Top 10 Things To Do In Key West


Your Perfect Vacation Awaits: Top 10 Things to Do in Key West

Ready for an unforgettable vacation with blue skies, clear waters and over 350 bars and restaurants on a 4×2 mile island?

Of course you are.

But you’ve only got a few days, and you don’t want to miss anything, right?  Here are our top 10 things to do in Key West so you can make the best of your vacation:

1) Get on the water.  From beaches to eco-tours to water sports, there really is something for everyone.  Our favorite water activity hands-down is snorkeling.  The Florida Keys is home to the only living coral barrier reef in the continental United States so it’s a no-brainer.  Not interested in swimming with the fishies?  Our 2nd favorite water activity is sipping wine while relaxing on a sunset sail.  Ask our Concierge for tips on which activity is best for you!

top 10 things to do in key west - Sunset Sail Nick Doll

Key West Sunset Sail, Nick Doll Photography

2) Lunch like the Locals.  Whether you want to dine on the waterfront, off the beaten path, or on Duval St, the options are plentiful.  But if you want fresh ingredients with a unique Key West atmosphere then you must try the popular food cart, Garbo’s Grill.  Featured on the TV show “Diners, Drive-ins & Dives,” they create big island flavors made to order.  Just be prepared to sit on a bucket while you eat.  Another local’s favorite lunch spot?  Stock Island’s Hogfish Bar & Grill for authentic Florida Keys cuisine and atmosphere with panoramic views of a working marina. Best of all, pets are welcome at both restaurants!

3) Check out the local art.  Surrounded by one of a kind sculptures, the red-roofed Custom House is in the heart of historic Old Town, steps from the harbor and Mallory Square.  This former post office, customs and security office now has two floors dedicated to two centuries of art, history, people and events.  Another favorite located on Eaton Street is The Studios of Key West.  This arts organization brings world class artists to Key West and is best known for their monthly event, “Walk on White.”

4) Tour famous homes.  Making everyone’s list of top things to do in Key West, you absolutely must take the opportunity to tour The Harry S. Truman Little White House, the Key West vacation home of President Truman for over 175 days while he was in office.  Then head over to The Ernest Hemingway Home & Museum just down the street.  Hemingway lived there from 1931 to 1939 and this beautiful piece of land has friendly 6 toed cats ready to welcome you.

top 10 things to do in key west - Hemingway House

Hemingway House and Museum located in Historic Old Town, Key West

5) Take unique Key West photos.  Your first stop: the Southernmost Point.  From this famous buoy, you’re closer to Cuba than you are to the nearest Walmart.  This is the most authentic souvenir (that’s also free!) you can get in Key West and every time you glance at the photo on your desk at work in the wintertime, you’ll get all warm and fuzzy inside.  Don’t forget to capture pics of Mile Marker Zero, conch cruisers, Key West sunsets and of course, lots and lots of roosters!  Extra points are awarded to those who grab a photo with the “girls from the 800 block” of Duval Street.  See #9 for more details.

6) Take a train or trolley tour.  Yes, we know this is considered “touristy.”  But guess what, you ARE a tourist!  It’s a great way to learn about our Conch Republic history and architecture.  You’ll find that there is much more to Key West than our world famous bars (ha!).  It’s also a great way to plan out your vacation since it will drive past all the hot-spots.  Ask our concierge to help you purchase tickets and skip the lines!

top 10 things to do in key west - conch train

The World Famous Key West Conch Train as it passes the Custom House in Old Town, Key West

7) Attend the nightly “Sunset Celebration.”  One of the longest living traditions in Key West, locals and tourists alike gather at Mallory Square on the waterfront each night to admire the breathtakingly beautiful Key West sunset.  Street performers and vendors make the event even more interesting with tight rope walkers, fire jugglers and the one and only cat show which features trained housecats and their “unique” trainer, the infamous Catman.

8) Create your own “Duval Crawl.”  It’s no secret that Key West is a great place to party.  Duval Street is covered with bars within steps of Old Town Manor that are oozing Key West’s unique and fun atmosphere.  Check out historic bars like Captain Tony’s and Sloppy Joe’s, then check out newer favorites like The Porch, The Other Side…the list goes on!

9) Catch a drag show.  Key West’s unofficial motto of “One Human Family” means everyone is accepted no matter your race, sexual preference, drink choices, etc.  The nightly shows at Aqua are a hoot.  The performers will sing along with the greatest hits while interacting with the audience.  Don’t forget your dollar bills – tipping is recommended!  Also, check out Drag Queen Bingo at 801 Cabaret every Sunday night at 5pm.

10) Learn about Key West’s Haunted Past.  Key West was originally named “Cayo Hueso,” which when translated means “bone key” or “bone island.” The land is said to have been covered with bones as a Native American burial ground.  Experience the stories first hand with a walking tour at the above-ground cemetery (dating back to 1847) or hop aboard a spooky and fun ghost trolley trip.  And guess what?  Old Town Manor is one of the Key West accommodations highlighted on the walking tour – eek!

We hope this list has given you plenty of options next time you’re trying to find things to do in Key West!  Read more Key West blogs or go back to our Old Town Manor home page.