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Why This Florida Beach Town Is The Perfect Fall Getaway This Year

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Key West is famous for its picturesque beaches, its near-tropical climate, and its uniquely quirky and off-beat vibes.

What’s not as well-known is that travelers can score some great deals on direct flights to Key West, making the dream of an easy-breezy Florida getaway more of an attainable reality.

So why should you fly to Key West to fall? Let’s check out what’s happening and show you some exciting new developments at this special southeastern corner of the United States.

Duval street in Key West

Why Visit Key West Now?

Though Key West may lack the flashy swagger of Miami to the north, Key West has its own special charm, as well as its own unique offerings.

This fall, Key West has plenty going on for everyone to enjoy.

Perhaps Key West’s biggest event of the fall is Fantasy Fest, a 10-day celebration (October 20-29) of the Halloween Spirit “Conch Republic style.” Not only are locals and visitors encouraged to dress up in their most creative costumes, but the festival also includes a parade, themed parties, visual and performing art events, family-friendly events, the signature pageant, and even a “Zombie Bike Ride!”

A "Rooster" Greets Visitors on the Street During Fantasy Fest in Key West, Florida

Key West has long been a popular destination for LGBTQ+ travelers, so it’s not too surprising to see the island kick off the fall season September 6-10 with Womenfest, a 5-day celebration of lesbians, trans women, other queer women, and allies featuring pool parties, drag shows, art exhibitions, sporting events, snorkeling outings, dance parties, and much more. 

Beyond Womenfest, several local hotels and resorts cater to LGBTQ+ travelers, including Island House, Alexander Guesthouse, and New Orleans House, and they usually host wild and fanciful parties every weekend.

In November, boat lovers of the world unite for the Key West Offshore World Championship, where the world's best offshore racers demonstrate their skills on the open waters. 

Then, on November 15, the Key West Film Festival kicks off. This is where new movies are premiered, international films that aren't easily found in the U.S. are screened, and everything from art house films to documentaries and specialty Florida films are presented. 

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aerial view of key west

What’s Also Available in Key West?

No matter when exactly you'll be coming to Key West, you will definitely have plenty to do. 

Even though Key West has had to deal with the sargassum seaweed situation that has plagued the entire state, the island nonetheless boasts some nice beaches, particularly the ones at Fort Zachary Taylor Historic State Park. Swimming, snorkeling, and diving opportunities abound, and November and December are usually prime times for exploring the water.

If you really want a fantastic beach day, head to Sunset Key for the most picturesque Caribbean-style shoreline. You can rent a cottage, book a spa treatment, and/or make a dinner reservation; plus they come with beach access. 

A Look at Sloppy Joe's Bar on Duval Street in Key West, Florida

As we hinted earlier, Key West is renowned for having fun around the clock, and this most definitely includes a lot of wild and crazy nightlife. Duval Street tends to have the most rocking bars and clubs (gay and straight) every night, plus it’s where you will find many of the island’s most iconic art galleries, restaurants, and other special storefronts. 

Keep in mind that during September and October, Key West is vulnerable to hurricanes (as is most of the rest of Florida). But starting in November, Key West enjoys its dry season, so late fall offers the area’s driest weather, and the island stays nice and warm. 

Thanks to Key West’s prime location, expect travelers to come and go throughout the fall season and into the winter holidays. Despite the obvious lack of fall colors and winter snow, the festive spirit of the season somehow persists throughout Key West.

The Entrance to Key West International Airport in Key West, Florida

How About Those Cheap Flight Deals?

So, what’s the deal with the chatter over cheap flights?

Earlier this week, The Points Guy spotted a bumper crop of cheap flights to Key West. Dates extend from September 2023 to July 2024, and American, Delta, and United are also offering lower ticket prices.

Some of these flight deals, such as an American round trip between Houston and Key West, involve a brief layover. But others, such as United’s round trip between Washington-Dulles and Key West, involve nonstop flights. 

delta plane

American offers baseline fares as low as $145 (from Houston), while United has fares as low as $188 (from Washington). 

As always, check the fine print for limits and potential surcharges. If you select the absolute cheapest Basic Economy fares with American, Delta, or United, seat selection will probably cost extra, and checked bags will definitely cost extra 

In addition, United does not permit carry-on bags with Basic Economy tickets, and Delta no longer allows passengers to earn SkyMiles with Basic Economy tickets. 

A Sunset View at Sunset Key and Wisteria Island Near Key West, Florida

Might This Be Your Time to Head to Key West?

Maybe so. Ultimately, that’s for you to decide. 

Hopefully now you have a better idea whether you can afford the ultimate Key West getaway. Key West may not always be the cheapest destination, but it always promises a great time. 

And now, you may at least be able to save some money on airfare this fall.

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Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.

Edward Orlando

Saturday 9th of September 2023

Looking forward to a fall vacation. at key west


Saturday 9th of September 2023

Too bad it's in Florida. I love key west but, I won't invest a dime into that state. Stop banning books and stop the witch hunt on drag queens.

J beard

Friday 8th of September 2023

No... key west is not known for their beaches.... they have 2 public beaches and they are not that great... its known for its character and small town feel..

Stew Shaw

Thursday 7th of September 2023

I lived in Key West for 30 years and it is completely misleading to characterize it as a beach town. The beaches are rocky, the sand is brought in from the Bahamas, they're man-made. When tourists ask me where the beach is I tell them Naples, Panama City or Ft. Lauderdale. Smathers Beach is the biggest one on the island and stinks with all the sargassum, the county Beach is big as a postage stamp, Truman Annex costs $ and is rocky, Simonton beach is as big as a walk-in closet but it's kind of nice, Sunset Key is nice but it costs $ to go to the most exclusive place in Key West. A great island for water sports, snorkeling, fishing, stuff like that, otherwise there are fabulous restaurants and a bar on every corner.


Thursday 7th of September 2023

I love, love, love Key West. The vibe and people are great. I drive down often from Ft Lauderdale and am amazed by the relaxed feeling that comes over me once I pass the 7-mile bridge. Then when I arrive in Key West I just feel happy.