We asked listeners to name the one thing they love most about Key West and, no surprise, most of them couldn’t pick just one. There’s something about America’s Southernmost City that sucks you in and makes you want to never leave.

Maybe it is the turquoise waters or the fact that when you’re there, you feel so detached from the world you left behind back on the mainland. When you’re in Key West you’re only 90 miles away from Cuba and far away from your problems back home. That is, unless you like to bring your work or your family problems with you on vacation.

Key West is about the closest thing to a tropical paradise you’ll find here in the continental 48. And it is tough to name the one thing we love most about Key West. So we put together a list of 12 things we love most about the Conch Republic.

Key West knows how to throw a good party. Special event season kicks off every New Year’s Eve when Sushi the drag queen is lowered from the top from a building on Duval Street inside a giant red high-heel shoe. The party never stops for the next 364 days. From seafood festivals and regattas to fishing tournaments, bridge runs, art exhibits and outdoor concerts, it seems there’s always something fun going on. The biggest events held annually include PrideFest, Fantasy Fest and Hemingway Days.

Because the island is only 4 miles long and just over a mile wide, Key West is extremely easy to navigate on foot, by bicycle or on a moped. If you didn’t pack a bike or a moped, there are plenty of places to rent one, usually for under $45 a day.


When it comes to lodging, there are plenty of options to choose from in Key West. But the best places to stay are the quaint bed and breakfasts that dot the island. Many have been updated with a contemporary touch and feature lush private garden areas with jacuzzis and small swimming pools. They’re all unique with plenty of character.

Each morning, you’ll want to get out of bed so you can find a cool place to eat breakfast. Our favorites include the Banana Cafe, Pepe’s Cafe, Sarabeth’s, and Blue Heaven. Eating breakfast in this tropical paradise is like heaven on earth.


There are plenty of activities to do on the water. You can scuba dive down to the Vandenberg, the second-largest artificial reef in the world, jet ski, paddle board, parasail or take a scenic boat ride. We highly recommend a sunset cruise on an old schooner like the Western Union.


Speaking of sunsets, they’re spectacular in Key West. Each night, hundreds of people gather at Mallory Square to watch the sun go down over the Gulf of Mexico. The carnival-like atmosphere attracts magicians, jugglers, flame throwers, musical acts, and artists. It’s an experience you won’t find anywhere else.


Key West has more bars per capita than any other place in the U.S. It seems there’s a place to have a drink on almost every corner of Old Town. Bar hopping between Sloppy Joe’s, Captain Tony’s, The Green Parrot and Hog’s Breath Saloon can kill an entire day.


This place is deep with history and culture. You can visit the homes of two famous Americans: the Harry S. Truman Little White House and the Ernest Hemingway Home and Museum. There’s also a house that showcases the art of 19th century naturalist John James Audubon, the Key West Lightouse and Museum, the Fort Zachary Taylor Historic State Park and multiple shipwreck museums featuring the collections of famous treasure hunters like Mel Fisher.

About 65 miles southwest of the city is an archipelago of seven reef islands known as the Dry Tortugas. This is the place to really escape from the world for a day. Only accessible by boat, this pristine national park is home to Fort Jefferson, built in the 19th century by the U.S. government to protect and control the Gulf of Mexico shipping channel. It also operated as a prison for Union deserters during the Civil War.

One of the most unique cemeteries in the country is located in Key West at the foot of Solares Hill. About 100,000 people are buried here. Many older graves date back to the mid-1800s with some of the newer ones put in above-ground vaults similar to New Orleans.

The best place to end a day of sightseeing is on Key West’s main tourist drag – Duval Street. A mix of locally-owned shops, clothing boutiques, art galleries, and several national chains can be found along the 5-mile street that runs north to south. If you can’t find it on Duval, you probably don’t need it.

Since 1983, tourists from all over the planet have been stopping by the famous red, yellow and black concrete buoy at the corner of South and Whitehead Streets marking the “Southermost Point in the continental United States.” This is the closest you’ll get to Cuba without leaving the country. And you can’t leave Key West without getting your photo snapped next to it.