49.5 in Marathon serves fresh seafood, cold drinks, and sunset views over Boot Key Harbor.

Sunday, August 9

Morning: Florida Keys Farmers Market

Sunday morning in the Upper Keys calls for a visit to the Florida Keys Farmers Market in Islamorada at 81001 Overseas Highway, running from 10:00 AM to 3:00 PM. This market features fresh local produce, artisan goods, tropical plants, handmade crafts, and live music. It is the perfect place to pick up fresh Key lime products, local honey, and tropical fruits to take home.

In Key West, Sunday is the final day of Lobsterfest. The street fair and Lobster Boil continue through the afternoon, making it a great last chance to enjoy the festival's offerings. The Summer Studio Series presents its final Performance & Dance Social #5 on Sunday evening at the Tennessee Williams Theatre at 7:30 PM.

Midday: Last Chance for Lobster Diving

Use Sunday morning for one more Keys adventure. Kayaking the mangroves in Key Largo, fishing the flats in Islamorada, or heading offshore for lobster diving are all solid options. The regular spiny lobster season runs through March 31, 2027, so this weekend is just the beginning of the eight-month season.

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.

Fresh Catch: Where to Buy and Dine on Lobster This Weekend

With the regular season opening, fresh spiny lobster is available at seafood markets and restaurants throughout the Keys. Here are the top spots:

• Robbie's of Islamorada (MM 77.5): Will prepare your fresh catch. Known for their dock-side tarpon feeding and casual atmosphere.
• Islamorada Fish Company (MM 81.5): Fresh seafood market and restaurant with outdoor seating overlooking Florida Bay.
• Key Largo Conch House (MM 100): Garden setting with fresh local seafood including spiny lobster.
• Burdines Waterfront (MM 49.5, Marathon): Tiki bar and grill with live music on weekends.
• Key West Lobsterfest (Duval Street, Key West): The Lobster Boil runs throughout the weekend with fresh spiny lobster served family-style.

Planning Your Weekend

Early August 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 which is common during August.

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 Lobsterfest, 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.