Key West | Travel News

The sun was just peeking above the horizon when we started our drive on Tamiami Trail towards Miami. For over forty-five years, I have driven this road and never tire traveling through the middle of the Everglades. The scenery is some of the most spectacular in Florida, from the “river of grass” dotted with clusters of palmetto and cabbage palms in the early morning mist. Alligators are already out on the side of the water waiting for the sun. Great blue herons, snowy egrets, and black anhingas, drying their spread-out wings, completed the magical marshy scenery. This impressive nature is now marred by one eyesore, almost at the halfway mark on the road by Alligator Alcatraz, the ICE detention facility. It is not that it can be seen from the road, but it is the only place where peace is disturbed by traffic and people.

On previous trips, we have stopped on the way South at the first main island on the “Overseas Highway,” Key Largo, to snorkel at John Pennekamp Coral Reef State Park, the only coral reef that is part of the continental United States. Next is Islamorada, often called the “Fishing Capital” of Florida, and Marathon, the home of the Sea Turtle Rehab Center and the Dolphin Research. This time we drove on, eager to get to Key West.

The gateway to Key West was a dream of the founder of Standard Oil, Henry Flagler, who originally connected St Augustine in North Florida to Miami, building the Florida East Coast Railway. However, he was determined to connect Miami to Key West as well and spent thirty million dollars to build the “Overseas Railway.” Today, that would be approximately $1,090,223,900. His dream was realized for him under the leadership of civil engineer William J Krome, who finished the seven-mile bridge in 1912, just a year before 83-year-old Flagler died. The hundred-plus-mile stretch was connected by 42 bridges that reportedly could withstand hurricane winds; however, in 1935, the Labor Day Hurricane, the strongest Hurricane of the time, did irreparable damage to the railroad.

The Category Five storm ravaged everything in its path with over 200 mph winds and 18-to-20-foot storm surge, bringing an end to the domination of Key West, which in the mid-eighteen hundreds was the largest city in Florida and, according to some data, the richest city in America.

In the meantime, our country had fallen in love with the automobile; consequently, three years later, the government repaired the bridges and covered the railroad in asphalt and concrete to create the “Overseas Highway,” leading to what is now again a tourist paradise with its own set of rules: Key West.

Arriving here, the atmosphere is more Caribbean, although I have never seen a policeman crossing the street on a horse anywhere in the Caribbean, either. He smiles at a group of revelers celebrating on the street. It seems anything goes in this town, which is located further away from Miami than from Cuba. Festive bars and restaurants line Duval Street and most side streets.

We had booked into a three-star property, called “Mansion On the Sea,” also called “Southernmost House Key West.” It indeed claims to be the farthest southern property on the US mainland, with rooms overlooking the azure, blue seas, their pool and private beach on the water, and a rooftop cocktail bar. The claim is somewhat confusing because several other hotels make the same claim. However, its location is indeed superb, right at the very end of the famous Duval Street. It is also a stone’s throw away from the much-photographed buoy that is 90 miles from Cuba and the “0-sign” indicating the start of the oldest road on the US East Coast, Rt 1, leading 2,446 miles all the way to the Canadian border in Ft Kent, Maine. The house was built in 1897 for the daughter of Florida’s first millionaire, Florida William Curry, and her husband. At the time, her father commissioned Thomas Edison to install electricity in the home’s one bedroom. Upon his departure, he left one of his original gramophones as a gift for the couple and it is still there today. Many famous people have stayed here, including Al Capone when he was on his way to Cuba. The story goes that a botched attempt was made on his life, and the bullet hole is still visible right behind the reception desk. Numerous celebrities and five Presidents frequented the Mansion, and it is said that Leonard Bernstein resided here when he wrote the music for West Side Story. The hotel has continued its colorful history into the latest years, with giant property and management disputes involving police intervention as recently as three years ago.

Controversial attorney Michael Halpern was the owner until his death at the very end of 2024. Many locals in Key West loved him and others, including city officials, clashed with him on occasion. Often, he came across as the strong-willed attorney he was, but employees and those who knew him loved the New Yorker who moved with his wife, Michelle, four sons, one adopted, to the outskirts of Key West in 1975 to work as a public defender. In 2011, Michelle lost her more than ten-year battle with cancer.

Unbeknownst to most, Michael was already involved in many local philanthropies and after his wife’s death, he assisted his sons in launching a non-profit, “Kids Fighting Cancer.” He provided continuous assistance with food for kids who would otherwise return home from school without having anything to eat. It paid for school trips that would have been impossible otherwise and even paid for sneakers. The list goes on and on, but he forbade people in the know to divulge his generosity and he refused to take credit. It was not publicly known that Michael had cancer and a shock to people when he suddenly passed away at the end of 2024 at age 72. His sons are continuing his legacy and his youngest son, Alex, now runs the Mansion on the Sea. As a result of the many storms, sand, and wind in Key West, properties sometimes seem somewhat weathered and neglected. Alex and his team are hard at work repairing, updating, and improving the property with its eighteen rooms. That helps in creating the very special atmosphere of this city at the most southern point of the United States, that was purchased from Spain in 1821 by John W. Simonton, who had large commercial interests in Havana, New Jersey, and Washington.

Our regular room, with a front balcony, was very comfortable and the breakfast enjoyed outside on the extended downstairs porch featured deliciously fresh delicacies from the local bakery.

For us, it was a perfect getaway for two nights of fun dining, prefaced by killer margaritas, rum cocktails, and conch fritters that Key West is renowned for. We felt justified in enjoying them all as a reward for all the walking we did from one end of town to the other and every cross-street in between!