Fantasy Fest, drag queen pageants and celebrations of citrus: a month-by-month guide to Key West

With high temperatures hovering between the mid-70s°F and lower-90s°F year-round, is there really a bad time to visit Key West? For those seeking a tropical island paradise and the warm vibes that come with it, there isn’t.

Waters spanning the blue color spectrum, international culinary delights and an aquatic underworld like no other are guarantees for any Key West adventure. But to avoid crowds, maximize your money and minimize your chances of a weather-related encounter, there are optimal times for a visit. Here's how to plan the perfect Key West trip.

Book a warm-weather getaway from January to March

Best time to escape frigid temps

For folks needing or wanting a reprieve from their normal frigid climates, winter is a dreamy – and popular – time for a vacation. Snowbird season, as it's known, traditionally happens between October and May, when folks from the northern states leave their often freezing-cold towns to reside in sunny Florida, and peaks between January and March, when Key West averages just three to four days of rain per month and daily temperatures hover in the mid- to upper-70s.

The Key West Food & Wine Festival, one of the area's biggest annual events, typically falls at the end of January, giving the masses another reason to visit early in the year.

Sweat it out between June and August

Best time for those who can handle the heat

Summer in South Florida is not a joke. It’s swampy, it’s humid, it’s hot and you should come prepared to sweat and sweat some more. For some people, this may be a deterrent and for others, a steamy delight. The hottest time of year is between June and August, with average temps floating in the upper-80s to low-90s.

The Atlantic hurricane season also kicks off June 1 and runs through the end of November; you’ll certainly want to pack some rain gear, but you'll be rewarded with generally cheaper hotel rates and quieter beaches than snowbird season.

Save some cash in September and October

Best time for budget travelers

Typically the heart of hurricane season, September and October are widely regarded as off-season in Key West. Still, this time can be hit or miss for any community along the Eastern US and Gulf of Mexico shores – you could go years without a hurricane-related event, or several could affect a specific area in a single year alone.

That inconsistency can result in stellar deals on accommodations and activities in the Florida Keys – just keep a close eye on the weather, opt for travel insurance and be flexible with your plans if need be.

January

The holiday spirit carries into January with big-time culinary festivities and delightful temperatures taking center stage.
Key events: Key West Literary Seminar, Key West Food & Wine Festival.

February

Presidents' Day and Valentine’s Day prove to be popular excuses for long-weekend adventures.
Key events: Old Island Days Art Festival.

March

Anchored by St Patrick’s Day and all its colorful glory, March sees an influx of visitors. Spring breakers emerge throughout South Florida, and Key West remains a lasting hotspot. This year Key West also celebrates its bicentennial, which culminates in a March heritage festival complete with a "silent" fireworks display by drone.
Key events: Conch Shell Blowing Contest, Tennessee Williams Birthday Celebration, St Patrick’s Day Bar Stroll, Bicentennial Heritage Festival.

April

The flood of snowbird and spring-break crowds noticeably slow to a trickle as spring blossoms. For outdoors activities, such as snorkeling, boating and beach lounging, April is bliss.
Key events: Conch Republic Independence Celebration, 7 Mile Bridge Run, Florida Keys Seafood Festival (typically held in January; postponed and rescheduled for April 2023).

May

Tangerine is the color in May. The island’s Insta-worth Royal Poinciana trees are blooming in vibrant shades of orange, which rival the breathtaking sunsets each day.
Key events: Key West Songwriters Festival, Queen Mother Festival.

June

Despite the start of summer and hurricane season, this is the last of the non-super-humid months before summer. Families embarking on summer vacation noticeably take advantage of it.
Key events: Key West Pride Week, Mango Fest.

July

The temps are as hot as the fireworks you’ll see over White Street Pier. Pack your sunscreen, or you’ll end up looking like a lobster. Speaking of crustaceans, Key West’s spiny lobster mini-season starts at the end of the month too.
Key events: Hemingway Days Festival, Key Lime Festival, Underwater Music Festival.

August

For fans of warm baths, this is the month the ocean is primed for you. Whether at your hotel pool or one of Key West’s beaches, you’ll want to take a dip to stay cool.
Key events: Key West LobsterFest, Tropical Heat.

September

The dog days of summer taper off, the kids are back in school and a tranquil buzz takes over the island.
Key events: Womenfest, Key West BrewFest.

October

It’s only appropriate that a quirky and artsy community like Key West does Halloween right. As hurricane season ends, stone-crab season begins.
Key events: Fantasy Fest, Goombay Festival.

November

Between a happening Halloween and Christmas, November is a comparatively quiet month in Key West.
Key events: Race World Offshore Key West Championships, Key West Film Festival.

December

All is lit up – bikes, boats and everything in between. The island is loaded with holiday-infused events, culminating in a New Year’s Eve fireworks spectacular over Key West Harbor.
Key events: BeLighted Bike Ride, Key West Hometown Holiday Parade, Key West Lighted Boat Parade, New Year’s Eve.

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