Fun Things To Do In Key West In September
September in Key West: The Underrated Sweet Spot
September is one of the best-kept secrets in Key West. With summer crowds fading and winter season not yet in full swing, this early fall window offers ideal conditions for laid-back adventures and unbeatable travel deals. From snorkeling in 86°F crystal-clear waters to catching live music at sunset, you’ll enjoy the best of island life with fewer crowds and a more local vibe.
In this guide, you’ll discover the top things to do in Key West this September – from iconic events like BrewFest and Womenfest, to relaxing boat rentals, sandbar trips, and farmers markets. Whether you’re planning Labor Day weekend or a full getaway, we’ll help you make the most of your trip.
Key West BrewFest
August 28 – September 1, 2025
Get ready to raise your glass at Brewfest, the tasting event in Key West! Hosted by Southernmost Beach Resort, soak up the sun, enjoy refreshing brews, and dance to live music. Experience this celebration & discover a variety of craft beers & seltzers! Learn more…
It’s 5 O’Clock in Key West: A Celebration of Jimmy Buffett
August 29 – September 1, 2025
Key West will host its annual Second Line Procession on September 1st, a vibrant event dedicated to celebrating the life and legacy of music icon Jimmy Buffett. This unique procession, which debuted in 2023 following Buffett’s passing at 76 after a battle with skin cancer, encapsulates the essence of Key West and Buffett’s spirit through music, stories, and his favorite things – rum, music, and stories. Learn more…
Key West Womenfest
September 3 – 7th, 2025
For decades, Key West’s Womenfest has attracted thousands of lesbians, bi-sexual, queer, transwomen, and allies to what is arguably the premier LGBTQ+ vacation destination in the country. Womenfest has a simple goal: to celebrate ALL women! See our Womenfest Guide
Get Out to a Sandbar!
Spend your vacation like a local, at the sandbar!
Explore the turquoise blue waters of Key West on your own boat rental. Stop at remote sandbars or just tour the island. There’s no better way to see Key West.
Be your own captain with a boat rental or let us do the driving and take one of our sandbar charters.
Green Parrot Charity Bingo
Join the Green Parrot Key West for Non-Profit Bingo. Every Monday night at 7:00 pm, we bring together the creative and artistic forces of our town to create a great fundraising opportunity benefiting one of the many local non-profits of our little island. Located at Green Parrot Key West, this event promises an evening of fun, games, and community support.
Cruise Around Key West
Cruise around Key West, island-style, with eco-friendly electric golf carts, Scooter Rentals, or gas-powered Golf Cart rentals. Discover the thrill of our roadworthy rentals, as they get you from one bucket-list spot to the next with a smooth and safe ride, perfect transportation experience for your vacation.
Truman Waterfront Farmers Market
Every Thursday, 2 pm to 7 pm
Wander along the harbor and harvest fresh produce, crafts, ready-to-eat delights, and art – all against a sunset backdrop at the Truman Waterfront.
You’ll find traditional farmer’s market fare including produce, seasonal fruits, cheese, pickles, nuts, honey, seafood, fresh breads, hot sauces and more. There are food stands and food trucks. It’s an eclectic group who collectively offer one-stop shopping at their weekly pop-up island bazar. Learn more.
Key West Artisan Market
Sundays discover an array of local artisans at the Key West Artisan Market. Located at Clarence S. Higgs Memorial Beach, this market offers a diverse selection of culinary delights, textiles, jewelry, woodworking, and more. Enjoy live entertainment, fresh produce, and delicious food while supporting local charities.
Double check their schedule
Local Tips for Visiting Key West in September
- Skip the Lines: September is off-season, which means walk-ins are easier at top restaurants – but locals still recommend reservations for dinner.
- Beat the Heat: Mornings and late afternoons are your best bet for outdoor activities. Midday? Head to Dante’s Pool Bar or get out to a sandbar like a local.
- Sunset Spots with Fewer Tourists: While Mallory Square gets the crowds, try Sunset Tiki Bar, White Street Pier or Fort Zachary Taylor beach for more local-friendly views. See our full Key West sunset guide.
- Rent Smart: Electric golf carts rentals and scooter rentals are a favorite for getting around Old Town – just make sure to book early.
- Storm Savvy: September is still hurricane season. It’s rare to get hit, but always check forecasts, buy refundable tickets, and consider travel insurance.
FAQ: Visiting Key West in September
What’s the weather like in Key West in September?
Expect warm and humid conditions with highs in the mid-to-upper 80s °F (around 30°C) and lows in the high 70s. Ocean temps hover near 86°F, perfect for snorkeling, boat rentals, and sandbar trips. Brief afternoon rain showers are common, but skies usually clear quickly.
Is September a good time to rent a boat in Key West?
Absolutely, be your own boat captain. September offers warm water, fewer crowds, and better availability. Ocean temperatures stay around 86°F, perfect for swimming, snorkeling, and sandbar hopping. It’s one of the best months for a boat rental without the high-season rush. Or, chose of our sandbar charters.
Unsure what to book? Contact us and we can find the best trip for your vacation.
Is September hurricane season in Key West?
Yes, technically – but direct hits are rare. Still, it’s smart to monitor forecasts and book accommodations with flexible cancellation policies just in case.
What’s the best type of boat to rent in September?
It depends on your vibe! For families or groups, pontoon boat rentals or deck boat rentals are perfect for relaxing and swimming at sandbars. For adventure seekers, center console rentals are great for faster rides, snorkeling, and fishing. Tiki boats are also popular for chill cruising and sunset tours.
See our boat rental guide or contact us to help you plan a vacation of a lifetime!
Is Key West busy in September?
Not really! After Labor Day weekend, crowds drop off significantly. You’ll find easier reservations, smaller tour groups, and a more local vibe.
Are restaurants and bars open in September?
Absolutely. Most businesses stay open year-round. A few might close briefly for renovations or staff breaks, like Blue Heaven. But you’ll still find plenty of options for dining and nightlife.
What should I pack for a trip to Key West in September?
Lightweight, breathable clothes, a swimsuit, reef-safe sunscreen, and comfortable sandals. A light rain jacket or poncho is also handy for sudden tropical showers. See our guide for what to pack on your boat day.
Do I need a license to rent a boat in Key West?
Florida does not require a boating license for most renters, but you may need to complete a short online boater safety course if you were born after January 1, 1988. We’ll walk you through it – super easy!
Can I visit a sandbar on my own rental boat?
Yes! Most of our guests choose self-guided sandbar trips. We’ll provide info, tips, and coolers. Wind and weather will determine which sandbar is best. See our Key West Sandbar Guide or hire a captain for a worry free day.
What’s the difference between a boat rental and a sandbar charter?
With a boat rental, you’re the captain. Perfect for freedom and privacy.
With a charter, our experienced local guides handle everything – driving, anchoring, and guiding you to the best sandbars and snorkeling spots.
Unsure what to book? Contact us and we can help plan your perfect boat day.
Are sandbar trips still running in September?
Definitely. In fact, September is a great month for them! You’ll find calmer waters and better availability. Sunset sandbar trips and mid-morning departures are especially popular this time of year.
