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19 Best Things To Do In Key West – Close to Perfect and Far from Normal

19 Best Things To Do In Key West – Close to Perfect and Far from Normal

Looking for the Best Things To Do In Key West, FL?

The Florida Keys is a tropical paradise known for its magnificent coral reefs, pastel homes, and low-key Caribbean attitude. A mecca for sports fisherman and treasure hunters alike, the Keys hum with a unique vibrancy.   

Key West is the very heartbeat of the Florida Keys and likely the most unique of all the small islands. Discovered in 1521 by Ponce de Leon while searching for the fountain of youth, Key West has a rich history filled with pirates, shipwrecks, and sunken treasure.

A trip to the Keys is not complete without exploring Key West; it’s culture, color, and local flair make it well worth the trip. The following is a list of 19 things you should try to fit in during your stay.

19 Best Things To Do In Key West, FL

Food and Drink

1.  A Key West Tradition Sloppy Joe’s

The origin story of Sloppy Joe’s is as colorful as one could imagine. The establishment opened for business on December 5, 1933; the day prohibition was repealed; prior to December 5, the owner Joe Russell had been operating an illegal speakeasy catering to the likes of Ernest Hemingway, which led to a lifelong friendship between the two.

Once the prohibition ban was lifted Russell was free to run a legitimate operation. In fact, it was Hemingway that convinced Russell to name the place Sloppy Joes, based on a Spanish bar owner from Hemingway’s past, who ran a “sloppy” business.

The Restaurant features nightly live music and fantastic bar food and is home to Joe’s Tap Room, a side bar away from the main area that has an exciting collection of beers on tap, including Florida Keys Brewing Iguana Bait, Sloppy Joe’s Island Ale and 3 Daughters Key Lime Apple Cider to name a few.

If your travels bring you to Key West in July, you will not want to miss Sloppy Joe’s Annual Papa-Lookalike-Contest, a yearly contest in homage to Hemingway. A do not miss destination.

See more: Best Beachfront Hotels in Key West

Sloppy Joe's Things To Do In Key West

Sloppy Joe’s/ Flickr

2.  Fresh Seafood at Half Shell Raw Bar

The original seafood restaurant in Key West, The Half Shell Raw Bar, opened in 1972 and is housed in what was originally a shrimp warehouse. Half restaurant, half fish market, Half Shell Raw Bar is a whole Key West experience.

From ocean to table, you will experience the freshest seafood imaginable. Enjoy the raw bar, oysters on the half shell, or freshly caught Mahi Mahi. You can take in the sunset while enjoying waterfront dining or watch the fishing boats return to dock with their daily catch. The Half Shell Raw Bar is perfect for families that want casual dining and the freshest fish imaginable. One of the best Key West attractions.

Half Shell Raw Bar

Half Shell Raw Bar/ Flickr

3. Cuban Coffee at 5 Brothers Grocery and Sandwich Shop

If you want the entire islander experience, you will want to make a stop at 5 Brothers, located at the corner of Southard and Grinnell Streets in Old Towne.

Their grab-and-go window has a steady stream of locals lining up for their authentic Cuban coffee and sandwiches. A family-owned operation and a staple in the community, they are renowned for their strong Cuban coffee (no vanilla latte’s here) and generous Cuban mix sandwiches.

Off the main path and well worth the visit, the early morning rush is your best chance to enjoy the sights and sounds of busy Key West waking up.

See more: Luxury Hotels in Key West

5 Brothers Grocery and Sandwich Shop

5 Brothers Grocery and Sandwich Shop/ Flickr

4. The Atmosphere at Blue Heaven

When you think of Key West, you think of the whimsical, free-spirited, and colorful, and all three of these collide at Blue Heaven, leaving you with a genuinely enriching Key West experience. Before you even take the first bite of your meal, there is so much to see.

From your seat in the courtyard paved with slate belonging to the tops of pool tables from the billiard hall it once housed, you can watch the roaming cats and feral chickens or take a quick stroll over to the rooster cemetery, an area paying homage to the lives lost during past cock fighting on the grounds. The property is rich in quirky, fantastical history (boxing matches refereed by Hemingway himself).

Blue Heaven, located in Bahama Village, is the creation of Suanne and Richard; armed with a bootstrap budget, some elbow grease, and determination, they have turned Blue Heaven into a foodies Mecca. Despite the fiesta-like atmosphere, the food is the shining star. Indulge in fresh seafood, sample the spices of Caribbean cuisine, and enjoy the extensive vegetarian options. Open for breakfast (they are known for their eggs benedict), lunch and dinner; you will not be sorry you stopped in. One of the best spots for breakfast in the Keys.

Blue Heaven Things To Do In Key West

Blue Heaven/ Flickr

5. Jimmy Buffet’s Beginnings at Captain Tony’s Saloon

You know you are in for a good time when you walk into a morgue that doubled as an icehouse turned into a celebrity-studded saloon. Welcome to Captain Tony’s!

Captain Tony Taraccino purchased the bar in 1958, and little has changed since then, right down to the “hanging tree” still growing in the middle of the bar. The smell of great food and the cheerful atmosphere hit you when you walk through the doors. The favorite watering hole of local legends such as Hemingway, Tennessee Williams, and Shel Silverstein.

Musician Jimmy Buffet got his start playing gigs at Captain Tony’s, and it is a favorite destination for his fans, Parrotheads. Perfect for a night out with live music and a full bar, be sure to wear your dancing shoes (or no shoes at all).

Captain Tony’s Saloon

Captain Tony’s Saloon/ Flickr

Beaches in Key West

6. Natural Beach at Fort Zachary Taylor Historic State Park

The historical significance alone makes the Fort Zachary Taylor State Park worth the visit. The fort was important during both the Civil and the Spanish-American Wars and is host to dramatic re-enactments once a month.

But the beach is why tourists and locals alike flock to the state park, located at the southern end Zachary Taylor Park is one of the only natural beaches (made of ground coral) in all of the Keys. The swimming area is shallow enough to be family-friendly and deep enough to snorkel (you can rent snorkel equipment at the park). Plan to spend the day enjoying the cool ocean water.

When it’s time to dry off, you can explore the hiking trails or bring some lunch and enjoy the tables and grills provided in the shaded picnic area.

There are plenty of reasons you should add this park to your “to-do” list; not only is Fort Zachery Taylor State Park a natural beauty and the southernmost state park in the continental U.S., but it also has one of the best sunset views in all of Key West. Reason enough to visit, wouldn’t you say? One of the best things to do in Key West with kids.

See more: Best Beaches in Key West

Fort Zachary Taylor Historic State Park Things To Do In Key West

Fort Zachary Taylor Historic State Park/ Flickr

7.  Jet Skiing at Smathers Beach

Most people think of Key West as an island of tropical breezes and white sandy beaches. But did you know there are only a few natural beaches in the Florida Keys? Most beaches are man-made. Smathers beach is one of them.

Smathers has crystal clear water and rock-free white sandy beaches making it one of the most popular beach destinations in Key West.

A half-mile in length starting at mile marker 0, Smathers is also the largest beach on the island. There is much fun to be had at Smathers, from swimming and snorkeling to enjoying catching rays on the sand. Energized after a quick dip in the Ocean, start a pickup game of volleyball at the provided nets.

Are you a fan of watersports? Want to try something a little more exciting? Smathers has jet skis and windsurfing equipment available to rent. Think of how much fun it would be to zip around in the Atlantic. Or maybe windsurfing has always been on your bucket list? Entry to the beach is free, but parking is $5/hour. Amenities include bathrooms and showers.

See more: Free things to do in Key West

Jet Skiing at Smathers Beach

Jet Skiing at Smathers Beach/ Flickr


8. Duval Street Nightlife

Key West’s main drag. Duval Street is the heart of Key West. If you like the party atmosphere, you will not be disappointed. Duval Street is party central of Key West.

There is so much to do, you are sure to find something to suit the whole family. You can shop till you drop at national retailers like the Banana Republic and Coach or local favorites like Key West Shells and Gifts and Tucker’s Provisions.

If all that shopping has left you hungry, there are several fantastic restaurants, including the laid-back Key West Fish & Chips to the elegant Nine One Five Restaurant & Bar, and everything in between. Known for its energetic nightlife and bar hopping, after dark is when Duval Street comes alive. From tiki bars to Irish pubs, there is something for everyone.

Duval Street Nightlife

Duval Street Nightlife/ Flickr

9. Sunset Celebration At Mallory Square

No excuses! The Sunset Celebration at Mallory Square is a MUST! Open 365 days a year, around 2 hours before sunset; Sunset Celebration is a nightly arts festival. Local artisans are exhibiting and selling their art, including jewelry makers, photographers, and crafters.

You can visit with a psychic or get your tarot cards read. Enjoy the live musical talent and amazing acrobatic entertainment. Food carts offering Conch Fritters, Chimney cakes, Pineapple drinks, and fresh coconut are available to satisfy your snack cravings while you wait for the main event, the sunset.

Mallory Square is ideally situated to display the most magnificent scene of the sun kissing the ocean just before setting. If you are in Key West, you need to experience this.

Sunset Celebration At Mallory Square Things To Do In Key West

Sunset Celebration At Mallory Square/ Flickr

10.  Southernmost Point of the Continental U.S.

Maybe visiting a concrete buoy isn’t at the top of your bucket list. But this one should be. The Southernmost point of the continental U.S. is marked by a brightly painted concrete buoy in Key West, Florida.

Anchored at the corner of Whitehead and South Streets, the buoy sits 18 feet above sea level and 90 miles from the coast of Cuba. The heavy concrete buoy replaced the sign that used to mark the spot (and was repeatedly stolen) and is built to last, surviving brilliant sunlight, fierce hurricanes, and thoughtless vandalism.

The buoy is one of the most photographed attractions in the United States. Be sure to stop by and add your photo to the countless list of people who have stood as far south as one can stand in the United States.

Southernmost Point of the Continental U.S.

Southernmost Point of the Continental U.S./ Flickr


11.  The Cats at Ernest Hemingway Home & Museum

The most popular tourist attraction in all of Key West, 907 Whitehead Street, was the home of the great American author Ernest Hemingway.

Hemingway penned various works of non-fiction, short stories, and novels during the years he called Key West home (1931-1939). The property boasts the first swimming pool in the Florida Keys and is home to a plethora of polydactyl (many-toed) cats.

The cats are famous in their own right and are thought to be direct descendants of Hemingway’s six-toed cat, Snow White. The museum is open daily for guided tours.

The Cats at Ernest Hemingway Home and Museum

The Cats at Ernest Hemingway Home and Museum/ Flickr

12.  Key West Cemetery

In 1846 a hurricane ripped through the keys and washed out the existing cemetery, scattering the dead into the surrounding woods.

The cemetery was reestablished in 1847 at the highest point in Key West. Tombstones were relocated, and for this reason, there are headstones present that are older than the cemetery itself.

Some dating back to 1829. Full of puns, sarcasm, and literary humor, this cemetery is sure to be unlike any you’ve ever witnessed. To make sure you make the most of your trip, use the northeast corner entrance (Passover Lane and Angela Street) and visit the office to pick up your free walking tour guide. With your guide in hand, you can walk back through history, the gravestones revealing the quirky characters of Key West’s past.

Key West Cemetery

Key West Cemetery/ Flickr

13.  Go Back in Time to the Oldest House Museum

Located at 322 Duval Street, the Oldest House in Key West, and for that matter, all of South Florida, was built in 1829.

Built by an immigrant from the Bahamas, Richard Cussans, the home features a simple wood frame design, reflective of the materials and technology available at the time. Instead of nails, mortise and tenon and posts and beams were secured with holes and pegs constructed in a fashion similar to shipbuilding which created the showcase that stands today.

Inside the home, you can observe original furnishings, family portraits, and memorabilia dating back to 1800s Key West. Outside you can tour the lush garden area, sit on the benches, and enjoy the natural beauty. The grounds are also home to the last remaining cookhouse (an outdoor kitchen, used to prevent house fires and curb excessive heat in the home) in the Keys, built around 1838.

Oldest House Museum

Oldest House Museum/ Flickr

14.  Sunken Treasure at Mel Fisher Maritime Heritage Museum

the Mel Fisher Maritime Heritage Museum is home to an assortment of items and artifacts recovered from the Henrietta Marie, Nuestra Senora de Atocha, and the Santa Margarita, all shipwrecked in the 17th Century.

The museum is also home to a rotating selection of items and exhibits relating to underwater retrievals, the actual pirates of the Caribbean, and slavery in the 1800s.

The Mel Fisher Museum is much more than just a museum; it is also a nationally recognized archaeology and research institute with an operating Archaeology and Conservation Lab that is open to the public via a private tour. Any history buff with a fascination for shipwrecks and pirates will not want to miss this one. One of the best key west activities.

Mel Fisher Maritime Heritage Museum

Mel Fisher Maritime Heritage Museum/ Flickr


15.  See Old Town with Conch Tour Train

With the first tour given in 1958, the Conch Train has been delighting tourists with the peculiar tales of Key West history for years.

The Conch Train is not only an excellent way to tour the island, but it’s also a perfect mode of transportation between the many attractions Key West has to offer. The Conch Train Tour is a 75-minute tour looping through Old Town. Be prepared to be delighted with tales of local celebrities and the quirky individuals who call Key West home.

Boarding at the Front Street depot, there are a few stops along the way; the Station Depot is a quick 10-minute stop allowing you time to shop and grab some delicious snacks. The next stop is located at Truval Village (corner of Duval St. and Truman Ave.), and the third stop is the Sails and Rails Museum.

The beauty of this tour is that you can wander about any of the stops and grab the next train. With trains running every 30 minutes, you should never have a long wait. So, hop aboard and explore all the local delights that Old Towne offers.

Old Town with Conch Tour Train

Old Town with Conch Tour Train/ Flickr

16.  Ghost & Gravestone Trolley Tour

Are you ready for a frighteningly fun time? Then the Ghost & Gravestone Trolley Tour is for you. Hop aboard the “Trolley of the Doomed” to explore Old Town Key West’s strange and macabre side.

A mixture of trolley rides and walking, this 60-minute tour is best scheduled for after dark, prepared to be regaled with folklore filled with ghosts, murder, and misfortune—a most interesting way to learn the peculiar history of Key West.

Several tour packages are available for every budget and level of fright. Due to the scare factor, some tours may not be appropriate for children under 13.

Ghost and Gravestone Trolley Tour

Ghost and Gravestone Trolley Tour/ Facebook

17.  Cruise around with Lloyd’s Tropical Bike Tour

Explore the Keys like a true islander. Lloyd’s Tropical bike tours are a fun-filled adventure for all ages. Ride a beach cruiser through botanical gardens, check out the homes of famous authors, and spend time at the Key West Wildlife Center. Lloyd’s tours are one of a kind and hosted by Lloyd himself; you can expect to have a relaxing afternoon gliding along at a leisurely pace exploring the sights, sounds, and tastes of Key West.

The tour is touted to be 90 minutes long, but Lloyd is known for his storytelling, and the rides can stretch out a little longer, not that you will notice; the nearly perfect weather and old Key West lore will surely distract you. You may want to only have a light snack before the ride because it is not uncommon to stop for fresh (right from the tree) fruit tastings.

Here is your opportunity to try fresh mango, limes, or coconuts. An authentic afternoon you won’t want to miss.

Lloyd’s Tropical Bike Tour

Lloyd’s Tropical Bike Tour/ Facebook

Key West Hidden Gems Off the Beaten Path

18. Robert the Doll at Fort East Martello Museum

The Fort East Martello was constructed by the United States Army in 1862 to protect Key West during the Civil War from a possible attack by sea from the confederacy. The museum has been restored to its original design. It is host to long-forgotten relics of the Civil War era and information about the industries that have shaped the keys, namely the wrecking industry and cigar manufacturing.

But the real star of the show on display at the Fort East Martello Museum is Robert the Doll. As the story went in 1906, Robert the doll was gifted to Robert Eugene Otto by his parent’s disgruntled housekeeper; it is suspected that the doll was cursed, as the woman was known to be involved in black magic and voodoo.

The doll was involved in many unexplained events and is thought to be the inspiration behind Chucky, the main character in the “Child’s Play” Movies. Robert is on display at the museum (behind glass, thank goodness), waiting for you.

Robert the Doll at Fort East Martello Museum

Robert the Doll at Fort East Martello Museum/ Facebook

19.  The Parrots at Nancy Forrester’s Secret Garden

Have you ever wanted to pet a giant macaw or ask Polly if she wants a cracker? Then the Secret Garden should definitely be on your list.

An environmental activist and pet lover, Nancy Forrester has spent the last 35 years rescuing, rehabilitating, and rehoming orphaned parrots. Twenty-eight years ago, she made it a mission to bring her activism to the public and started the Secret Garden. Home to a plethora of large birds such as macaws, cockatoos, and Africa Grey Parrots, a trip to the Secret Garden allows you to get up close and personal with these birds. An excellent way for animal lovers and anyone who appreciates nature to spend the day. A perfect family destination that is sure to delight and educate.

A day in Key West is better than a day not in Key West, or so it is said. Whether you are just walking down the street watching the feral chickens running about or enjoying the display of Hemingway cats (with their big paws) basking in the sun, you are bound to see something exciting and peculiar everywhere you look. This list is just the tip of the iceberg regarding the strangely wonderful things you can do in Key West.  Grab a pen and write down your favorites!

The Parrots at Nancy Forrester’s Secret Garden

The Parrots at Nancy Forrester’s Secret Garden/ Facebook


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