Best Things to Do in Key West During Fall

Key West, the southernmost point of the United States, is a tropical paradise that lures visitors year-round. While summer brings the sun worshippers and winter the snowbirds, the fall season offers a unique and enchanting charm of its own. As the island settles into a gentle and welcoming rhythm, it's the perfect time to explore Key West's fall activities and immerse yourself in its vibrant culture.

In this blog, we'll guide you through the top fall activities in Key West, from festive events to outdoor adventures. Start planning your fall getaway to Key West today and book your boutique accommodations with Dwell Key West! So, check it out, the top fall things to do in Key West:

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In this Blog:

• Enjoy Key West's Best Fall Weather
• Attended Fall Festivals and Events in Key West
• Fantasy Fest
• Sunset Celebration at Mallory Square
• Key West Film Festival
• Fall Water Activities in Key West
• Visit Dry Tortugas National Park
• Take a Sunset Cruise
• Sunset and Starlight Kayak Tour
• Explore Old Town Key West
• Ghost Tours and Halloween Events in Key West
• Zombie Bike Ride
• Robert the Doll After Dark
• Key West Firehouse Paranormal Investigation
• Book Your Fall Getaway with Dwell Key West!

Enjoy Key West's Best Fall Weather

The best thing about Key West's weather in the fall is that it is essentially an extension of the summer beach season, with seasonal averages starting in the mid to high 80s and hanging around the low 80s until November. November can be very rainy, but September and October are also firmly in the area's wet season, so we'd advise packing a few layers suited for the rain. Despite this, the fall time stays ripe for plenty of outdoor adventures, including snorkeling, swimming, and spending evenings watching beautiful sunsets.

Attended Fall Festivals and Events in Key West

Fantasy Fest

Fall kicks off with a bang in Key West, thanks to the world-renowned Fantasy Fest. Held at the end of October, this 10-day extravaganza is a must-see. It's a celebration of creativity, self-expression, and all things flamboyant. Imagine colorful costumes, elaborate masks, and whimsical floats parading down Duval Street. Each year has a different theme, ensuring that no two Fantasy Fests are alike. It's an event that showcases Key West's unique spirit and invites everyone to embrace their inner fantasy.

Sunset Celebration at Mallory Square

Although not exclusive to fall, the daily Sunset Celebration at Mallory Square is a timeless Key West tradition that's especially magical during this season. As the sun dips below the horizon, a carnival-like atmosphere unfolds. Street performers, artists, and vendors gather to create a vibrant spectacle. It's the perfect way to wind down a day of exploration and witness a breathtaking sunset over the Gulf of Mexico.

Key West Film Festival

This mid-November film festival features a mix of major award-season contenders, independent films, and documentary features, as well as several projects made in Florida. The festival has featured works by talents like Sean Baker, Sofia Coppola, and Pedro Almodovar. The festival will also include a focus on LGBTQ+ films, opening and closing ceremonies, and special screenings, with former installments featuring guests such as Miles Teller and Elizabeth Olsen.

Fall Water Activities in Key West

Visit Dry Tortugas National Park

A visit to Dry Tortugas National Park is a fantastic fall adventure. Located about 70 miles west of Key West, this remote and pristine park is accessible only by boat or seaplane. Explore Fort Jefferson, a 19th-century coastal fortress, and soak in the beauty of unspoiled beaches and crystal-clear waters. It's a peaceful escape from the hustle and bustle of daily life.

Take a Sunset Cruise

Get the famous sunsets of Key West in the best possible place to see them, right on the water! Sunset cruises offer a relaxed outing, panoramic views, and, in many cases, delicious food and beverages to go along with your ride. Most rides last 90 minutes to 2 hours, and most operators allow you to customize your ride to your liking. 

Sunset and Starlight Kayak Tour

For something a bit more stripped back, book yourself a kayak tour under the gorgeous Key West sky. The guided tours typically begin an hour before sunset, offering you a paddling experience through shallow waters and mangrove tunnels. Most providers will offer LED lights to accompany you during your trip, leaving the stress of preparation out of the picture. 

Explore Old Town Key West

Take a nice, long walk around the historic Western half of Key West. Observe the historic saloons, restaurants, and shops, with sections featuring 19th-century Conch-style architecture. The area also features stunning pastel homes and plenty of street entertainment, making the whole walk feel vibrant and exciting. If you're there during sunset, we'd recommend heading to Mallory Square, known for its beautiful waterfront views.

Ghost Tours and Halloween Events in Key West

As the nights grow longer, Key West's history comes alive in a spooky and entertaining way. With its long history of travelers and explorers, there are bound to be ghosts and goblins around. Join a guided ghost tour to hear tales of pirates, shipwrecks, and haunted houses. It's a fun and slightly eerie way to delve into the island's rich history, perfect for the spooky season!

Zombie Bike Ride

This Fun and Spooky Event takes place in the last week of October, celebrating the season with a bike ride featuring tons of themed costumes inspired by rock and roll, horror, and, of course, zombies. Zombie Bike Ride consistently draws thousands of visitors from across Florida and other states. Registration is only $10, making it easy for just about anyone to get in on the fright-filled fun!

Robert the Doll After Dark

Enter this fun, permanent display at the Fort East Martello Museum. The experience is based around the reportedly haunted doll, once owned by painter and Key West resident, Robert Eugene Otto. The tour begins after the museum closes, offering you exclusive access to the premises as you dive into the secrets of Key West's past. 

Key West Firehouse Paranormal Investigation

Another after-hours museum tour, although this one takes place over at the Alex Vega Key West Firehouse Museum. The two-hour tour is limited to 13 guests per night, with visitors walking through an immersive storytelling experience featuring audio narration and complimentary beverages.

Book Your Fall Getaway with Dwell Key West!

As you plan your fall adventure in Key West, consider staying at Dwell Key West. Our boutique hotel accommodations offer the perfect blend of comfort, style, and convenience. At Dwell Key West, we pride ourselves on providing personalized service to ensure your stay is nothing short of exceptional, with amenities including full kitchens, shared pools, and convenient parking. Our dedicated team is here to assist you with any inquiries, offer local recommendations, and make your Key West experience truly memorable.

Don't miss these fall activities in Key West, Florida. Book your vacation rental with Dwell Key West and embark on a journey filled with adventure, culture, and relaxation. Your Key West adventure begins with us!