A Traveler's Guide to Fall in Key West

With endless sunshine and good vibes, Key West is a great place to visit anytime, but as we locals can attest, there’s something extra special about the fall. Whether you want to relax and soak up the sun on the beach, immerse yourself in some haunted history for Halloween, or dive into some Duval Street debauchery for Fantasy Fest — fall has it all in the Florida Keys.

If youÂ’re ready to trade sweater weather and hot apple cider for beaches and margaritas, Key West is the perfect fall getaway. DonÂ’t worry; thereÂ’s still plenty of festive fun with pumpkin patches, ghost tours, and Thanksgiving dinner cruises. You can avoid the noise and crowds of hotels and enjoy all the comforts of home in a private vacation villa.

Here are all the fun details of fall in Key West to help you plan your trip!

 

Fall Weather in Key West

Fall weather in Key West fluctuates from warmer in early fall to cooler in late fall, but overall, temperatures tend to stay within the 70s and 80s, with plenty of sunshine and Caribbean breezes.

September is considered an extension of summer with hotter and sometimes wetter weather. ItÂ’s also still part of storm season, so visitors should watch for any local storm warnings.

October and November are typically cooler and drier, and the threat of potential hurricanes diminishes by late fall, making it the perfect time to be outdoors.

 

Best Things to Do in the Fall in Key West

ThereÂ’s plenty to do when you visit Key West in the fall. Conditions are still favorable for outdoor recreation, and there are lots of festive fall happenings.

 

Beaches and Watersports

With warm, sunny weather, fall is a great time to enjoy the beaches and be out on the water in Key West. Enjoy kayaking, paddleboarding, snorkeling, parasailing, and much more. You can also book a boat tour, fishing charter, sunset cruise, or many other water activities and excursions.

 

Outdoor Recreation

Fall is the perfect time to be outdoors in Key West, especially in the later months when itÂ’s a bit cooler. Enjoy hiking, biking, and exploring the nature preserves and botanical gardens. ItÂ’s also a great time to take the ferry out to Dry Tortugas National Park.

 

Shopping, Dining, and Entertainment

Key West is full of unique shops, great restaurants, and eclectic bars and nightclubs. Hunt for treasures in local boutiques, dine on fresh seafood and Key Lime Pie, kick back with cocktails and live music on Duval Street, and stroll through Mallory Square for the sunset celebration.

 

Visit Museums and Historical Sites

From the historic Hemingway House to the Civil War monuments of Fort Zachary, Key West is full of historic sites and fascinating museums. Step back in time at the Truman “Little White House,” see replicas of ancient shipwrecks at the Shipwreck Museum, and climb the famed 88 steps at the historic Key West Lighthouse.

 

Ghost Tours

ThereÂ’s no better way to celebrate the spooky season than in one of AmericaÂ’s most haunted cities. From haunted pub crawls to graveyard ghost hunts, Key West is home to numerous paranormal sites, historic haunts, and ghost tours that are unforgettable experiences.

 

Fall Events in Key West

Fall is one big party in Key West with holiday happenings and some of the biggest festivals of the year.

 

Fantasy Fest (October)

An event that probably needs no introduction, Fantasy Fest is one of the islandÂ’s most famous festivals, pulling in a whopping 75,000 attendees every October.

Fantasy Fest is a 10-day festival featuring elaborate costumes, parades, drag shows, music, pool parties, and much more. It’s been described as Mardi Gras mixed with Halloween — but with a typically little extra spice.

Although most events at Fantasy Fest are best for adults, they do offer some family-friendly options. Enjoy the Bahama Village Goombay Festival, an all-day event on Friday and Saturday filled with kid-friendly activities, the Zombie Bike Ride, ideal for the kids that would love to dress up as zombies for the day, and ChildrenÂ’s Day on Sunday.

For more details on all of the events that Fantasy Fest offers, browse through the schedule.

Whether you come with your kids or are eager for the adults-only fun, we recommend you book your vacation rental early; accommodations are known to sell out well in advance.

 

Halloween Events (October)

What better place to celebrate Halloween than in the haunted city of Key West? While you can partake in paranormal tours and ghost hunts all year round, itÂ’s an extra fun way to celebrate Halloween, and many tour operators offer special events.

YouÂ’ll also find other Halloween fun around the island, from costumed pub crawls and block parties to kid-friendly trick-or-treat events and pumpkin patches.

 

Key West Film Festival (November)

If youÂ’re a fan of the cinematic arts, youÂ’ll want to score tickets to the Key West Film Festival. This 5-day festival in November features special screenings of films, documentaries, and short stories. YouÂ’ll also get to participate in panel discussions, meet with filmmakers, and shop for unique film memorabilia. ItÂ’s a must for film buffs.

 

Trib Fest (November)

A culmination of some of the best tribute bands from around the world, Trib Fest pays homage to some of the most iconic performers of our time. From rock legends like Elvis and Queen to the legendary reggae artist Bob Marley and modern pop acts like Lady Gaga — you’ll find every kind of music at Trib Fest in November.

 

Thanksgiving Dinner Cruise (November)

You may not think of Key West as a traditional Thanksgiving destination, but the island offers a welcome break from the ordinary. You can still have your turkey and pumpkin pie, but youÂ’ll also get to enjoy conch fritters and Key Lime Pie. Celebrate Thanksgiving with a tropical twist at one of the many restaurants around Key West that feature a special menu, or book a Thanksgiving Dinner Cruise.

 

Packing for Your Fall Getaway

Ready to visit Key West in the fall? Here are some packing essentials:

• Swimsuits/beachwear


• Flip-flops and/or water-shoes


• Casual or athletic clothes for daily wear and outdoor activities


• Comfortable walking shoes


• Sun protection - hats, sunglasses, and reef-safe sunscreen


• A light rain jacket or poncho


• Mosquito repellent


• Waterproof phone case with floaties


• A small beach tote or backpack to carry your essentials


• A few dressier pieces, like sun-dresses or linen pants for upscale dining

DonÂ’t worry if you forget anything; Key West is full of shops that have everything you might need. And, of course, if youÂ’re planning to come for Fantasy Fest or Halloween, donÂ’t forget your costumes or festival wear.

 

Where to Stay for Your Key West Fall Getaway

Whether you’re coming for one of the festivals or just want to break away from the traditional fall destinations and enjoy some sunshine and warm water — Key West makes a fantastic fall getaway.

Stay close to all the best fall activities and events by booking your stay with Vacation Homes of Key West.

Choose from Duval Street bungalows, where you can be right in the heart of the party, not far from the secluded villas on Sunset Key, or beachside condos with epic views around the Truman Annex. ThereÂ’s a vacation home for every type of traveler and every size group in the Conch Republic!