The Best Things To Do In Key West Florida

Sunshine, clear water, and Margaritaville, the Florida Keys are known for some of my favorite things in the world. Key West is the southernmost city in the continental United States and only about 95 miles north of Cuba.

While modern Key West is known for resorts, fishing, and some great ice cream, it was once an ancient Indian burial ground. Cayo Hueso is the original Spanish name for the island of Key West, it literally means “bone cay”. It is said that the island was littered with the bones of prior native inhabitants, who used the isle as a communal graveyard.

Luckily, none of this guide on things to do in Key West will have you messing with any ancient human remains or graveyards!

At the corner of South and Whitehead Streets, you will find a concrete replica of a buoy, claiming it is the southernmost point in the contiguous United States. The monument is often surrounded by tourists waiting in line to take their photo. It is often the most photographed tourist spot in the Florida Keys.

It is kind of funny because it isn’t the actual southernmost point. The southernmost point of the contiguous United States is actually Ballast Key, a privately owned island south of Key West. Whitehead Spit is the southernmost point on Key West, but it is on US Navy property just west of the buoy and cannot be entered by civilian tourists. The southernmost location that the public can visit is the beach at Fort Zachary Taylor Park.

So should you see the concrete buoy? Sure! Now you know the “truth” and can even share your knowledge with your friends back home when you post the picture.

If you want to go to Key West, it is partially due to Jimmy Buffett. Jimmy Buffet put Key West on the map with a happy-go-lucky attitude preaching the Caribbean gospel of cold drinks, hot sand, and no worries. As a fan of Key West, Jimmy Buffett leveraged the success of his 1977 hit song into something more than just music.

In January 1985, Jimmy opened the Margaritaville Store in Key West. However, customers continued to enter the store in hopes of getting a Margarita, which they didn’t sell. In late 1987, the Margaritaville Cafe joined the Margaritaville Store at 500 Duval Street.

While many will claim this is the “original” Margaritaville, they are mistaken. This was the first successful Margaritaville. Buffett opened a failed Margaritaville in Gulf Shores, Alabama. The Original “J.B.’s Margaritaville” in Gulf Shores opened in 1984 but closed in 1988.

I guess you consider “J.B’s Margaritaville” different from “Margaritaville”, then yes, the Key West Margaritaville is the first.

Speaking of famous drinkers, Ernest Hemingway was a big fan of Key West as well. In 1928, writer Ernest Hemingway and his wife moved to Key West. They eventually purchased a house and had it restored, installing the first-ever swimming pool in the Florida Keys. Rumor has it, Ernest installed a wall around the property so he could swim nude.

The current owners intended to use the Hemingway House as a private residence, but due to interest from tourists, they opened the house to the public as a museum in 1964. It is one of the most popular tourist sites on the island.

The house grounds are inhabited by a bunch of “Hemingway cats”. Legend has it that the cats are descended from Snowball, a white six-toed cat. However, only around half of the cats today have six toes (known as polydactyl).

Word of warning, Key West is not known for its beaches. Obviously, being where it is located in the world, it has beaches, but nothing to rival Tahiti or the rest of the Caribbean. Funny enough, the majority of beaches in Key West and the Florida Keys are not natural. The sand has been imported from the Caribbean to make it nice. There are three main beaches on Key West: Smathers, Higgs Beach, and Fort Zachary Taylor Historic State Park Beach.

Smathers Beach is the largest public beach in Key West. The beach is free to visit every day between 7 a.m. and 11 p.m. and is worth the quick stop. The beach offers picnic areas, restroom facilities, volleyball courts, Jet Ski rentals, and free parking. 

Higgs Beach is a smaller beach right next to the Casa Marina Resort. It does offer free parking, Lounge chairs, umbrellas, kayak rentals, paddleboards, volleyball, and even Wi-Fi. Depending on the time of year, you may get a lot of seaweed buildup on Higgs Beach. If you don’t, it is a great atmosphere. If you do, it may not be as pleasant. 

Fort Zachary Taylor Historic State Park Beach is “Key West’s favorite” beach. It is located in the civil war-era Fort Zachary Taylor State Park. The fort was built in the mid-1800s to defend the nation’s southeastern coastline. Fort Zachary Taylor played roles in the Civil War and Spanish-American War. The beach itself is a solid beach with clear water, good snorkeling, and a shaded picnic area. If you want to catch some rays and learn about some US Military history, this is the spot for you.

Ok, so this may not make a lot of sense, but Key West has some amazing ice cream. We visited during May, so we needed something to cool us down during our walks around town (no matter how many Pina Colada and Margaritas you have, nothing cools you down faster than some ice cream).

Key West is a party town. If you want to party, you can find one on Duval. Duval street is a bit over a mile long and starts near the cruise port and Mallory Square area on the Northside of the island. It is not hard to have a good time on Duval.

Duval is home to many famous restaurants and bars, including Sloppy Joe’s, Margaritaville, Fogarty’s, “The Flying Monkeys Bar”, The Bull and Whistle, Rick’s Cafe, and Bourbon Street Pub. Each place has a great atmosphere and nightlife. Duval is also known for drag shows. 801 Bourbon, Aqua, and LaTeDa all put on different shows and make for a fantastic time.

This list of things to do in Key West didn’t even cover the hundreds of tours, excursions, and min-day trips you can take from the island. If you like to fish, dive, snorkel, boat, or lay on a beach with a drink in your hand, there are tours and excursions for all of those. 

Key West is a fun place to spend a few days soaking in the history, nightlife, and natural beauty of the islands.

If you want the fastest way to Key West, you can fly. Key West’s airport has all major carriers including Delta, American, United, and Southwest. 

If you are already itching for a water adventure, you can also arrive to Key West by boat. There are several charters available from various cities through Florida and the Bahamas. Ferry service is available between Key West and Ft. Myers all year round. During the winter, you can also catch a ferry from Naples. 

Of course, if you would like to take the scenic route, US Highway 1 connects Key West to mainland Florida for a nice easy drive. However, during hot travel weekends (like Labor Day or Memorial Day) this stretch of road will be very packed, so plan accordingly.

Depending on what you want to do, you have a few options for getting around in Key West.

Key West is only about 7 miles in total size, so you can walk the entire stay if you stay near Old Town. For example, we stayed in Casa Marina Key West and had no problem walking to everything we wanted to see in Key West. However, it gets hot. If you are visiting during the summer, you won’t want to be far from a pool with a Pina Colada in your hand. If you are visiting during Spring, Fall, or Winter, then walking during the day is no problem.

 As always, my thoughts and opinions are my own. Be sure to check out more destinations on the blog here!

Angie xoxo