Ever been to Key West?

Yes? No? Don’t remember?

It doesn’t matter!

Sit back, and we’ll give you a glimpse of the city and its history plus a character or two.

From our location, here on Cudjoe Key, 23 miles northeast of Key West or as they say in the Keys, Mile Marker 23, we proceed down the Overseas Highway or Route 1, the only road in and out of the beautiful Florida Keys.

The Overseas Highway, a 113-mile road that extends from Key Largo to Key West is one of the most scenic drives in the world. For much of the ride, you feel like you are driving in the middle of the ocean with the Atlantic to your left and the Gulf of Mexico on the right.


There are 42 bridges on the overseas highway connecting the Keys. The Seven Mile Bridge at Marathon, MM 47 is the most well-known.  You may have seen this remarkable bridge in the movies, 2 Fast and Furious 2, True Lies with Arnold Schwarzenegger or Mission Impossible III just to name a few filmed on the bridge.

The spectacular ride down the Overseas Highway, completed in 1938 follows the trail of the Railroad built by Tycoon Henry Flagler between 1905-1912. What took almost seven years to build got wiped out in 1935 with a Labor Day hurricane that destroyed more than 30 miles of track. Remnants of the Railroad can be seen parallel to the highway.

Breathtaking beauty along the drive reaches its peak at sunset when the orange ball like sun slowly descends into the sea. If you arrive in Key West near sunset, be sure to head over to Mallory Square for the nightly sunset celebration.  Performers of all types from musicians, clowns to jugglers and artists delight the hundreds who gather before sunset at the waterfront plaza just off the northern end of Duval Street.

Yes, New Orleans has Bourbon Street, but Key West has Duval Street, a 1.1-mile street, lined with pubs, restaurants, and shops that extend from the Atlantic Ocean to the Gulf of Mexico.  Live entertainment is a staple in the bars and restaurants where you can hear everything from Country, Rock, Irish, to reggae. If you are so inclined, take a pub crawl which many people visiting Key West recommend highly.

Some of the better know places are Sloppy Joe’s, Captain Tony’s Saloon, Margaretville owned by Jimmy Buffet, Hog’s Breath, Irish Kevin’s and the Green Parrot, just to name a few.

It has been said that Ernest Hemingway who first came to Key West in 1928 spent most evenings from 1933 to 1937 at Sloppy Joe’s located at 428 Green Street, a bar run by his friend Joe Russell.

Hemingway wrote feverously in the early morning but by three p.m. left his home on Whitehead Street ready to indulge in a libation or two with his adventurous friends who became known as the “mob.”  From this association, his nickname “Papa” emerged.

In 1938, the property owner of Sloppy Joe’s raised Joe Russell’s rent one dollar per week which did not sit well with Russell and his friends, so they moved the entire bar during the night to 201 Duval Street where it remains today. The former Sloppy Joes, one of Key West oldest bars became Captain Tony’s Saloon.

For the past 37 years, there is an Ernest “Papa” Hemingway Look-Alike Contest held at Sloppy Joes during “Hemingway Days,” July 18-23 which commemorates the iconic author’s legacy.  This year’s Look-Alike contest runs from July 20 to July 22.  After the final judging, the party spills out onto the street, where everyone has a good time.

Two or three years ago, many people got the chance to meet former Food Network star Paula Deen who was on hand to support her husband Michael, a Hemingway Look-Alike contest finalist.
        CAPTAIN TONY’ S SALOON                          SLOPPY JOE’S

Besides the lively entertainment and exciting adventures available in Key West, the city has an abundant history. The Harry S. Truman “Little White House” located in the Truman Annex off Whitehead Street built around 1890 gives a glimpse of Truman’s life in the 175 days during his presidency that he spent in Key West. The tour, available daily is both entertaining and informative while it takes you back to the late 1940’s.

Everyone visiting Key West should get their picture taken at the Southernmost point in the continental United States.

Lauren and Liam Gibbs on their first visit to Key West from Pittsburgh, PA joined the more than 30 people waiting in line to get their photo taken next to one of Key West’ most famous attractions.

The city of Key West erected the large, brightly colored, concrete buoy in 1983. On the Southernmost Point buoy visitors can read “90 Miles to Cuba” which they round off when it fact it is about 94 miles to Cuba which is still a lot closer than Miami.

Just a few feet to the right of the Southernmost Point Buoy is the bronze life-size statue of Albert Kee affixed in 2015 to the spot where Kee blew on a conch shell and welcomed everyone who visited the Southernmost Point.  With a toot from the conch shell and a wave, Kee greeted Southernmost Point visitors with, “Welcome to the Island.”

Tourist “Dr. Bill” high fives the hand of Kee’s statue. Kee was known as Key West’s unofficial greeter, ”The Conch Ambassador.”

From the southernmost point, the next stop is the beach.

Key West has three beautiful beaches: Smathers, Higgs and Fort Zachery Taylor Park, a personal favorite.

The 54-acre Fort Zachery Taylor Park is a National Historic Landmark with a historic fort and beautiful beach that stretches around the tip of Key West. You can swim and snorkel out to the rocks, but don’t forget water shoes because the coral is a bit rough on the feet.

A café, umbrella and chair rental, picnic tables and grills plus a separate area for fishing provide for a day filled with fun and adventure.

The Park’s magnificent beauty make it a favorite location for weddings and family fun.

“I made it!”

Here we have Dr. Bill again after a proud swim out to the rocks and he didn’t lose the hat.
Another interesting aspect of the Park is Fort Taylor itself. It dates to the mid-1800’s. The Union held the fort during the Civil War to protect the nation’s Southeastern coastline.  Still, on the site today are the ten-inch cannons with a range of three miles that proved a deterrent to Confederate ships.

The abundant history, fun-filled events, excellent fishing and beauty of Key West draws about three million tourists per year. Tourists have ample opportunity for sea, snorkeling and dive adventures, boating, jet ski trips, offshore and backcountry fishing as well as excursions out to the Dry Tortugas, a national park located 70 off the coast of Key West in the Gulf of Mexico.

Key West offers many exciting attractions, but let’s not forget about food.  Fine dining, as well as casual fare, can be found throughout the city. From the raw oysters, Key West pink shrimp at the Raw Bar in the historic seaport to the stunning beauty of Latitudes situated on Sunset Key a short boat ride across the harbor, diners will not be disappointed.
Board the small ferry boat docked in the harbor near the cruise ships for a ride over to Latitudes. Enjoy an incredible meal either outside or inside with a beautiful water view of the Gulf of Mexico.

Randy Smith of Palm Springs, California visits Latitudes on every visit to Key West citing it as one of his all-time favorites.

Many people refer to Key West and the Florida Keys as “Paradise.”  The tropical climate, lush vegetation, turquoise colored waters and sometimes quirky people make it more than interesting.

Walking on a beautiful day in Key West, you’ll see an abundance of gray-haired ponytailed men with tattoos, chickens, and rooster roaming freely, many fishing shirts, bicycle riders, scooter with people ranging in age from their teens to nineties,  and a happy population mostly wearing flip flops.

In most cases, you can stroll down Duval Street with a cocktail hidden in a plastic cup, converse with attractive strangers many just off a cruise ship and listen to music playing in the street. No one puts much thought into what they wear or how they look. Many enjoy life without too many cares amid the natural beauty of the Florida Keys.  Does that sound like paradise to you?


This story does not mention Fantasy Fest, one of Key West’s premier events because that is a story all its own which is coming in October.


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