Upper Keys, Florida Upcoming Events

Team Walters July 20, 2022

Upper Keys, Florida Upcoming Events

The Upper Keys is the first stop on your journey through Florida's tropical and charming chain of islands. An outdoor and water lover's paradise, it’s surrounded by the glittering crystal waters of Florida Bay, the Florida Straits, the Atlantic Ocean, and the only living coral reef system in the United States.

The Upper Keys include Tavernier, Islamorada, Marathon, and Key Largo, the latter of which is the longest of the islands in the Florida Keys.

Are you looking for something to do in the Upper Keys? Whether you're a local, new in town, or just cruising through, the following are some of the Upper Keys’ best, most colorful, and most unique upcoming events.

33rd Annual Hemingway 5k Sunset Run and Paddle

Photo courtesy of Hemingway 5k Sunset Run and Paddleboard Race

Prove your stamina—on foot and on your paddleboard—during the Hemingway 5k Sunset Run and Paddleboard Race on Saturday, July 23 as part of Key West’s annual Hemingway festivities. Celebrating the life of author Ernest Hemingway, who lived in Key West during the 1930s, this nationally acclaimed, two-sport race sees hundreds of racers compete on both land and sea.

The paddleboard race will begin at 5:30 PM beside the Southernmost Beach Café, where racers will paddle a 3-mile ocean course before finishing back at the beach. At 7:30 PM, runners and walkers will set off from the southernmost point of the continental United States (located at the corner of Whitehead and South), traversing a 3.1-mile course that will take them through the picturesque beauty of Old Town Key West and the Ernest Hemingway Home & Museum itself.

The fun doesn’t stop once the two races are over! Attend the pre-race brunch the morning before, take part in post-race recovery yoga (presented by Salute to the Sol) on Sunday morning, and celebrate at the Sunday afternoon Hemingway Rum Bar Stroll. Register online for either or both races. There are even virtual participation options available for those who aren’t in Key West or prefer to compete on their own.

38th Annual Underwater Music Festival

Photo courtesy of The Florida Keys & Key West

Have you ever thought of attending an underwater party? If yes, your dream has come true at the Florida Keys' Underwater Music Festival. This quirky celebration is held annually on Saturday after July 4th. The concert is held at Looe Key Reef, part of the world's third-largest and North America's only living coral reef. Bill Becker founded the festival for public entertainment and raised awareness for coral reef preservation.

Hosted by the Lower Keys Chamber of Commerce and a local radio station, US1 104.1 FM, the ocean celebration encourages environmentally responsible diving and the preservation of the world's coral reefs. The festival's primary purpose is to promote reef protection and eco-conscious diving, and offer a bucket list underwater experience.

The music program consists of pre-selected radio playlists. Ocean-themed songs are streamed through waterproof speakers hung from boats floating above the reef. The experience is unique as sound travels 4.3 times faster in water than in the air. Several hundreds of divers and snorkelers come to enjoy such an ethereal experience where you can listen to music with your entire body, not just with your ears.

Lobster mini-season

Photo courtesy of The Florida Keys & Key West

Did you know that the Florida Keys has not one, but two lobster seasons? The longest season—dubbed the regular season—will run from August 6, 2022, to March 31, 2023, while the two-day-long “mini-season” runs from the last Wednesday of July to just after midnight the following Thursday. Thousands of Florida Keys visitors and locals go diving for spiny lobsters each year during the mini-season. Whether it’s your first time diving for these spiny crustaceans or an annual tradition, it’s essential to follow the rules and regulations set out by the Florida Fish and Wildlife Conservation Commission to make sure you have a fun and safe sporting season while helping to maintain the Key’s marine ecosystem.

Make sure any lobster you catch has a carapace (the hard part of the shell) that measures greater than three inches, stay within 300 feet (or 100 feet if you’re in a channel) of your dive flag, and catch no more than six lobsters per person per day. Avoid taking or touching any lobsters in traps (recreational trapping is prohibited in Monroe County), and ensure your recreational saltwater fishing license and lobster permits are up to date.

Follow these rules, practice safe boating procedures, and you’ll be ready to make the most of this short—yet exciting!—lobster season.


Calling all ocean lovers! REEF Fest is an annual celebration of marine conversation hosted by Reef Environmental Education Foundation that features a bevy of diving, snorkeling, kayak tours, ocean-themed seminars, social events, and so much more! Held each year in October since 2015, REEF Fest welcomes divers, snorkelers, and ocean enthusiasts alike for a weekend of sun, surf, and sea along the Florida Keys.

All are invited to REEF Fest, and most events are free, although pre-registration is required. From nature tours at John Pennekamp Coral Reef State Park to silent auctions, book signings, and a For the Love of the Sea celebration overlooking the Florida Bay, make sure you clear your calendar for October 13-16 this year—you won’t want to miss a day of festivities! 

Morada Way Art Walk

Photo courtesy of Morada Way Arts & Cultural District

Organized by the Morada Way Arts & Cultural District and held on the third Thursday of each month, the Morada Way Art Walk is the place to be for all things arts and culture in the Florida Keys. Each month, artisans, craftspeople, musicians, visitors, and locals meet on Morada Way in beautiful Islamorada for late-night gallery openings, vendors teeming with local, Keys-inspired crafts and artworks, live music, and delicious food and drink.

While the Art Walk primarily features fine artworks such as sculpture, ceramics, paintings, printmaking, and photography, they are always looking for emerging and established artists, musicians, and other creatives to join them each month! Find more vendor information here, but also check out all of the great fares on display—you may just find your new favorite artwork, piece of jewelry, or local band!

Florida Keys fishing tournaments

Fishing is a huge part of the makeup of the Florida Keys—after all, where else can you fish in such gorgeous, deep blue waters under clear, cloudless skies? It makes sense, then, that monthly fishing tournaments are a long-standing tradition that gives visitors and locals a chance to participate in some friendly competition to see who can snag the biggest saltwater catch of the day.

Take part in the currently ongoing Key West Fishing Tournament (it runs from January to the end of July each year), where anglers catch and release more than 40 species of fish, or sign up for the Stock Island Marina Village Key West Marlin Tournament, which runs from July 20-23 during Key West’s annual Hemingway Days. This exciting event sees marlin fighters vie for $50,000 in cash prizes (or $25,000 if you’re in a team) by catching the biggest marlin around.

You and the whole family can try your hands at catching dolphin fish during the inaugural Caloosa Cove Dolphin Tournament in Islamorada. This family-friendly angling challenge is for a good cause, too—the event is being held to raise funds for the Alligator Lighthouse Restoration Project spearheaded by Save Alligator Lighthouse. This aging beacon stands approximately four miles off the coast of Islamorada, and funding efforts—such as this dolphin fish tournament—are being held to restore, preserve, and maintain it.

Whatever kind of fish—or fishing!—you’re drawn to, you’re sure to find a fishing tournament that’ll bring the thrills, the catches, and the camaraderie.

Are you looking for a luxury property in the Upper Keys?

Are you looking for a property in the Upper Keys? Whether you're a local or new in town, Team Walters has a complete inventory of incredible properties to show you. Please don’t hesitate to contact us today, and let's find you a property that's perfect for you.

Work With Us

The Walters Luxury Group in Florida shares the dedication and commitment required to deliver exceptional service with the world's most discerning sellers and buyers. Their local expertise, combined with Sotheby's one-of-a-kind relationships in most influential media outlets worldwide, artfully connects people with extraordinary homes for sale in the Florida Keys and beyond.