When is the best time to go to Key West?

With sun-drenched shores and temperatures that hover between the mid-70s°F (23°C) and lower 90s°F (33°C) year-round, Key West appeals all year long. Indeed, anyone who seeks out this free-spirited island’s pleasures will find something to love almost every month of the year.

Still, some months in Key West are more popular than others – and certain times of year let you avoid crowds, maximize your money and minimize your chances of a weather-related encounter.

Here’s how to choose the perfect moment for your next Key West trip.

At a glance

• While there are pros and cons to each season, there’s never really a bad month to visit Key West.

• October to May in Key West are peak months, when “snowbirds” decamp to South Florida from cold northern states.

• The peak of peak season falls in March, when spring breakers descend on Key West.

• Summers in Key West are hot and humid. This is a great season to enjoy the island’s famous water sports and fishing.

• Hurricane season starts June 1 and peaks in September and October. Though the weather can be unpredictable, and you should be flexible in your plans, you can enjoy fabulous deals in Key West during hurricane season.

December to March is best for winter sun and spring break

Weather in Key West in winter: Key West is where people flock to escape the winter chill in their own hometowns. Temperatures hover around 78°F (25.5°C), rainfall is limited to a couple of days per month, and almost every day is drenched in sunshine.

For folks needing or wanting a reprieve from frigid climates, winter is a dreamy – and popular – time for a vacation in Key West. So-called snowbird season happens between October and May, when folks from northern states leave their freezing-cold towns to set up shop in sunny Florida. The peak falls between January and March, and an overlap of snowbirds and spring breakers in March makes this month the pinnacle of peak season in Key West. This is when you’ll find some of the highest prices for lodging, along with swelling crowds. 

The island is swathed in colorful lights throughout December to ensure everyone feels the holiday spirit in the sunshine. The calendar is packed with holiday-infused events, culminating in a New Year’s Eve fireworks spectacular over Key West Harbor. Get involved at the BeLighted Bike Ride and the Key West Hometown Holiday Parade.

One of the area’s biggest annual events, the Key West Food & Wine Festival typically falls at the end of January, giving folks another reason to visit early in the year. Also in January, Mile 0 Fest draws crowds with a multiday lineup of live music on stages big and small. 

Valentine’s Day and Presidents’ Day bring welcome excuses for long-weekend adventures during February, while the Key West Art and Craft Festival brings creative energy to the waterfront. Spring breakers start rolling into town in March as visitor numbers rise. The celebrations for St Patrick’s Day always draw big crowds.

Planning tip: While you should expect to pay a premium during peak season in Key West, there are a host of things to do on the island that are free all year long. Indeed, some of the quirkiest and most memorable Key West activities don’t cost a dime.

Sweat it out between June and August

Weather in Key West in summer: The weather in South Florida in summer is no joke. Things are very hot and humid, with average temperatures in the upper 80s°F to low 90s°F (31–34°C) – and you should arrive prepared to sweat.

From fishing and kayaking to swimming and scuba diving, the best way to cool off when visiting Key West in the summer is to head for the water. The easy-to-access beach near Fort Zachary Taylor is a popular spot for snorkelers, with many fish surrounding the beautiful coral reefs. (Note that there’s a small entry fee to access this beach.) 

On the southern side of Key West, just off Hwy A1A, Smathers Beach is a popular free option for sunbathers, swimmers and snorkelers. Higgs Beach is a small, lesser-known beach with a pier, playground, nearby dog park, tennis and pickleball courts and a short fitness trail. Although you’ll need a reservation on the ferry or your own boat to get there, remote Dry Tortugas National Park is an incredible spot for underwater and on-land exploration. 

Though the nearby key of Islamorada claims the title of “Sportfishing Capital of the World,” Key West also has plenty of prime locations to cast a line. Charter a boat to fish offshore, where you might catch tarpon, yellowtail, snapper, grouper, marlin, tuna or redfish. If you want to stay landside, Knight Pier and Fort Zachary Taylor Park are popular shore- and pier-fishing spots. Tournaments and events dedicated to the sport take place throughout the year, including the Key West Fishing Tournament, which has many events from January through July. 

The worst of the humidity won’t have really kicked in during June – a welcome relief, as locals and tourists take to the streets to celebrate Key West Pride Week with a spectacular rainbow of color and fun events. Typically held in mid-July, Hemingway Days celebrates one of the Keys’ most famous residents: Ernest Hemingway. Festivities include look-alike contests, poetry readings, rum tastings, a sunset run, beach parties and a multi-day marlin fishing tournament. 

Also held in July, the Key Lime Festival celebrates the islands’ iconic dish, the key lime pie. Be sure to sample Blue Heaven’s authentic-style pie topped with meringue; the whipped-cream-topped version at Kermit’s; or other interpretations from such local favorites as Old Town Bakery and Kaya. 

Pride isn’t the only big LGBTQ+ event during summer: Tropical Heat brings the party for 5 days in mid-August at a variety of events and pool parties.

The Atlantic hurricane season kicks off June 1 and runs through the end of November. You should count on packing some rain gear for travel within this period – and on the reward of generally cheaper hotel rates and quieter beaches than in snowbird season. The ocean is like a warm bath during August, yet a dip still provides welcome relief from hot weather. Check if your hotel has a pool, as it will be sweet relief during this month.

Planning tip: No matter what time of year you visit, you can learn about Ernest Hemingway’s relationship to Key West at the gorgeous colonial house he lived in. You’ll also encounter some 60 cats supposedly descended from the author’s own pet.

Save some cash in September and October

Weather in Key West in fall: While stormy weather in peak hurricane season is to be expected, there are still lots of balmy days to enjoy, with highs in the high 70s° and low 80s°F (25–29°C). The weather is famously volatile, so keep an eye on local weather reports. Pack a bathing suit and light, comfortable layers.

Typically the peak of hurricane season, September and October are widely regarded as the low season in Key West. When it comes to storms, these months can be hit or miss for any community along the Eastern Seaboard and Gulf of Mexico. Many years can pass without a hurricane-related event, or several could batter a specific area in a single season alone.

The upside of such unpredictability? Stellar deals on accommodations and activities in the Florida Keys. Just keep a close eye on the weather, opt for travel insurance and prepare to stay flexible with your plans, should contingencies be necessary. If the weather behaves, you can enjoy balmy days on the beach, walk the streets of Old Town or cycle around the island.

Everything calms down a little after the summer rush, when kids go back to school in September and a tranquil buzz sets in on the island. Another LGBTQ+ event that brings in lots of visitors is the annual Womenfest at the beginning of the month, a warm and wonderful celebration of women.

October brings Fantasy Fest, an annual 10-day extravaganza that lets grown-up revelers deck themselves out in imaginative costumes, as they enjoy creative art, music and theater exhibitions. The event began in 1979 to revitalize the slow month of October with a massive party, uniting the island’s artistic spirit with the mischief and mayhem of Halloween. Themed events occur across the island, from pool parties and burlesque shows to ghost tours and masquerades. Don’t miss the Fantasy Fest Parade as the party makes its way down Duval St. The Fantasy Market, Living Art Expo and Robert the Doll’s Fantasy Facade are also staples of this one-of-a-kind event. 

Planning tip: September and October are when some (though far from all) Key West businesses close for a short annual break. If there are any must-visit bars, restaurants or attractions on your Key West list, check their plans before you make your own.