Best Time to Visit Key West: A Month-by-Month Guide
When is the best time to visit Key West?
Good news: there isn’t really a bad one.
Winter brings warm, dry days while most of the country is reaching for another coat. Spring hits a sweet spot for sunshine and time on the water. Summer turns up the heat and slows down the pace. Then fall brings some of the island’s biggest events.
At The Perry Hotel & Marina, every season comes with marina mornings, two pools, dockside dining and Key West close enough whenever the mood strikes.
The agenda? That part is up to you.
When Is the Best Time to Visit Key West?
While there’s no wrong time to visit, the best overall balance would be late winter through spring (December to May), especially April and May, for the driest weather and most comfortable temperatures.
But the best time really depends on the Key West trip you want.
| Time of Year | Typical Weather | The Pace | Best For |
| December–February | Warm, dry days with highs around 76–78°F | Lively | Escaping winter, dining outdoors, events |
| March–May | Highs climb from around 80°F into the mid-80s | Busy early, easing later | Boating, sightseeing, spring getaways |
| June–August | Hot, humid and tropical with highs around 89–91°F | Easygoing | Pool days, water activities, slower island trips |
| September–November | Warm with more rain early, becoming milder later | Changes with the event calendar | Festivals, fall escapes, flexible trips |
Key West has a tropical-maritime climate. December through April is its dry season, while June through October accounts for most of the annual rainfall. May and November tend to act as transition months.
Planning around something happening on the island? Check The Perry’s Event Calendar for live music, dockside gatherings and seasonal events happening during your stay.
Winter in Key West: December Through February
Want to trade grey skies for marina views?
Winter is one of Key West’s most popular seasons for good reason. Days are mild, rainfall is relatively low and outdoor plans rarely need much convincing. Average highs sit in the mid-to-upper 70s from December through February.
December
December brings warm days, cooler evenings and plenty of reasons to stay outside.
Key West also gets surprisingly enthusiastic about the holidays. Expect lights, festive events and decorated boats throughout the island, including celebrations built around its waterfront setting.
Sunshine and holiday lights. Not a bad combination.
January
January is one of the coolest months in Key West. Which, around here, means an average high of about 76°F.
It’s a great month for walking Old Town, getting on the water and eating outside without summer heat. Food lovers can also keep an eye out for the annual Key West Food & Wine Festival, taking place Wednesday, January 27 through Sunday, January 31, 2027.
February
February keeps the dry, comfortable weather going, with average highs around 77°F.
Think easy afternoons exploring Key West and dinner outside once the sun starts to dip.
No complicated itinerary required.
Spring in Key West: March Through May
If you’re trying to decide when to visit Key West, spring deserves a serious look.
Temperatures steadily warm from around 80°F in March to 86°F in May, while March and April remain among the drier months of the year.
March
March brings warm days without full summer heat.
It’s a natural month for spending more time outdoors, whether that means walking Duval Street, heading out on a fishing charter or simply finding a spot beside the pool.
April
April might be one of the easiest months to love.
Average highs reach around 83°F, rainfall remains relatively low and warmer water makes boating and other outdoor plans increasingly tempting.
Late April also brings some of the island’s signature celebrations, including the annual Conch Republic festivities.
May
By May, Key West has settled firmly into warm-weather mode, with average highs around 86°F.
Music is often part of the plan too. The Key West Songwriters Festival, held around late April and early May, brings songwriters and live performances to venues across the island.
Then there’s the water.
Fishing, snorkeling, sailing or absolutely nothing beside the pool. All valid choices.
Summer in Key West: June Through August
Key West in summer runs warmer, wetter and a little more laid-back.
Average daytime highs sit around 89–91°F, so this is the season to build the day around water. Early starts, pool afternoons and sunset plans work nicely.
Summer also falls within Atlantic hurricane season, which officially runs from June 1 through November 30. Travelers visiting during this period should keep an eye on forecasts and build some flexibility into their plans.
June
June marks the start of the wetter season, with warm days and tropical showers becoming more common.
Translation?
Get on the water early. Keep the afternoon flexible.
July
July is hot, sunny and made for a slower schedule.
It’s also traditionally the month of Hemingway Days, celebrating the writer’s Key West years with events ranging from literary gatherings to the famous look-alike contest and Running of the Bulls.
August
August keeps the tropical weather going, with average highs around 91°F.
Foodies have another reason to visit: Key West Lobsterfest celebrates the start of Florida spiny lobster season with dinners, live music and festivities around town.
Pool. Lobster. Repeat.
Fall in Key West: September Through November
Fall starts tropical and finishes noticeably milder.
September is historically Key West’s wettest month, while conditions begin transitioning toward the drier season during November.
It also happens to contain one of Key West’s biggest parties of the year.
September
September is warm, humid and firmly within hurricane season.
The Atlantic season reaches its historical peak around September 10, so flexibility matters particularly at this time of year.
The upside? There’s something appealing about Key West when the schedule feels a little less crowded.
October
October comes with costumes.
Lots of them.
Fantasy Fest takes over Key West each October with parades, parties, costumes and events throughout Old Town. It’s one of the island’s biggest annual celebrations, so travelers planning around it should book ahead.
Stay on Stock Island and you can join the party when you want it.
Then come back to the marina when you’ve had enough.
November
November is the reset.
Average highs ease to around 81°F, rainfall drops and Key West begins shifting toward its dry winter season.
For travelers who like warm weather without peak-summer heat, it’s an underrated time to arrive.
Planning Your Key West Stay Around the Season
Found your month?
Now give yourself enough time to enjoy it.
If your travel dates are set, The Perry’s Advance Purchase offer can reward planning ahead, with current savings available for eligible prepaid stays booked in advance.
If your plan involves lingering a little longer, browse current Key West hotel offers, including any active offers for longer stays, to see what works for your dates.
Because one more marina morning rarely hurts.
So, What Is the Best Month to Visit Key West?
Our recommendation is April. It offers one of the best balances of warm weather, relatively low rainfall and plenty of time on the water, while arriving as the busiest winter period begins to ease.
That said, the right month depends on the trip you want. Come in winter for the driest, mildest weather; choose late spring for warmer days; visit in summer for pool and water time; or plan an autumn trip around Key West’s festival calendar.
At The Perry, you’ll have the marina outside, Old Town within easy reach and a waterfront base for exploring Key West in any season.
Key West Weather & Travel FAQs
What is the best time of year to visit Key West?
Late winter through spring is a particularly appealing time for warm weather and relatively low rainfall. April and May offer warmer temperatures as Key West transitions toward summer.
What is the weather like in Key West by month?
Average highs range from around 76°F in January to around 91°F in August. December through April is generally the drier period, while June through October receives more rainfall.
When is hurricane season in Key West?
Atlantic hurricane season officially runs from June 1 through November 30, with activity historically peaking around September 10. Travelers visiting during these months should monitor forecasts and consider flexible travel plans.
Is Key West good to visit in winter?
Yes. Key West winters are mild, with average daytime highs in the mid-to-upper 70s from December through February and comparatively low rainfall.
Is Key West worth visiting in summer?
Yes, particularly if your ideal trip revolves around pools, boating and water activities. Expect hotter, more humid conditions and a greater chance of tropical showers, and remember that summer falls within hurricane season.
