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Perfect Day in Key West

Perfect Day in Key West

Perfect Day in Key West

Kit Williamson from Eastsiders shares his must-see itinerary for Key West's hottest attractions. 

OUT sent newlyweds Kit Williamson and John Halbach, from the acclaimed series, Eastsiders, to our favorite gay mecca, Key West. From breakfast pineapple pancakes to poolside margaritas, and from private tours of the Hemingway Home to nude snorkeling off the Florida coast, these guys experienced and discovered all that Gay Key West has to offer. Follow along as Kit and John take you OUT in Key West. 

There’s so much to see and do in Key West. You can take in the history, the community, and the natural beauty all around you. This is our perfect day in Key West. 

Key West Butterfly & Nature Conservatory

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Located right on the famous Duval Street, the Key West Butterfly & Nature Conservatory is a must-see for any visitor to Key West. Nowhere else will you have the chance to get up close and personal with hundreds of the most beautiful butterflies you’ve ever seen flying and floating amongst an amazing collection of exotic flowers, birds, plants, and trees. 

Kit's Take: This is a great spot to see something special and take some incredible photos. Get a selfie with a monarch, but be careful not to accidentally bring any “hitch-hiking” butterflies out with you; they all have to stay at the conservatory. 

Southernmost Point

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Only 90 miles from Cuba, the Southernmost Point Buoy marks the Southernmost point in the continental United States. One of the most visited spots in Key West, guests line up to take each other’s photo here. 

Kit's Take: It’s really cool to know that you are standing at the southernmost point in the continental United States and standing in line to get your photo taken is a great opportunity to meet locals and fellow travelers. Pro tip: beat the heat by visiting the coconut salesman nearby. He’ll drill a hole in the shell for you and hand you a straw!

The Ernest Hemingway Home & Museum

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Right in the heart of old town Key West, The Ernest Hemingway Home & Museum gives you a look at where one of America’s most legendary authors lived for ten years and wrote over 70 percent of his work. Step back in time and see the rooms where he wrote “For Whom the Bell Tolls,” and where he threw some incredible parties with notable guests such as Tennessee Williams. The property also serves as home to more than 50 polydactyl (6-toed) cats! Hemingway was given a white six-toed cat by a ship's captain and some of the cats who live on the museum grounds are family members of that original cat, whose name was Snow White.

Kit's Take: The house has an informative app for a self-guided tour. It also includes names and descriptions of all of the Hemingway House cats if you want to try and meet all 54 of them. Bring some cat treats, and make sure you ask the curator about all the celebrities that have gone swimming naked in Hemingway’s pool. 

Rainbow Crosswalk

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In 2015 Key West permanently installed 4 Rainbow Crosswalks at the intersection of Duval and Petronia Streets to show unity with their LGBT residents and visitors. It is estimated that about 2/3 of the Key West population is LGBT. The rainbow crosswalks are the perfect embodiment of the Key West motto that was adopted in 2000, “One Human Family.” Accepting diversity has been going on for generations in Key West, even when it was an island that could only be reached by boat. It’s a tradition that is still very important to the community today. 

Kit's Take: Everyone we met in Key West was welcoming and hospitable. They are really proud of the city’s motto that we are all “One Human Family,” and it’s clear they really try to live by that philosophy.

Sunset Celebration at Mallory Square

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Every night, about two hours before the sunset, tourists and locals alike gather at Mallory Square to watch the sun disappear into the Gulf of Mexico. There are a ton of food carts, bars, and street performers to take in while you enjoy the scenery. 

Kit's Take: I love a trained cat show, and the Sunset Celebration has an AMAZING one. There was also incredible fire-juggling, music, and shopping. Be sure to get a  mojito from one of the bars on the pier to drink while taking it all in. 

For more coverage of Kit and John's trip to Key West, head to, and to book your own OUT in Key West experience, visit

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Kit Williamson