Key West in September: Weather, Events, and What to Expect

Ask a Key West bartender about their favorite month and a surprising number will say September. The island is as empty as it ever gets. You can park, you can walk straight into a table at the places that turned you away in March, and the regulars at the bar outnumber the visitors. The water is still close to 86°F, lobster is on every menu, and the sunsets have started coming a little earlier, and a little more orange, every evening. There’s also a reason it’s empty. Key West in September sits at the statistical peak of the Atlantic hurricane season, and it’s the wettest month of the year. For the right traveler, it’s a wonderful, cheap, uncrowded month. For the wrong trip, it’s a gamble you shouldn’t take.

This guide is about knowing which of those you are. It covers the September weather and rain, an honest look at hurricane risk and how evacuations work, the water, the handful of events (Labor Day, Womenfest and the Poker Run), the lowest prices of the year and the businesses that close, what’s worth doing, what isn’t, and how September compares with August and October. Weather figures are NOAA 1991–2020 normals for Key West International Airport. Prices and dates were checked in September 2026; treat prices as the right order of magnitude and confirm 2027 dates before booking.

§ 01

Key West in September at a glance

§ 02

What a September trip costs

September has the lowest hotel rates of the year, and it isn’t close. Good Old Town guesthouses and even some of the big resorts drop to prices that would be unthinkable in February. The one rule is to book a rate you can cancel. Everything else here was checked in September 2026:

§ 03

September weather

September is still fully summer in Key West. The average high is about 89°F, the average low about 79°F, and the humidity is as heavy as it was in July. It’s the wettest month of the year, averaging about 7.2 inches of rain on around 16 days. Much of that falls in the usual short afternoon and evening thunderstorms, but September is also when tropical waves and disturbances pass through, and those can bring a gray, drizzly day or a full day of heavy squalls. Of all the summer months, September is the most likely to give you a day where the beach simply isn’t an option.

The flip side is that September also has plenty of beautiful days: bright, hot and still, with a flat sea and the kind of clear light that makes the reef glow. The days are shortening, and by the end of the month the sun sets around 7:15 p.m. A late-September evening, when the heat finally breaks around sunset, can be gorgeous.

§ 04

Hurricanes in September: what you need to know

The Atlantic hurricane season runs from June 1 to November 30, and its statistical peak falls around September 10. More major hurricanes have formed in September than in any other month, and several of the storms Key Westers still talk about came in this month or the next. Hurricane Georges passed directly over Key West on September 25, 1998. Hurricane Irma made landfall at Cudjoe Key, about 20 miles up the road, on September 10, 2017, as a Category 4. It flattened parts of the Lower Keys and wrecked Bahia Honda State Park’s campgrounds, and recovery took years. In late September 2022, Hurricane Ian passed well to the west of the island and still pushed storm-surge flooding into Key West’s streets.

None of that means a September trip is reckless. In any given week, the odds of a hurricane hitting Key West are low, and many Septembers pass without one. But the probability is higher than at any other time of year, and the consequences are real. Here’s how it plays out when a storm threatens:

• You’ll get warning. Hurricanes are tracked for days, and the National Hurricane Center’s forecasts give plenty of notice. Nobody gets surprised by a hurricane in Key West.
• Visitors leave first. Monroe County issues evacuation orders for visitors ahead of residents, often several days before a storm arrives and sometimes before its track is certain. Hotels close, and the trip is over.
• There’s one road. Everyone leaves on US 1, the Overseas Highway, through 100-plus miles of islands and bridges. It’s slow, and it’s the only way out by land.
• Flights sell out. Key West International is small, and seats disappear fast once an evacuation looks likely.
• A near miss still ruins days. Storms that pass well away can still bring rough seas, canceled boats, closed beaches and heavy rain.

How to book a September trip sensibly:

• Book refundable rooms and, if you can, refundable or changeable flights.
• Read the hotel’s hurricane policy. Many Key West properties waive cancellation fees if a mandatory evacuation is ordered.
• Buy travel insurance that covers hurricanes when you book. Policies won’t cover a storm that already has a name.
• Check the National Hurricane Center’s outlook daily in the week before you leave and while you’re here.
• If an evacuation order comes, go promptly. Don’t wait to see if it turns.

For the full seasonal picture, see our Key West weather and best time to visit Key West guides. If you’re driving down, our drive to Key West guide explains the Overseas Highway, which is also your way out.

§ 05

The water in September

The sea is still about 86°F in September, only a touch cooler than August’s peak, and between weather systems the reef can be wonderful: calm, warm and uncrowded, often with only a handful of people on the snorkel boat. After a tropical system passes, though, visibility on the reef can stay murky for a few days, and seas can stay lumpy long after the rain has cleared. If a reef trip or the Dry Tortugas ferry matters to you, build a spare day into the trip so you can move it.

Sargassum usually starts to ease by September, though heavy years can linger into the fall. As always, Fort Zachary Taylor and the sheltered beaches are the safer bet. Some years coral spawning, which usually comes in August, falls a few nights after the September full moon instead.

§ 06

September events

September has the thinnest events calendar of the year. That’s a big part of its appeal, but a few weekends do fill up.

Labor Day weekend (September 4–6, 2027)

The last long weekend of summer brings a burst of Floridians driving down, busy boat ramps, a lively sandbar and higher room rates for three nights. It’s the busiest weekend of the month. If you want the empty-island September, come the week after.

Womenfest

Key West Womenfest is one of the largest gatherings of LGBTQ+ women in the country, and it fills the island around Labor Day with pool parties, themed parties, live music, sunset sails, snorkel trips, bike and trolley tours, art events and food experiences. The 2026 festival ran September 2–6 under the theme “Lost Women in the Arts”. Expect the 2027 edition in the same early-September slot, and book the women-friendly guesthouses early because they fill.

The Key West Poker Run

On a weekend in September, thousands of motorcyclists ride down the Overseas Highway from Miami for Phil Peterson’s Key West Poker Run. The event started four decades ago with 46 riders and grew into South Florida’s biggest motorcycle party. Riders draw cards at five stops on the way down, the best hands play Texas Hold ‘Em at the end, and eight blocks of Duval Street close for a bike show and a weekend of noisy, good-natured biker celebration. If you like chrome and loud pipes, it’s great fun to wander. If you came for a quiet September, it’s the weekend to avoid Duval. Dates are announced during the summer.

Book Fantasy Fest now

September isn’t Fantasy Fest, but it’s your last realistic chance to book it. The island’s biggest party takes over the last ten days of October, and rooms sell out well ahead. If you’re thinking about it, sort your room in September at the latest. Our Fantasy Fest guide explains what you’re signing up for.

The rest of the month

Otherwise, September is quiet. The nightly sunset celebration at Mallory Square carries on, the bands on Duval still play every night, and the bars along the harbor feel like locals’ bars again. Key West Brewfest, which was traditionally held over Labor Day weekend, moved to early October in 2026, so check the current date if you’re planning around it. For the full calendar, see our Key West events guide.

§ 07

Crowds, prices and what closes

September is when Key West takes its own vacation. A good number of restaurants, bars and small shops close for a week or three, while owners travel, staff take time off and kitchens get renovated. Some hotels schedule refurbishments too. Most of the island stays open, but if there’s a particular restaurant or tour you’ve set your heart on, check its website or call before you book the trip. It’s a small price for having the rest of the island almost to yourself.

For more ways to make a low-season trip go further, see our cheapest time to visit Key West and Key West trip cost guides.

§ 08

What to do in Key West in September

Take your pick of the restaurants

This is the month to eat at the places you couldn’t get into in winter, often with the owner working the floor and time to talk. Lobster is in season and fresh, and the fish is local. Go early in the week, since some kitchens close a night or two more than usual in the low season.

Snorkel and dive between the weather

On the good days, the reef is warm, calm and quiet. Stay flexible, book mornings and let the dive shop tell you which day looks best. See our Key West snorkeling guide.

Catch your own lobster

With the mini-season crowds long gone, September is a relaxed time to try lobstering on a guided snorkel trip. Our Key West lobster season guide covers licenses, limits and technique.

Explore the museums on stormy afternoons

Rain days are what the island’s museums are for. The Shipwreck Treasure Museum, the Mel Fisher Maritime Museum, the Custom House, the Hemingway Home and the Key West Lighthouse and Keeper’s Quarters can easily fill a wet day. Our Key West museums and rainy day activities guides have the full list.

Find the quiet corners

With the crowds gone, September is the month for the parts of Key West most visitors never see: the cemetery at dawn, the lanes of Bahama Village, the tiny beaches at the end of Old Town streets, and the backcountry in a kayak on a still morning. Our Key West hidden gems guide is a good place to start.

Hear the music without the crush

Live music on Duval and in the harbor bars goes on every night of the year. In September you can get a seat at the bar, and the musicians have the time and space to take requests. See our Key West live music guide.

§ 09

What isn’t worth it in September

• Non-refundable anything. September’s low prepaid rates look irresistible until a storm cancels your trip. The flexible rate is worth the difference.
• A wedding with guests flying in. A September Key West wedding is a lovely idea with a real chance of being evacuated. If you do it, insure it and have a plan B date.
• A trip built around one boat day. If the Dry Tortugas is the reason you’re coming, September is the month most likely to cancel it. Build in a spare day, or come in spring.
• Driving down with a storm in the Gulf. If a system is forecast to approach during your dates, postpone. The Overseas Highway is no place to be heading the wrong way.
• Counting on a particular restaurant. Check it’s open before you plan an evening around it.

§ 10

A five-day September itinerary

• Day 1: Arrive and walk Old Town. Sunset at Mallory Square around 7:40, then dinner at a restaurant you’d never get into in winter.
• Day 2: Morning snorkel or dive, if the sea is calm. Afternoon at the Shipwreck Treasure Museum and the Mel Fisher Museum.
• Day 3: Dry Tortugas if the forecast is good. If not, a lazy day at Fort Zachary Taylor and the Hemingway Home.
• Day 4: Dawn kayak through the mangroves, a long lunch, and live music in the evening.
• Day 5: Early bike ride to the cemetery and Bahama Village, Cuban coffee, key lime pie, and home.

Treat the order as a suggestion. In September, you slot the water days in around the weather.

§ 11

What to watch out for in September

• The tropics. Check the National Hurricane Center outlook every day, and follow evacuation orders at once.
• Lightning. Afternoon and evening storms are frequent and electric. Get off the water, the beach and the pier when you hear thunder.
• Street flooding. Heavy rain and high tides can flood low streets in Old Town and New Town. Don’t drive or scoot through salt water.
• Heat and humidity. September is still summer. Drink plenty of water.
• Mosquitoes. The wettest month is also the buggiest. Bring repellent.
• Closures. Check restaurant, tour and attraction hours before you set out.

§ 12

September for different kinds of travelers

Budget travelers

It’s the cheapest month of the year, often by a long way, if you book flexible and accept the risk. See our Key West on a budget guide.

Solo travelers

An empty island, chatty bartenders and easy seats at the bar make September surprisingly sociable. See our Key West solo travel guide.

LGBTQ+ women

Womenfest makes early September one of the most welcoming weeks of the year.

Families

Schools are in session, so September is a quiet month for families. If you have preschoolers and flexibility, it’s cheap and uncrowded, but the heat and storm risk make it a harder sell with little ones.

Anyone with a fixed date

If the date can’t move, as with a wedding, a big birthday or a reunion, choose another month. November and April give you warm, calm weather without the hurricane risk.

§ 13

Beyond Key West in September

September’s great natural spectacle is up the Keys. From mid-September into November, migrating raptors funnel down the island chain on their way south, and the volunteer Florida Keys Hawkwatch at Curry Hammock State Park, near Marathon, counts them from a platform by the beach. The site is known for some of the highest counts of migrating peregrine falcons recorded anywhere. Even if birds aren’t your thing, Curry Hammock’s calm waters are among the prettiest paddles in the Middle Keys. See our Marathon guide.

• Bahia Honda State Park (MM 37), rebuilt after Irma, is quiet in September. See our Bahia Honda State Park guide.
• Looe Key Reef, off Ramrod Key at MM 27, is superb on calm September days. See our Looe Key Reef guide.

§ 14

What to pack for September

• Light, breathable summer clothes
• A good rain jacket and a compact umbrella
• Sandals and shoes that can get soaked
• Swimwear, a rash guard and reef-safe mineral sunscreen
• A hat and polarized sunglasses
• Strong insect repellent
• A phone power bank, useful if storms knock the power out
• Printed copies of your insurance policy and hotel hurricane policy

See our Key West packing list for the complete checklist.

§ 15

September vs August vs October

For the month before, see Key West in August, and our Key West month by month guide for the whole year.

§ 16

Is September a good time to visit Key West?

For flexible travelers who value space and price above certainty, September can be the best-value month of the year. Hotel rates are at their lowest, the water is still bath-warm, lobster is in season and the island feels like a small town again. Many repeat visitors swear by it.

But September is the peak of hurricane season and the wettest month on the calendar, and there’s a real chance your trip gets rained on, cut short or canceled. Book it only if you can book flexibly, insure it properly and genuinely shrug off a lost day or two. If you can’t, move the trip to November, when the storms have mostly passed, the humidity has broken and the island is still calm. Our best time to visit Key West guide compares the months.

§ 17

Frequently asked questions

Related Key West Guides

• Key West month by month: every month compared
• Key West in August: the month before
• Best time to visit Key West: weather, crowds and prices
• Cheapest time to visit Key West: the savings and the risks
• Key West weather: the climate explained
• Key West events: the full calendar

§ 19

Photo Credits

Flooded Key West street during Hurricane Georges: Hurricane Georges effects in Key West MM00014972 (2634866926) by Florida Keys–Public Libraries from Key West, Fla., USA, CC BY 2.0, via Wikimedia Commons.

Kayaking at Curry Hammock State Park: Florida Keys Scenic Highway – Kayaking in Curry Hammock State Park – NARA – 7718446 by Unknown author Unknown author or not provided, Public domain, via Wikimedia Commons.