What is There To Do in Key West, Florida?

Paradise, admittedly, is an overused phrase these days, to which I am absolutely guilty of. A word that has lost its meaning and also means something different to every single person. To some, an ice fishing hut on a frozen lake when it’s -50F outside is paradise, though far from mine idea of a good time. Most others would default the word to a beach with a cold drink as their version of paradise. If you follow Route 1, starting all the way up in Maine, you’ll cross many versions of paradise. But it’s the terminus of Route 1, where you’ll find an island chain, littered with palm trees overhead, ice cold drinks along an endless party on Duval Street, and a healthy marine environment that surrounds it all. Plus, a shocking amount free range chickens roaming the city streets.

Key West, of the Conch Republic, with its historic and embattled past, has transformed itself through the centuries and decades into a winter escape for the northern residents of this country. Once owned by Spain, then Britain, and eventually the US, all before the 1800s and the civil war, where it remained in Union hands. Following the wars, industries like fishing, turtling, salt manufacturing, and wrecking became sole focus of the island’s inhabitants. Fast forward through two world wars, a railway, an overseas highway, a few devastating hurricanes, an influx of soldiers and tourists, you now have the steady population of Key West into what it is today. But that history is not what draws most people to this island each year, though it probably brought famous Americans like Ulysses S. Grant, Grover Cleveland, William Taft, FDR, Truman, JFK, Jimmy Carter, and most notably, Ernest Hemingway.

Bars, Restaurants, & Shops

Key West is a place you can spend a day, a weekend, week, month, or the rest of your life in. At the surface, Key West is a party town, famous for Duval Street. Across its 14 blocks, spanning 1.1 miles from the Gulf of Mexico to the Atlantic Ocean, has over 100 bars and restaurants where you will have the time of your life. You don’t even need a plan, you can simply walk up and down the street, and let the endless live music that pours out onto the sidewalk decide for you. But if you need some suggestions, the Green Parrot, Hogs Breath, The Rum Bar, Captain Tony’s Saloon, Willie T’s, and of course the Southern Most Beach Cafe. The average night in Key West can take you all over the place, to a single bar followed by a good night’s sleep, or half a dozen bars that will have you jamming to live music until last call. Take Captain Tony’s Saloon for example. This place hasn’t changed since the 1970s, when Jimmy Buffet graced the stage and was paid in free tequila.

To list every bar and restaurant would take up an entire article in itself, and, well, to be honest, I’m no food blogger. Key West is a place that you just roam. But I will mention the REQUIREMENT to get some Key Lime Pie from either the original Key Lime Pie Bakery or Kermits Key Lime Pie Shop. Whether it’s north up to the harbor where the cruises come into port, or down to the southern most tip of the continental USA, you are never more than a block from an amazing restaurant and bar. Tucked between all those drinking establishments, are all the tourist stores you could ever dream of visiting to remember your trip by. From knick-knacks to fancy clothes, and ornaments to fishing gear. So just start walking and you can pretty much find anything, and everything that you’d want on vacation.

Rum Stroll & Running Races

Tied into the Key West Half Marathon weekend, you can never be too far from a drinking-themed party. And in this case I’m talking about the Papa’s Pilar Rum Stroll after the races in the morning. By races, I’m referring to the 5K, 10K, and Half Marathon over the Runfest weekend. Starting before the sunrise on a Saturday, the 5K kicks off with hundreds of runners starting from Higgs Beach, taking to the empty Atlantic Blvd for a once in a lifetime running experience. But this is not speaking from experience, because I was on dog-duty with my father-in-law, while my wife, Courtney, and her mom crushed the 5K. But all that running was just a precursor to the real plan for the day.

The rum stroll itself is far from an organized 5K, but rather a great excuse to get like minded drinkers spread out across Key West. Spanning 8 designated bars, each establishment has a signature rum drink that you prepay for in your registration. Then, you just show up with your ticket and get a “free” rum drink. To add to the fun, you get an event stylized wick-away t-shirt. Following the them of the great Earnest Hemingway, you’ll recreate his many drunken afternoons in Key West as he wrote countless works including To Have and Have Not and Green Hills of Africa. The bars included the Southernmost Beach Cafe, Celtic Conch Public House, Key West Legal Rum, and the Island Dogs Bar. If you make it to all 8 before the time runs out, I’d love to say you win a prize, but best you can get is the satisfaction of crushing an amazing day out in Key West.

Beaches & Coastline

If you’re looking to enjoy the emerald green and mostly clear waters that surround Key West, you have a few beach access options. Unlike most beach towns that have a sprawling coastline of sandy beaches boarding one side of the town, Key West is definitely closer to some Caribbean Islands in the way that the beaches are hard to find and tucked away. Fear not, there are Fort Zachary Taylor, Southernmost Beach Cafe, Dog Beach, Higgs Beach, County Beach, Rest Beach, Smathers Beach, and Simonton Beach. 

Sure all these beach access points will get you into the tropical waters, but really, the Fort Zachary Taylor beach is the only real beach in Key West. Make sure you get up early and into the Fort, which you do have to pay, to ensure you get a good spot because it inevitably fills up. But once you do get there, you’re left with over a 1/4 mile of pristine beaches covered in palm trees and the backdrop of a historic fort that has played part in America’s history predating the Civil and Spanish-American Wars. Plus, it’s far from a lot of the boat traffic that plagues the small town allowing for great snorkeling and swimming opportunities.

Dog Friendly

While the town itself is quite dog friendly, there are some limitations. Sure, you can’t pass more than a single block or bar patio without stopping to let a cute dog hanging out in the sun, but access to water is definitely a problem. As mentioned before, the water access is a bit limited compared to the beach towns further up the Florida coast where sandy shores are endless from Miami to Maine. This is further limited to where dogs are also allowed to access those limited places. And with that, dogs are pretty much limited to the Key West Dog Beach. But as far as dog beaches go, this one is pretty awesome! Located on Vernon and Waddel Ave, right next to Louie’s Backyard bar and restaurant, this is a great place for both dogs and owners to hang out in the turquoise waters of the Caribbean Sea! And if your dog doesn’t mind a little alone time, you can grab a drink at Louie’s and watch your dog from your table. And though they’re technically not allowed on the beach, some people take their dogs up to Smather’s beach and get into the water right from the bullhead rather than across the beach area. 

Besides my ramblings of the limited beach access for dogs, everywhere else is shockingly dog friendly. Since the weather is amazing year round, nearly every restaurant and bar has an outdoor patio or is just entirely outdoors. And it’s not uncommon for all times of day, and night, to see patrons drinking the night away with their furry companion laying down at their feet. The best option obviously being Hanks Hair of the Dog Saloon. And to add to the dog friendly nature, most places have dog water bowls outside of every door or in the restaurant themselves so the dogs are never far from water during those hot days.

Just be careful, there are a ton of truly free-range chickens and roosters roaming the town. So if your dog likes to chase critters, be aware, because those roosters will fight back.

SCUBA Diving

The scuba diving here is absolutely incredible. The coral reefs, though challenged like many other reefs around the world, are still very vibrant. The Florida Keys National Marine Sanctuary protects the reefs from Key West up 100 miles to Key Largo. And between the ends of the Keys to are countless dive sites and shipwrecks to explore. Lucky for us, we’ve been able to dive out of Key West, Islamorada, and Key Largo. Of course there are many more, but I can speak very highly of the following dive sites: Western Dry Rocks, Sand Key Reef, Molasses Reef, French Reef, Davis Reef, and I think Hen & Chickens. We went through Southpoint Divers in Key West and Islamorada Dive Center.

I barely scratched the surface when it comes to the plethora of diving opportunities, and I still haven’t dove on any of the countless shipwrecks. But there are more than 60 dive shops to take you diving or even just get you certified to dive. Under the ocean’s surface, you can expect to see live, flourishing coral reefs with both hard and soft corals, parrot fish, butterfly fish, angel fish, lobsters, and even sharks. But any time you can go scuba diving, whether it’s in 10 feet of water or 100 feet, is a great way to spend a day. Especially since you can normally be back on land and exploring town by the afternoon after heading out for an early morning dive.

Renting Golf Cart

One of the most memorable things to do in Key West is to rent a golf cart! They are everywhere, being utilized by both the tourists and locals alike! Super functional, efficient, and can fit anywhere in this crowded tourism-driven town. But that has nothing to do with why it’s so much fun. Even though, functionally, a golf cart is the same as a car, it feels so much more free when the wind hits your face rather than being deflected by a wind shield. Having your legs dangling out when you go around a turn or sitting backwards in the second row of seats as the world passes by in reverse. Plus, the ease of just hopping in and out to get a beer and popcorn from the Green Parrot, grab a bite to eat from Amigos Tortilla Bar, or just to see the sights. To be honest, I still can’t rationalize why it’s so much fun, but it’s something the family talks about still to this day. So maybe, it’s just the removal of the sense of safety a car provides and feels more open and free, but I cannot recommend it enough. We picked ours up from Minty’s and it was an effortless process, so I’d check’m out.

Here in Key West, there is really something for everyone. And with warm weather year round (especially in summer), it’s a great place to wander the town and explore the world below the water as well. Flights into Key West aren’t uncommon from most hubs, or you could fly into Miami or Fort Lauderdale and take the 4 hour drive to the terminus of Route 1. What are you waiting for? It really does feel like a piece of the Caribbean that you can drive to!