Composed of hundreds of islands (or keys) that stretch nearly 200 square miles, the Florida Keys is ripe for exploration. But when should you make your tropical journey happen?

Compared to other corners of the United States, the Florida Keys has consistently warm temperatures, with highs rarely dropping below 70 degrees Fahrenheit. While the pleasantness of its climate and the vibrancy of its residents are constants, factors – spanning quirky cultural attractions to the likelihood of weather-related events – will help you nail down your plans. So, let’s find that perfect time for your next trip to the Florida Keys. 

Two people at a food stand with signs reading Key Lime Pie
While the rest of the US deals with winter weather, the Florida Keys are just getting started © Matt Munro / Lonely Planet

Go November through February to feel the energy and heat

As much of the rest of the country combat cold temperatures, snow or a mix of the two, the Florida Keys remain delightfully sunny. In fact, there's a name for those that opt to hibernate for months on end or own a seasonal residence in South Florida (or other traditionally warm locations): Snowbirds.

During these snowbird-filled months, things feel noticeably busier in some of the bigger towns and popular places to visit (e.g., Key Largo, Islamorada, Tavernier, Marathon and Key West) – there is a bit more traffic, restaurant waits are longer and the bar scene is, well, just as crazy as it is any other time of year. With a primed climate – high temperatures are typically in the mid- to upper-70s – and a unique tropics-meets-winter holiday charm, it’s no wonder so many opt to hit the Florida Keys this time of year.

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A band playing in a bar under colorful lights
Although the Florida Key's bar scene is perennially crazy, winter brings revelers from all around  © Justin Foulkes / Lonely Planet

Enjoy festivals and parties before the heat arrives from March through May

If you want to sneak in a Florida Keys adventure before the thermostat reads a very humid 90 degrees, this is the time to do it. March through May is optimal for a number of activities: fishing, spring festivals and a wonderful balance of locals and tourists.

Throughout the Florida Keys, you can visibly notice the snowbirds heading back north. But, between raucous St. Patrick’s Day celebrations, the Conch Republic Independence Celebration in Key West and an influx of Spring Breakers, there's plenty to keep folks heading here, too.

A man and woman kayak in calm waters
Summers get hot in the Florida Keys, but you can cool off by heading out onto the water © Corey Rich / Getty Images

Get a bargain travel deal from June through October

Those dreamy waterside resorts and cottages that the Florida Keys are known for certainly aren’t cheap. For those looking for a bargain, the summer to early fall time frame is the time to make it happen. These bargains come with a few asterisks.

It is typically super-humid and hot during the summer months, so you’ll want to pack accordingly. Also, June 1 through November 30 is the Atlantic hurricane season, with September and October typically being the most active. So, you’ll want to keep an extra-close eye on the weather this time of year. But, for many, these caveats are easily worth the extra dough you’ll save.

Enjoy cultural events in January

With divine temperatures and cultural events galore, it’s no wonder so many folks opt to ring in a new year in the Florida Keys.

Key events: Art Under the Oaks (Tavernier), Coconut Crawl (Key Colony Beach), Florida Keys Celtic Festival (Marathon), Florida Keys Seafood Festival (Key West), Key West Food & Wine Festival.

Head to the art festivals in February

Love may be in the air on Valentine’s Day. But, art is in the air throughout the Florida Keys for much of the month, with two of the islands’ biggest annual attractions for art lovers.

Key events: Coral Head Music Fest (Marathon), Old Island Days Art Festival (Key West), Pigeon Key Art Festival (Marathon).

A large brown pelican on a dock
March brings Spring Breakers to the Florida Keys © romrodinka / Getty Images

Experience the energy of Spring Break in March

South Florida is a Spring Break hotspot and the Florida Keys are certainly a part of the mix starting in March and running through mid-April. If you’re not a college student, St. Patrick’s Day is always an all-ages spectacle with festivities throughout the islands.

Key events: Islamorada Seafood Festival, Key Colony Beach St. Patrick’s Day Parade, Marathon Seafood Festival, St. Patrick’s Day Bar Stroll (Key West).

Go fishing in April

For fishers, April is one of the best months of the year for snagging a big one. Mahi mahi, tarpon, wahoo, blue marlin and yellowtail are in their prime, so plan for a fishing adventure or two.

Key events: Conch Republic Independence Celebration (Key West), 7 Mile Bridge Run (Knights Key to Pigeon Key).

May brings the start of the heat

You can feel the spring temperatures slowly starting to shift to summer heat. With this, the snowbirds and masses of tourists that had taken advantage of cooler temps start to taper off.

Key events: Cuban American Heritage Festival (Key West), Key West Songwriters Festival, Queen Mother Festival (Key West).

Cannons under a brick fort hallway
Rows of cannons in Fort Zachary Taylor in Key West © Nagel Photography / Shutterstock

June is the start of hurricane season

The heat is on and so is hurricane season. June through November, you’ll want to keep an eye on weather systems developing in the Atlantic Ocean and Gulf of Mexico that may affect your trip.

Key events: Florida Keys Guitar Festival (Marathon), Key West Pride Week, Mango Fest (Key West).

July celebrates one very famous pie

A darling of dessert menus everywhere, you can celebrate your love of key lime pie at the Key Lime Festival this month. You’ll want that slice of pie extra cool as the weather is scorching throughout July.

Key events: Hemingway Days Festival (Key West), Key Lime Festival (Key West), Spirit of Islamorada 4th of July Festival, Underwater Music Festival (Looe Key).

Get your lobster fix in August

The ocean water is at its hottest in the Florida Keys in August, so dive in. You can celebrate a fellow ocean swimmer – the lobster – at the Key West LobsterFest, too.

Key events: Key West LobsterFest, Kilts in the Keys (Marathon), Tropical Heat (Key West).

An old-fashioned typewriter in an office
 Ernest Hemingway House is a popular attraction on a visit to the Florida Keys © Kris Davidson / Lonely Planet

Enjoy less crowds in September

Family road trips come to a screeching halt and the islands have a noticeably less family-filled vibe. 

Key events: Florida Keys Birding & Wildlife Festival (Big Pine Key), Womenfest (Key West), Key West Brew Fest.

Get dressed up for an ultimate Halloween celebration in October

For Halloween fans, if getting creatively bedazzled for just one day isn’t enough, you can dress up and party for 10 consecutive days at Fantasy Fest in Key West. For the Halloween traditionalists, there is plenty to do throughout the islands on the big day and leading up to it.

Key events: Fantasy Fest (Key West), Goombay Festival (Key West), Reef Fest (Key Largo), Zombie Bike Ride of the Living Dead (Big Pine Key).

Enjoy the slower pace and cooler temperature of November

Wedged between Halloween and a holiday-filled December, November feels somewhat quiet. High temperatures hover around a pleasant 80 degrees Fahrenheit.

Key events: Key West Film Festival, Taste of the Islands (Marathon).

Bring in the holidays in December

The holidays are celebrated on land, by boat and via seemingly every mode in between. As colorful as The Florida Keys are year-round, things feel that much more cheery and vibrant to close out the year.

Key events: Big Pine & Lower Keys Island Art Festival, Key West Holiday Parade, Key West Lighted Boat Parade.

You might also like:
The best things you can do for free in Key West
12 best things to do in Florida, from rockets and rollercoasters to the Everglades
Plan your next vacation to one of these top destinations in Florida

This article was first published Sep 30, 2021 and updated Dec 18, 2021.

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