Is September a Good Time to Visit Key West? You Bet It Is!
Welcome to the heart of hurricane season in the Florida Keys—but don’t worry, it’s still a great time to visit Key West. September may fall in the wet season, but if you’re flexible, it can be the perfect time for an unforgettable experience. Just keep an eye on the weather (and maybe invest in travel insurance).
Why visit Key West in September? Well, school is back in session, summer crowds are gone, and you’ll enjoy a little peace before the high season kicks off. It’s what I like to call the sweet spot of the year.
Key West Weather in September: What to Expect
Let’s talk Key West weather. On any given day, expect high humidity and average high temperatures in the mid-80s. Nighttime doesn’t cool off much—low temps hover around 80°F.
September is one of the wettest months of the year, with around 3 inches of average precipitation and over 20 days of rain. Yup, you’ll want a poncho.
But don’t worry! Rainy days in Key West just mean it’s time to explore indoor attractions like the Key West Museum of Art, the Key West Lighthouse, or Fort Zachary Taylor. Or, enjoy people-watching over a slice of key lime pie at a cozy café.
It can be a bit of a rainy season, this time of year… so what to Do on Rainy Days? So much to do!
Why September Might Be the Best Time to Visit
September brings a mellow, breezy vibe to the Conch Republic. Hotel rates tend to drop, the weather starts to mellow out (just a bit), and the island is refreshingly less crowded.
It’s the perfect time of the year to explore historic sites, take a walking tour through Old Town, or visit the Historic Seaport for cocktails and conch fritters.
Looking to relax under the palm trees? Head to Higgs Beach and soak in those crystal clear waters of the Gulf of Mexico and Atlantic Ocean. The water temperature stays warm—around 87°F—and it’s ideal for spotting marine life like tropical fish and sea turtles.
Water Activities you must check out in Key West
Water Adventures and Outdoor Activities
September still offers plenty of daylight for outdoor activities and Key West adventures. Try a snorkeling trip to our coral reefs, book a romantic sunset cruise, or head to Dry Tortugas National Park for a day trip to what feels like a private island.
Want something more low-key? Enjoy wine on a waterfront deck, watch the sun set with a view of the ocean, or stroll Duval Street for live music, tasty treats, and drag queen karaoke. It’s all part of the charm.
Fun Events in Key West in September
September might be off-season, but the party doesn’t stop:
- BrewFest (Labor Day Weekend): This annual event features craft beer, pool parties, beach games, and plenty of good times.
- Key West’s Womenfest: A celebration of diversity and community with drag shows, beach parties, and fun-loving revelers from around the world.
Toward the end of the month, the island starts buzzing with early events tied to Fantasy Fest—Key West’s biggest party. This annual 10-day party officially kicks off in late October, but the excitement starts early.
Travel Tips for September
Flying in? The Key West International Airport makes it easy to get here from just about anywhere in the continental United States.
Driving down? Make a stop in Key Largo—the first of the small islands in the Florida Keys—and ease into island time.
Hungry? It’s a great time to explore the best restaurants in town without waiting hours for a table. Plus, September is ideal for sampling local Key West food.
Packing tip: Don’t forget your umbrella, a waterproof bag, and a few backup outfits—just in case the tropical showers roll in.
Final Thoughts: September in Key West Is Still a Vibe
Whether you’re sipping frozen drinks under the sun, snorkeling with sea turtles, or dancing to live music on Duval Street, September offers the chance to enjoy Key West before the peak season kicks in.
Sure, it’s hurricane season—but there’s never really a bad time to visit Key West. With the right mindset and a flexible itinerary, September just might become your favorite time of year to visit this tropical island paradise.
Top things in Key West not to miss
Activities in September
Womenfest Key West – September 3 – 7, 2025
The popular festival for lesbians and their friends is designed to allow singles, couples and groups of women to experience the atmosphere of openness and acceptance that has made Key West an internationally acclaimed lesbian and gay vacation destination. Activities range from beach parties, snorkeling, sunset cruises, to live entertainment, an art workshop and much more.
History of Diving Museum Presents – Celebrating 20 Years! Featured Exhibit – until December 31, 2025
The History of Diving Museum’s new limited-time featured exhibit is open to the public! Starting May 21st, dive into the Museum’s 20th Anniversary Special Exhibit to learn about what it took to create the world’s largest collection of diving equipment on public display, how the Museum has evolved and grown over the past two decades, and what visitors have to look forward to in the future. Info: (305) 664-9737; www.divingmuseum.org
Truman Waterfront Farmers Market – Every Thursday – September 4
Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.
Expressive Painting Class Inspired by William DeBilzan’s Work – September 4
In a relaxed and welcoming environment, you’ll explore DeBilzan’s signature style—characterized by bold colors, elongated figures, and themes of love, identity, and connection—and create your own interpretation on canvas. No prior experience needed!
This is not your typical paint night—it’s an artful experience that invites you to connect with the emotional depth and storytelling behind DeBilzan’s work.
Studios of Key West: First Thursday Open House – September 4
Studios of Key West invites all to visit during First Thursday Open House, where art, conversation and community come alive after hours. Wander through the galleries showcasing the newest exhibitions, sip drinks under the stars at the Hugh’s Rooftop terrace, and explore the creativity in the third-floor artist studios. Take in the vibrant energy, connect with fellow art lovers, and discover hidden gems at Books & Books. Mingle, marvel, or make memories!
Exclusive 4-Course Dinner Featuring Guest Chef Ken Shiro Lumpkin – September 4
Experience a night where fine art meets fine dining in this unforgettable culinary event inspired by the bold and emotional work of artist William DeBilzan.
Under the open sky, guests will enjoy a 4-course dinner crafted in collaboration with the renowned guest chef Ken Shiro Lumpkin, whose culinary artistry mirrors the creativity and storytelling found in DeBilzan’s Caribbean-influenced paintings.
This is more than dinner—it’s a curated celebration of art, flavor, and story, designed to leave a lasting impression.
Truman Waterfront Farmers Market – Every Thursday – September 11
Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.
Swim for Alligator Lighthouse – September 13
Join Islamorada’s annual world-class, 8-mile open-water swim out to the iconic Alligator Reef Lighthouse and back. This unique and challenging experience can be conquered solo or on 2-, 3- or 4-person relay teams. Proceeds from the race go toward the effort to fully restore and re-light the 152-year old lighthouse.
Sheriff’s Animal Farm Open House – September 14
Visit the family-friendly Monroe County Sheriff’s Animal Farm, open the second and fourth Sundays of each month from 1 to 3 p.m. Animals include a capybara, possum, sloths, goats, birds and many more. Visits are free of charge, but donations of cash or fresh produce are always welcomed. Stock Island Detention Center, 5501 College Rd.
Free Immerse Yourself! Creating a World-Class Museum – September 17
Islamorada: Join the History of Diving Museum and its co-founder Dr. Sally Bauer as she takes us through what it took to build the Museum, and what challenges she and Dr. Joe Bauer faced in their 40 years of collecting and researching their historic collection. Presentation will be both in-person and virtual, and take place at 7 PM on September 17th at the History of Diving Museum, 82990 Overseas Hwy (MM 83 Bayside). Be sure to come early for the Museum’s extended hours and see Celebrating 20 Years! Featured Exhibit. Donations welcome. Info: (305) 664-9737; www.divingmuseum.org
Truman Waterfront Farmers Market – Every Thursday – September 18
Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.
Morada Way Third Thursday Art Walk – September 18
The Morada Way Arts & Cultural District’s Third Thursday Art Walk in Islamorada is the organization’s landmark, monthly event. This Thursday, enjoy a holiday-flavored edition of the art walk with Keys-inspired fine artists, vendors, residents, and visitors congregating on Morada Way in Islamorada. Enjoy a relaxing evening from 6-9 p.m. perusing local fine art, imbibing local craft beer and wine and listening to music, in the area between mile markers 81 and 82 at 151 Morada Way.
Walk on White Third Thursday Art Walk – September 18
Explore an array of arts-focused offerings at more than 20 locations showcasing the works of painters, photographers, sculptors, ceramic and mixed media artists, and artisan jewelry makers at this monthly third Thursday event from 6 to 9 p.m. Take in views of beautiful island architecture, exhibit openings, creative demonstrations, musical, literary and performance offerings and complimentary libations. White Street between Southard and United Streets.
Truman Waterfront Farmers Market – Every Thursday – September 25
Shop with a view every Thursday from 2 to 7 p.m. at the Truman Waterfront Farmers Market located on the harbor by the USCG Ingham Museum. Find great food options including ready-to-eat items, fresh Florida produce and other grocery items, along with gifts, home decor, art and more. Located at the corner of Southard Street and Weech Way.
Take Stock in Children Backcountry Challenge – September 26 – 28, 2025
This annual tournament offers anglers the opportunity to win coveted trophies for trout, snook and redfish. Fishing is allowed around the clock from Friday night through Sunday afternoon. A popular weekend auction showcase and Sunday evening dinner are open to the public. Proceeds support local vocational scholarships for all ages and Take Stock in Children scholarships for financially challenged Upper Keys students.
Conch Scramble Charity Golf Tournament – September 26 – 27, 2025
The Conch Scramble is a charity golf tournament that uses boats instead of golf carts. Costumed teams boat to “holes” located at area marinas, bars and restaurants where players tee off from land to hit holes situated in the water. The legendary kick-off party – open to the public – takes place on Friday, Sept. 26 from 5 to 9 p.m. at SD Marine, mile marker 85.5 bayside, with the tournament on Saturday. Spectators can watch the wacky play from several favorite Islamorada watering holes on Saturday including Lorelei, Marker 88, and Oceanview Inn.
Sheriff’s Animal Farm Open House – September 28
Visit the family-friendly Monroe County Sheriff’s Animal Farm, open the second and fourth Sundays of each month from 1 to 3 p.m. Animals include a capybara, possum, sloths, goats, birds and many more. Visits are free of charge, but donations of cash or fresh produce are always welcomed. Stock Island Detention Center, 5501 College Rd.
Rams Head Presents: Puddles Pity Party – September 28
Puddles Pity Party, the 7-foot sad clown whose golden voice is comparable to rock legends like Tom Jones and Freddie Mercury, has amassed over 900K YouTube subscribers and performed sold out shows around the globe including The Kennedy Center in D.C., San Francisco’s Palace of Fine Arts, London’s Soho Theatre, and a residency at Caesars Palace in Las Vegas.
Looking to head down toward the end of October? Be sure to check out all of the activities with Key West’s biggest festival… Fantasy Fest
