Island Style

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There are many architectural highlights that visitors must check out while in Key West.

Hemingway House, Truman’s Little White House, Key West Lighthouse…just to name a few.

While these are amazing attractions, one of the best things to do is set out on foot and discover all of the small historic sites that are scattered throughout the city. As my husband and I made our way throughout the island, we encountered many homes, theaters, bars, churches, boats, gardens and other structures that give Key West its charm and style.

Shopping

You can start emptying your pocketbook in Mallory Square. There are a great many souvenir shops located here as well as local vendors, street performers and live music. The Key West Aquarium is positioned here and it is the starting point for the Old Town Trolley Tours. If setting out on foot is not your forte, then hop on board the trolley and see the city! If you do decide to take your own walking tour, make sure to watch out for the markers on some of the historic sites. You can call the number listed at the bottom of the marker for free audio description.

Restaurants and Bars

Just around the corner from Mallory Square your will find El Meson De Pepe restaurant. While the Cuban food was good, what I enjoyed most was the interior. The restaurant is filled with murals and art by Mario Sanchez, information on author Jose Marti and even an antique airplane hanging above diners! Since I had been to Cuba a few months prior, it felt very familiar and comfortable.

Sloppy Joe’s Bar and Restaurant is a favorite on Duval Street. Touted as a Key West tradition, it is usually filled with revelers until the early hours of the morning. Because of Covid restrictions, it was extremely quiet while we were visiting as was many of the numerous bars and restaurants that line the famed street. However, we have been there on other visits and it is one of the highlights if partying is your thing!

Churches

The Basilica of St. Mary Star of the Sea was one of the churches that I had marked high on my to-do list while in Key West. Adjacent to the Convent of Mary Immaculate, built by the Sisters of the Holy Names of Jesus and Mary in 1878, the church dates back to 1905. The church is a single nave structure and decorated quite simply with touches of gold and light blue, paying homage to the sea. There is a beautiful stained glass window located above the altar and some nice sculptures scattered throughout. Since the church is not air conditioned, the many sets of double doors that line each side of the church are opened for the comfort of the parishioners.

As we walked down Duval Street, we encountered St. Paul’s Episcopal Church. Though we only were able to admire the structure from the outside, we did learn that this church was preceded by three others on this historic site. The first and third was destroyed by hurricanes in 1846 and 1909 and the second was devastated by the Great Fire of 1886. This church was completed in 1919 and designed to stand the test of time and nature.

Historical Homes

On many of Key West’s main and side streets, you can find beautiful, historic homes of great significance. Whitehead Street boasts the Philip L. Cosgrove House, dating back to 1872. This house once belonged to Captain Philip L. Cosgrove, Sr. who commanded the U.S. lighthouse tender Mangrove, the first rescue ship to aid victims of the 1898 explosion of the U.S.S. Maine in Havana harbor. Incorporating the former house of federal judge James Locke, the house was expanded to two and a half stories in the Greek Revival style.

A few steps away from the Cosgrove House is the William Lowe Delaney/Theodore Holtsberg House which has a long line of owners dating back to 1844. The first owner, Benjamin Sawyer, built the first house on the property for his family and also used the structure for Key West’s port business until the completion of the Customs House. The next owner, Deputy Custom Collector William Lowe Delaney bought the property from Sawyer’s widow and built the house that stands today, a two story, Queen Anne revival with an asymmetrical floor plan. The home was transferred to Lavinia Artolozaga in 1918 upon Delaney’s death, and then again in 1925 to Romanian immigrant Theodore Holtsbert, one of the island’s first Jewish immigrants. Today, the home is part of the Banyan resort.

At the head of Whitehead Street is the Audubon House and Tropical Gardens. The house was built in 1830 by Captain John H. Geiger, pilot and master wrecker. The house was dedicated in 1960 by Mitchell Wolfson, to act as public museum to be named Audubon House commemorating John James Audubon’s visit to the island in 1832 to study the key’s birds.

Alexander Cruz/Julia Gardner House is located on the corner of Eaton and Whitehead Streets. A three story cigar factory was built on the site in 1889 by the Cruz Brothers, Andres, Alexander and Jose. Acting as a business and residence for the family the cigar factory was then bought by Alexander in 1900 where he then erected a two and a half story Neoclassical home in 1904. Fourteen years later, Julia Gardner, daughter of prominent land owner Richard Henry Albury, purchased the residence and lived there for thirty years.

On Duval Street, the Martin Hellings House was constructed in 1892 by Captain Martin L. Hellings and is one of only a few homes that was not built during the Civil War. Hellings, accepted the position of cable manager of the International Ocean Telegraph Company in Key West, an important position as telegraphs were the means of rapid long distance communication. Upon his death in 1908, the house was converted into offices and then purchased by the Key West Woman’s Club which later converted it into a public library.

Government Buildings and Museums

One of the most beautiful landmarks in Key West is located on Duval street. Founded in 1871 by Cuban exiles as an educational, civic and patriotic center, the multi-purpose facility serves as a museum, library, art gallery, theater and school. The famed Jose Marti united the exile community in 1892 and affectionately referred to the San Carlos as “La Casa Cuba”.

On Simonton, between Eaton and Caroline Streets, you can find the Federal Courthouse, which also houses the Social Security Administration and U.S. District Court. The building, as evidenced by the wording on the face of the building, acted as the Customs House.

On Front Street, you can find the Key West Museum of Art and History at the Custom House, built in 1891, which also acted as the island’s custom office, postal service and district courts. This four story construction was built in the Romanesque style and was the site of many significant historical events. In later years, it was transferred to the United States Navy and then abandoned for almost twenty years. It was purchased by the State of Florida in 1991 and leased to the Key West Art and Historical Society for use as a museum. Visitors can now experience two floors of exhibitions which tell the tale of Key West’s history, art and people.

The Monroe County Courthouse, located on Fleming Street, was completed in 1890 in a traditional county courthouse style and features a 100 foot tall clock tower that can be seen from almost any part of the island. Make sure to check out the massive Kapok (or Ceilba tree), located in front of the courthouse.

The Southernmost House holds the distinction of being (yes, you guessed it) the southernmost house in the United States. The house is located near the Southernmost Point attraction and although it acts as a hotel, it also acts as a museum with displays of collections of important and interesting documents, many signed by presidents of the United States, including John F. Kennedy’s inaugural address. Even if you don’t have time to visit the museum, take the time to inspect this impressive Queen Anne Victorian architectural gem.

If you are a maritime enthusiast, you can visit the U.S. Coast Guard Cutter Ingham Maritime Museum, on the waterfront near Fort Zachary Taylor. The museum ship served during WWII and Vietnam and is the most decorated ship in the United States service. It was the last American Warship afloat to have sunk a German U-Boat and you can learn about its illustrious history in its exhibit room. We took a quick picture in front of the cutter, however, we planned to return at the end of the day on Friday or Saturday…this ship is known for being one of the best places to view the beautiful Key West sunsets…and it serves wine and beer!

Other Historic Structures and Attractions

If you are an Ernest Hemingway fan, of course, you would visit his former home. If that leaves you wanting more, take a walk on Simonton Street and check out the Old Trev-more Hotel where Hemingway and his wife stayed in 1928. It was here where he penned Farewell to Arms from his second story room. In 1978, the hotel was converted to a private residence and renamed Casa Antigua.

There are two prominent art-deco style theaters in the historic district of Key West. The Key West Theater, originally built in 1848 as the First Baptist Church of Key West, has also operated as a dance club and concert venue. Today, it now operates as a performing arts center.

Further down Eaton Street is Tropic Cinema. Of the two, this is the one to take a moment to see. Showing independent movies on four screens, this cinema’s exterior is beautifully styled with neon signs and a statue of Marilyn Monroe standing over a vent, dress blowing surrounded by a sidewalk interspersed with stars.

Finally, at the end of your days (if you still have the stamina), venture down to the Historic Seaport Harbor Walk where you can have drinks and dinner, gaze (wistfully) at the beautiful boats, people watch and then wander over to nearby Sunset Pier to watch the awesome sunsets that grace Key West’s skies on most evenings.

The style of Key West, both natural and man made, can’t be beat!

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Mallory Square

El Meson de Pepe Restaurant

Sloppy Joe’s Bar

The Basilica of St. Mary Star of the Sea

  • https://stmarykeywest.com/
  • Address: 1010 Windsor Lane, Key West, Florida 33040
  • Hours: Monday-Friday, 0900-1500, Saturday, 0900-1400, Sunday, after all masses
  • Admission: free

St. Paul’s Episcopal Church

Philip L. Cosgrove House

Address: 323 Whitehead Street, Key West, Florida 33040

William Lowe Delaney/Theodore Holtsberg House

  • Address: 323 Whitehead Street, Key West FL 33040

Audubon House and Tropical Garden

  • http://audubonhouse.com
  • Address: 205 Whitehead Street, Key West, Florida 33040
  • Hours: 0930-1615, Monday -Sunday
  • Admission: free (not verified)

Alexander Cruz/Julia Gardner House

  • Address: 403 Eaton Street, Key West FL 33040

Martin Hellings House

  • Address: 319 Duval Street, Key West, Florida 33040

San Carlos Institute

Customs House and Museum

  • https://www.kwahs.org/museums/custom-house/visit
  • Address: 281 Front Street, Key West, Florida 33040
  • Hours: 1000-1600, daily
  • Admission: Adults, $16.00 ($14.40 online), Senior/Local/College ID/Retired Military, $12.00 ($10.30 online), Youth (ages 7-18), $8.00 ($6.30 online), Children (under 7), free, Military, free

Monroe County Courthouse

Southernmost House

U.S. Coast Guard Cutter Ingham Maritime Museum

  • https://www.uscgcingham.org/
  • Address: Truman Waterfront On The Western Edge of Key West Foot of Southard Street at new Park Seawall, Key West, FL 33040
  • Hours: Tuesday-Saturday, 1000-1600
  • Admission: Adults (ages 13+), $10.00, Children (ages 7-12), $5.00, Children (under 6), free, Active Military, $5.00

Casa Antigua

Key West Theater

  • https://thekeywesttheater.com/
  • Address: 512 Eaton Street, Key West, Florida 33040
  • Hours: vary according to events scheduled
  • Admission: varies according to event

Tropic Cinema

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