Everything you need to know when visiting Key West Florida

Key West Florida

KEY WEST, FLORIDA – It’s the most southern point in the continental U.S. (and a mere 90 miles from Cuba), and yet, when you leave mainland Florida and make your way further south along the Florida Keys region, you’re going to discover a place that’s a whole other world where the living is truly easy and the atmosphere is a mixture of culture, history, great food and an encompassing mellow feeling. A good path to take would be to visit boat rental Hollywood FL and travel quickly to Key West and enjoy your stay in a luxury boat.

When you finally reach the end of the line at Key West, you’ll discover that you can enjoy the conch (pronounced “conk”) way of life, whether you’re a lifelong resident or a tourist who is getting some much needed warmth and sunshine.

Key West Florida
Most southern point – Key West

But don’t take my word for it, just ask any conch (which is the term used to describe a lifelong resident of Key West), or find out why famed American writer Ernest Hemingway spent nearly a decade of his life there, or former U.S. President Harry S. Truman, who established a Little White House in Key West during his presidency, and continued to vacation there for years after his second term was completed in 1953.

Key West
Stuart Nulman having a cocktail with Ernest Hemingway

As I made my way southwest along highway US 1, I made a stop at Islamorada, the halfway point enroute to Key West. An overnight stay at the Postcard Inn Beach Resort and Marina (www.holidayisle.com) that’s located on US 1 was the perfect remedy after a long day of travelling. This city-within-a-city is more than just a resort hotel. There is an onsite marina and boat ramp where you can charter a boat for some cruising or fishing along the coast; fully outfitted cottages and suites (my suite had a wonderful view of the ocean); beaches, pools, guest services (like a general store where you can purchase bait and tackle for a day of fishing), pool and beachside bars and restaurants such as the Kokomo, the Tiki Bar, the Lao Hound Italian restaurant, and the Raw Bar Islamorada; and even a Starbucks to satisfy your caffeine fix.

* * *

Following my departure the next morning, it was a two-hour drive to the Keys’ most southern tip, Key West. The tropical scenery and the people doing some rod and reel fishing along the bridges was like an introduction to the serene way of life that awaited me.

My home base during my stay was the Perry Hotel & Marina (www.perrykeywest.com),  located on Stock Island, which was recognized by Architectural Digest as one of the 12 best-designed hotels. To put it simply, the Perry offers the resort hotel experience at its best. Where to begin … how about the beautifully-decorated guest rooms with property-wide high speed WiFi; or the free shuttle service to the Old Town district every hour on the hour from 9 a.m. to 10 p.m. (with return service to the hotel every hour on the half-hour between 9:30 a.m. and 10:30 p.m.); or a 288-slip state of the art marina; or a fitness centre and F45 training studio; or a selection of shops and services; or a charter service for diving, snorkeling and sailing; or three restaurants (Sloppy Joe’s, Matt’s Stock Island and the Salty Oyster) complete with pool and dockside bars; or a welcome glass of champagne when you check in? And that’s just scratching the surface.

Best way to see the water

If you’re a first-time visitor to Key West and you require a means to familiarize yourself and get your bearings so you can navigate the city properly, taking the Conch Tour Train (www.conchtourtrain.com) is highly recommended. A tourist fixture since 1958, the Conch Tour Train echoes the legacy of Henry Flagler, whose railroad and bridges he built connected Miami to Key West in 1912, which had a lasting effect on the island city.

On the morning when I took the tour, I rode on train number 110, which was engineered by Kenny, a Key West Conch whose family has resided there for over 150 years. A former chef who cooked for former Presidents Jimmy Carter and Bill Clinton, Kenny gave us a highly informative and entertaining tour, which was a mixture of fascinating history and curious tidbits (“There are three ways of communicating in Key West. By television, by telephone and by tele-conch,” he told our tour group).

The tour will take you to many of the sights and points of interest that have made Key West famous (such as the Southernmost Point marker, which had a huge line-up of people who wanted to take a picture with it as early as 9 a.m.), and those sights with a touch of hidden history (such as the La Concha Hotel on Duval Street, which is the tallest building in Key West, where Tennessee Williams did the entire rewrite for his best-known play A Streetcar Named Desire). And then there’s the tidbits of trivia that Kenny dropped during his narrative. For example, Key West was the site of the first Coca-Cola bottling plant to be established outside of Atlanta, where their version of the world famous soft drink was made with rainwater until 1941. And Kenny will also tell you why the green-and-white Mile 0 road sign that marks the end of US Highway 1 (and shares the same post as the sign marking the beginning of US 1) is the road sign that is most often stolen in Key West.

Probably one of Key West’s best known past residents was Nobel Prize-winning writer and novelist Ernest Hemingway, who made it his home throughout most of the 1930s. Key West as a retreat from a tourist-laden Paris was recommended to Hemingway by friend and fellow novelist John Dos Passos. As Michael Palin, a former member of the Monty Python comedy troupe, diarist and travel writer in his own right, stated in his 1999 book Michael Palin’s Hemingway Adventure, “once he’d got used to the heat, Hemingway became wildly enthusiastic about Key West. He sent out a flurry of letters to tempt his friends to visit him in what he called ‘the St. Tropez of the poor.’”. He even tried to persuade Max Perkins, his editor at Scribners, to visit by saying the shooting and the fishing there were “fantastic”, and that that he had 14 bottles of a well-aged brand of champagne that he personally salvaged from a nearby shipwreck and wanted him to sample.

Although those incentives to visit Key West sounded tempting, they were not necessary for me to make the trip way down south. In fact, one of the reasons I wanted to make that trek was to follow in the footsteps of one aspect of the life of Ernest Hemingway, who is one of my favorite writers.

If that is one of your raisons d’etre to visit Key West (short of doing some deep sea fishing and hopefully catching a marlin), there are two places that you must visit. First is the Hemingway Home and Museum (www.HemingwayHome.com) located on Whitenhead Street. This is the house where Hemingway and his wife Pauline lived from 1931 until 1937 and wrote a number of his works there, including the novel To Have and Have Not, the short story The Snows of Kilimanjaro, and his nonfiction work about bullfighting in Spain called Death in the Afternoon. After Hemingway’s untimely death in 1961, his sons decided to sell the property. Bernice Dickens bought the property for $80,000 to live in it as her new home; however, there was a slight dilemma with living in a house that was once owned by Ernest Hemingway. Bernice had a constant stream of tourists knocking on the door inquiring if this was the previous residence of the famous writer. So, realizing that her new home was more popular than she anticipated, she decided to open the home to those tourists, in which the curious tourists were charged $1 per person and allowed them to entre from the back of the property. This became the genesis of turning the Hemingway Home into a museum that paid tribute to his life, his time in Key West, and his life as an adventurer and writer.

The tour of the house takes about 30 minutes (and visitors are allowed to roam the property afterwards) and doubles as a museum to different aspects of Hemingway’s life, such as his stint as a World War I ambulance driver, his craft as a writer (where you also get to see his preserved writing studio, where he churned out about 70% of his total literary output), his fondness for African safaris, and his love for the sea (where pieces of his beloved boat the Pilar are on display).

Visitors will get to learn about some of the curiosities that surrounded the Hemingway family during their time in Key West, in which two really stand out. One is the 57 cats (that’s right … 57!) that reside on the premises. These felines, many of whom are descended from the original six-toed (polydactyl) cat that the family owned. Although the sign at the admission gate boldly states that the cats should not be picked up, many of the visitors defy that edict, because those 57 cats are just as popular as their original master. The other curiosity is Pauline’s quirky household design passions, in which she replaced the ceiling fans with chandeliers and designed the bathroom floors with art deco tiles. Perhaps the quirkiest was when Pauline built the very first swimming pool in the Keys, at a cost of $20,000 (and in 1937 dollars to boot). Hemingway was so furious by the pool and its exorbitant cost that he angrily declared to Pauline that she spent every dollar he had on the pool except his very last penny, which he flung on the ground near the pool, and is now encased in clear plastic on that exact spot.

The Best things to see on Duval Street Key West

Another way to enjoy the Hemingway experience in Key West is to visit the Hemingway Rum Company Distillery (www.papaspilar.com), where the Papa’s Pilar brand of rum is made and bottled. 

“This brand has a very large following amongst three groups of people. There’s the blue water people, who enjoy fishing, sailing, yachting and jet skiing; there’s the adventure seekers, who love to travel and explore; and there’s the Hemingway group, who are literature and history buffs,” said Tricia Constable-Flannigan, who is the company’s Director of Operations and Marketing. She added that the Papa’s Pilar brand of rum (which is named after Hemingway’s second wife, as well as his treasured boat, which is now moored in Cuba) has the backing and support of the Hemingway family. “They fell in love with the brand, and have actively supported it on a partnership level,” she said.

The distillery is housed in one of Key West’s oldest buildings, that dates back to the late 1800s, and housed a tobacco warehouse. The building, which lay empty for 16 years, was chosen to be the current home of the company and distillery because it was the perfect location for a working rum distillery that would be safe for tourists as well (it also doubles as a museum, with large displays of photos of Ernest Hemingway that traces his life as a writer and bon vivant).

I took a tour of the distillery with “Bahama Bob”, its chief rum maker, who gave a fascinating, step-by-step explanation of the rum making process, from its copper pots, shotgun cylinder, blending tank, and the selection of used bourbon barrels and Spanish Sherry casks to store and blend the rum. About 450 cases (of six bottles each) of either the blonde or dark rum are made each day, in which the only automation that is utilized is the machine that pours the liquid into the bottles; the sealing and packaging are all done by hand (there is also a second bottling plant located in Lakeland, Florida). The distillery also contains a small laboratory where the rum is scientifically quality-tested and new flavours are experimented with. “Bahama Bob” added that the key to making Papa’s Pilar a quality rum is how it’s made with a derivative of sugar cane, and a blend of ingredients that are sourced from Florida, Panama, Venezuela and the Dominican Republic, as well the fermentation process, which is set to a temperature range between 76 and 96 degrees Fahrenheit.

He also mentioned an interesting fact about the shape of the bottle that’s used to sell the rum in the continental U.S. and Ontario. It’s modelled on the canteen that was used by American soldiers during World War II, and is a tribute to Hemingway’s work as a war correspondent during the war.

When you are finished with the tour, take a look at the distillery’s gift shop that offers a selection of quality merchandise and souvenirs for purchase, such as t-shirts, hats, drinking glasses, a selection of Hemingway’s books and of course, bottles of Papa’s Pilar, which is available individually or in a two-bottle set. And with all that rum making in mind, stop by Hemingway’s Library, a pub that is adjacent to the distillery, where you can enjoy live music in a book-crammed venue with leather armchairs, while imbibing Hemingway-inspired cocktails that are made with the rum, such as Rumming with the Bulls, The Sun Also Rises After the Hurricane, Hemingway’s Daiquiri, and Papa’s Express Punch. And don’t forget to toast the good life (and take a picture with) at the life-sized statue of Ernest Hemingway that can be found, appropriately enough, at the bar.

Key West
Harry Truman Little White House – Key West

Throughout the history of the American presidency, many of its 46 chief executives always had a place outside of Washington, D.C. as a retreat where they can have a restful change of scenery, and where they can unwind and conduct the business of the nation at the same time. For example there’s Monticello (Thomas Jefferson), Hyannis port (John F. Kennedy), Hyde Park and Warm Springs (Franklin Roosevelt), and San Clemente (Richard Nixon). 

For Harry S. Truman, the 33rd President of the U.S. from 1945-1953, his presidential retreat was an oceanfront former U.S. Navy station commander’s house in Key West that was built in the 1890s, in which Truman made it his own and converted it into a little White House. Today, what is now known as the Harry S. Truman Little White House (www.TrumanLittleWhiteHouse.com) is the only presidential museum that is based in Florida.

Before Truman made the house his own (where he paid 11 visits between 1946 and 1952, which started by orders from his doctor after the stressful workload he experienced during his first year in office), it was also a retreat for former U.S. Presidents William Howard Taft, Dwight Eisenhower (where he recovered after he suffered a heart attack in 1955), Jimmy Carter, Bill Clinton, as well as inventor Thomas Edison. The volunteer guides (many of whom are dubbed “Harry’s Girls”) are very knowledgeable about – and show an amazing enthusiasm for – Harry Truman the president and the person. That was quite evident with the numerous stories they told about the 33rd president throughout the tour, such as his rule of having any visitor dress informally during their stay (especially Hawaiian print shirts, in which one of Truman’s is on display); having a nearby moored navy ship provide the necessary electric connections to the house, so that Truman can do his necessary phone calls every day with other leaders, members of Congress and his staff; the bar where he began his day with what he called his “heart starter”, which comprised of orange juice and a shot of bourbon; and the regular poker games he had with guests at the table that was a gift from the sailors at the nearby naval base (and under strict orders that no photos were to be taken of anyone sitting at the table during those poker games). 

Although the taking of photos are not permitted during the tour, the impression that you get after visiting the Truman Little White House is that Harry, Bess, Margaret and their famous and not-so-famous guests enjoyed their time in Key West in a place that was comfortable, uncomplicated and had that mid-western charm that defined the Trumans (gun shell casings converted to ashtrays notwithstanding). It’s a piece of American history that is a definite must-visit.

* * *

One of the good qualities about visiting Key West is that it is a very walkable city, with many of its attractions located within walking distance of each other. That is the case when it comes to doing some shopping. In Key West proper (or known as the Old Town district), the shopping district is concentrated in the city center, with Duval Street as its nucleus. Among the 19th century architecture, art galleries, retail chains (such as a newly discovered chain of beach wear stores called Salt Life), ice cream parlours, restaurants and souvenir shops, Duval Street has 31 bars along its north-south island-wide thoroughfare, including the original location of Jimmy Buffet’s Margaritaville Café. It’s a great place to shop, dine, relax and absorb the conch way of life.

* * *

A wonderful way to get your nightlife in Key West off to a great start is to follow the mass of people who make their way to Mallory Square on the island’s northwest corner to view probably one of the most beautiful, picturesque sunsets that you will ever experience. Don’t forget to take a picture of that sunset, which could give your photo album that coffee table book quality. Finally, before or after that sunset, check out the many shops and kiosks that pepper Mallory Square, where you can buy some Key Lime Pie, sample a cup of Cuban coffee, visit the Key West Shipwreck Treasure Museum, try a conch fritter, which are part of the many of the unique sights and shops that make Mallory Square a must on your to-do list.

* * *

If you happen to see a great deal of chickens and roosters roaming free along the streets of Key West, don’t think they escaped from a nearby chicken coop. There is no need to call the ASPCA or the police. In fact, there is a reason why these fowl have such a free reign to wander wherever they want to. And it goes back to the time when Florida was occupied by the Spanish; when Spain left the territory, somehow they left behind a number of roosters and chickens, where they were able to breed and crow as much as they want (even after the sun rises). Key West became a sort-of “chicken nirvana” for these Spanish fowl, and after Florida joined the union, laws were passed in which they were officially recognized as a protected species, and were not allowed to be caged. Hence, their “fowl” reign of the streets of Key West, which has lasted for over 500 years.

* * *

And now, a word about the food: When it comes to food in Key West, two things quickly come to mind: fresh seafood and Key Lime Pie. And during my stay in the Keys, I happily had my fill of both. But I managed to visit four different restaurants that defined the Florida Keys dining experience for me. 

On my way to Key West, I made a stop at the Morada Bay Beach Cafe (www.moradabaykeys.com) in Islamorada for dinner. After a long day of travelling by air and road, dinner at the Morada was the perfect antidote to enjoy a freshly-cooked meal in a very tranquil atmosphere. That was accomplished with Keys-style dining al fresco, meaning tables on the beach, lit up by torches, with live music and the sounds of waves crashing on the shore serving as the soundtrack. The Key West pink shrimps with pasta was delicious, and the courteous, friendly and person-to-person service made this dinner a perfect welcome to the Florida Keys. 

My Hemingway experience on Key West became a troika with a stop for lunch at Sloppy Joe’s (www.SloppyJoes.com), which was his favorite bar. The moment you set foot in Sloppy Joe’s, you can feel the testosterone in the air, and can’t wait to taste the offerings on its menu. The fried chicken tacos was the perfect lunchtime dish, and that was well complemented with one of Sloppy Joe’s specialty drinks (I chose the Key West Lemonade), and was topped off with a generous piece of Key Lime Pie, complete with whipped cream and raspberry drizzle. As well, the restaurant and bar is a mini-museum dedicated to their favorite famous customer, complete with photos and memorabilia (including “Skinner’s Peacemaker”, a blunt baseball bat-like device that was owned by one of its longtime bartenders, which certainly did its job of keeping the peace in the event of a disagreement or brawl). And if you hear a bell ringing loudly on a semi-regular basis, don’t worry; it means that one of the servers just received a generous tip from a customer.

Aviation history buffs will certainly appreciate a meal at the First Flight Island Restaurant (www.firstflightkw.com). The site of the restaurant was actually the birthplace of the legendary Pan American (Pan Am) World Airways, where in 1927 its first plane tickets were sold, especially for the first ever flight service between Key West and Havana, Cuba. It’s also the location of Havana Red, the southernmost brewery in the U.S., which is served at the Crash Bar, where the drinking surface is an actual aluminum plane wing to commemorate the time when a Sikorksy sea plane plunged through the ceiling. The menu has a variety of seafood, meat, chicken and pasta dishes including my favorite, the Brewery Burger, which is an 8-ounce kobe beef patty, complete with aged white cheddar, a beer battered onion ring, arugula and served on a brioche bun.

For a true seaside seafood dining experience, check out the Half Shell Raw Bar (www.halfshellrawbar.com).  Located at the historic Bight seaport on the northern part of the island, the Half Shell offers a large variety of oysters, clams, lobsters and other fresh catches of the day straight from the fishing boats to your table. I decided on a succulent dish of grilled shrimp with a choice of two sides, and glass of Texas Tea (vodka, iced tea, and lemonade served over ice); and for dessert, bread pudding, a specialty of the house, which is made with Cuban bread and garnished with a creamy bourbon sauce. Dee-licious!

* * *

A special thank you goes out to the Florida Keys & Key West bureau for putting this tour together. For more information of what to see and do in the Florida Keys and Key West, go to www.fla-keys.com.

Stuart Nulman
By: Stuart Nulman – [email protected]

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