28 Hours in Key West

“That is what we are supposed to do when we are at our best – make it all up – but make it up so truly that later it will happen that way”  Earnest Hemingway

Key West…physically it is only 4 miles long and 2 miles wide, but psychologically it has an enormous impact; one never forgets time spent within its boundaries. It first showed up on maps beginning in the 1600’s, and the U.S. claimed from Spain’s  “North Havana” as an official port of entry in the early 1800’s. Agriculture and cigar manufacturing were the largest activities until the 1920’s, when Prohibition created a ravenous appetite in the country for all things alcoholic. Many fortunes were made and properties purchased in Key West by enterprising individuals who smuggled beer and rum to its thirsty citizens until the law was repealed. Marijuana became the smuggler’s product of choice in the 60’s through 80’s, and even though tourism is Key West’s main industry today, it is rumored that occasionally wafts of Cannabis can be detected in the surrounding air. Key West is famous for its “live and let live” attitude; a walk down Duval Street might make Grandma’s pace-maker work overtime; and annual events such as Fantasy Fest, Survivors Party, Pride Fest, Pirates in Paradise Fest, and Fool Fest (they do love their Festivals) are not for the feint of heart, however often over the years we have encountered a quiet, laid back, and sleepy Key West which was exactly what we encountered on this April trip.


8:00 a.m.

Everyone in the car and heading south by 8:00 a.m…the lunch plan is right on schedule; An early departure is necessary when the lunch restaurant is 229 miles away in Key West, and you live in Wellington, a village outside of West Palm Beach. Now some people might think that is a long way to go for lunch, and those people would be right; that is why the four early-risers (my wife Peg; her sister Barbara, my son Sean, and myself) decided to spend the better part of two days visiting old favorite locations while at the same time giving a mini-tour of Key West to Sean, who had never been. Just outside of Miami, we made a brief stop for coffee and a breakfast sandwich and shortly thereafter we swing onto U.S. Route 1 at Key Largo, the largest of the Keys. Key Largo is a premier destination for 1) kayakers and ecotourists because of its proximity to the Everglades and 2) for snorkelers and divers as it is the home to Pennekamp Coral Reef State Park; Pennekamp is the country’s singular park which happens to be completely under water! But no time for exercise right now because we still have to traverse 51 islands with the assistance of 42 bridges before reaching our first Key West stop – lunch at Louie’s Backyard. Taking a cue from the Talking Heads, you may ask yourself, well, how did I get here? How can we have 51 islands and only 42 bridges? It seems that one Key activity is land-filling with rock and coral to create overland connections on U.S. 1, so some of the islands are now linked by land and not completely surrounded by water. Elsewhere perhaps they would no longer be considered islands, but in the region of Hemingway and Tennessee Williams, facts sometimes are made up “so truly that later it will happen that way.” One island down, 50 to go.

12:30 p.m.

Louie’s Backyard has long been our favorite and now traditional first stop in Key West. Why? Because the Caribbean inspired food is superb, the drinks refreshing and the backyard offers a spectacular oceanfront setting that to me symbolizes laid-back tropical living. The parking gods smiled and produced a spot directly across the street, and with reservations previously established, we were seated right away on the requested outside deck. We prefer lunch at Louis’s because of the daylight view, but dinner is most popular, together with watching the sunset or a late evening rendezvous at their outside deck bar. Seated, cocktails in hand, massaged from tropical breezes, it is time to treat the senses with perfect island ambience.


3:00 p.m.

After a well-deserved leisurely two and one-half hour lunch,  a short walk from Louie’s brings us to the touristy photo-op object of our affection, the large concrete buoy indicating the southernmost location in the continental U.S.. It was built in 1983 as the final replacement for all those signs taken by tourists as a souvenir of their visit. No one is going to steal this baby. There’s a short line for exclusive space in front of the buoy, and we each take turns offering to take pictures of the party immediately before us, which makes it perfect for all in involved. The people behind us were very patient with our request for the 12th shot (three cameras, combination of four people…you get the idea).

4:00 p.m.

For the first time visiting Key West, we stayed at a hotel outside of “Old Town“, where the historic district and the classic bungalows and guest mansions are located. A special offer of two rooms for approximately half the cost of one room in Old Town compelled us to do so. It was too good to pass up and the hotel was very modern and comfortable with a free shuttle to most locations, but Old Town lodging provides convenience with atmosphere that is preferable to most people.


4:30 p.m.

The shuttle drops us off a short walk from Front Street and the Key West Conch Tour Train; this in my opinion is a must-do for anyone visiting for the first time, and especially if the visit will be brief. In a little over 90 minutes, you drive by all the famous sights and hear about many of the legends and lores of the area, and get a very good idea of what direction you want to head in when the tour is over. In our case, there was no doubts…time for libations in anticipation of watching a Key West sunset!

7:30 p.m.

“Sunset Celebration” is in full swing on Mallory Square and Pier, located in the heart of Old Town, facing the Gulf of Mexico. Once upon a time this is where U.S. Navy ships and other massive vessels came to port and where Cuban cigar makers and sponge collectors sold their goods. Do you like the hustle and bustle combination of arts and crafts, street performers, food carts, and hundreds of tourists? Well then this is the place to be. If you happened to be there courtesy of a cruise ship, it is a city law that your ship has to leave port two hours before sunset and return after sunset, however without an additional docking fee. On the night we were there the sun bid adieu precisely at 7:48 with the coral painted sky beginning it’s journey into darkness. So much to do and so little time, we called ahead to one of our favorite dinner restaurants to inform we were on our way. A little bit of heaven was only a invigorating walk away.


8:30 p.m.

Of the 210 restaurants in Key West, Trip Advisor ranks Petronia Street’s Blue Heaven #8, although I would quibble for a lower ranking. Whatever the ranking, we never miss going there when visiting, either for dinner or breakfast, and sometimes both; it is that good. One hundred years ago it was a bar, and through the ensuing years it has hosted cock fighting, gambling and Friday night boxing matches – Earnest Hemingway sometimes was one of the fighters, and sometimes the referee. For many years, the downstairs operated as a billiard hall and ice cream parlour. Oh for the good old days where one could get a double scoop, sink the eight ball, and bet on both men or beasts getting pummeled. Atmosphere my friends, atmosphere. Tonight there are no pugilistic events on the menu, but it’s OK because we will stay alert by people watching, keeping,  an eye out for falling almonds, Spanish limes, coconuts and of course, roaming roosters. And besides, how can you not have a good time at a place where the menu states “we serve heaven on a fork and sin in a glass”?


10:30 p.m.

Satiated from good food, drink, and company, one option is always cutting over to Duval Street, which of course is humming at this time, but having consumed one day’s complete ration of sin and heaven, an evening swim before retiring sounded both refreshing and relaxing. Good night Key West…we will dream of an assortment of scalawags, ship wrecks, authors and poets, fishing, … … snz  snnzz  snzzz  snzzzz  snzzzzzzzzzzzzzzz


10:00 a.m.

The ladies have slept in…the guys are hungry! We’re finally off to, yes another favorite eating establishment; “the eldest eating house in the Florida Keys; a fairly good place, for quite a long while. Open under old management.” We arrive at Pepe’s Cafe on Caroline Street and for the first time in my experience, are seated in their beautiful outside courtyard without a wait. (No doubt it was the tardy arrival time!) For one hundred and two years, Pepe’s has been serving breakfast, lunch and dinner; 7 days a week since 1984. The first thing I notice is three people at the bar drinking Mojitos, the breakfast of revelers. We all agreed it was a little too early for alcohol, so coffee, fresh squeezed orange juice and a starter order of home made coconut toast are ordered while we peruse the menu. For sheer excitement, Pepe’s features oyster races twice weekly with the winning oyster delivering a $100 pot for the winning oyster handicappers. I’d share the oyster motivation factor , but it would be more satisfying for you to ask staff when you go. We had fun just guessing what gets an oyster to move. Breakfast outside under a shade tree in Key West…that’s living!

12:00 p.m.

Walking the side streets, the group is now heading for a very special and meaningful Key West address, 408 Williams Street.  It was here that my wife Peg, her sisters Barbara and Pattie, and their parents lived from 1955-59. Dad was a career Navy man and had his duty station here at the time. The sisters were in elementary school in the mid-fifties, and when we arrived at the house, Peg and Barbara regaled with tales of those years such as what it was like to live in Key West without air conditioning, and climbing out the 2nd floor window onto a tree limb over to the house next door. That special tree is no longer there today, but with the stories, it was easily imagined. Their house originally was in Green Turtle Cay, Abaco, Bahamas, where it was completely disassembled, floated across to Key West and reassembled in 1847. Today, this “Bahama House” is on the National Registry of Historic Places. Also today I fantasize how this magnificent structure could have remained in the family if only it had been bought at the time. I should have met Peg when I was 11 and advised them all of what a wise investment opportunity was at hand. Of course at 11, I was in Philadelphia trying to master tying laced shoes, but I digress.

Touristy and tacky, Duval Street is the main drag with most of the bars and restaurants in Key West. However on this day it is fun to walk because the number of pedestrians is very manageable, one side of the street offers ample shade, and there is plenty of beautiful architecture, uncommon souvenirs and gifts, and just so many things you simply don’t see back home. The street is named after Florida’s longest serving Governor in Florida’s history (1822-1834) and interestingly, on the northern end  of Duval you are looking at the Gulf of Mexico, and at the southern end, the Atlantic Ocean. What you find in between are restaurants and shopping to fit every taste. Locals call bar hopping the “Duval Crawl” which is probably an ample description of what you may be doing at the end of the evening. Yes it is true that at night Duval Street is usually very crowded and noisy, however one or two blocks removed on either side, the night sounds are filled with birdsong, whirling fans, and trickling fountains. But for now, it is in the middle of the afternoon, and with shopping and sightseeing finished, we head back to the car for the ride home.

5:30 p.m.

Two hours north of Key West we arrive in Islamorada (purple island) and head straight to the “world famous” Tiki Bar at Holiday Isle (over the years I have never gone wrong by visiting any place with “Tiki” in the title.) for shucked oysters (incapable of racing), and fresh grilled Mahi fish sandwiches. Sitting on stools overlooking a breathtaking ocean vista, it provides the perfect ending to our trip along the Florida Keys. Cheers!

Key West is a place and a state-of-mind. It’s allure calls us back often and it never disappoints. It’s impossible to tell which of the legends and tales are true or not, but as Hemingway wrote,  “make it up so later it will happen that way” captures the spirit that whether fact or fiction, it really doesn’t matter in  the minds and hearts of those who share the experience.

Although you can fly into Key West,  any opportunity to have the experience of driving from Miami on the Overseas Highway should not be missed. Recently, the Overseas Highway was awarded the high honor of “All-American Road” by the U.S. Department of Transportation. “To become All American, a roadway must have very unique features and possess characteristics of national significance that make it a visitor destination in and of itself.” There is no doubt in my mind we shall return to Key West again and again…but for now, it’s time to be moving on.


About Alan G Billingsley

My career has been varied, including time as a newspaper deliverer, lifeguard, bubble gum maker, door-to-door detergent promoter, telephone book proofreader, short order cook, private employment agency counselor and owner, office and credit manger, infantryman, pots and pans salesman, Chinese restaurant cook, Chinese restaurant owner, public employment counselor, budget analyst, tax analyst, grant administrator, radio announcer, radio and television show host, disk jockey, automobile valet, child advocate, and now retiree. I've seldom been bored.
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2 Responses to 28 Hours in Key West

  1. Barbara says:

    Loved it!

  2. Pingback: 28 Hours in Key West | Travel Smart: Florida vacations, staycations, beaches, resorts, attractions, tourism & more | The Palm Beach Post

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