What is the first thing that comes to mind when someone mentions Key West? The gorgeous sunsets at Mallory Square? The tenacious pub crawlers along Duval Street or the eclectic festivities that give the island its signature flair?
I didn’t know what to expect on my first visit to Key West. I was only 19 years old working on a cruise ship and it was the first stop on our itinerary before traveling to Cozumel. My fellow pursers guaranteed that I would love Key West, but I could not have imagined how many memories I would make here. This magical place seemed more like a Caribbean island than a Florida port of call.
There was so much to learn about Key West that summer. I booked a lobster dive, visited the Treasures of the Atocha museum and watched Jimmy Buffett perform at a local bar. Rich with history and a unique culture unto its own, it is no doubt, Key West is unlike any other place I have ever visited in the US.
Originally given the Spanish name Cayo Hueso (Bone Cay), Key West was once a settlement of the Calusa people, an Indian tribe known for their fierce, war-like disposition. The English, mispronouncing the name, would later call it “Key West”.
The island was also a popular hideout for pirates who attacked Spanish treasure ships sailing from the Caribbean to Spain.
By 1912, the coral islands of the Keys would become accessible by rail with the completion of Henry Flagler’s railroad. Damaged by hurricane winds in 1935, the rail line was abandoned and replaced by the 123-mile Overseas Highway.
Touring the island by trolley was my favorite way to explore the island. The open-air tram made its way through town, stopping at several historical landmarks.
I remember how excited I was to reach one of Key West’s most popular sites, the Southernmost Point of the Continental U.S. Standing at the corner of South and Whitehead Streets, I was surprised to learn I was closer to Cuba than Miami. This cute little bouy-like structure attracted visitors from all over the world and the line for a photo was worth the wait.
At the top of the monument, there is a reference to Key West as “The Conch Republic.” The trolley guide explained that on April 23rd, 1982, the island seceded from the mainland with the desire to establish itself as its own country. The events leading to this decision began when US border patrol set up a checkpoint at the entrance to Key West. This border stop infuriated residents when a 17-mile traffic jam occurred and began to interrupt Key West’s tourism industry. When the government refused to listen, Mayor Wardlow decided to declare war on the United States. Within one minute, he quickly surrendered and applied for foreign aid in the amount of one billion dollars. This publicity stunt resulted in the US government agreeing to remove the inspection station and life in Key West went back to normal.
For the conchs of Key West, the 1982 Conch Republic secession is celebrated each year with a ten-day festival taking place around April 23rd. Among the festivities are a Pirate’s Ball, the Conch Crawl and a Musical that reenacts the events of the secession.
I caught the next trolley from the Southernmost Point and disembarked at the Ernest Hemingway Home. The beautifully restored two-story home is located at 907 Whitehead, across from the Key West Lighthouse. Hemingway wrote many of his great novels here from 1931 to 1939 including “The Snows of Kilimanjaro”, “The Short Happy Life of Francis Macomber”, “Green Hills of Africa” and “To Have and Have Not”.
I enjoyed a tour of Hemingway’s home, the property and his inspirational studio overlooking the pool. Following the guided tour, I opted to take a second stroll of the home to explore the gardens of hibiscus, jasmine and gardenias.
One of the highlights of my visit was watching the Hemingway’s cats lounging among the lush tropical plants outside. Descendants of Hemingway’s beloved polydactyl (many toes) cat Snowball, the nearly fifty felines have taken up residence in this luxurious estate.
My final ride on the trolley returned me to Duval Street. A popular hub of restaurants, bars, shops and museums, cruise ship passengers could participate in the “Duval Pub Crawl” with a stop at the Bull and Whistle. Known as the “oldest Open Air Bar in Old Town Key West”, it is located on the corner of Duval and Caroline Street. The Bull, located on the ground level, showcases a beautifully hand-painted mural, paying homage to a number of the island’s influencers. Yankee Jack has been entertaining patrons of the Bull with his performance of “On the Walls of the Bull”.
The Whistle is the bar upstairs providing great views of Duval Street and the opportunity to shoot a few games of pool. The Garden of Eden is the bar located on the third floor for visitors interested in a clothes optional environment.
Before leaving the Bull and Whistle, I begged one of my colleagues to pose next to “The Bull” on Caroline Street.
Duval Street is just over a mile long running north and south of the island. The most well-known bars of Key West include Sloppy Joe’s, Rick’s Bar Key West, Jimmy Buffett’s Margaritaville Cafe, Irish Kevin’s, Captain Tony’s and Hog’s Breath Saloon.
Each year, Sloppy Joe’s pays homage to famous author Ernest Hemingway by staging its annual Ernest Hemingway look-alike contest.
My day in Key West had come to a close but I had one more attraction to experience. I had arrived at Mallory Square with plenty of time to enjoy the live entertainment and secure a pier-side seat to watch the spectacular sunset. The plaza was bustling with arts and crafts stands, food carts and street performers. I waited in anticipation as sailboats glided by and catamarans drifted off into the horizon. I took several photos of this unforgettable moment and looked forward to experiencing it again on my return.
What is one of the most memorable sunsets that you have seen in your travels? I would love to hear about it! Tell me about your experience or recommendations for places to visit in the comments section below! Many thanks for reading my post about Key West and wishing you many Happy Travels!
What to See and What to Do:
The Southernmost Point
At the corner of South and Whitehead Streets
Key West, FL 33040
- Admission Fee: Free
- Hours: Open 24/7
- Tips for Your Visit: The trolleys drive by The Southernmost Point and a drop off location for the shuttle is nearby. There may be a line to wait to take your photo at the buoy.
The Ernest Hemingway Home and Museum
907 Whitehead Street
Key West, FL 33040
Phone: 305 294 1136
- Admission Fee: Adults, $13 and Children, $6, group rates may apply (12 or more)
- Guided Tour: Admission includes a 30-minute guided tour
- Hours: 9AM to 5PM, 365 days per year, including ALL holidays
- Tips for Your Visit: The museum is home to many cats and may affect those with cat allergies.
Mallory Square
Address:
400 Wall Street
Key West, FL 33040
- Cost: Free
- Hours: Open 24/7; best time to visit is during sunset
- Tips for Your Visit: Arrive early because the square fills up with spectators who are visiting to watch the sunset. Festivities begin 2 hours before sunset.
Where to Stay:
Heron House
512 Simonton Street
Key West, Florida 33040
Toll Free Number: 800 294 1644
I absolutely loved this property with the accommodations surrounding the pool. The plants and foliage are thick and provided much appreciated privacy during our visit! The rooms were spacious and there was a complimentary breakfast provided each morning!
Where to Eat:
There are so many colorful restaurants with a variety of cuisine in Key West that selecting one place is incredibly difficult. Because I have a love for Cuban Sandwiches and Oysters, here are my two recommendations:
Half Shell Raw Bar
Waterfront dining
231 Margaret Street – 305 294 7496
Oysters, oysters and more oysters! Food & Wine Magazine voted the restaurant “Best Local Oysters.” I ordered a half dozen lightly steamed oysters with hot sauce and crackers along with an order of the conch fritters appetizer which included six fritters served with cocktail sauce.
What to Eat:
- Key West pink shrimp – said to be sweeter than other shrimp
- Conch – a tough, hardy mollusk usually cooked as fritters
- Seafood – snapper, grouper and lobster
- Key Lime Pie – a tangy, creamy dessert made from key limes
Where to Drink:
The Bull and Whistle
On the corner of Duval and Caroline Streets
Key West, FL 33040
Phone: 305.296.4545
- Hours: 10AM to 4PM, daily
- Tips for Your Visit: Note that the rooftop bar, the Garden of Eden is clothing optional. Check out the website for coupons before you visit.
Cuban Coffee Queen (two locations)
284 Margaret Street – 305 292 4747
5 Key Lime Square – 305 294 7787
I started with a Cafe con Leche, the strong Bucci coffee with steamed milk. I loved the Cuban Mix sandwich because it was the closest to an authentic Cuban sandwich with a side of black beans. Save room for Key West’s famous Key Lime pie!
What to Read:
- Ernest Hemingway books
- Jimmy Buffet: The Key West Years, by Tom Corcoran
- Hemingway’s Girl, by Erica Robuck
- The Best Key West Trivia Book Ever! by David L. Sloan
Photo Guide for Key West:
- 801 Bourbon Bar (cabaret and karaoke) for interesting characters
- Duval Street for the drinking crowds and colorful shops
- Higgs Beach Pier, for amazing sunrises
- Mallory Square, especially at sunset
- San Carlos Institute for Cuban history
- Smather’s Beach for long exposures during the day
- The Strand, after dark for the neon lights
- The Tropic Cinema, at night for the neon lights
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