Key West. The last main island of the Florida Keys. Mile 0 on US Highway 1. The “southernmost point” in the Lower 48. It’s hard to find the right adjectives to describe the place. Quirky? Weird? Festive? Titillating? Paradise? Paradise lost? We’ve visited Key West several times, and revisited it recently to use as a base for exploring the Dry Tortugas National Park (about 70 miles further west.) In this post we’ll share some stories from our adventures in this odd island town, and some tips on what to see and do if you choose to drop in for a spell.
The island has a colorful history and rich cultural heritage. The early inhabitants included Cubans, Bahamians, and many European shipwreck survivors. “Wrecking,” or the salvaging of shipwrecks, was the main source of income for many of the early residents. It was a profession so lucrative that 1860 Key West was the wealthiest city per capita in the United States, and the largest city in Florida. That last bit isn’t really saying much, since in 1860 the rest of Florida was still mostly an inhospitable, mosquito infested, alligator ridden swamp.
Today locals by birth are called “Conchs” (rhymes with “bonks”) presumably after the conch shells harvested on the sandy shoals around the island. The shells are beautiful and contain critters that are the main ingredient for the island’s famous “conch fritters.” In 1982 the locals got a little sideways with the Federal Government over immigration restrictions and symbolically declared sovereignty from the US Government, forming the Conch Republic. According to local lore the uprising reached its climax when the Conch Navy attacked the US Coast Guard Cutter Diligence with a barrage of water balloons, conch fritters, and stale Cuban bread. Defeat came quickly for the Conch Navy under sustained assault from the Dilligence’s fire hoses. The rebellion was quashed, but the spirt of the Conch Republic is alive and well today in Key West. Did I mention the place was a little weird?
Sloppy Joe's Bar - entertaining folks since 1937.
Folks come to Key West for many reasons, but the most common reason is apparently to party. The streets downtown are lined with bars to help revelers celebrate, drink to remember, and drink to forget. We are not big bar people, but there are a many worth checking out if you interested. Sloppy Joe’s Bar is one of the oldest in town. It is large, by bar standards, and features live music almost continuously. Key West is one of those “small world” places where you never know who you might run into. One of the members of our party actually knew the bongo player in the band playing one night while we were there. And while we are on the topic of small, you might also want to check out The Smallest Bar, just down the street from Joe’s. The self-proclaimed “world’s smallest bar” is set up in an alley between two buildings and is a fun place to grab a cold beverage and take a photo – no wide-angle lens required. And if you are a Jimmy Buffet fan no visit would be complete without at least one visit to Margaritaville – flip flops are optional, but highly recommended.
All aboard! The Conch Tour Train - fueled by tall tales, and a bit of rum.
There are a wide variety of diversions to entertain visitors while they are letting their livers recover. A great way to tour the island and learn about its history and charm is to hop on the Conch Tour Train. This open-air “train” makes a narrated tour of the historic downtown, with options to hop on and off at several locations around town.
The "Southernmost Point" in the Continental USA.
One of the locations you won’t want to miss is buoy that marks the “Southern Most Point” in the Continental United States. Locals like to brag that Key West is closer to Cuba than the nearest Walmart. Don't get hung up on the fact that you can clearly see more of the island extending to the south – that’s all on a restricted military base. Just enjoy the photo op and keep an eye out for rouge waves that like to sneak up and make a liquid photo bomb!
Seaplane adventure to the Dry Tortugas.
For the more adventurous there are many outfits that provide jet ski tours, parasailing, snorkeling, dive excursions, and fishing charters. If your schedule allows, we highly recommend visiting the Dry Tortugas National Park. The Yankee Freedom Ferry provides day-long trips to the island, and Key West Seaplane Adventures provide both half-day and full-day excursions. We took the seaplane tour and it was amazing! If you missed it you can read about it here.
Yes, this is actually a pretty good place to eat.
In between bar hopping and touring you are going to get hungry, and Key West has no shortage of fun and interesting dining options. One of our favorite spots is B.O.’s Fish Wagon. This one takes a little courage. It looks like a food truck that got buried under debris from a hurricane and the owners just said “yeah, whatever, it’s fine.” But if you are okay with dining in an open-air shack with chickens running in and out of the kitchen you will be rewarded with some of the best fresh seafood on the island.
A proud island resident.
A word on the chickens. They are everywhere. These birds are descendants of the original chickens brought to the island by the Europeans and are protected by law, so don’t mess with them. Don’t do it. If you do, a rooster will be posted outside your bedroom to wake you up promptly at 4:30 in the morning. Well, that’s not totally true. You will probably get a wakeup call from the neighborhood rooster regardless. It’s all part of the Key West charm!
For those that are looking for something a little more main stream the Conch Republic Seafood Company is another favorite. They can accommodate large groups, have a great selection of food and specialty drinks, and have a very friendly staff. It is the only place I have had a hurricane accidentally dumped in my lap and didn’t even care. Of course, the fact that it was the third hurricane of the day may have had something to do with that.
Be sure to save room for the islands signature desert, Key Lime Pie. There are dozens of shops selling the slightly tart treat, but for the perfect pie you need to seek out Kermit’s Key Lime Pie Shop. If you are lucky you might get to meet Kermit and his dog Pirate. Just look for eccentric old man wearing a lime color apron and chef’s hat. And if pie isn’t your thing there are cakes, cookies, and plenty of other tasty lime-flavored treats at Kermit's.
Key West is very walkable, and having a car can actually be an expensive pain in the bumper as parking is very limited downtown and none of it is free. If you need to venture further out, we recommend using a ride-share service – especially if you have been celebrating. We’ve never had to wait more than a few minutes for a ride and you can get anywhere on the island for under $10. There are also concessions that rent scooter, bicycles, and golf carts. I would only recommend these options if you are an adrenalin junky and have a very good insurance policy. The roads are narrow and full of tourists that don’t know where they are going and aren’t paying attention. We saw “near misses” at just about every intersection. If you are brave enough to give it a try, just make sure you save room for your guardian angel to ride shotgun!
This trip we opted for a "resort condo" experience.
If you are looking for a cheap place to stay on the island, well, there aren’t any. You can occasionally get deals in the off-season, also known as peak hurricane season, August through early November. We’ve stayed off-island in the RV, at ABnB’s in old town, and in resort style condos on the outskirts of town. Downtown is the place to be if you want to be within walking distance to all the action, but you need to expect limited parking, late night revelry, and the possibility of a local rooster infection. The resort condos are a good option if you are interested in enjoying amenities like pools and fitness centers. Most resorts are too far to comfortably walk downtown, but you are more likely, but not guaranteed, a rooster-free experience. Staying off-island can be less expensive, but you will need to either use your own car or take a shuttle bus to get into town. We would 100% not recommend taking an RV into Old Town Key West. The roads are too narrow and congested. It would a miserable and nerve-wracking experience!
No matter where you stay, or how long you are there, you need to take at least one night to head downtown to Mallory Square to participate in the Sunset Celebration. Visitors from around the world gather for this nightly festival that includes musicians, magicians, jugglers, clowns, artists, food vendors and more. The festivities begin two hours before sunset. It is a great opportunity to meet folks from all over, and maybe make a few new friends. They will probably be from Ohio or Michigan.
There is a little something for just about everyone in Key West. It’s kinda like the conch fritters. You may not love them, but you oughta give ‘em a try!
Other things to know before you go:
Key West is generally very dog friendly. Most restaurants with outdoor/open air seating will welcome your fur babies. Be aware that it can be very crowded, so if your pup doesn’t do well around strangers, you might have some challenges. Also remember that there are chickens running wild everywhere so it is not a great place for dogs that are prone to chasing after other critters.
If you are beach bum you may be disappointed. Despite the tropical island vibe, Key West has modest offerings when it comes to beaches. The few that do exist are mostly small manmade affairs built to attract tourists and created with sand that was brought in from the Bahama’s. But if you want to check them out, we suggest either Higgs Beach or Smathers Beach. Both offer great swimming, snorkeling, and sun bathing.
Finally, Key West is one of the most LBGTQ+ friendly places on the East Coast and you will see some interesting and colorful folks about town. All are welcome. Except for intolerant, loudmouth, jerks. They run the risk of being barraged with water balloons, conch fritters, and stale Cuban bread and being assigned a dedicated wake up rooster. Don’t be that guy. Grab a cold drink and chill. After all, as patron saint of Key West Jimmy Buffet teaches us, “it’s 5 o’clock somewhere.”
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