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14 Hidden Gems in Key West Off the Beaten Path! [From a local!]

14 Hidden Gems in Key West Off the Beaten Path! [From a local!]

There are seriously so many hidden gems in Key West! You just need to know where to look to find them 😉

As a sailor who has extensively sailed the Florida Keys, I have visited Key West a lot of times before and in my travels I have uncovered some seriously unique activities to do in the Keys.

So if you are planning a trip to Key West but want to add some more eclectic, off-the-beaten-path attractions, you have come to the right place! Maybe this is not the first time you’ve visited and you feel like you’ve done all of the quintessential Key West activities.

Below I’ve put together a list of some of my top-rated Key West hidden gems that are great additions to your itinerary if you want to experience the quirkier, goofier side of the city! Trust me, it is totally worth it to venture off the beaten path in Key West!


Quick list with pinpoints to their location on google maps

  1. Key West Cemetery | Google maps location
  2. Key West Martello Tower | Google maps location
  3. African Burial Ground at Higgs Beach | Google maps location
  4. Blue Heaven Rooster Cemetery | Google maps location
  5. Mel Fisher Maritime Heritage Museum | Google maps location
  6. Five Brother’s Grocery | Google maps location
  7. USNS General Hoyt S. Vandenburg | Dive location is 6 miles (10 km) off the Florida Keys 
  8. Captain Tony’s Saloon | Google maps location
  9. Pan Am’s First Office | Google maps location
  10. Curry Mansion Inn | Google maps location
  11. Key West’s First Legal Rum Distillery | Google maps location
  12. Nancy Forester’s Secret Garden | Google maps location
  13. Joseph ‘Bum’ Farto’s Desk at the Firehouse Museum | Google maps location
  14. Rodriguez Cigar Factory | Google maps location

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14 Must See Hidden Gems in Key West Off the Beaten Path!

1. Key West Cemetery

The Key West Cemetery is a 19-acre time-capsule piece of land sitting at the foot of Solares Hill in the northwest corner of Old Town. The entrance lies at the intersection of Margaret and Angela Streets.

Key West is an expensive place and this is one of the best free things to do in Key West if you are short on cash. It might not sound the most fun activity in Key West but we really enjoyed our visit due to the history around the cemetery.

If you want to know a bit more about the history when you visit, we would recommend buying a Cruise Through Key West’s Black History Audio Tour.

A lot of people choose to rent bikes to visit the Key West Cemetery which is a fun afternoon activity. You can rent bikes in shops all over Key West such as Fury Key West Bike Rentals.

For a short run down of the history, the cemetery is said to be the final resting place for over 100,000 individuals. This is remarkable considering Key West’s population of 30,000 people.

There are about 100 people who are buried there yearly. In 1847 it was established at this location because a hurricane that passed through in 1846 caused havoc in the previous cemetery. There were corpses littered throughout the dunes on Whitehouse Point. Because of this, this cemetery was built sixteen feet above sea level, which is considered “high ground” for Key West.

Walking through the cemetery you will find graves from soldiers of both the Spanish-American War and the Civil War. There is also a separate section devoted to Cuban freedom fighters.

In 1898 USS Maine exploded in Havana Harbor, in Cuba. A monument was constructed in the cemetery in honor of the 260 sailors who lost their lives. The Key West Cemetery also contains the grave of the original Sloppy Joe. He was Ernest Hemingway’s fishing guide and his name was “Sloppy” Joe Russell. He lived from 1889 to 1941 leaving his profound mark.

Address: 701 Passover Ln, Key West, FL 33040, United States

Cost: Free

hidden gems on key west

2. Key West Martello Tower

You may have heard about the Key West Martello Tower before, but maybe you don’t know about its history and what makes it such a unique construction. If you like history or haunted places in Florida, you will love making a visit to the Key West Martello Tower. The best part about the tower is that it is entirely free!

Interestingly, although the state of Florida decided to side with the Confederate army, Key West sided with the Union.

The West Martello Tower was built during the Civil War as a fortification of the island and a supportive stronghold of Fort Zachary Taylor. Originally, the plans were to build five towers to look out and protect Fort Zachary Taylor Unfortunately, Key West’s “island time” lifestyle led to the building not being completed until after the Civil War was concluded.

Although it was used later on during the Spanish-American War for housing troops, storage, and a lookout point for the military. Between the years 1914 to 1944, the tower was used as a radio station control center.

The Martello Tower is also home to the haunted Robert the Doll. Legend says that Robert the Doll is possessed and wreaked havoc in every life he was introduced to. Even visitors of the tower today occasionally say they can see his eyes follow them and facial expressions change.

Address: 1100 Atlantic Blvd, Key West, FL 33040

Cost: Free 


3. African Burial Ground at Higgs Beach

Making a visit to the African Burial Ground at Higgs Beach is interesting as it is a unique part of Key West’s history. Higgs Beach is also one of the best beaches in Key West.

After the Civil War, the trading of slaves was made illegal. Owning slaves wasn’t yet illegal, but the transportation of them was. In 1860, the U.S. Navy intercepted three illegal transatlantic slave trade ships and rescued close to 1500 slaves.

They were then brought to Key West where they were provided food and clothing. There were also housing units and hospitals that were constructed to accommodate the refugees.

Many of the Africans were malnourished and sick due to the horrific and filthy living conditions on the transport ships. Unfortunately, close to three hundred of them passed away within three months of being rescued. People were first made aware that souls were laid to rest on this beach while the West Martello Tower was being constructed and there were bodies found in the dunes.

In 2002, an exert radio detector was able to find the exact locations of the graves. Pedestals were then put at gravesites, along with Adrinkas, which symbolized slavery. The burial ground was added to the National Register of Historic Places as a place of “unique archaeological significance”. There is free parking available and entrance to the cemetery is also free.

An interesting but one of the more unusual and unique things to do in Key West.

Address: 1074-1094 Atlantic Blvd, Key West, FL 33040

Cost: Free


unusual things to do in key west

4. Blue Heaven Rooster Cemetery

Blue Heaven Rooster Cemetery exhibits Key West’s history of and continued weirdness. It is a poultry graveyard inside the courtyard of a prominent Key West restaurant.

The eatery is called Blue Heaven, and they are known for their delicious and decadent breakfast dishes. They adhere to Key West’s tendency of following “island time” so it may not be the quickest meal of your life, but they have tons of entertainment for you while you wait.

Ping-pong tables or rooster ghosts, whatever suits your fancy. The graveyard was initially dedicated to fighting cocks, however, it has had some additions of different species as well. There are multiple six-toed Hemingway cats buried within this pet cemetery. The property is said to be haunted by six-toed cats and fighting cocks, which were the bravest and most aggressive roosters on the island.

There is a secret garden on the property. You can grab a mimosa and explore the secret garden if you’re brave. The building has a long-standing history with tons of different functions.

In the past, it was a brothel, tavern, ice cream parlor, and pool hall with a regular boxing match that Hemingway referenced in some of his novels.

Address: 729 Thomas St, Key West, FL


Cost: Purchases from the restaurant

Blue-Haven-Rooster-Cemetery off the beaten path key west

5. Mel Fisher Maritime Heritage Museum

If sunken ships and treasure spark your interest, this museum is a must on the itinerary for your Key West trip. It is for sure one of the top hidden things to do in Key West.

Entry costs $20 per person and includes an audio guide and access to the conservation and archaeology lab. The building itself was constructed in 1901 and originally served as a Navy storehouse.

Inside, you can see $450 million worth of treasure found by Mel Fisher off the coast of Key West in 1985. The treasure originated from a Spanish ship, Nuestra Señora de Atocha, that sunk in 1622 during a brutal hurricane. There are also relics from the sunken Henrietta Marie.

This ship sunk in 1701 returning from Jamaica after transporting slaves there. You will also find artifacts from the Santa Margarita wreck, a Spanish galleon stocked to the max with New World gems and treasures. With all of the shipwrecks on display, including the St. John’s Wreck, there is an enormous amount of emeralds, gold bars, gold and silver coins, cannons, and more.

Initially, there was a gold bar on display that tourists could pick up through a plexiglass case. The gold was stolen in 2010, chopped up, and sold off in Las Vegas. The two men were eventually caught and served time and paid fines as a result.

Address: 200 Greene St, Key West, FL 33040


Cost: $20 per person

Mel Fisher Maritime Heritage Museum

6. Five Brother’s Grocery

5 Brothers Grocery and Sandwich shop may be the most authentic Cuban experience you will find outside of the island. You will find this local favorite at the intersection of Southard and Grinnell Streets. If you are looking for non touristy things to do in Key West this is a great place to go!

It is located just a block away from the Key West Cemetery, so you could check both of them out on the same day if you’d like. It is both a sandwich shop and a grocery store and offers a diverse variety of fruit, vegetables, meats, breads, desserts, and Cuban staples. The shop is a frequent stop for locals and tourists alike.

It is family-owned and has been in the family since 1979 and has seen three generations. The current owner is the son of one of the original five namesakes whose images make up the logo.

They are known for their unbeatable cafe con leche, pan Cubano, Cuban sandwiches, oxtail, ropa vieja, picadillo, mixto sandwiches, fried grouper, BBQ pork sandwiches, and bollos which are buns made out of corn.

They claim to go through twenty-four pounds of coffee beans daily. They also offer hand-rolled Cuban cigars. The restaurant is counter service, making it a quick ordeal to secure your meal.

Address: 930 Southard St, Key West, FL 33040

Cost: Whatever you order


7. USNS General Hoyt S. Vandenburg

If you like diving, you’ll find this one of the best hidden gems in Key West! USNS General Hoyt S. Vandenburg is the newest addition to the Florida Keys Shipwreck Heritage Trail.

The ship had many functions and many names before she was laid to rest in her final resting place just off the coast of Key West. Her original name was USS General Harry Taylor, in honor of the US Army Chief of Engineers. She was a part of a General G.O.

Squier class of transport ships that were built for the US Navy during World War II. She served for some time as an army transport ship under the name USAT General Harry Taylor, before being reacquired by the Navy in 1950 and renamed USNS General Harry Taylor.

While she was under the ownership of the Navy, she was decked out with the newest technology and gadgets before being placed in the reserve in 1958. She was officially transferred to the Air Force in 1961 and renamed USAFS General Hoyt S. Vandenburg.

In 1964, she was transferred to the Navy once more and designated as a missile range instrumentation ship, or a tracking ship. Reefmakers, a Key West-based economic development company, sunk USNS General Hoyt S. Vandenburg on purpose with the intention of it becoming an artificial reef. It was the largest artificial reef at the time it sank on May 27, 2009.

Location: 6 miles (10 km) off the Florida Keys in the Florida Keys National Marine Sanctuary

Cost: Price of the dive at local PADI dive shops in Key West like Southport Divers.


8. Captain Tony’s Saloon

Captain Tony’s Saloon is one of the best unique places to have a drink or a bite to eat in Key West as it was a popular hang out of many famous people in years gone past.

Like many other things in Key West, Captain Tony’s Saloon has a weird history. The building was originally constructed in 1851 functioning as an ice house and occasionally a morgue. In the 1890s the building contained a wireless telegraph station, which became very important during the Spanish-American War.

In 1912, the location was transformed into a cigar factory before becoming a brothel. The property then was transformed into a saloon known as the “Duval Club”, a popular watering hole for Navy soldiers. The Navy later deemed the Duval Club “off limits” and it slowed down traffic so much to the establishment that the owner was forced to close its doors.

It then became multiple different speakeasies, the last of which was named the Blind Pig and was known for its gambling, women, and bootleg rum. In 1933, Joe Russell bought the business and created “Sloppy Joe’s Bar”. The name was inspired by Hemingway as a tribute to his friend Jose Garcia, who owned a bar in Havana known as “Sloppy Joe’s”.

In 1968, Tony Terracino, a local fishing guide bought the building and turned it into “Captain Tony’s Saloon. It was at this bar that Jimmy Buffet got his start in Key West. He often played music there in the early seventies and was sometimes paid in Tequila. Other notable guests of the saloon include Ernest Hemingway, Bob Dylan, Shel Silverstein, and Tenessee Williams.

Location: 428 Greene St, Key West, FL 33040


Cost: Whatever you order

Captain Tony’s Saloon

Captain Tony’s Saloon/ Flickr

9. Pan Am’s First Office – a unique historic building turned brewery

Dine and enjoy a beer at one of Key West’s most unique historic buildings turned brewery.

Pan American World Airways was America’s largest airline from the 1920s to its collapse in 1991. Its humble beginnings started in a tiny little office on Key West.

On October 27, 1927, Pan Am Flight Number One left Key West en route to Havana, Cuba. It was the first international air service in scheduled operation. The company was created by Juan Trippe to provide mass air transportation for the everyday man at affordable rates.

After Trippe secured the air postal routes between Cuba and Florida, he transformed his small airline business out of his Key West office into the world’s biggest air carrier.

The office is now First Flight Island Restaurant Brewery, with the “Crash Bar”. It is Key West’s only microbrewery and the southernmost brewery in all of America.

There is an elegant red brick patio where luscious tropical plants create a canopy above you. Off the main garden area through a set of French Doors, you will find the “Crash Bar”. The bar is made out of an aluminum airplane wing, and the ceiling fans appear to be rotary engines of an airplane. Definitely worth a visit for dinner!

Location: 301 Whitehead St Key West, FL 33040


Cost: Whatever you order

first flight

10. Curry Mansion Inn

If you haven’t chosen where you are going to stay while you are in Key West, then the Curry Mansion Inn should definitely be on your list. Staying at the Curry Mansion Inn will give you access to historic details and architectural features that will show off aspects of the colorful history of the building.

The property has 21 separate guest rooms across three different buildings, including the James House. The mansion is named after its builder, William Curry. Curry came to Key West as a poor Bahamian immigrant at the age of sixteen in search of economic opportunities. He began his career working as a clerk in the office of Weever and Baldwin.

He then fought in the Spanish-American War for several years before returning to Key West and climbing the corporate ladder. He then built a successful merchandising, wrecking, and ship-building company.

He had eight children with Euphemia Lowe and passed away in 1896.His estate was worth $1.5 million when he died. He was Florida’s first self-made millionaire and the richest man in the state at the time of his death. Curry’s son, Milton, completely demolished the property and rebuilt the home as a lavish Victorian mansion, which still stands today.

Location: 511 Caroline St, Key West, FL


Cost: As low as $300 a night if you book in advance. Book your stay here.


11. Key West’s First Legal Rum Distillery

Key West’s First Legal Rum Distillery is a cool place to visit in Key West if you are looking for something a bit different. They have free tours available every day between 12 pm and 5 pm, pets and kids are also welcome.

Key West’s First Legal Rum Distillery’s has a colorful history of its own. In 1900, it was originally Jack’s Saloon, known to be the go-to place for wines, spirits, and cigars.

Coca-Cola Company bought the building in 1903 and turned it into a bottling facility. Paul Menta bought the building in 2012, and Key West’s First Legal Rum Distillery was born. Paul Menta is a chef by trade, so he has created the Chef’s Distilled Rum, with the premise of making rum as a chef first and, a distiller second.

All of the rum is distilled with natural Florida ingredients. The distillery’s most well-known rum is the 80-proof rum. This dark rum is aged in American oak barrels that are soaking in seawater at nearby Simonton Beach. After they are soaked, the casks are then dried, leaving sea salt in the oak and adding interesting notes of the sea in every rum bottle.

If you are looking for something a little more decadent, check out the Chef’s Line. It includes flavors such as Key Lime, Mojito Mint, Glazed Pineapple, Green Coconut, and Vanilla brûlée dark. 

Location: 105 Simonton St, Key West, FL 33040

Cost: Free tours. Purchase of rum additional cost.


12. Nancy Forester’s Secret Garden

Nancy Forrester created this sanctuary over thirty years ago to care for abandoned and neglected parrots. At the rescue, you will get a chance to hang out with, chat with, and even dance with some cheeky birds.

It is the smallest parrot rescue in all of the United States. They also offer parrot guidance and background information to public visitors. Forrester gives a parrot 101 every day at 10 a.m.

The rescue was at one point the last undeveloped acres in all of Key West. Unfortunately, in 2012 Forrester was overwhelmed with taxes and finances and was forced to downsize by selling off parcels of land to developers. The rescue is now reduced to a small backyard on Elizabeth Street but still holds much of its passionate character.

If you visit, you will likely get a chance to meet Nancy Forrester herself and get to hear her speak about her passion. The rescue specializes in macaws. They have eight different species of macaws and two hybrids in captivity.

The entrance fee for adults is $10, for kids between the ages of 5 and 11 is $5, and kids under five get in for free.

Location: 518 Elizabeth St, Key West, FL 33040

Cost: Adults $10, Kids between the ages of 5 and 11 $5, kids under five get in for free.


Nancy Forrester’s Secret Garden

Nancy Forrester’s Secret Garden/ Flickr

13. Joseph ‘Bum’ Farto’s Desk at the Firehouse Museum

Visiting the Firehouse museum to see Joseph ‘Bum’ Farto’s Desk is for sure one of the best hidden gems in the Florida Keys.y.You can book a haunted firehouse tour which is really fun if you want to explore this part of Key West’s history.

Who was Bum Farto? Besides having a notoriously unfortunate name, he was also the infamous fire chief who turned criminal before disappearing. Joseph was born in Key West in 1919 and grew up across the street from the fire station. He had an obsession with firemen and often solicited change from the firemen, earning him the nickname “Bum”.

Farto grew up and took on the role of fire chief in 1964. He was known for sporting red suits, flashy gold chains, and rose-colored glasses. His arrest was a result of the investigation known as “Operation Conch”.

He was caught on camera selling cocaine to an undercover cop outside of the fire station. His criminal career consisted of grossly misusing department funds, drug trafficking, and selling cocaine out of the firehouse. After his arrest, he was facing thirty years in prison.

While he was awaiting his sentence, Farto completely vanished from Key West on February 16, 1976. Some believe that he escaped to Central America. Some believe that he was kidnapped and murdered by a drug cartel. There was even a musical created in his honor, “Bum Farto- the Musical”.

If you visit the Key West Firehouse Museum, you will be able to see Farto’s desk exactly how he left it, along with having an immersive experience of Key West Fire Station history.

Location: 1024 Grinnell St, Key West, FL 33040

Cost: $15


14. Rodriguez Cigar Factory

The Rodriguez Cigar Factory is the oldest cigar company in Key West. It is a family business that was started in Cuba in 1947 and was the birthchild of Angel and Daniella Rodriguez.

The most prized cigar that you can buy at the Rodriguez Cigar Factory is a bundle of the Reserva Privada cigars. You can also take a $35 tour of the factory. This tour includes a cigar wrapping class, a cigar, and a Cuban espresso. You may even get a chance to meet Danny, the current owner, and get a glimpse of his generous spirit and passion for sharing his family’s cigar-making heritage.

The family began on their private tobacco plantation in Siguaney. The tobacco plantation was called “La Finca de Carmencita”. Eight years after the plantation had been opened, the rise of communism made its way into the Cuban government. The Cuban government nationalized the plantation, forcing the family to immigrate to Florida to continue their business.

The family continued making and selling cigars with the main goal of producing consistent products enriched with Cuban heritage. To this day, they still produce cigars with Cuban manufacturing techniques. All Rodriguez Cigars are constructed only with vintage leaves sourced from Nicaragua, Honduras, and Ecuador.

Location: 113 Fitzpatrick St, Key West, FL 33040

Cost: You can book a tour at a cost of $35 per person.



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  • Reilly Mulligan

    Reilly is a sailing enthusiast from Florida who has spent her life sailing and exploring the Sunshine State. A native Floridian born who raised in St. Petersburg, Florida, Reilly has spent her whole life going on interesting, off-the-beaten-path trips around the state of Florida and has a plethora of information and experiences to share! While she is not sailing her boat around the Sunshine State she is sharing her experience traveling around the State with the readers of Florida Vacationers!

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