September might sound like an in-between month. A pause after the summer rush and before the winter crowds hit, but Key West in September is often one of the most rewarding times to visit. You’ll find a lively calendar packed with unique festivals, fewer lines at top attractions, warm ocean temperatures, and a local atmosphere that lets you dive deep into everything offering in a little less hectic environment. Whether you dream of diving alongside vibrant reef fish, wandering through art-filled alleys, or relaxing on a quiet beach, this guide has the most up-to-date advice to help you plan your perfect early fall trip to Key West.

Why Visit Key West in September?

When Labor Day crowds disperse and vacationers head back north, Key West starts slipping back into its easygoing, island groove. September is the sweet spot for travelers who want a more authentic Key West experience. Imagine no waits at the best restaurants, easy bookings on the best day trips, and a friendly, local vibe all over Old Town. The summer humidity lingers, but only in brief spurts. Expect daytime highs in the mid-80s and comfortable evenings. While brief showers can pop up, you’ll often be rewarded with clear skies and gorgeous sunsets. Visitors who plan ahead almost always snag stellar hotel and tour deals, sometimes at rates you’d never see during high season.

Key West September Events and Festivals in 2025

Wondering what to do in Key West in September beyond hitting the usual sights? Here’s where the town truly shines. Forget just sticking to Duval Street. September’s event calendar brings out the best in local culture, sports, and artistry with something to match nearly every interest and mood.

Marathon International Bonefish Tournament

Anglers looking for bragging rights won’t want to miss the 66th annual Marathon International Bonefish Tournament held September 25-28th This iconic sporting event attracts pros and passionate amateurs alike. Even if you’re new to the sport, you’ll witness some of the area’s best fishing action and get a feel for generations-old local traditions. For up-to-date registration and schedule info, check community boards or visit local tackle shops when you arrive.

Gallery Nights and Arts Festivals

If you want a night out that feels distinctly Key West, plan to stroll a Gallery Night or pop into one of the September arts festivals. Local studios and galleries open their doors for after-hours browsing, often paired with live jazz, wine tastings, or talks with featured artists. Look up the Studios of Key West and the Key West Art and Historical Society’s events calendar before your trip. You might catch an impromptu printmaking workshop or a pop-up sculpture show in an old cigar warehouse.

Womenfest Key West 2025

Mark your calendar for September 3–7, 2025. Womenfest has grown into one of the largest LGBTQ+ women’s festivals in the country. You’ll find everything from dance parties at Aqua to snorkel sails, trivia nights, inspiring workshops, and community networking events across the island. There’s no experience more welcoming or empowering in the Florida Keys and visitors of all stripes are genuinely invited to join in.

Best September Activities in Key West in 2025

Water Adventures and Excursions

September offers some of the best ocean conditions for snorkeling and diving Key West has all year. Warm waters mean comfortable swims even early in the morning plus, with fewer boats out, you’re more likely to spot the good stuff like sea turtles, eagle rays, and nurse sharks around the reefs. It’s also a great time to get certified to dive with fewer students in the area.

Snorkeling tours to Sand Key Lighthouse and the Western Sambo Ecological Reserve
Dolphin watching and glass bottom boat trips departing daily from the Historic Seaport
Kayak or paddleboard rentals for winding solo journeys through lush mangroves
Iconic sunset sails with live music and a local rum punch toast as the sky lights up over Mallory Square

Here are some of the best water sports companies in the Key West:

Eco-Tourism and Nature Exploration

September brings a migration boom for birders. White-crowned pigeons, warblers, and ospreys sweep through the Lower Keys. Learn more about where to bird in Key West.
Sign up for a guided kayak or paddleboard eco-tour through the Key West National Wildlife Refuge, where you’ll spot juvenile sharks and maybe even a manatee.
For independent adventurers, hike the shaded trails of Fort Zachary Taylor State Park and catch glimpses of fall wildflowers along the Old Town walking routes.

Adventure Sports and Active Exploration

Feeling ambitious?

The consistent breezes of September open up the island’s best kiteboarding and windsurfing conditions. Several outfitters near Smathers Beach offer lessons and gear rentals.
For a slower pace, locals swear by early-morning bike rides through the residential streets of Bahama Village and along the Atlantic shoreline. Most hotels provide complimentary bicycles, or you can snag a rental for the week at reasonable rates.

Best Restaurants, Culinary Experiences and Local Flavors in 2025

A Key West September feels delightfully unscripted for food lovers. Local chefs take advantage of the early fall seafood catch (spiny lobster season runs through March!) and get creative with menus. Ignore the guidebooks telling you where to eat. Just follow your nose to pop-up food truck gatherings or the Saturday morning market at Truman Waterfront Park.

The Lobster Shack is regularly voted the best lobster roll in Key West
Try some Key West “Dinnertainment” cooking classes at Key West Cooking School
Sample island-inspired tapas and fresh ceviche at popular Duval Street happy hours
Don’t miss September-only specials at Eaton Street Seafood Market and Fisherman’s Cafe—perfect for travelers on a budget

Culture, History, and Local Art

Step under the shade of gumbo limbo trees and into the past with a self-guided tour of the Ernest Hemingway Home. September is ideal for skipping the crowds at hotspots like the Key West Lighthouse and the Mel Fisher Maritime Museum.

In the evenings, gather your courage and set off on a local ghost tour or hunt for quirky bits of island lore with a walking storyteller. Several workshops offer the chance to paint your own seascape or join in a found-art project. These creative sessions sometimes stretch late into the night when the vibe is just right.

Wellness and Relaxation in Key West

Not every moment on the island needs an itinerary. Recenter with sunrise yoga on Higgs Beach or book a hammock massage in a private tropical garden. Try a reiki workshop at a local studio to slow down and reconnect. From infrared saunas to oceanfront meditation circles, you’ll find plenty of options that recharge both body and mind.

Practical Tips for Visiting Key West in September 2025

Where to Stay: Look for September specials at family-owned B&Bs in Old Town, where innkeepers are always happy to recommend their favorite events that week. Big-name hotels often drop rates by 20–35% after Labor Day, particularly on weeknights.
Getting Around: Ditch the car. Bike rentals are everywhere and make zipping from Smathers Beach to Mallory Square a breeze. The Duval Loop bus is free and covers the heart of downtown. If you do rent a scooter or golf cart, check parking rules closely.
Packing Guide: Bring light, breathable clothing, rain gear for passing showers, sunscreen, and a refillable water bottle. Don’t forget water shoes or sandals for the coral beaches and reefs.
Weather and Safety: Stay informed by bookmarking the National Hurricane Center’s website and signing up for local alerts on your phone. Most businesses share their storm protocols and usually remain flexible with last-minute travel changes.

Frequently Asked Questions (FAQs)

Is September a good time to visit Key West for weather and crowds?

It is! You’ll enjoy warm ocean temperatures, quieter evenings around Old Town, and lower prices at times. While short rain showers happen, they often clear up quickly. September’s chill, uncrowded atmosphere lets you experience Key West more like a local.

What are some unique, off-the-beaten-path activities in Key West in September?

Consider a sunrise kayak through Boca Chica Channel or Cow Key Channel.
Santiago’s Bodega for is awesome for tapas and wine.
Rent a bike and explore hidden murals in neighborhoods like the Meadows. Here are some other ideas for public art.

Are there any special travel deals or discount events during September?

Travelers notice flash sales on both hotel rooms and water excursions once school starts. Several restaurants offer local pricing on drinks and menu items to encourage business during the slower season. Bundle your ferry, snorkel trips, and museums with passes from tourism kiosks near the Seaport for additional savings.

How do hurricane season risks affect travel plans for September in the Keys?

Stay flexible. Check forecasts in the two weeks leading up to your visit and confirm cancellation or rescheduling policies with hotels and tour operators. Buying comprehensive travel insurance in late summer is a smart move and rarely costs much extra.

Are water sports and diving safe and available throughout September?

Yes. We monitor weather reports closely and adjust schedules when necessary. Visibility is generally still great post-summer. Diving, snorkeling, sunset cruises and sandbar trips are all great options for Fall activities in Key West.

Plan Your Ultimate Trip to Key West in September 2025

September in Key West brings out the island’s best-kept secrets and one-of-a-kind events. With a little planning, you’ll grab the best hotel deals, sip cocktails at uncrowded bars, and catch sunsets that feel practically private. Whether you’re here for Womenfest, kayaking in the backcountry, hopping from gallery to gallery, or simply soaking up the salty air and easy pace, September is your window into the heart of the Keys.

Things to Do in Key West in September