Key West, Florida.
September 2023.

Before we ever set foot on the island, Key West began with a journey. As we travelled across the sea on a highway of concrete and steel, we got a glimpse of the islands known as the Florida Keys. The Overseas Highway, often called the “Highway That Goes to Sea,” stretches 113 miles (182 km) from mainland Florida to Key West, leaping from key to key over 42 bridges that span the Atlantic Ocean, Florida Bay, and the Gulf of Mexico. Built atop the remnants of Henry Flagler’s early 20th-century railroad, this engineering marvel can be slow going at times. The highway is busy, but the sights along the way soothed the impatience we felt. As we journeyed, turquoise waters shimmered on both sides, and the salt air told us the ocean calls.

At the southernmost tip of U.S. Route 1, where the highway meets the sea, we found End of the Road, a souvenir shop that celebrates the spirit of Key West. This colorful storefront is a magnet for travelers seeking a tangible memory of their journey.

We chose to tour the island and its laid-back architecture on the Conch Tour Train. One of Key West’s iconic attractions, we chose the open cars that offer a narrated journey through the island’s rich history without the distraction of photos through glass windows. Along the way, knowledgeable tour guides (we had two) shared stories about the island’s past. The tour lasted about 90 minutes, and I captured many more photos than I can present here.

One of the first things we learned about the island features one of its celebrated residents, the conch. The mollusk holds deep cultural and symbolic significance in Key West, far beyond its role as a culinary staple. The term “Conch” originally referred to Anglo-Bahamian settlers who made conch a dietary mainstay and later migrated to Key West in the 19th century. Over time, locals embraced the name, and today, native-born residents are proudly called “Saltwater Conchs,” while those who’ve lived on the island for at least seven years earn the title “Freshwater Conchs”.

It was near City Hall that the tour guide told us about the Conch Republic. A “revolution” was born out of protest and humor on April 23, 1982, when Key West symbolically seceded from the United States in response to a Border Patrol roadblock that disrupted tourism and daily life. Led by then-mayor Dennis Wardlow, the tongue-in-cheek declaration of independence was a clever way to draw attention to the issue—and it worked. Since then, the Conch Republic has evolved into a beloved local identity and tourism booster, celebrating its “sovereign state of mind” with annual Independence Day festivities, passports, and merchandise that reflect the island’s irreverent, free-spirited culture.

On our tour, we learned that the Southernmost Point monument is not technically the southernmost spot in the continental U.S. The actual southernmost point is located on a restricted military installation just a short distance away. The monument was placed at its current location to serve as a symbolic, accessible landmark for tourists. At the same time, the actual southernmost tip remains protected due to national security and operational reasons. A lot of AI manipulation was required for this photo. We weren’t allowed to get off the train to photograph the buoy. There were many people at the site, and I was lucky enough to get a view without someone blocking the buoy. I cropped the image closely, then used AI in Photoshop 2025 to remove people at the monument’s edges. From the road, we couldn’t even see the entire text of the memorial, which reads,
The Conch Republic
90 Miles to Cuba
Southernmost Point
Continental U.S.A.
Key West, F.L.
Home of the Sunset

Nestled along one of Key West’s quieter residential corridors, this house exemplifies the island’s signature Conch architectural style, blending Bahamian simplicity with Victorian style. Its wrap-around veranda, gingerbread trim, and tall sash windows are typical of the bygone era when sea breezes were the island’s natural air conditioning. Elevated slightly above ground, the structure reflects traditional tropical design principles: raised foundations for ventilation and flood protection, steep metal roofing to shed rain, and louvered shutters for shade and privacy.

The Red Doors building is another example of Key West’s Conch architectural tradition, blending utilitarian design with historical depth. Initially constructed in 1868 by the Pinder and Curry families, its layout reflects classic Conch principles: commercial space on the ground floor with residential quarters above, maximizing both function and airflow in the island’s tropical climate. From its beginnings as a cigar factory to its current incarnation as a shrimpers’ bar, the structure’s vibrant red doors make it one of the more picturesque and historic landmarks on the Key West waterfront.

Tucked behind a white picket fence on Whitehead Street, the modest wooden structure with blue shutters and a metal roof marks the birthplace of Pan American World Airways, founded in 1927 by aviation pioneer Juan Trippe. The building’s classic Key West architecture, the raised foundation, louvered windows, and tropical landscaping mirror the island’s knack for blending charm with utility. I would have loved to see the interior of the former home where Trippe launched what would become one of the world’s most iconic airlines.

The Pan Am house is now home to the First Flight Island Restaurant & Brewery. This historic building marks the site where Pan American World Airways sold its first tickets in 1927. While it doesn’t operate as a traditional museum, it retains a strong sense of its aviation heritage. Inside, visitors will find a bar shaped like an airplane wing—aptly named the Crash Bar—along with ceiling fans designed to resemble rotary engines and a small display case featuring Pan Am memorabilia.

Mallory Square is one of Key West’s popular gathering spots. The rustic shipwreck in the plaza evokes the island’s maritime heritage. Mallory Square is best known for its nightly Sunset Celebration, where street performers, musicians, and food vendors create a festive atmosphere as the sun dips into the Gulf. We spent some time exploring the quirky shops, enjoying waterfront views, and admiring some of the sculptures.

“The Wreckers” commemorates the 19th-century wrecking industry that once made Key West the wealthiest city in America. It depicts two salvagers—one pulling a rope, the other working among debris, symbolizing the licensed crews who rescued cargo and passengers from ships that ran aground on nearby reefs.

On our Conch Train tour, we traveled past a tree-lined street and the well-hidden home of Ernest Hemingway from 1931 to 1939. Our guide explained that at his Key West home, Hemingway wrote three novels: Green Hills of Africa (1935), The Snows of Kilimanjaro (1936), and To Have and Have Not (1937).

Key West was more than a tropical escape for us. After our tour, we enjoyed the beautiful weather, enjoyed a seafood dinner with a friend who’d moved to the island, and returned to our hotel, tired and happy. Our plan for the next day was to visit Dry Tortugas National Park. We departed Key West on the Yankee Freedom III ferry from the Key West Ferry Terminal. This high-speed catamaran takes visitors on a 70-mile (112 km) journey across open water to Garden Key, home to historic Fort Jefferson and the park’s main facilities. It was there that we met our third tour guide, the docent at Garden Key. A future post will focus on our journey to the Dry Tortugas.

From the pastel-hued porches of Old Town to the echoes of aviation history at the Pan Am house, our stay was shaped by those island vibes of sea breezes and sun-soaked days. Key West invited us to slow down, explore, and feel the rhythm of an iconic island.

About the photos: You can find metadata and more information about the pictures in this gallery, along with many more images from our Key West adventure, on my Flickr site here. Some photos were enhanced using AI distraction removal tools in Adobe Photoshop and Lightroom Classic.

John Steiner