As many followers of this site will know, Key West is unlike anywhere else in the United States, and not exactly like anywhere else in the Florida Keys for that matter. It is a tropical hideaway closer to Cuba than it is to the US mainland, with a laidback lifestyle that is enticing. It’s not difficult to see why it attracted writer and adventurer Ernest Hemingway, whose former house is now a major tourist attraction in the city.
Getting here by road is an adventure in itself. We travelled in a rental car from Miami, driving down the magnificent Overseas Highway, a 182-kilometre (113-mile) road taking US-1 through the Florida Keys to Key West. We saved our sightseeing along the way for the return trip, so drove pretty much non-stop in a little over three hours.
We stayed for a few days at The Grand Guesthouse, a charming establishment at 1116 Grinnell Street with attractive and secluded outdoor areas outside the rooms. Those looking for more upmarket accommodation might like to try the Marquesa Hotel, recommended by Travel + Leisure magazine and voted one of the best resorts in Florida by its readers in 2023. It is classically styled with dark wood flooring and tropical island furnishings, and a bright blue exterior that matches the nearby sea. But there are dozens of eclectic accommodation houses to choose from.
Old Town is the original Key West settlement on the western part of the island, which contains the classic bungalows and guest mansions and now the major tourist destinations as well. These include Duval Street, Mallory Square, Fort Zachary Taylor State Park and the Ernest Hemingway home and museum at 907 Whitehead Street.
Hemingway’s writing study.
The historical building was where Hemingway lived with his second wife, Pauline Pfeiffer, while he wrote A Farewell to Arms and Death in the Afternoon, among other literary works. The house was built in 1851 by Asa Tift, a marine architect and wreck salvager, and was Hemingway’s private residence from 1931 to 1939.
If you’re only here for a short time it’s best to find accommodation as close to Duval Street as possible since this is where the night-time action is and where most of the bars and restaurants are – it is said there are more than 300 of them. Don’t leave without trying the exquisite Key lime pie.
It is de rigueur to go to the pier at the northern end of Duval Street at sunset for a drink, and then to Mallory Square for the best views of the sun going down. Our excursions to these points can be seen in the following pictures.
The southernmost point of the continental United States is marked (not strictly accurately) by a massive buoy erected in 1983. It is one of the most photographed locations in Key West, and of course we had to contribute to that reputation.
You can get to most of these places on the Conch tour train, which leaves from Front Street every 30 minutes from 9.00am to 4.30pm. The round trip takes 75 minutes and there are three scheduled stops.
Fort Zachary Taylor Historic State Park is home to the largest archive of Civil War armament in the world. It also has a gorgeous beach that is open to the public for swimming, snorkelling and outdoor dining. It is the southernmost state park in the continental United States.
Boating, fishing, scuba diving and snorkelling are all popular in Key West. Those more interested in aesthetics will be delighted by the local architecture of mainly wooden buildings dating back to the 19th century, including the distinctive conch houses.
The conch-house style was developed in Key West by Bahamian immigrants and can also be seen in Miami. The conch house is built of timber and set on wooden posts or stumps, which allow air to circulate under the floor, much like the Queenslander-style homes in Australia.
Why did the chicken cross the road?
New Town occupies the eastern half of the island and features more modern (and less interesting) infrastructure – large shopping centres, retail developments, cinemas, residential areas and schools. It does, however, have some very nice homes, many in the authentic Key West style.
I’ll let the remaining photos speak for themselves.
Key West is a fabulous hideout that I could go back to time and time again. On the return trip to Miami we stopped off at various places including Key Largo, but that’s another story.
Photos © Judy Barford
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