The Best Time to Visit Key West

Seaside promenade at Key West Pier

Peter Unger / Getty Images

The best time to visit Key West is between March and May. Falling right between peak tourist season and hurricane season, this time of year promises temperatures in the low 70s and 80s Fahrenheit, limited rainy days, smaller crowds, and better flight and hotel prices. Winter (November through February) is the busiest season, and while the island is lively and fun, expect expensive flights and car rentals and for hotels and vacation rentals to be at capacity. Conversely, you’ll find unbelievable deals every June through October, but at a price—it's during Atlantic hurricane season.

Hurricane Season in Key West

Key West, like the rest of Florida, is no stranger to hurricanes. Hurricane season runs from June 1 through November 30 every year, with the most powerful storms typically forming in August, September, and October. Because Key West is surrounded entirely by water, an oncoming hurricane often leads to a mandatory evacuation of the island.

Peak Season in Key West

When the weather gets colder up north, winter travelers flock south to Key West for its blue skies and warm sunshine. For that reason, November to February is peak travel season in Key West. Thanksgiving week officially kicks off tourist season in the Florida Keys. After that, restaurants and hotels are at capacity, flight prices are more expensive than usual and traffic in and out of Key West gets pretty heavy. The island isn't that big, so added crowds are definitely noticeable. If you’re looking to visit at this time of year, make sure you book your flights, hotels, and rental cars early for two reasons: to make sure you get one before they’re all gone, and to save money on what is already a more expensive time to visit Key West.

Fantasy Fest in Key West

Key West’s most popular event is Fantasy Fest, a 10-day costuming and masking festival that takes place at the end of every October. For a week and a half, expect funky costumes, public nudity, X-rated parties, a “Kinky Carnival,” appearances by adult film star Ron Jeremy and the main event: a nighttime costume parade down Duval Street on the last Saturday of Fantasy Fest. If you’re planning to go, wear your wildest costume and join the tens of thousands of locals and visitors crowding the streets of Key West—the island has been hosting it for more than 40 years.

January

While Key West never gets cold, January is the coldest month of the year there—with temperatures averaging between 64 and 74 degrees Fahrenheit. This is peak of “snowbird” season, that time of year when residents of colder climates escape to the warmth of South Florida, so flight and hotel room prices are higher and hotels fill up quickly.

Events to check out:

  • The annual Key West Literary Seminar brings together book lovers and contemporary authors for readings, lectures, book discussions, and more.
  • Dubbed one of the top ten winter half marathons, the Key West Half Marathon & 5K Run follows a 13.1-mile course that takes runners through picturesque Old Town Key West and along the idyllic Florida Keys coastline.

February

Similar to January, high and low temperatures are in the mid-70s and 60s Fahrenheit, respectively. February is the tail end of peak tourist season, so flight and hotel room prices will be at a premium.

Events to check out:

  • Eat your heart out at the family-friendly Key West Food Truck Festival, where food lovers can spend an entire Saturday jamming out to live local music and tasting the delights of Key West’s top food trucks.

March

March marks the official end of tourist season in Key West. This is a great time to visit the island, as hotel and flight prices are cheaper, temperatures are mild and Key West isn’t as crowded.

Events to check out:

  • Start March with the Conch Shell Blowing Contest, which has been a tradition on the island for more than 50 years. This friendly competition, which celebrates the historical importance of conch in Key West, has people of all ages attempting to play music on fluted conch shells.

April

During April, visitors start to feel the transition from spring to summer. By the end of the month, the higher temperatures start to creep into the 80s Fahrenheit, but the cool Gulf of Mexico breezes keep nights mild.

Events to check out:

  • Don’t miss the Conch Republic Independence Celebration, an eccentric, 10-day party with bar crawls, an arts and crafts fair, hat contest, drag show, dog festival, and a famous reenactment of the Conch Republic’s “Great Sea Battle.”
  • The Key West Paddle Classic includes both a 12-mile Elite Race and a 4-mile open race around the island, all on paddle board.

May

Summer has arrived in Key West. The sun beats down hard during Key West summers, so bring light clothing, plenty of sunblock and bug spray.

Events to check out:

  • The Key West Songwriters’ Festival is an annual showcase of America's top performing songwriters in an intimate setting. It’s the largest festival of its kind in America, and includes five days and nights of meet-and-greets, artist talks, concerts, and more.

June

This is both the heart of summer and the official start of hurricane season in Key West. Many people think that South Florida summers are all sunshine, but don’t believe the myth. When there isn’t a hurricane, sunny mornings and afternoon thunderstorms are the norm. It’s still hot, however, so wear light clothing and pack an umbrella.

Events to check out:

  • Start June with Key West Pride, a five-day celebration of all things LBGTQ+ with pool and beach parties, late-night drag shows, snorkeling, kayaking, glass-bottom boat tours, a street fair, and, of course, pageants to elect Mr. Key West Pride, Miss Key West Pride, and Ms. Key West Pride.
  • Mango Fest Key West celebrates Florida’s favorite fruit with a day-long festival that includes mango tastings, mango daiquiris, culinary competitions between local chefs and residents, live music, art, and food vendors.
  • Mystery Fest Key West brings together mystery writers, aspiring authors and true crime experts and fans to America’s “Southernmost City” for meet-and-greets, book signings, workshops, panel discussions, and lectures.

July

July is the hottest month of the year in Key West. During this time of year, highs are in the 90s Fahrenheit and temperatures rarely dip below 80 degrees Fahrenheit. It’s still hurricane season, however, so afternoon thunderstorms are common and there is always a threat of devastating tornadoes and hurricanes.

Events to check out:

  • Key West’s annual Key Lime Festival is one of the tastiest events of summer, with pie-eating and cooking contests, culinary showcases, the Key Lime Cocktail Sip & Stroll, and The Key Lime Pie Hop.
  • Join Key West’s oldest ongoing 5K, the Hemingway 5K Sunset Run/Walk & Paddleboard Race, which is part of the annual Hemingway Days Festival. Runners will compete in a scenic flat course that takes them through the island’s most famous landmarks, like the Ernest Hemingway Home, the iconic Southernmost Point and Key West’s famous Green Parrot Bar.

August

August in South Florida is typically when humidity is the highest. Much like July, expect hot days and frequent thunderstorms. August is also the peak of hurricane season, so prepare for the worst and make sure all flights and hotel rooms booked during this time are refundable.

Events to check out:

  • Marking the start of lobster season, don’t miss the annual Key West LobsterFest. It’s a four-day festival, right on Duval Street, offering lobster cooked every way possible.

September

As the unofficial start of fall, temperatures in Key West start to cool down (slightly) in September. This is also the peak of hurricane season, so while there might be more of a pleasant breeze, visitors should pack for both sunny and rainy climates. Luckily, this is also shoulder season—so hotel room and flight prices are cheaper.

Events to check out:

  • Kick off September with Womenfest, the largest celebration of lesbians in America, which brings together thousands of women from all over the world.  
  • During Labor Day weekend, head to Key West Brewfest, a craft beer festival with more than 200 beer and ale samples, oceanside tastings, beer-focused brunches, pool parties with specialty beers, daytime tap takeovers, and beer-pairing dinners.

October

October is one of the most popular times to visit Key West! The first couple weeks are quiet and perfect for a romantic or family-friendly getaway—but when Fantasy Fest comes to town at the end of the month, Key West turns into a giant, 10-day party. It’s the last month of hurricane season, but if one doesn’t hit, days are typically sunny and temperatures go as low as the mid-70s Fahrenheit.

Events to check out:

  • Fantasy Fest, a costuming and masking festival that takes place at the end of every October, includes 10 days of parades, X-rated carnivals, adult film stars, and a general celebration of all things kinky. It’s been taking place in Key West for over 40 years, and is undoubtedly the island’s most popular festival.

November

November is an important month in Key West because hurricane season is finally over. As fall and the start to winter set in, the island gets cooler. While the weather is perfect, this is the start of the winter “snowbird” season, so expect crowded hotels and higher flight prices.

Events to check out:

  • Every year, the Key West Film Festival takes over the island with four days of films, screenings and special events for filmmakers, actors and film enthusiasts alike.
  • As the holiday season approaches, so does the Lighting of the Bight: Key West Harbor Walk of Lights. This kick-off event is the official lighting ceremony for the “Harbor Walk of Lights,” which lights up the island nightly through New Year’s Eve with a lit Fishing Buoy Tree, Nautical Christmas Tree, the original Key West Lobster Trap Tree, and more.

December

As the holiday season comes to sunny South Florida, expect warm days and cooler, more breezy nights. Key West is busy with tourists at this time of year, so book your flights and hotel rooms early before they are all gone.

Events to check out:

  • Celebrate Christmas with the Key West City Home Holiday Parade, which includes marching bands, local schools, floats, a live Santa Claus and more parading down Truman Avenue.
  • The annual Schooner Wharf Bar Lighted Boat Parade is a holiday tradition in Key West. Enter your own boat, or grab a seat at a waterfront bar to watch all the fun—festive, lit boats, from holiday-inspired rowboats to tall ships, will set sail around Key West's Historic Seaport and harbor areas.
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