If you’re looking for world-class snorkeling, sunset cruises, and an unforgettable trip to the southernmost point in the continental United States, the perfect time to visit Key West is between March and May. For folks who are heading south for the winter (or anyone who wants to experience Key West’s incredible Christmas festivities!), peak season is Thanksgiving through February.
Key West is a tiny island and a tourist hotspot, so it should come as no surprise that flights, hotels, and beaches fill up quickly. To find the perfect timing for your island getaway, you’ll need to put on your expert-travel-planning hat—which is where car insurance
super app Jerry
can help. From festivals to ferry rides, Jerry is here to walk you through the best times to visit Key West, so that your trip to the southern tip of the Sunshine State is as fun-filled and stress-free as can be.
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The best times of year to travel to Key West
If you’re ready to brave the crowd and pony up top-dollar for your trip to the Florida Keys, a winter adventure might be best for you. But if you want to save some cash and still experience all that Key West has to offer, aim for the shoulder season (March to May) for great prices.
Peak season: November to February
The good: Holiday festivities, beautiful weather
The bad: Busy and expensive
The weather: Sunny and 75
By Thanksgiving, peak season has officially begun in Key West—hurricane season has come to a close, allowing the holiday festivities to spring to life. Though each month of the peak season is busy, the priciest time to swing through the Keys is Thanksgiving through the New Year.
If you happen to be in town the week before Thanksgiving, check out the Key West Film Festival
—the perfect place for film fanatics to find entertainment and inspiration. Things really get going, though, with the “Bight Before Christmas
”, which illuminates the seaside with vibrant Christmas lights, glowing trees, concerts, and a lighted boat parade! The festivities last from Thanksgiving eve until the New Year’s Eve celebrations
in Mallory Square. Finally, if you’re less of a midnight party-goer and more of a late-night bookworm, the Key West Literary Seminar
focuses on a unique literary theme for four days each January, which will enrich your trip no matter how long you’re staying. Pro Tip Ready to conquer Key West in peak season? Book your trip well in advance—even two or three months early—to secure the lowest rates!
Off-season: June to October
The good: Cheap, less crowded
The bad: Rain and hurricanes
The weather: Upper 80s and lower 90s
In June, temperatures will creep towards the triple digits, and the threat of hurricanes and tornadoes will grow—but, if you’re willing you take your chances with the weather, you can get some of the cheapest plane tickets and hotel rooms in Key West.
Even during the off-season, Key West is chock-full of revelry, starting with the Hemingway Days Festival
in late July. This one-of-a-kind celebration honors the bullfighting, Pulitzer Prize-winning, larger-than-life American author Ernest Hemingway
, and it features a short story contest, Marlin fishing tournament, and Hemingway-lookalike competition (imagine lots of jolly, large-bellied fellows with white beards). If you miss the Hemingway Festival, don’t sweat it—you can still visit the Hemingway Home and Museum
year-round. Other activities to keep an eye out for during the low season include the Goombay Festival (a kid-friendly two-day festival that boasts live music and delicious food like conch fritters) and Fantasy Fest
(its not-so-kid-friendly, riotous 10-day counterpart). Shoulder season: March to May
The good: Fewer crowds and better prices
The bad: Not as many attractions, not as cheap as off-season
The weather: High 70s and low 80s
The shoulder season, which falls between the high and low seasons, is the sweet spot for visiting Key West. Rates begin to fall as winter visitors disperse, and hurricane season hasn’t yet kicked into gear.
March begins with the Conch Shell Blowing Contest
, a 60-year-old tradition where participants try to make the most beautiful (and loudest!) music on a fluted conch shell. The conch-related merrymaking doesn’t stop there, though—in April, watch out for the Conch Republic Independence Celebration
, an eccentric 10-day event with shows, festivals, fairs, and more. The shoulder season winds down in May with the Key West Songwriters Festival
, a five-day series of concerts and meet-and-greets with famous musicians. It's the largest festival of its kind in the country—so don’t miss it! The cheapest time to travel to Key West
You’ll find the cheapest flights to Key West in August and September when the hurricane season is peaking and humidity is at its highest. The potential for damaging weather wards off lots of tourists in these months, so travel is inexpensive—but it’s a great idea to make sure that your flights and hotels are refundable, just in case.
Even if you can’t find a cheap flight during these months, there are other times you might be able to sneak into a hotel for a low fee. For example, in between the Halloween and Thanksgiving activities, during the first weeks of November, you might be able to score an inexpensive flight and a low-cost room.
Find the best month for your visit to Key West
So, you’re certain that you want to head to South Florida for your vacay—but which month is the best one for you? Here’s a table that we’ve put together to help you plan your stay, centered around different activities in Key West:
| | |
|---|
| | Breezy, sunny weather is perfect for aquatic activities off the coast of the Keys. |
| | Along with the Songwriters Festival, the seaside is loaded with restaurants that perform live music in May. |
| | October is one of the busiest months for tourism in Key West, largely due to the rowdy and raucous Fantasy Fest. |
| | One of the top winter runs in the country, the Key West Half Marathon and 5k takes you right along the picturesque Florida coastline. |
| | In 2009, the missile-tracking ship Vandenberg was intentionally sunk to create a bustling artificial reef. |
| | The Key West express provides an awesome way to arrive at (or depart from!) Key West via the ocean. |
| | Best to aim for the cooler months for a bike tour, which is a fantastic way to get an insider’s perspective on the city. |
Pro Tip Since most activities in Key West run year-round, you should plan your stay first and foremost around your budget and specific interests.
How to save money on car and rental insurance
Whether you hop into your own car for a cross-country road trip or grab a rental after you fly into Key West, you’ll want to be sure that your car has the best insurance. Jerry
, our car insurance
comparison super app, is the perfect place to find the lowest rates. Just download the app, sign up in 45 seconds, and let Jerry work its magic. Within minutes, you’ll have the best prices on the market. Best of all, Jerry can even help you cancel your old policy and get started on your new one—as stress-free as a stay in the Florida Keys.
Still not convinced? Check out the numbers—the average Jerry user saves $887 on car insurance!
MORE: 7 ways to save money on car rentals
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