Rebecca Engel
Key West has a reputation, and most of it fits on one street. People picture a bar crawl down Duval, a photo at the buoy, and a crowd clapping at the sunset. All of that is real, and plenty of people fly home having done nothing else.
The island is small enough to see properly in a few days, though, and the best parts of it sit a few blocks off the main drag. These are the underrated things to do in Key West Florida, the ones that regulars go back for, from a fort you can snorkel straight off to a garden growing inside an old brick tower.
1. Snorkel Straight Off The Beach At Fort Zachary Taylor
Most people picture a boat trip when they think about snorkeling in the Keys. At Fort Zachary Taylor you just walk in from the sand and start swimming, which makes it the easiest water in Key West to get into.
The shoreline here is rock and old coral instead of soft sand, so water shoes make a big difference. Once you’re past the edge you’ll see parrotfish, yellowtail snapper, and the occasional lobster tucked under a ledge.
The park is worth time out of the water too. The fort dates to 1845, it held for the Union through the Civil War, and it holds the country’s largest collection of Civil War seacoast cannons, many of them dug out of the walls during restoration work in the 1960s. There’s a hut near the beach renting chairs, umbrellas, snorkel gear and bikes, so you can turn up with nothing.
2. Take The Early Ferry To Dry Tortugas National Park
Seventy miles west of Key West, out where the phone signal quits, there’s a huge brick fort sitting on a small island surrounded by water the color of a swimming pool. Fort Jefferson is the biggest brick building in the Americas, and almost nobody makes it out there.
The ferry takes a little over two hours each way, which is why it stays quiet. Your ticket covers the park entry, breakfast and lunch, and snorkel gear, and there’s a guided walk around the fort that runs about forty minutes once you land.
Book it well ahead. The boat sells out weeks in advance in the busy months, and it’s the one thing on this list you can’t decide on the morning of. If the ferry is full, a seaplane runs out there too and turns the crossing into part of the trip.
3. Climb The 88 Steps Of The Key West Lighthouse
The lighthouse sits right across the street from the Hemingway house, and almost everyone walks past it to stand in line for the cats. That’s a shame, because the view from the top is the best free look at the island’s shape you’ll get without paying for a plane.
It’s 88 steps to the lantern room. From up there you can see the tin roofs and back gardens of Old Town, the cruise ship docks, and water on three sides.
The keeper’s quarters at the base is a small museum, and it’s better than it sounds. The families who ran this light lived through hurricanes that flattened the town, and their photos and belongings are what stay with you afterward.
4. Read The Epitaphs At Key West Cemetery
The island’s water table is too high for normal burials, so the graves here sit above ground in whitewashed vaults. The result looks like a small town with its own narrow streets, and somewhere between 80,000 and 100,000 people are buried in 19 acres.
It was laid out in 1847, after a hurricane washed the old seaside cemetery away the year before. Bones turned up in the streets, and the town moved its dead inland.
What people actually come for is the writing on the stones. One reads “I told you I was sick.” Another remembers a woman as a devoted fan of Julio Iglesias, and one honors the best flan maker. It’s a strange, funny, very Key West place to spend a quiet hour.
5. Eat Breakfast With The Roosters At Blue Heaven
Blue Heaven sits on a corner in Bahama Village, and you eat outside on a dirt floor under a tree while chickens walk between the tables. The roosters are descendants of birds Cuban families brought over generations ago, and they run the island now.
The building has had a life. It was a bordello, a bookmaking parlor and a cockfighting pit, and Hemingway is said to have refereed boxing matches in the arena on the property in the 1930s.
Breakfast is the meal to come for, and there’s usually a wait, so put your name down and walk the block while you wait. The key lime pie comes with meringue piled ridiculously high, and it’s worth ordering even if you’re full.
6. See The Atocha Treasure At The Mel Fisher Maritime Museum
A Spanish galleon called the Atocha went down in a hurricane off the Keys in 1622 carrying silver, gold and emeralds. Mel Fisher spent sixteen years looking for it and found the main pile in 1985.
The museum holds what came up: gold chains, silver bars stamped with their weights, emeralds still rough from the mine, and everyday things off the ship that make the story land harder than the treasure does.
One good detail the guidebooks skip. For years there was a solid gold bar in a case you could reach in and lift with one hand. Two men stole it in 2010, so the case is empty, which is somehow an even better story.
7. Find The Garden Hidden Inside West Martello Tower
From the road it looks like a pile of old brick by the beach. Inside, the ruins of a Civil War era battery have been planted top to bottom with palms, orchids and flowering vines, and the whole thing is run by the local garden club.
The tower was finished in 1863 and never armed, and it was nearly demolished before the garden club took it over. Now the gun rooms are garden rooms, with arches framing the sea.
Admission is free, it’s open most days, and it takes twenty minutes if you’re moving or an hour if you’re the kind of person who reads plant labels. It sits right beside Higgs Beach, so it pairs with a swim.
8. Kayak The Mangrove Tunnels Outside Town
A few minutes out of downtown, the shoreline turns into a maze of mangroves with channels running through it. Some are wide and calm, and some narrow down until the branches close over your head and you’re paddling through a green tunnel.
The water is shallow and clear, so you see things: sponges, little sharks, rays, upside down jellyfish, and birds standing in the roots waiting for lunch. Outfitters run guided trips from Geiger Key and from the channel between Key West and Stock Island.
Go in the morning if you can. The wind is usually down, the light comes through the leaves at a low angle, and you’ll have the tunnels to yourself.
9. Sit With The Parrots At Nancy Forrester’s Secret Garden
This one is small and easy to walk past. It’s a garden on Elizabeth Street that doubles as a home for rescued parrots and macaws, most of them birds whose owners couldn’t keep them.
Mornings are the time to go, when Nancy talks people through who the birds are and how they ended up here. The birds sit on stands out in the open, close enough that you can see how much attention they’re paying to you.
Admission is a few dollars and goes to feeding them. It takes half an hour and it’s one of the few places in town where nobody is trying to sell you a boat trip.
10. Watch The Sunset From A Schooner Instead Of The Square
The sunset here really is the event everyone says it is. The mistake is watching it from shore with a few thousand other people when you can be out on the water instead.
Several old wooden schooners sail out of the seaport every evening. You clear the harbor, the engines go off, the sails go up, and you drift past the square, the naval docks and Fort Zachary Taylor while the sun goes down.
Most trips run around two hours and include drinks and something to eat. It costs more than standing on the pier, and it’s the single easiest upgrade to a Key West evening.
11. Pay Respects At The African Cemetery At Higgs Beach
In the summer of 1860 the Navy stopped three American ships running slaves to Cuba and brought more than 1,400 Africans to Key West. They’d spent weeks in conditions that killed people, and 294 of them died here.
They were buried in unmarked graves on the sand at what is now Higgs Beach. The site was lost for over a century until ground penetrating radar found it again in 2002, and it went on the National Register ten years later.
There’s a memorial by the water now, and people swim and play volleyball a few steps away. Standing there for five minutes changes how the rest of the island reads.
12. Order A Drink At The Green Parrot
The Green Parrot has been on the corner of Southard and Whitehead since 1890, first as a grocery with a saloon attached. During the war it filled up with submarine crews from the base a block away, and it picked up the parrot name in the 1970s.
It’s open to the street on two sides, the ceiling is covered in odd things, and there’s no television showing you anything. Locals drink here, which in a town this touristy is worth noting.
The music is the real draw. Bands play several nights a week, the good ones are genuinely good, and you can usually hear them from the sidewalk before you commit.
13. Tour The Harry S. Truman Little White House
Truman came down to Key West in November 1946 worn out and under doctor’s orders, liked it, and kept coming back. He spent 175 days of his presidency in this house, working in shirts loud enough that they became part of the story.
The rooms are kept the way he had them, down to the poker table he had built with a lid so it could pass as a coffee table. The guides are good, and the tour runs about an hour.
It’s a quieter kind of history than the Hemingway house next door in the same town, and far less crowded. Later presidents used the place too, which the guides get into if you ask.
14. Get Key Lime Pie On A Stick At Kermit’s
Every restaurant in town claims the best key lime pie, and arguing about it is part of being here. The version worth going out of your way for isn’t a slice on a plate at all.
Kermit’s on Elizabeth Street freezes a slice, puts it on a stick and dips the whole thing in chocolate. It sounds like a gimmick and it absolutely works, especially when you’re walking the seaport in the afternoon heat.
Real key lime juice is pale yellow, not green, so any pie the color of a lime is telling on itself. That’s the one piece of pie knowledge you need here.
15. Rent A Bike And Stop Driving
Key West is four miles long and two miles wide and almost perfectly flat. You can bike from one end to the other in about half an hour, and a lot of people who live here don’t own a car at all.
Driving is the worst way to see the place. Old Town streets are narrow and one way, parking is scarce and expensive, and you end up walking from a spot you were lucky to find anyway.
Rentals are everywhere and cost less per day than parking does. Once you’re on a bike the island shrinks, and side streets you’d never have driven down become the best part of the trip.
16. Watch The Sunrise From White Street Pier
Everyone talks about the sunset here. Almost nobody gets up for the sunrise, which is the quietest good thing on this list.
White Street Pier runs about a quarter mile straight out into the Atlantic, and locals call it the unfinished road to Cuba. At dawn there are a few people fishing, a few walking dogs, and that’s about it.
The AIDS Memorial sits at the foot of the pier, flat granite panels with the names of more than a thousand people the town lost. It was dedicated on World AIDS Day in 1997, and the early quiet is the right time to read it.
17. Wander The Conch Houses On Old Town’s Side Streets
Old Town has more than 3,000 wooden houses, most of them built between the 1880s and the 1910s, and walking them is free. Bahamian ship carpenters built the classic conch house: wood on piers so air moves underneath, a porch the full width of the front, louvered shutters and a tin roof.
Look for the eyebrow houses while you’re at it. The roof comes down low over the upstairs windows like a half closed eye, which shaded the bedrooms back when nobody had air conditioning.
Pick any street off Duval and go two blocks. You’ll get gingerbread trim, chickens, cats asleep on porch rails, and gardens spilling over the fences, and you’ll understand the island better than any ticketed attraction will teach you.
The Things To Do In Key West That Get All The Attention
None of the famous stuff is bad, and skipping it entirely would be silly on a first trip. It’s just that the famous stuff is where everyone already is.
Duval Street runs the length of Old Town and is the island’s bar strip, with Sloppy Joe’s at the middle of it and a good daytime version of itself before the crowds build. Mallory Square holds a sunset celebration every night, an outdoor arts festival with jugglers, magicians and food carts that fills up about an hour before the sun goes down.
The Southernmost Point buoy has a line for the photo most of the day, and the Conch Tour Train and the trolleys loop past all of it with narration. The Hemingway house and its six toed cats are genuinely worth the ticket if you’ve never been.
Do them early in the trip, then spend the rest of your time on the list above. That’s how people who keep coming back end up spending their days here.
Final Thoughts
Key West is a small island with a loud reputation, and the loud part takes up about six blocks. Walk past those blocks and it turns into gardens, forts, old wooden houses, chickens and water clear enough to see your feet.
Pick a few of these things to do in Key West, rent a bike instead of a car, and get up for one sunrise while you’re here. That’s the version of this island people fall for.
