The Keys Have a Fall. It Just Doesn't Show Up in the Trees.

Florida Keys Road Trip | October 20, 2026

Hey Keys lovers! Everybody says the Keys have no seasons.

No maples turning. No sweaters. No reason to own a rake. Just summer, and then more summer, and then Christmas decorations on a palm tree.

That is mostly true about the trees.

It is not true about the weather, and the numbers are more dramatic than almost anybody realizes. There is a real seasonal change down here. It is just measured in inches of rain instead of color.

Once you see the actual figures, you start picking your trip differently.

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❓ Keys Trivia

Key West does not get fall color. But one weather measurement drops by more than seventy percent between September and November.

Which one?

Answer at the bottom of the newsletter.

📣 The Mile Marker Roundup

Fall things, not year-round things. Most of these only exist for a few more weeks.

North to south.

🦞 The whole chain: Spiny lobster season Florida spiny lobster runs August through the end of March, which means right now it is on every good menu between Key Largo and Key West. No big front claws like a Maine lobster. All the meat is in the tail, and it is sweeter. Order it grilled and do not let anybody put it in a roll.

🦅 MM 56, Marathon: Curry Hammock Hawkwatch Fall is raptor migration season, and the counters set up at Curry Hammock to track birds funneling down the chain. Peregrine falcons, kestrels, broad-wings. Some days the sky genuinely has hundreds of them in it. Runs through roughly mid-November. Directions →

💀 Stock Island: Scarecrows and Skeletons in the Forest This is the one almost nobody knows about. The Key West Tropical Forest and Botanical Garden fills its trails with scarecrows and skeletons built from recycled materials by local artists, students and community groups. September through November. It is the Keys version of an autumn garden walk, except the foliage is tropical hardwood and there are birds passing through overhead. Directions →

🏁 MM 0, Key West: Offshore World Championship Powerboat racing on the Key West waterfront, November 1 through 8, with race days on the 4th, 6th and 8th. The harbor becomes a racecourse with a historic town sitting right behind it. Worth seeing once even if you have never cared about boat racing.

🎬 MM 0, Key West: Key West Film Festival November 18 through 22, centered on the Tropic Cinema on Eaton Street. Screenings and filmmaker programming in a town with a long creative history of its own. A good reason to be on the island in a month most people overlook.

🎭 MM 0, Key West: Fantasy Fest, final weekend If you are already down there, it runs through Sunday. This year's theme is Musical Icons and Iconic Musicals, and the parade is Saturday night.

🌴 Partner Spotlight

November Is the Month to Book

Here is the case, and it is a strong one.

By November the average high in Key West settles around 81 degrees. Rainfall drops to about two inches for the month. The water is still warm enough for everything you came to do. And the winter crowds, the ones who push rates to their annual peak, have not shown up yet.

So you get summer water, spring weather and off-season pricing, in a month with a real calendar of things happening.

That combination does not exist at any other point in the year.

FloridaKeysResorts.com can help you compare places to stay from Key Largo to Key West, with nobody taking a commission out of the middle.

See Florida Keys resorts →

🧩 Deep Dive

Three Different Islands in Ninety Days

Pull the National Weather Service climate normals for Key West and the fall looks like this.

September. Average high 89 degrees. About 7.2 inches of rain. The wettest month of the year.

October. Average high around 86. About 5.7 inches of rain.

November. Average high around 81. About 2 inches of rain.

Look at that rainfall column again.

September to November is a drop of roughly seventy percent. That is not a nudge. That is a different climate arriving over the course of about ninety days, and it is the single most useful thing a visitor can know about timing a trip down here.

Up north, fall announces itself. The trees do the work for you. You look outside, you know what month it is, and you dress accordingly.

Down here it is quieter than that, and people miss it entirely. Nobody looks at a palm tree and thinks "ah, November." The seasonal shift happens in the humidity, in how hard it rains on a given afternoon, and in how long you can stay outside before you need to go find air conditioning.

Which produces three genuinely different versions of the same island chain.

September is hot, wet and empty. It is the Keys with nobody in them. If you want to drive US-1 and feel like you have it to yourself, that is the month, and you accept the heat and the afternoon storms as the price.

October is the pivot. Still warm enough for everything on the water, starting to ease in the evenings, and then the back half of the month belongs to Fantasy Fest and the island changes character entirely.

November is the one people underestimate. Cool enough to walk around all day. Dry enough that outdoor plans mostly hold. Calendar still full. Rates still reasonable.

Most visitors pick winter because winter is obvious.

The people who come down every year quietly pick November.

🐦 The Last Gas Station Before Cuba

Here is a fall thing about the Keys that almost nobody thinks about, because everybody down here looks at the water instead of the sky.

Every autumn, a very large number of birds fly south through Florida. Hawks, falcons, songbirds, warblers. They come down the peninsula, and then the peninsula runs out.

What is left is the Keys. A hundred-mile chain of small islands, and then ninety miles of open water to Cuba.

So they stop.

The Keys become a staging area. Birds come down the chain, feed, rest, wait for the right wind, and then launch across the Straits. The hammocks and the botanical garden and the scrubby bits of green you drive past without noticing are all functioning as a rest stop for something that is about to attempt a very long flight over the ocean.

Some of them have come from Canada. Some are going to South America.

And for a few weeks in the fall, they are sitting in a tree at mile marker 56 on US-1, waiting on the weather, exactly like everybody else in the Florida Keys.

🍹 Four Things We'd Tell a Friend

Book outdoor stuff for the morning, even in November.

The rain pattern down here is afternoon-shaped. A ten o'clock plan survives a lot of days that a three o'clock plan does not.

Order the lobster while it lasts.

Spiny lobster is on menus the length of the chain right now and it is the best seafood value in the Keys. Grilled, with butter and lime, and nothing else getting in the way.

Look up once.

Specifically on Big Pine, Bahia Honda and Curry Hammock. You will see more birds in the air in a single October morning than most people see all year, and the whole thing is free.

If you have a flexible November, go then.

Warm water, dry weather, open restaurants, shoulder-season rates. It is the best combination of the year and it is the one month people forget to consider.

📖 One More Thing

Lost in the Keys: Mile Marker Thoughts is out.

It is about this drive. The bridges, the bars, the stops you mean to make and the ones you make by accident, and what goes through your head on a road that is mostly water.

If you have read it, a review helps more than you would think.

Get the book → 

🕰️ Lore & Legends

The Month That Gets Overlooked Every Single Year

There is a pattern to how people book the Florida Keys, and it has been the same for decades.

Winter sells itself. Somebody in Ohio looks outside in January, sees grey, and books March. Spring break fills in behind that. Summer runs on families and school calendars.

And then there is fall, which has spent a very long time being the part of the year nobody markets.

That is the whole reason Fantasy Fest exists. In 1979, Key West business owners looked at an October with nothing in it and invented a festival to fill it, and it worked so well that the back half of that month is now one of the busiest stretches of the year.

But look at what they left alone.

September is still quiet. Early October is still quiet. And November, which has the best weather of the three by a comfortable margin, is still the month almost nobody thinks to book.

Nobody has invented a holiday for it yet.

Give it time.

✅ Trivia Answer

Rainfall.

Key West averages roughly 7.2 inches of rain in September, its wettest month of the year, and about 2 inches in November. That is a drop of more than seventy percent in ninety days.

The temperature changes too, from an average high near 89 down to about 81.

So the Keys do get a fall.

It just happens in the rain gauge instead of the trees.

If you have a favorite month down here, hit reply and tell us which one and why. We have a theory that the answers from people who come every year will look nothing like the answers from people who have been once.

And if you have never seen the Keys in November, consider it.

Eighty-one degrees. Two inches of rain for the entire month. Water still warm. Restaurants open and not slammed. Birds overhead working their way toward Cuba.

The whole island chain in its best condition of the year.

And most people are not there to see it.

Until next week, keep your windows down and your watch off.

The Florida Keys Road Trip Team

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