Things to do in Key West: Historic Whitehead St

Nov 15, 2021

When I was looking for things to do in Key West my friend mentioned, “Why don’t you take a stroll down Whitehead St?” This historic Key West street spans from the Southernmost Point of the Continental United States and ends at Mallory Square. Please enjoy the play by play as we took in the sights, sounds and good eats along the way.

The Southernmost Point

The Southernmost Point of the continental United States of America is Key West, Florida. At the beginning of the historic Whitehead Street we visited the large concrete buoy where thousands go to take pictures to say “I have been to the Southernmost Point!.” You can check out the webcam to get a peak of the view here.

Southernmost Point Key West
Key West has a lot to offer in the clear waters from snorkeling to sailing to dolphin watching the list goes on. When you are in town strolling through Duval street you can hear the sounds of live music being played at the various tiki bars and restaurants. We rented some bikes and scooters to get around with ease so we could take as much in as possible.

Key West Lighthouse

Next up on the journey we took 88 steps up the Key West Lighthouse. The lighthouse was opened by a woman in 1848. At the time it was nearly unheard of to have a woman as a keeper so it was a historic moment! “In the years following, the Key West Lighthouse underwent a number of upgrades including the installation of a Third Order Fresnel Lens, an extension to the tower which allowed the light to be seen from a greater distance, the addition of Keeper’s Quarters, and finally the electrification of the light.” (Source)

Key West Lighthouse

In 1969 it was decommissioned due to tech advancements that didn’t require a full time keeper. We got to see the belongings, photos, and words of the lighthouse keepers as we perused the 19th century beauty. It’s open 7 days a week from 10:00 a.m. – 5:00 p.m. It’s located at 938 Whitehead Street and you can check out the website here.

Hemingway House & Museum

The next stop on Whitehead Street is the Hemingway House & Museum. Ernest Hemingway was an American novelist and short story writer who lived an adventurous life.

“His succinct and lucid prose style exerted a powerful influence on American and British fiction in the 20th century.” (Source) In 1931 Hemingway’s wealthy Uncle Gus purchased a home for Ernest and his wife Pauline. The 1851 homestead located on Whitehead Street in the heart of Key West was renovated by the Hemingway’s in the 1930’s and it turned into the National Historical Landmark that thousands of tourists visit and enjoy today.

Ernest Hemingway Portrait

Hemingway, “received the Pulitzer Prize in fiction for The Old Man and the Sea (1952), a short heroic novel about an old Cuban fisherman who, after an extended struggle, hooks and boats a giant marlin only to have it eaten by voracious sharks during the long voyage home.” (Source) As a journalist he spent a lot of time in the field during the war. He saw a lot of action in the Battle of the Bulge in Normandy and he even impressed the soldiers he was with in his journey as not only a brave man but someone who was well educated on war, strategy, etc. He wrote several novels about the war, “A Farewell to Arms he focused on its pointlessness, in For Whom the Bell Tolls on the comradeship it creates.” (Source) He made his way to London and participated in several missions with the Royal Air Force. He even crossed the English Channel with the Americans during D- Day. (Source)

When he wasn’t writing he was on the water with his boat, Pilar, as he was an avid fisherman. He spent his summers in Wyoming at his second residence – hunting elk, deer, and grizzly bears. A writer, husband, father, adventurer… Hemingway was many things throughout his life. It was neat to see how well preserved his legacy is through the home and museum.

You can find all the information about the home and tours etc. by visiting here. The address is 907 Whitehead Street, Key West, Florida and you can call the office at 305-294-1136.

Bahama Village Market

The Bahama Village Market is home to some of the best food on the island! The Market “is a 12-block area between Whitehead and Fort and Angela and Catherine Streets, you’ll be able to see the original area in which the first Bahamian settlers arrived in the 19th century.” (Source) Ram’s Head Southernmost was our pick for brunch. It is located at 804 Whitehead Street in Key West, Florida only a few, “steps from Duval, at the entrance of the historical Bahama Village.” It features an open outdoor tropical setting with a tiki bar offering an eclectic Caribbean cocktail list which is home to their signature “Rum Punch”.

Rams Head Southernmost Nightlife and Music

The colorful walls mixed with a unique weathered wood bring it all together as the local live music plays on daily. The beachy signage behind the bar and the palm ceiling fans pull it together to be the perfect setting for a vacation beach brunch.

Their website says, “Rams Head was founded in Annapolis, Maryland and has been family owned and operated since 1989. With roots in Key West, Rams Head is proud to be part of the local community and is committed to providing the best in food, fun, and beer.” You can, “enjoy breakfast, lunch and dinner, among lush foliage, water fountains, and the Key West sunshine.”

The hours of operation are 9:00 a.m. -11:00 p.m. every day with food being served until 10 p.m. The “Happy Hour” is 4:00-6:00 p.m. Monday through Friday and features $4 drafts, domestics, $2 off wine and liquor, and half price apps. There are a lot of places to explore in the Bahama Market but this restaurant had rave reviews and it was located nearest Whitehead Street.

Cornish Memorial AME Zion Church & The Kapok Tree

Walking off the tasty brunch at Ram’s Head we made our way down the sunny sidewalks of Whitehead Street. We didn’t take a tour but we did stop to take in the beautiful architecture of the Cornish Memorial AME Zion Church. Sandie Cornish was born into slavery in Maryland in the 1700’s and through some miraculous events he was able to be free! Through this process he and his wife moved to Key West and helped start this church. “It is the oldest African American church in South Florida.” (Source)

Kapok Tree Whitehead St, Key West

The Kapok tree was not far from the church. “It is a tropical tree, native to Mexico, Central America, the Caribbean, northern South America, and tropical west Africa.” (Source) It is a sacred tree in the Mayan mythology and it grows to be 130 plus feet tall with a gargantuan trunk that spans nine or more feet! It is one of the most popular trees to get a picture of in Key West.

Mallory Square & More!

Mallory Square is the historic shopping center that we were making our way towards. Before the end of Whitehead Street we made a few stops and notes for other days (adventures). We had a pint at First Flight Island Restaurant & Brewery located at 301 Whitehead St, Key West, Florida. I tried the Maverick IPA (love the Top Gun reference!) and it is described as a, “medium pale ale using our specialty blend of unique malts, grains and hops, to create a perfect balance of aromas with a clean crisp finish.” (Source) It paired nicely with the Bavarian Pretzel with Maverick IPA cheese. Be sure to check out their full menu here.

Mallory Square Key West

We made note on our way past the Comedy Key West club that we needed to schedule a night of laughter! It is the only comedy club in the Florida Keys and features comedians from HBO, Netflix and Comedy Central.

The last stop on Whitehead Street is the Key West Shipwreck Museum. They offer tours and it, “combines actors, films and the actual artifacts from the 1985 rediscovery of the wrecked vessel Isaac Allerton, which sank in 1856 on the treacherous Florida Keys reef.” (Source) This is a great experience for the whole family! There is a rich history of shipwrecks in Key West but that will have to wait for another blog…

We made it to Mallory Square! You could easily spread out the Whitehead Street stroll over several days as there are a lot of fun options. Be sure to check with the restaurants before you go as some prefer reservations for lunch and dinner.

key west travelers sign off