Top Landmarks of the Florida Keys

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Visiting the Florida Keys is like taking a trip to paradise. Everyone knows the crystal blue waters beckon, the drinks are cold, and the fish are biting. But not every visitor knows about the top landmarks of the Florida Keys. Join in exploring these iconic places in paradise.

The Overseas Railroad

Approaching the Florida Keys by car? Then you’re already on the path to history as you drive across what remains of Overseas Railroad. In 1905 Developer Henry Flagler, extended his existing East Coast Railway 100 miles off the Florida peninsula to Key West.

In 1935 this “Eighth Wonder of the World” was partially destroyed by a hurricane. The State of Florida used the salvageable parts of the railway to create a roadway.

A new roadway was constructed next to the original in the 1980s. Some of the ruins are visible as you drive next to them or fly over. Some portions of the old railway have been converted to paths or fishing piers.

Curious to know more about this fascinating landmark? Click here.

In addition to the loss of the railroad, and most buildings, over 420 people died during the storm. A monument to the victims is installed on the Overseas Highway at Mile Marker 82.


Gay Road Trip Guide to the Florida Keys

Key Largo

John Pennekamp Coral Reef State Park

Mile Marker 102.6

John Pennekamp State Park’s crystal clear waters and reefs draw many visitors. Explore the 70 nautical mile park by snorkeling or scuba diving. Or you can explore the sea from above. For great views of the reef and fish without getting wet try a glass-bottom boat tour.

Pennekamp also features two small beaches for swimming and sunbathing. Admission to the Park is a reasonable $9 for two visitors, and just $10 for up-to four. Learn more about all this unique park has to offer by clicking here.

The Christ of the Abyss Statue Dive and Snorkel Site

Adventurous travelers will appreciate this replica of a 1954 Italian statue of the same name. The catch, it’s located 25 feet beneath the Atlantic off the Key Largo Dry Rocks, approximately 6 miles northeast of Key Largo.

Non-divers can see another replica of the statue in the main sanctuary of St Justin’s Martyr Catholic Church at mile marker 105.5 in Key Largo.

The U.S.S. Spiegel Grove Artificial Reef

130 feet below the coast of Key Largo

Extreme adventurers will want to check out this former U.S. Navy ship. The Spiegel Grove is one of the largest ships sunk for an artificial reef.

Since 2002 this massive vessel has been attracting marine life and experienced divers to what has become one of the top landmarks (or is that seamarks?) of the Florida Keys.

Insider Tip: This site is only for advanced divers. Consult local dive masters about expectations and suitable equipment. Learn more about the Spiegel Grove here.


Explore Arts and Culture in the Florida Keys

Key West

West Martello Gardens & Fort

1100 Atlantic Boulevard

One of two Civil War era forts in Key West, this tower is now home to the Key West Garden Club. This is not just a landmark because of its historic status, it gets a mention as one of the last attractions in Key West to not charge for parking or admission!

History lovers will enjoy the landmark tower, which has not been altered since its construction in 1862. Plant lovers can learn about tropical gardening and explore the lush, beautifully maintained grounds.

Insider Tip: If you have an actual camera bring it! The textures of the fort and the unique plants make for great photos.

See what awaits you at the West Martello Gardens and Fort here.

African Refugee Cemetery

1074 Atlantic Boulevard

This landmark honors Africans who died after being rescued from illegal slave trade. 1,500 individuals were rescued from three ships in 1860. The nearly 300 that did not survive were buried here.

This cemetery was lost to time until 2002 when it was re-discovered by a team of archaeologists. This sacred space is now on the National Register of Historic Places. An exhibit at the Mel Fisher Maritime Museum (200 Greene Street) provides details of this story.

Key West Aids Memorial

White Street at Atlantic Boulevard

Stroll down to the end of White Street to the pier, that extends over the Atlantic.

At the foot of the Pier is the Key West Aids Memorial. This monument was established in 1998 to pay tribute to those who have died of AIDS. Further, they had some connection to the Florida Keys. For more information about this thoughtful Memorial, including how to nominate a new name for addition, visit here.

Key West Memorial Sculpture Garden

401 Wall Street

This garden honors individuals who have contributed to the history and development of Key West. It’s an easy stroll from bustling Mallory Square, and the rest of downtown to this quiet, free space. Visitors can learn the names and stories of the famous, and some infamous, people who helped shape this slice of paradise.


Where to Eat in the Florida Keys

Key West Cemetery

701 Pauline Street

At any given time’ Key West has a population of approximately 130,000 residents. But only around 30,000 of them are still alive.

Come meet some of the permanent residents of Key West’s historic cemetery. Visitors can take a guided tour or explore the 19 acre park-like setting on your own. Here people from all backgrounds rest side-by-side, reflecting Key West’s historic diversity.

Insider Tips: This is still an active cemetery. Please be respectful if you encounter any services taking place. Keep an eye out for amusing sayings on headstones like “I Told You I Was Sick!”

Make your final arrangements, or rather, plans to visit here.

Truman Little White House

111 Front Street

Even world leaders need a change of scenery sometimes. United States President Harry Truman made this 1890 former Spanish-American War headquarters his winter home. Other U.S. Presidents used this location during the Cold War because of its proximity to Cuba.

The rooms have been restored to the way they were while Truman stayed there. There are many interesting objects to view. Be sure to ask about the “secrets” of the poker table!

Insider Tip: There is no charge to visit the front two rooms of the museum. However, tickets are required for full access. Ticket prices are lower online. Get yours here.

Tennessee Williams Exhibit

513 Truman Avenue, off Duval

Key West has been home to many artists and writers over the years. Author Tennessee Williams began spending vacations on the island in 1941. In 1949, he made Key West his permanent residence and lived on the Island with his partner until his death in 1983.

However, fans of the man and his many classic works can check out this exhibit honoring his life and career. Visitors can see Williams’ typewriter, other personal items, and view some of the paintings he created.

Insider Tip: In March Key West honors Williams with a birthday celebration over several weeks. The party includes productions of his plays and other fun. This is not the home Williams lived in. That is now a private resident and is not open to the public.

Learn more about this literary star and his life here.

Audubon House & Tropical Gardens

205 Whitehead Street

In the midst of bustling Old Town Key West is this small, quiet oasis. This restored house and gardens date to the 1840s. Visitors can get a sense of what life would have been like in the Keys during the mid-19th Century.

Today, the house is a showcase for the original artwork of John James Audubon (who never actually visited the property). The home’s builder, Captain John Geiger, made his living salvaging and auctioning cargo from shipwrecks. This was big business in the Keys at the time and Geiger was one of the ten wealthiest men in the area.

Plan your visit to learn more about this fascinating industry and the history of the Audubon House here.

Insider Tip: Visitors with mobility issues will only be able to access the gardens and the first of three floors. There are rocking chairs on the porch for relaxation.


Top Beaches of the Florida Keys

Key West Shipwreck Museum & Observation Tower

1 Whitehead Street

This museum in a replica 19th Century warehouse, tells the history of Key West’s wrecking industry. The history of this dangerous business is brought to life by actors, videos, and actual artifacts from shipwrecks.

Visitors can explore the museum and then climb up the 65-foot lookout tower. This replica landmark offers spectacular views, if no actual shipwreck sightings.

Insider Tip: The climb to the top is worth the reward of the amazing view. Check the museum’s website for info and occasional discount offers.

The Ernest Hemingway Home and Museum

907 Whitehead Street

Ernest Hemingway’s love affair with Key West prompted him to move here permanently. In 1931 Hemingway, his wife, and their six-toed pet cat moved in to this 1851 home.

Hemingway wrote his novel “To Have and to Have Not, ” about depression era Key West while living here.

The descendants of Hemingway’s six-toed pet cat still live in and around the house. While the historic furniture is off limits to humans, don’t be surprised to see these cats sleeping on it.

Learn more about Hemingway and his former home here.

Key West Lighthouse & Keeper’s Quarters

938 Whitehead Street

Key West is an island of pioneers and many “firsts.” One of the first female lighthouse keepers, Barbara Mabrity, served here for over 30 years. The lighthouse, built in 1848, was critical in keeping ships safe from the reefs around the island.

Now visitors can explore the grounds of this historic structure. The keeper’s cottage provides a glimpse into what life was like on the island in the 1800s.

Get your exercise in by climbing the 88 steps to the top of the light. You’ll be rewarded with a good workout and the amazing view.

Get all the details you need to plan your visit here.

Southernmost Point

Whitehead Street at South Street

Top Landmarks of the Florida Keys come in all shapes and sizes. Head on to the “southernmost point” of the continental United States to grab your selfie at this quirky buoy. The view of the sea, and the architecture of the neighborhood make this worth a quick stop.

Insider Tips: There is no parking here so plan to walk a few blocks. Arrive early, or at dusk, to avoid lines.

Fort Zachary Taylor

601 Howard England Way

This Civil War Era Fort overlooks the Atlantic. Daily tours offer interesting info about the fort’s construction and history.

Military buffs will enjoy seeing guns and ammunition excavated from the site. Trails around the grounds offer stunning views of the Atlantic. Many are ADA accessible for visitors with mobility devices.

Insider Tip: Bring your swimsuit and beach gear for time on the shore at the park’s beautiful beach. Plan your visit to Fort Taylor by clicking here.

Dry Tortugas National Park/Fort Jefferson

68 miles south of Key West is the day trip of a lifetime in this unique national park.

For Jefferson is the true gem of this top keys landmark. The massive fort and prison served as safe harbor and refueling station for ships traveling to Gulf ports and the eastern seaboard.

Overnight primitive camping is available. Adventurous visitors wanting this memorable experience should read these guidelines to help plan.

Insider Tips: No matter how you get here, this is a long day trip. There are no concessions on the islands. Bring everything you think you will need. Carefully research and select the best mode of transportation for you and your traveling companions. Communicate directly with your chosen transportation provider to find out all rules and regulations of their operation, and what, if any, amenities they offer.

Start planning your one-of-a-kind adventure to the Dry Tortugas here.

Explore from a New Perspective

Whatever your interests and vacation goals the Florida Keys has something to interest you and your travelling companions. Including some off-the beaten path landmarks might just open your eyes to new passions.

**Disclaimer: There is a good chance that this post contains affiliate or sponsor links. If you make a purchase through them, we may receive a small commission at no extra cost to you (for which we are extremely grateful).

Also, while we do our best to highlight LGBTQ-friendly destinations and businesses, info provided is based solely on personal experience and recommendations by community partners. We hope that nobody experiences discrimination or homophobia while visiting Florida, but we make no guarantees. Please inform us if you experience discrimination or homophobia while visiting any destination so we can make updates to our recommendations.

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july, 2024

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