Post originally published on September 27, 2018; Post update published on September 30, 2021
Is taking a trip to Key West, Florida on your radar? That’s great! It should be! In fact, let’s take it one step further from your radar to your calendar right away. First thing’s first, let’s discuss the best times to visit Key West!
There is so much to be found on this Southernmost US island, located at the southern tip of Florida. Sunshine abounds most of the year. This makes it appealing for those seeking solace from the bitter winds and dreary weather found throughout the northern and midwestern states during the winter months.
It’s incredibly important to have an idea of what you want out of your vacation, and also what you want to avoid (hurricanes maybe?). This guide will provide you with all the details you need to understand the best (& worst) times to head south.
But let’s be honest….. Is there really a bad time to go to Key West? Yeah, I didn’t think so.
KEY WEST IN JANUARY
January is a great time to visit Key West. The weather is amazing. A typical day would be mid to upper 70s and sunshine for the majority of the waking hours. The annual Key West Half Marathon happens on the nation’s southernmost island every year in January and one year we had hopes of going to get our run on, but found the island to be pretty well booked up during that week/weekend and the rates of rooms were astronomical compared to normal. So, if you’re planning to start your new year off right, just plan around one of the biggest marathons Florida sees all year. That is of course, unless you’re going specifically for the marathon. Then, duh, go during that week but know you’ll be paying those premium rates.
January, February and March are considered to be the “high season” and you’ll find that most of the lodging costs, etc., are higher than normal during this time.
FEBRUARY TRAVEL
February is a lovely time to be in Key West. The temperatures will start slowly rising, although if you live in the Midwest, you’ll take whatever level of warm up you can get. We found February to be just a little chillier than we would have liked one year (70s instead of 80s) but were told by the locals that the temps had been running about 10 degrees cooler than normal.
We were stoked for some water activities and chanced it with booking a tour with Danger Charters. I wore a light jacket out to sea that day and only made it a few minutes in my snorkel suit before calling it quits because it was just too cold in that water for me. If being in the water isn’t something you’re looking for and you just want to lay back and relax, February is a great time. You’ll get all the sunshine you could hope for, without having to suffer in hypothermic water conditions (I’m only embellishing a little).
MARCH AND APRIL
During March and April, the temps remain relatively warm with sunshine-y skies but in April, you’ll have more chances for those pop-up showers that always seem to come in out of nowhere. The water temps are still going to be a bit chilly for things like deep sea snorkeling and scuba, but for some lazy days at the beach, the sun has already warmed the water up quite nicely.
The last week in March, as with anywhere else in the world, is a busy time because Spring Breakers from all over the US and Europe vacation on Key West.
MAY TRAVEL
Your May stay could go one of two ways. Cloudless blue skies or spotted thunderstorms with overcast skies. During our last stay in May, pop-up storms were pretty well a daily occurrence, and easily happened several times in one 24-hour period. When the sun does come out, the temps are in the upper 80s and feels great but be prepared to possibly spend some time indoors.
KEY WEST IN JUNE, JULY AND AUGUST
You will find pretty consistent weather patterns during the summer months in KW. June, July and August will bless you with hot temps (90s to 100s) and lots of sunshine. The hot summer months deter folks who aren’t able to tolerate heat well or who simply don’t enjoy profusely sweating every minute of the day. This is a great time to avoid some of the in-season crowds (this is KW’s off-season) and take in some great water adventures. May I suggest a day spent out at the sand bar?
SKETCHY SEPTEMBER
The honorable month of September tends to wreak havoc on the Keys. Many businesses close their doors for the month to prepare for busy, busy, busy October. Blue Heaven and Louie’s Backyard, two Key West favorite dining options, close for the entire month.
Most importantly, however, September is primo hurricane season. If you think that purchasing travel insurance will save your potentially ruined trip, think again. Most companies do not refund based on poor weather. You could be up a creek without a paddle. Literally.
A group trip we planned in 2017, barely happened after Hurricane Irma nearly decimated the Keys. Luckily for the residents of Key West, the hurricane changed paths enough that the island was mostly spared. Sadly though, the storm turned north into the other Key islands and left those folks without services for weeks.
September is risky. Don’t say I didn’t warn ya.
OCTOBER TRAVEL
So, you wanna party, huh? Then October is going to be your month! If you’re planning a trip during October, book early and plan to fork out a little more dough on room and board. There are three (yes three!) festivals in the month of October. The biggest, most famous, most craziest, loudest, most obscene of them all is Fantasy Fest. During the 10 days of Fantasy Fest, I’ve been told that the island triples in residents all in the name of partying and producing lewd ridiculousness along with the rest of them. Fantasy Fest isn’t until the end of the month so if you hit it right at the beginning, you should still be good. If you’re not one to be in the party crowd, do yourself a favor and skip Key West during the month of October.
KEY WEST IN NOVEMBER AND DECEMBER
Key West vacations during the months of November and December can be thoroughly enjoyed with nice temps and lesser crowds. The snow birds haven’t started heading down in droves yet and you can enjoy some of the great holiday events that are hosted in Key West every year.
The Lighted Boat Parade, for example, is something that should not be missed. Also, who doesn’t want to lounge on the beach when the rest of the states are hunkered down for the winter?
January through December, it really doesn’t matter. Pick one and you’ll be glad you did. To each their own, you just need to make sure your vacay time matches your activity wish list.
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Other Key West articles that may interest you:
Key West Travel Advice: Where to Stay
The Top 10 Reasons I Love Key West
Renting a Vacation Home in Key West
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What do you think is the best time to visit Key West? Do you have some other helpful information to add to the discussion? We’d love to hear from you! Please enter your comment below to help others!
