What To Do This Weekend in the Florida Keys | August 14-16

Things to do this weekend in the Florida Keys span a full spectrum of experiences, from the spirited Rum Fest Key West celebration running through Sunday to the athletic Key Largo Triathlon on Sunday morning. Mid-August brings classic Keys summer weather with warm Gulf Stream waters, calm mornings, and spectacular sunsets. Whether you are looking for a rum-fueled island adventure, a weekend of watersports, or a relaxed few days of sunset dining and farmers market browsing, this guide covers the best events and activities across the island chain from Key Largo to Key West.

The regular spiny lobster season continues through March 2027, so fresh local lobster is on menus all over the Keys. For a complete overview of the area, our Islamorada community guide and Key Largo community guide cover the neighborhoods, dining, and attractions in the Upper Keys. For real-time event updates, the Florida Keys tourism events calendar is the most reliable source.

Rum Fest Key West: The Weekend's Signature Event

Rum Fest Key West is running August 12 through 16, making this the final weekend of the multi-day festival celebrating Caribbean rum culture. The Grand Tasting Event takes place Sunday, August 16 from 3:30 to 5:30 PM at the Key West Theater, featuring premium rum samples from distilleries around the world. The festival also includes a Rum Cake Competition, Ti Punch Brunch, and an optional Day Trip to Cuba.

On Friday, August 14, the Key West Theater hosts Cliff Cody and Sharese in concert from 8:00 to 10:00 PM (doors at 7:00 PM). Saturday, August 15 brings Jesse Rice to the same stage. Throughout the weekend, Rum Fest events spread across Key West's bars and restaurants, with rum-paired dinners, cocktail workshops, and tasting sessions. For the full schedule, check the Rum Fest Key West official website.

Friday, August 14

Morning: On the Water

Friday morning is an excellent time for a snorkeling trip before the weekend crowds arrive. John Pennekamp Coral Reef State Park at Mile Marker 102.5 in Key Largo runs multiple daily snorkel tours to the living coral reef formations. The Molasses Reef and Grecian Rocks sites are particularly vibrant in August when water clarity is at its peak. For a full guide to the best dive and snorkel sites, see our diving and snorkeling guide.

In Islamorada, the patch reefs off Upper Matecumbe Key and Lower Matecumbe Key offer excellent snorkeling conditions with water temperatures in the mid-80s. Several local operators run half-day trips that combine snorkeling with a stop at a sandbar or a visit to Indian Key Historic State Park. For more on the area, explore our Islamorada community guide.

For anglers, August fishing is productive across the Keys. The flats hold bonefish and permit on the early morning tides, while the reef produces yellowtail snapper, mutton snapper, and grouper. Offshore, dolphin (mahi-mahi) and blackfin tuna are active. Our complete guide to fishing in the Florida Keys has details on the best charters, species, and seasonal patterns.

Afternoon: Arts, Culture, and Rum Fest Kickoff

Friday afternoon in Key West, Rum Fest activities are in full swing. The Key West Theater hosts "The Art and Impact of Archival Research with Monica Berra (PEAR)" from 1:00 to 2:30 PM, a lecture-style workshop for those interested in creative inspiration from historical archives. Later, Rum Fest tastings and cocktail events are taking place at venues throughout Old Town.

In Islamorada, the Morada Way Arts District remains a relaxed Friday afternoon destination. Galleries, boutiques, and the Florida Keys Brewing Company tap room are all within walking distance. The Craft Beer Tasting Room at Florida Keys Brewing Company offers a rotating selection of island-inspired craft beers in a dog-friendly outdoor setting.

In Key Largo, the Florida Keys History and Discovery Center at the Islander Resort features exhibits on Keys maritime history, shipwrecks, and the natural environment. It is open Friday afternoon and offers a cool, air-conditioned break from the August sun.

Evening: Sunset Dining and Live Music

Friday night in the Upper Keys means waterfront sunset dining. Marker 88 at Mile Marker 88 in Islamorada offers one of the most iconic sunset views in the Keys, with an outdoor deck facing west over Florida Bay. Lazy Days Restaurant at the marina is another excellent choice, serving fresh seafood in a casual, open-air setting. Both restaurants fill up quickly on summer weekends, so reservations are recommended.

In Key Largo, Snook's Bayside Restaurant and Grand Marina at Mile Marker 100 serves fresh seafood on a dockside deck with live music on Friday evenings. The Caribbean Club at Mile Marker 104 is a classic Keys watering hole with a storied history and a lively atmosphere on weekend nights.

In Key West, the Cliff Cody and Sharese concert at Key West Theater runs from 8:00 to 10:00 PM, followed by rum-themed events at Duval Street bars and clubs. The Rum Fest after-parties continue late into the night at several venues throughout Old Town.

Saturday, August 15

Morning: Boondocks Open-Air Market and Beach Time

Saturday morning starts with the Boondocks Open-Air Market at Mile Marker 27.5, running from 9:00 AM to 2:00 PM. This market features local artisans, handmade crafts, tropical plants, and Keys-made products. It is worth the drive if you are staying in the Upper or Middle Keys, offering a unique shopping experience with island character.

For beach time, Anne's Beach on Lower Matecumbe Key at Mile Marker 73.5 in Islamorada is a local favorite. The shallow, calm water and scenic boardwalk make it a pleasant morning destination. Sombrero Beach in Marathon offers natural white sand, clear water, and a playground, with restroom facilities and ample parking. August sun is intense by mid-morning, so arrive early and bring plenty of water, sunscreen, and a sun hat.

For those looking to paddle, the mangrove trails at Curry Hammock State Park near Marathon offer excellent kayaking conditions. The calm waters of Florida Bay side provide a peaceful paddling experience through the mangrove tunnels, with opportunities to spot wading birds, rays, and small sea turtles. Kayak rentals are available at the park.

Afternoon: Live Music and Rum Fest Saturday

Saturday afternoon in Islamorada features live music and community energy. Sippin' Fire kicks off at 1:00 PM at a venue in the Islamorada area. Later, LatchkeyKidsMusicFL performs at Sandbar starting at 8:00 PM. The main Saturday music event is Brothers of Others at Lorelei Restaurant and Cabana Bar at 6:00 PM, with free entry and one of the best sunset views in Islamorada. Lorelei's at Mile Marker 82 is an institution, with its iconic mermaid statue, tiki bar, and waterfront deck.

In Key West, the Jesse Rice concert at Key West Theater on Saturday evening adds to the Rum Fest entertainment lineup. The Rum Fest village and tasting events continue throughout the day and into the evening, with rum samples, food pairings, and live music at multiple venues.

Evening: Sunset and Nightlife

Saturday night offers multiple entertainment options across the Keys. In Islamorada, the Brothers of Others set at Lorelei starts at 6:00 PM and continues through the evening. The Florida Keys Brewing Company in the Morada Way Arts District is a relaxed option for Saturday night, with craft beer, live music, and a welcoming outdoor space. Burdines Waterfront at Mile Marker 49.5 in Marathon serves dinner with sunset views over Boot Key Harbor, with live music on weekend evenings.

In Key West, the Rum Fest evening events are the highlight of Saturday night. The Grand Tasting preparations are underway for Sunday, but Saturday features the largest party crowds, with Duval Street bars hosting Rum Fest specials and events throughout the evening.

For a more subdued evening, a sunset sail from Key West or Marathon offers a tranquil end to the day. Several operators run sunset cruises with drinks and light snacks, providing an unforgettable view of the sun sinking into the Gulf of Mexico.

Sunday, August 16

Morning: Key Largo Triathlon and Islamorada Farmers Market

Sunday's headliner event is the Game On! Key Largo Triathlon Summer at John Pennekamp Coral Reef State Park. The event features Olympic distance (1.5K swim, 40K bike, 10K run) and Sprint distance (750m swim, 20K bike, 5K run) categories, plus duathlon and aquabike options. The swim takes place in the protected waters of Pennekamp Park, the bike course follows the scenic Overseas Highway, and the run winds through tropical landscapes. This is a well-organized event that draws athletes from across Florida.

For a more relaxed Sunday morning, the Florida Keys Farmers Market in Islamorada at 81001 Overseas Highway runs from 10:00 AM to 3:00 PM. This Sunday market is a highlight of the Keys social calendar, featuring 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, tropical fruits, and island-made gifts. The market is dog-friendly and has a genuine community feel.

Another Sunday morning option is a visit to Founders Park in Islamorada, which has a one-acre fenced dog park, sports fields, and a community pool. The park is open to the public and offers a cool, shaded area for a relaxing morning.

Midday: Rum Fest Grand Tasting Event

The centerpiece of Rum Fest takes place Sunday from 3:30 to 5:30 PM at the Key West Theater. The Grand Tasting Event features premium rum samples from distilleries around the world, with mixologists, brand representatives, and rum enthusiasts all in one place. This is the flagship event of the five-day festival and draws the largest crowd. Tickets are available through the Rum Fest website.

For those not attending the Grand Tasting, Sunday midday is a great time for a final Keys adventure. Snorkeling at Sombrero Reef in Marathon, kayaking through the mangroves in Key Largo, or a leisurely lunch at one of the Keys' many waterfront restaurants are all excellent options.

Evening: Final Sunset of the Weekend

Sunday evening calls for one last sunset experience. In Islamorada, the Lorelei Restaurant and Cabana Bar is a perfect spot for a farewell dinner and sunset toast. Marker 88 also offers a memorable sunset dining experience. For those heading north, Snook's Bayside in Key Largo is a convenient last stop before crossing back to the mainland.

A word on traffic: Sunday afternoon and evening northbound traffic on the Overseas Highway (US-1) builds significantly as weekend visitors return to the mainland. If you are driving north from Key West or Marathon, plan to leave by early afternoon or wait until after 7:00 PM to avoid the heaviest congestion. US-1 is the only road in and out of the Keys, and summer weekend traffic can add an hour or more to the return drive.

Ongoing Summer Activities

Beyond the weekend-specific events, mid-August in the Keys offers a full menu of ongoing activities. Snorkeling and diving remain excellent, with warm water and calm conditions. The regular spiny lobster season is open through March 2027, so fresh local lobster is on menus across the island chain. Popular seafood restaurants include Marker 88 and Lazy Days in Islamorada, Snook's Bayside in Key Largo, and Burdines Waterfront in Marathon.

The summer heat and humidity are at their peak in August, with temperatures in the upper 80s to low 90s. Pack water, sunscreen, a wide-brimmed hat, and mosquito repellent for evening activities near the mangroves. Afternoon thunderstorms are common, so plan outdoor activities for the morning and early afternoon hours. Check the National Weather Service Miami forecast before heading out.

For a deeper look at each Keys community, check out our guides to Islamorada, Key Largo, Tavernier, and Marathon. Each guide covers the neighborhoods, dining, and lifestyle that make these communities unique. And if a weekend in the Keys makes you consider 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.