The Conch Connection

Key West Has Always Been Happily a Little Different

Key West does not do ordinary especially well. This is an island where a cemetery comes with a self-guided map, a legendary bar has a tree growing through the middle of it, and a day on the water can end with you climbing, sliding and trying not to splash off a floating playground.

That is part of the charm. The usual beaches, boats and sunset views are still here, but leave a little room in your plans for the stranger side of the island. These five experiences are a good place to start.

Wander the Key West Historic Cemetery

A cemetery may not sound like vacation material until you get to Key West. The Key West Historic Cemetery is a 19-acre, park-like piece of Old Town history, established after the 1846 hurricane destroyed the island's earlier burial ground. Today, it remains an active cemetery—and a place where the island's sense of humor has clearly refused to rest.

Photo Credit: CedarBendDrive from USA, CC BY 2.0, via Wikimedia Commons

Look for the famously cheeky epitaph, “I Told You I Was Sick,” along with family plots and memorials that reflect generations of Bahamian mariners, Cuban cigar makers, veterans, artists and longtime island families. Pick up the free self-guided map at the entrance, keep your voice low and give yourself time to wander. It is equal parts history lesson, outdoor walk and Key West oddity.

Pull Up a Stool at Captain Tony's

At Captain Tony's Saloon, the building is nearly as entertaining as the people inside. Before it became the bar everyone knows today, 428 Greene Street was an ice house and city morgue, then a telegraph station, cigar factory, bordello, saloon and speakeasy. It was also the original home of Sloppy Joe's before that bar moved to Duval Street in 1938.

Photo Credit: Steven Miller, CC BY 2.0, via Wikimedia Commons

Captain Tony Tarracino bought the place in 1958, and Jimmy Buffett later played there early in his Key West years. Today, bras hang from the ceiling, names cover bar stools and a tree grows right through the room. Stop by for the atmosphere, a cold drink and the easy feeling that just about anything could have happened there—and probably did.

Play on a Water Park That Floats Offshore

Some vacation activities are hard to explain without sounding like you made them up. An inflatable water park in open water is one of them. Fury's Ultimate Adventure packages snorkeling, parasailing, jet skiing, a banana boat and time on a floating water park into one very energetic day.

Photo Credit: Fury Watersports

The ocean water park is an obstacle-course-style collection of inflatable climbs, slides and platforms. It is the kind of place where adults suddenly remember how much fun it is to race someone to the top of something. Our Fury Ultimate Adventure guide has more on what the experience feels like. Check the operator's current requirements, trip length and weather policy before booking.

Lean Into the Island's Spooky Side

Key West has a long memory, plenty of old buildings and no shortage of stories that get better after dark. A Ghosts & Gravestones tour brings the island's haunted reputation to life with theatrical storytelling and nighttime stops around Old Town.

You will hear about Robert the Doll, strange happenings and local legends that make even a familiar street feel a little more mysterious. Are the stories true? That is between you, the guide and whatever may be standing behind you. Either way, it is a fun, slightly spooky change of pace from another sunset cocktail.

Get Your Southernmost Selfie

The Southernmost Point Buoy is one of those Key West stops that is both completely expected and still worth doing. The big painted landmark at South and Whitehead streets has become the island's classic photo backdrop, usually with a cheerful line of visitors waiting for their turn.

Go early in the morning or later in the afternoon for a better shot, be patient with the people ahead of you and offer to take a photo for the next group. It is a tiny bit of island goodwill that tends to come back around. Before you go, see the latest visitor information in our Southernmost Point Buoy guide.

Let Key West Be a Little Weird

The best Key West trips usually include at least one story that starts with, “You will never guess what we did.” Maybe it is finding an outrageous epitaph, sitting beneath a barroom tree, slipping off an inflatable obstacle or listening for ghosts in Old Town. The island has plenty of polished, postcard-perfect experiences—but its quirks are what make it unforgettable.

Travel from Fort Myers Beach to Key West aboard Key West Express, then give yourself permission to wander beyond the expected. Check the current Key West Express schedule and fares, and reserve your trip when you are ready for a delightfully different island escape.

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