The Best Things To Do in the Florida Keys By Month

Indian Key Historic State Park

The Florida Keys are a year-round destination with many celebrated events, attracting tourists essentially every month of the year.

Of course, wonderful warm weather drives plenty of visitors during the winter months, but folks still brave the heat and humidity in the summertime for the escapism and the events this destination offers.

The best time to visit the Florida Keys and deciding which Florida Key to visit really depends on the experience you desire. To help, we outlined a few main attractions and events divided across the three main seasons. So now, let’s review and discover the best time to visit the Florida Keys.

Visit in the Winter Months (December – March)

The winter months remain the most popular in the Florida Keys with good reason — the best weather is here. Warm tropical breezes provide and an often needed escape from the northern winters. Plus, festivals nearly every weekend delight visitors.

From massive nautical markets to food and wine events and even the classic Duval Street bar crawls, there is always something to do in the Florida Keys. Of course, all of this comes with a price too, as the popular places to stay in the Florida Keys charge their high season rates during the winter. But for those still considering the high season and its beautiful weather, here are a few highlights.

Key Largo Boat Parade

After the Thanksgiving turkey slumber fades, the holiday season kicks into high gear in the Florida Keys with the annual themed Key Largo Boat Parade.

In early December, a local tree lighting occurs and the Florida Bay is filled with decorated boats. Spectators watch the parade from the shore and a committee awards a winner while everyone gets into the spirit of the season.

New Year’s Eve in Key West

Key West remains a popular destination for New Year’s Eve. TV networks often report live at the dropping of a drag queen celebrity in a high heel shoe on Duval Street, but that is just one of the events in this island party town. A big conch shell gets lowered from atop Sloppy Joe’s Bar, a key lime wedge is lowered onto Sunset Pier, and also the historic seaport lowers a pirate from the mast of a schooner. There’s no doubt that Key West starts the New Year off in style.

BayGrass Bluegrass Festival

baygrass bluegrass festival florida keys

Every winter, Bluegrass comes to Islamorada and this American music form is celebrated with a multi-day concert series that brings the blues to the bay. Located in Founder’s Park, this event is one of the more popular concerts to appear in the Florida Keys and is held annually in January.

Marathon Seafood Festival

Most visitors can’t wait to dive into the fresh local seafood delicacies the Florida Keys offers. One place to try everything imaginable including fresh Florida lobster and coveted stone crabs (both in season) along with the local catch, shrimp, conch, and Cuban croquettes is the Marathon Seafood Festival.

This family-friendly event in March provides live entertainment and access to over 200+ vendors to satisfy all your shopping needs. Patrons can also expect a boat show, rides and games for children, and a military service tribute.

READ MORE: 7 Florida Keys Beaches to Visit

Visit in the Spring (April – June)

When the weather starts to heat up in the Florida Keys and the deep crowds recede as the snowbirds start to migrate back north, many turn to the open waters for fishing tournaments. Fishing occurs all year round between the Gulf of Mexico, the Florida Bay, and the Atlantic Ocean, but the weather starts to steadily cooperate once spring arrives. Listed below are a few popular tournaments for multiple fish and more spring events.

Nick Sheahan Dolphin Rodeo

Nick Sheahan Dolphin Rodeo

Normally at the end of April, a fishing tournament to honor a local teenager who lost his life because of a shallow water blackout provides a way for the community to gather and also educate the public on the dangers of freediving. All the fishing proceeds from the Nick Sheahan Dolphin Rodeo provide scholarships to local high school seniors.

REEF Lionfish Series Derby

The slogan still remains, “eat them to beat them” in many circles as local conservationists aim to protect the local coral reefs by sponsoring a fishing derby to remove the invasive and harmful Lionfish. Sponsored by REEF (Reef Environmental Education Foundation) this annual Earth Day derby contest is for both experienced and novice spearfishing anglers.

The 7 Mile Bridge Run

It’s not all fishing during the spring — many running, biking, and swimming outdoor events occur in the Florida Keys too. The most popular? The 7-mile bridge run held every April. The limited capacity event (since it closes down the sole roadway in the Florida Keys), fills up quickly and provides a thrill for everyone who makes the run across the water on this 6.8-mile bridge. Begun in 1982 to commemorate the creation of the bridge, runners have just 90 minutes to complete the run.

READ MORE: Which Florida Key Should I Visit?

Visit in Hurricane Season (June to November)

Summer and fall are just one season in the Florida Keys, and it’s called Hurricane Season. From June to November, everyone watches the weather channel to make sure no storms head through these small flat islands. This hurricane threat lowers hotel prices, as does the heat, humidity, and mosquitoes. Yet plenty of visitors still make the journey to perhaps some of the best events of the year.

Hemingway Week

With Ernest Hemingway’s birthday on July 21st, an entire week of celebrations and events are planned in Key West — from a Running with the Bulls (the Bulls are made of wood) and a fishing tournament to a 5k race and paddle and the famed lookalike contest held one of his favorite watering holes, Sloppy Joe’s, there’s plenty going on. The week was designed to celebrate the bold adventurous life of everyone’s favorite Pulitzer-prized Papa.

Lucerne Memorial Backcountry Fishing Championship

Created in honor of one of Everglades National Park’s most respected backcountry anglers and “Mr. Everglades,” himself, Herman Lucerne, the goal of this tournament is to bring like-minded anglers together to raise funds and awareness to the many issues facing Florida Bay today. The 2021 dates are for September 17 to 19.

Annual Swim for Alligator Light

alligator lighthouse swim

For those wanting to go the extra mile and get in the water, the annual eight-mile swim to Alligator Lighthouse provides a challenging open water swim in Islamorada every September. With the website dictating, “Not for the faint of heart,” this swimming race was created by local artist Light House Larry. From the first event in 2013 it ballooned from a local south Florida friendly gathering to a world-class competition attracting top open water swimmers from around the globe. The limited spots sell out quickly, and swimmers can sign up solo or in groups of two, three, or four.

Fantasy Fest

Leading up to Halloween every year, Key West created a 10-day party for grown-ups during hurricane season in 1979 to attract visitors in the once quiet season. It was a success.

Fantasy Fest has grown every year since its inception, and is now one of the wildest island parties not only in the Florida Keys, but in the entire world. Fun-loving folks of all adult ages come from around the globe bring their creativity, imagination, and the desire to have a good time to Key West. The calendar is complete with countless parades, themed parties and events, libations, art, and events where truly anything goes.

Key West Songwriters Festival

The Key West Songwriters Festival remains one of the largest festivals of its kind in the world. For five days and nights, live music covers Key West as the songwriters introduce crowds to the faces, stories, and voices behind the songs we’ve come to love and know by heart.

For some travelers, anytime is the best time to visit the Florida Keys since the calendar is packed all year round with events.

For others, the weather is the deciding factor. But regardless of when you decide to vacation in the Florida Keys, events like the 12 listed here will help ensure that you make the very best of it.

READ NEXT: The 9 Most Popular Restaurants in Islamorada, Florida

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