23 Oct 10 Things To Do in Key West, FL

Key West is so much more than partying and beaches–ok, well those do happen to be top activities on the island, but I want to share with you some of our favorite spots as well. Even though the island is less than 7 square miles, there are an abundance of activities waiting to be discovered, so here is our list of 10 things to do in Key West!

1. The “Must See’s”

First off, you have to check out the cheeky tourist sites: the Southernmost Point and Mile Marker 0–they may be silly, but they are such iconic sites in Key West, it would be a shame to miss them, at least on your first visit. The Southernmost Point is a concrete block painted to look like a buoy; however, it is not actually the southernmost point of Florida. The southernmost point of Florida is actually on a private island south-west of Key West, and the southernmost point of the island is on Navy property not accessible by civilians. Mile Marker 0 is the end of the last mile of highway 1 which runs all the way down the east coast.

You can also hop on an Old Town Trolley, Conch Train or Ghost Bus tour to catch a glimpse around the island and learn a little history in the process.

2. Museums

The history of Key West is very interesting; from pirates and ghosts to presidents and authors, there is always an interesting story around any corner. Here is a quick look at some of my favorite Key West museums.

The East Martello Museum has an eerie past and a fair share of bizarre stories, such as a haunted doll and a man who tried to keep a decaying body “alive” for years. The museum also displays local art and historic artifacts and stories.

Ernest Hemingway was one of Key West’s famous residents, and you can now tour the home of the brilliant author. The house is now home to over 40 cats, many of them with six-toes, and they are all named after famous people to keep with Hemingway’s tradition. You can tour the house and garden to get a peek into the past.

My favorite part of the Custom House is the sculptures outside–there are an array of statues depicting people in everyday situations, and they are fun to pose awkwardly with. Inside, the museum houses displays and galleries depicting the history and traditions of Key West.

If you like searching for treasure, check out the Mel Fisher Maritime Museum as it brings you through the pirate history of the Keys–you will learn all about famous pirates, shipwrecks, and treasures found and still waiting to be found today.

The Key West Historic Memorial Sculpture Garden is a courtyard area close to Mallory Square where you can wander amongst the 36 busts of influential people in Key West’s history. Permanent residents such as Henry Flagler, Ernest Hemingway, and Harry Truman are depicted with a bronze plaque sharing who they are and the influence they had on making the island what it is today.

3. Water Activities

Enjoying the water in the gorgeous weather is a must in Key West, and there are so many activities to choose from. Take a spin on a jet ski or cruise around on a paddle board or kayak. Board a catamaran and search for dolphins or dive and snorkel around North America’s only living coral reef. Go for a leisurely sail or hop on a jet boat for a speedy tour around the island. As you can see, the options are almost limitless!

4. Fly in the Sky

If you would rather fly above the water rather than on it, try your hand at flying on a jet pack, flying behind a boat on a parasail tour or plummet out of a plane with a skydiving adventure.

5. Restaurants

My favorite restaurant in Key West is Blue Heaven–grab a seat at this eclectic cafe known for their breakfasts, with equally delicious lunches, and watch the local chickens run around while you listen to the live bands that often grace the stage.
Other famous restaurants on the island include Jimmy Buffett’s Margaritaville, which is great for atmosphere and drinks and only decent for food. Sloppy Joe’s Bar always has entertaining live music and a delicious sloppy joe sandwich.

Fogarty’s has surprisingly delicious and affordable food all with a great setting right in the middle of the Duval Street action, while the Hog’s Breath Saloon serves good food in a laid back Key West atmosphere.

Conch Fritters and Key Lime Pie both scream Key West signature foods, so you might want to give them both a try at any of the multitude of restaurants that serve both. Tip: Find a slice of key lime pie with real meringue for a top-notch taste–it is way better than the alternative of whipped cream.

There are many other restaurants and bars along Duval Street and the side streets too, so you are sure to find something you enjoy. And, if you are feeling adventurous, stop in at the top floor of the Bull Bar for a visit to the Garden of Eden’s clothing optional bar; although, fair warning, I’ve heard you may not actually want to see all that you find…

6. Take in Duval from Morning to Night as well as the Historic Seaport nearby

There is always something crazy happening on the mile long Duval Street in the downtown area of Key West. Filled with bars, restaurants, shops, art galleries and inns, the activity seems to run nonstop around the clock.

The Historic Seaport area of Key West is near Duval Street and is also home to shops, restaurants and the seaport area with a multitude of boats, sailboats and catamarans.

7. Celebrate the Sunsets

Sunsets are a big deal in Key West, so make sure you don’t miss the multitude of celebrations. Every night there is a party at Mallory Square overlooking the water and Sunset Key in the distance, with street performers and vendors abound. Join the hundreds of celebrators and watch the sun dip below the horizon. If you would rather watch from a distance, hop on either a sailboat or catamaran for a beautiful sunset cruise. Another option to escape some of the crowds is to find a restaurant or bar and watch the sun set while relaxing and sipping a tropical drink–one good option is the bar at the Ocean Key Resort right next to Mallory Square.

8. Wildlife

On land you will find wild chickens roaming the streets–apparently there is a big debate on whether the chickens should be free to roam–half the town says yes the others say they don’t want them around, and so, the debate continues.

If you enjoy seeing wildlife in the wild, you can take a glass bottom boat, go snorkeling or diving, or go on a dolphin watching boat ride. If you are more into seeking out wildlife in controlled atmospheres, you can visit the Key West Aquarium or the Key West Butterfly and Nature Conservatory. Both of these locations are home to numerous species of wildlife so you are sure to see a great variety. Another option is to head to the Key West Wildlife Center where they seek to rehabilitate the animals they care for so they can go back to their families and natural habitats.

9. Beaches

Ok, so there aren’t as many beaches on the island as one would think, but there are still a few beaches that are great for relaxing. Smathers Beach and Higgs Beach are man-made beaches both located along the south side of the island. Both beaches boast sparkling white sand imported from the Caribbean, and although they are not natural, they are sure beautiful and enjoyable.

For a natural beach, head over to the hidden Fort Zachary Taylor Historic State Park for crystal clear water with a slightly more rocky beach. This beach is gorgeous as well and is my favorite on the island. It doesn’t hurt that there is shade and some interesting civil war history nearby either.

Although these are the main beaches on the island, there are a few hotels with small beaches as well. The only hotel beach I have been to is the Casa Marina Resort’s beach, and I must say the hammocks lining the shore are lovely. As for the beach itself, it’s not super sandy but it isn’t exactly rocky either–in my mind it’s a decent beach since it has private access.

10. Festivals

Key West definitely knows how to party and their many festivals and celebrations are a testament to this fact. The most famous, wild and naughty festival of the year is Fantasy Fest, where partygoers dress up in skin-baring costumes, covered in body paint and party through the night every October. The main event is the Fantasy Fest Parade, and other notable events are a coronation where they crown 2 locals as the Conch King and Queen, a drag queen contest and even a pet costume contest.

New Years Eve is done right as the city has three different Times Square style ball drops. When the clock strikes 12, instead of dropping a ball, Key West drops a conch shell, a giant, red high-heel shoe with a drag queen inside and a pirate wench dressed in next to nothing, all of which are dropped in different areas of the city.

Another bizarre festival once again has to do with the islands famous past resident, Ernest Hemingway. To honor Hemingway, there is a multi day festival which is appropriately named Hemingway Days Festival. During the festival there is a short story competition, a fishing tournament, a mock “Running of the Bulls” and a “Papa” Hemingway look-alike contest held at the famous Sloppy Joe’s Bar which was often visited by Hemingway himself.

What crazy Key West antics do you/would you enjoy the most?