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When’s the best time to visit Key West? This party island is one of the warmest places in the contiguous United States! You may want to go in the winter for that reason — but the very best time to go to Key West is in the spring: from March to May.
I adore Key West. It’s one of my favorite destinations in the US — not only a beautiful island but a guilty pleasure as well, and one that continues to improve with age.
Of course you’re sure to have a blast in Key West at any time of year! There are historic sites to explore, sunset cruises to take, and slices of key lime pie just waiting for you to order them. But it’s no lie that certain times of year in Key West are kinder to your body and your wallet.
I’ve visited the Florida Keys at a few different times of year. Having visited in the peak of July and during the colder months, I can personally attest to the vibe and environment in Key West changing dramatically based on when you visit.
Whether you’re looking for the cheapest time to go to Key West or you want to hit up a legendary festival, you’ll want to read on for the best times to visit Key West and the Florida Keys!
Best Time to Visit Key West
The best time to visit Key West is during the spring months: March, April, and May. This is when the tourist crowds from the winter high season have finally dwindled, the weather is mild and warm, and prices begin to come down from their peaks.
You might think that the fall shoulder season would also be a great time to visit, but it’s not — hurricane season peaks in September and October, and this can easily derail a fall trip to Key West.
Key West has the best weather in March, April, and May. There are fewer rainy days and temperatures are in the 70s and 80s Fahrenheit, or 21-30 Celsius.
April is the best month to visit Key West. Right in the heart of spring, this is when you’ll find the best temperatures, fewest crowds, and most affordable prices.
Key West is famed for its fun, lively, and bizarre festivals. Some of the best ones are Fantasy Fest in October, Key West Pride in June, Hemingway Days in July, or the “Bight” Before Christmas.
Couples will love visiting Key West during the spring months, in March, April, and May. The winter crowds have dispersed, prices are lower, and the island is a bit quieter and more romantic.
Key West Weather
The weather in Key West is warm year-round, making it a popular winter destination for snowbirds fleeing the cold. While all of the Florida Keys have warm weather, Key West tends to be a little warmer than the others, especially in winter. Key West was the one Key where I didn’t need a cardigan or light jacket at night in February.
As for rain, know that rain in Florida and the Caribbean tends to be brief and intense. You won’t get the all-day drizzles of the Pacific Northwest or New England. Rain doesn’t derail a whole day in Key West; it gives you a reason to get a drink and wait for it to pass.
Key West in Spring
There’s no question — spring is the best time of year to visit Key West. March, April, and May experience warm, sunny weather; tourist crowds have reduced to a more manageable level. Spring is the first time many locals are willing to sunbathe or go swimming.
Humidity in the spring is much less than in the summer months, making it more comfortable to be outside and take advantage of Key West outdoor activities during the day. While there are occasional rainstorms, there is zero risk of hurricanes during the spring, making it a solid weather option for Key West.
Key West in Summer
Summer weather in Key West is very hot and extremely humid, which makes it more difficult to spend time outdoors. Many people in Key West stay inside during the peak heat hours of noon to mid-afternoon. This can make it tough to enjoy outdoor activities. For this reason, evenings are the peak time to be out and about in Key West during the summer.
Most importantly, though, summer in Key West marks the start of hurricane season, which runs from June through November. Most hurricanes don’t hit Key West until late August, though some occasionally hit earlier than that. Hurricane season can be a very risky time to visit Key West. See more on that below.
Summer brings a few major festivals, including Key West Pride and Hemingway Days. Both prices and crowds balloon during these festivals.
Key West in Fall
Fall is the riskiest season to visit Key West. Most hurricanes tend to hit in September and October, though hurricane season officially ends on November 30.
While heat drops a bit during this months, making it easier to do outdoor activities, rain is more common. When it rains, it tends to be a short, intense burst rather than an all-day drizzle.
Fall also hosts some of Key West’s most popular festivals including the iconic Fantasy Fest before Halloween and the Bight Before Christmas. Prices shoot up for these times of year, particularly Fantasy Fest, and the crowds can be intense.
Key West in Winter
Winter is peak season in Key West and hordes of tourists converge on the island in order to beat the cold up north. This is when you’ll see the highest seasonal prices for flights and hotel accommodations and you can expect there to be booked out activities and long waits for restaurants.
If you decide to visit Key West during the winter, you’ll want to make sure to book your trip well in advance to ensure availability. You may want to book your connecting flight through a less-snowy city — think Orlando rather than Chicago — to ensure that a snowstorm doesn’t disrupt your trip.
Key West weather in the winter is warm and sunny during the day and a bit cooler at night. Expect a few rainy days throughout the season, but overall the days will be sunny.
High Season and Low Season in Key West
High season in Key West is during winter, from November to February. This is when tourists flock to the Florida Keys to evade the cold.
But the absolute peak periods in Key West, when prices and crowds are at their worst, are during the biggest festivals: Hemingway Days in July, Fantasy Fest in October, and Pride in June. The other peak times are major travel holidays — New Year’s Eve, Memorial Day, Labor Day, even Martin Luther King Day and Presidents’ Day.
If you want to book a trip during these times — great! But don’t accidentally book a trip during these times!
Shoulder season in Key West is during the spring, in March, April, and May. This is when the winter crowds have started to slow and the crowds have dissipated a bit.
Low season in Key West is during the summer and fall months — with the exceptions of Pride, Hemingway Days, Labor Day weekend, and Fantasy Fest. Lower prices? Yes. Humidity and hurricanes? Also yes.
Best Time of Year to Visit Key West
Some months are better than others when it comes to the best time to visit Key West.
Here’s a rundown of what to expect in Key West each month:
January in Key West
January is in the heart of peak tourist season in Key West. It’s the coldest month of the year, though this is Key West we’re talking about, so it may be. Temperatures range from 65 to 74 degrees Fahrenheit (18 to 23 degrees Celsius). You can expect rainfall approximately 12 days throughout the month, though these storms are brief.
January sees larger crowds and higher prices due to the influx of tourism, so you’ll want to avoid January if you’re looking for the cheapest time to go to Key West.
The Key West Literary Seminar happens annually in January. It’s an awesome event that brings together book lovers and some of the world’s most acclaimed authors. (Did you know that Judy Blume owns a bookstore in Key West?)
February in Key West
February is the final month of Key West’s peak tourist season, so expect high prices through the end of the month. Temperatures range from about 68 to 76 degrees Fahrenheit (20 to 24 degrees Celsius).
There will only be about five rainy days in February, though it is cloudy for most of the month. Humidity climbs throughout February.
The Key West Food and Wine Festival takes place annually in February and is a popular event for culinary enthusiasts.
March in Key West
March marks the end of peak season in Key West, making it an optimal time for travelers hoping to avoid the crowds. Prices start to come down and the weather is mild and warm. Temperatures in March range from 70 to 78 degrees Fahrenheit (21 to 25 degrees Celsius).
March boasts warm, dry weather with even more sunny days than in January and February. There will only be about six rainy days, which is perfect for those hoping to take advantage of nice weather!
Head to Key West in March to experience the iconic Conch Shell Blowing Contest, which has been a local tradition for over 50 years.
April in Key West
April is the sunniest and least humid month in Key West, with temperatures ranging from 72 to 81 degrees Fahrenheit (22 to 27 degrees Celsius). With barely any rain, fewer crowds, and affordable prices, April is the perfect month to visit Key West.
April brings the annual Conch Republic Independence Celebration. This wacky festival includes an arts fair, bar crawls, a drag show, and more.
May in Key West
In May, the warm and sunny days continue. Though there is low humidity, the weather starts to get a bit hotter and wetter as spring begins to turn into summer.
Temperatures in Key West in May range from 76 to 85 degrees Fahrenheit (24 to 29 degrees Celsius). There will be up to a week of rainy days throughout the month, but you can expect majority hot and sunny weather.
The Key West Songwriters Festival occurs in Key West in May. This festival hosts over 200 artists annually.
June in Key West
June marks the beginning of summer in Key West — and technically the beginning of hurricane season, though hurricanes often don’t hit this early. With hot, humid temperatures and severe summer storms, June is one of the worse weather months in Key West.
Temperatures range from 79 to 88 degrees Fahrenheit (26 to 31 degrees Celsius) and it’s typically sunny during 75% of daylight hours.
Key West Pride takes place in June, and since Key West is an LGBTQ hub under ordinary circumstances, the celebrations here are legendary. The festival includes pool and beach parties, drag shows, pageants, and more, and happens over the course of five days and nights.
July in Key West
July is Key West’s hottest month and lands travelers in an often stormy part of year. Afternoon thunderstorms and tropical storms are common, and hurricanes become a potential threat during this time of year.
Temperatures range from 80 to 89 degrees Fahrenheit (27 to 32 degrees Celsius), which is perfect if you plan to go swimming and partake in water activities.
July in Key West brings Hemingway Days. With a legendary Ernest Hemingway lookalike contest, a short story competition, a fishing tournament, and so much more, this is one Key West festival you won’t want to miss!
August in Key West
August tends to be one of Key West’s most humid months and is known for bearing the brunt of hurricane season. Make sure your hotels and flights are flexible or refundable if you plan to visit in August, as storms this month can get particularly tough.
Temperatures range from 80 to 89 degrees Fahrenheit (26 to 32 degrees Celsius). Travelers should plan for very hot days and regular (brief but intense) thunderstorms.
The annual Key West Lobsterfest happens in August, and visitors can experience lobster in every way imaginable. The event also hosts live music, street fairs, pub crawls, and much more.
September in Key West
September is the rainiest, stormiest month in Key West. During this month Key West experiences some of the strongest storms of hurricane season.
The weather begins to cool off — by Key West standards, at least — with the coming of fall. Prices remain affordable throughout the shoulder season. Temperatures in September range from 79 to 88 degrees Fahrenheit (26 to 31 degrees Celsius).
Key West Womenfest brings together lesbians from around the world for a colossal celebration of womanhood in September. Key West Brewfest happens over Labor Day Weekend and hosts a number of exciting craft beer events.
October in Key West
October is an unusual month in Key West. Though hurricanes are often at their most fierce at this time of year, October is the month of one of Key West’s biggest festivals: Fantasy Fest! Fantasy Fest attracts thousands of visitors to the island over its 10-day period.
Though October puts visitors at the greatest risk for experiencing a tropical storm or hurricane, October days are typically sunny and dry. Temperatures in October range from 76 to 85 degrees Fahrenheit (24 to 29 degrees Celsius).
November in Key West
November is the most humid month in Key West, though temperatures start to cool down significantly. Marking the end of hurricane season and the migration of tourists coming from up north, November tends to see more expensive prices, larger crowds, and less availability.
Temperatures range from 72 to 80 degrees Fahrenheit (22 to 27 degrees Celsius). There is much less rain in November than earlier in the fall, making it a pleasant month for visiting Key West.
Check out the Key West Film Festival in November and don’t miss the annual Lighting of the Bight: Key West Harbor Walk of Lights event to kick off the holiday season.
December in Key West
December brings nice weather with warm, sunny days and cooler nights. This is peak tourist season in Key West, so make sure to book your flights and accommodation well in advance.
Temperatures range from 67 to 76 degrees Fahrenheit (19 to 24 degrees Celsius). Expect a lot of humidity and a few rainy days throughout the month.
The Key West Bight Before Christmas and New Year’s Eve in Key West are major events that travelers will definitely want to experience if you plan to visit in December. Of course, with popular events come peak prices.
Hurricane Season in Key West
Hurricane season in Key West technically lasts from June 15 through November 30, but the worst storms tend to hit between August 15 and October 1. The tough thing about hurricane season is that it’s unpredictable — you could have a perfectly fine time, or you could endure a once-in-a-century storm.
It’s important to take hurricane season seriously in the Florida Keys, as some hurricanes have forced mandatory evacuations in the last few years.
I urge you to avoid the Florida Keys during the peak of hurricane season. Why spend the months leading up to your trip wondering if your dream tropical trip will be stormy? Or worse, if you’ll have to evacuate?
Travel insurance is important for every trip — but it’s essential for a trip to Florida during hurricane season. It could save your life or your finances. I use and recommend World Nomads for trips within the US.
If you do end up in the Florida Keys during a hurricane, please listen to the authorities and evacuate if they tell you to evacuate. Don’t ride out the storm. Someone could die trying to rescue you.
Best Key West Festivals
Key West is a party town — and they put on some incredible festivals! Travelers from all over the world flock to the island to experience them, some returning year after year. Here are some of the major Key West festivals you’ll want to check out:
Fantasy Fest: Easily the most famous of the Key West festivals, Fantasy Fest occurs over the 10 days leading up to Halloween. Expect 10 days of partying, including street fairs, parades, drag contests, a masquerade costume contest, and more. This event is NOT for kids — this is a sex-positive celebration with many x-rated costumes.
Key West Bight Before Christmas: Beginning on Thanksgiving and running through Christmas, the Bight Before Christmas showcases festive floats and parades, Christmas lights, a tree trimming party, a boat parade, concerts, and more.
New Year’s Eve: Who needs a ball drop? Key West has a Dropping of the Conch Shell at midnight! Similar quirky festivities also happen throughout the island at Bourbon St. Pub and the Historic Seaport.
Hemingway Days Festival: One of the most iconic festivals in Key West, the Hemingway Days Festival draws a huge crowd every July. I attended a few years ago and loved every minute of it. With a Hemingway Lookalike Contest, a short story competition, a marlin fishing tournament, and more, this is one Key West festival you have to experience once in your life!
Key West Pride: Key West is a major LGBTQ destination year-round — so you can imagine how Pride is here! Pride in Key West is absolutely legendary and draws people from all over the country. The celebration includes a week of festivities, ranging from pool parties to street fairs to talent shows, parades, and so much more.
Best Time to Visit Key West with Kids
Is Key West a good destination to visit with kids? Honestly, Key West is more of an adult-oriented destination, but you can definitely have fun with kids here! They’ll especially enjoy the sunset celebration. If you’re visiting the Florida Keys with kids, I recommend spending the bulk of your time in other parts of the Keys, which tend to be more family-friendly.
The best time to visit Key West with kids is during the spring. Whether your kids’ spring break is in March or April, it’s a great excuse to escape the cold, head down to the Keys and soak up the sun with your family. The weather isn’t too hot and humid, and prices are good.
Winter is another great time to check out Key West with the kids — though it tends to be more crowded and expensive. The weather is warm, making for a great escape from cold winter weather in the rest of the country, but it might not quite be swimming weather yet. You know your kids best — they may jump in anyway!
Though summer is a popular time for family vacations, summers in Key West tend to be extremely hot and humid. If your kids can’t handle intense heat and humidity, you may want to consider visiting during a different time of year.
I recommend avoiding hurricane season in Key West, which peaks in September and October. It’s bad enough if you have to evacuate on your own — but with kids? Even scarier.
Cheapest Time to Visit Key West
The cheapest time to visit Key West is from March to May. Spring marks the end of peak tourist season, so crowds begin to dwindle, the weather becomes more pleasant, and prices drop waaaaay down. Flights to Key West from within the US often tend to be inexpensive during these months.
Key West also tends to be inexpensive during the summer and early fall (excluding the major festival dates — Key West Pride, Hemingway Days, and Fantasy Fest, as well as Labor Day weekend), largely due to hurricane season.
If you decide to take advantage of cheap prices during hurricane season, don’t even think of booking a trip without travel insurance! I use and recommend World Nomads.
Overall Best Time to Visit Key West
Though you can have a great time in Key West any time of year, the best time to visit Key West is during the spring months. March, April, and May experience warm, mild weather, crowds of tourists have dissipated, and prices are lower than what you’d pay during the winter.
A springtime trip to the Florida Keys is a solid choice. Now go on your trip — then come back and tell me all about it!
More on the Florida Keys:
See all posts on Florida here.
Have you been to Key West? What time of year did you visit? Share away!