Key West, Florida — Fun and Sun At the End of the Road | To-Do List
Key West — a tropical Caribbean island you can get to by car.
At the very tip of the Florida Keys, and only 90 miles from Cuba, Key West is a tropical island paradise that you can drive to.
Key West
In the fall of 2018, Rick and I met in Key West for a little tropical vacation. Rick arrived on the island in mid-October after a short East Coast tour. We hadn’t seen each other since August. After flying into Atlanta, I hopped a puddle jumper to Key West.
In the parking lot, I was surprised to see a red rooster followed by a plump, doting hen and three fluffy yellow chicks. Oddly, the rooster behaved like he owned the place. I found myself smiling ear-to-ear as I watched the fearless cock crowing and strutting, frantically tailed by his apprehensive spouse and their little “peeps.” I was perplexed by the unusual sight. Rick gave me the Coles notes version of the Key West chicken story.
Apparently, the Key West chickens were initially brought to the island by its original inhabitants as a food source. Folklore says many yardbirds escaped after a hurricane. Later, others were released onto the streets after cockfighting was banned.
The Key West chickens are now highly revered residents and protected under the Migratory Bird Treaty Act. Eating, or even merely annoying these iconic birds is a crime.
Key West is certainly full of surprises!
Key West is the last island in the Florida Keys. It’s the end of the road for the Overseas Highway — a two-hour island-hopping drive from the mainland.
Check out this video featuring a drive through the Overseas Highway put to Kid Conch’s (Rick’s) surf instrumental masterpiece, “Big Wave Surfer.”
Key West boasts the southernmost point in the continental U.S. It’s also a stop-off point for several cruise ship lines. The massive ships sometimes tower over Mallory Square and the surrounding resort hotels.
Often referred to as Miami’s backyard, Key West has designated an Official U.S. port of entry in 1828.
The entire island is approximately 4.2 miles in length with most of the tourist attractions grouped toward the southern end of the island. Parking is scarce in Key West, but numerous bicycle, moped, and golf cart rental lots dot the island. There’s also a sightseeing Trolley that regularly circles the island as well as free buses.
The uber-relaxed attitude in Key West makes you feel as if you’ve entered a surreal adult storybook realm. This multi-hued holiday destination is atop the bucket list of tipsy, fun-loving partiers in fedoras and flip flops, who unabashedly revel in their newfound freedoms.
It’s not uncommon to see people walking around with drinks in their hands or smell the musky aroma of cannabis. The police won’t bother visitors unless they cause real trouble. In fact, Key West is one of only two cities in the U.S. where folks openly consume alcohol in public, the other being the French Quarter in New Orleans.
Rick found lodging in a room in a lovely home a quick two-minute drive from the airport. We pretty much had the house to ourselves! The house is run by local music legend, C.W. Colt, a super-talented singer/songwriter and a long-time fixture in the Key West music scene and a good friend of the late, great Capt. Tony whose live music bar is a historic fixture in Key West.
C.W. rents out the three-bedroom main house to guests. The place is spotless and airy with comfortable bedrooms, a cozy living room, and a charming kitchen. The house is ensconced with tropical gardens and palm trees. It lies just a block away from two of the biggest beach resorts on the island — Casa Marina and The Reach — places we frequented for sunset.
Rick has a knack for finding himself at House Concert venues. C.W.’s backyard has been transformed into a performance venue that seats about 30 people. C.W. entertains guests with heartfelt original songs and shares hilarious stories. He knows musicians from all over the world who frequent Key West and he often invites them to accompany him on stage, much to the delight of his visitors.
While we were there, C.W. graciously invited Rick and me to open his weekly show. We were enthusiastically received by the audience members, especially a couple of fellow Canucks who had stumbled across the private venue in their afternoon meanderings.
The night was pure magic. C.W. and his partner are amazing cooks! They whip up an astonishing tropical buffet and open bar for their guests at every show. The temperature was warm and the tropical air sweet — the ocean and swaths of aromatic tropical flowers competing for my olfactory attention.
The crazy story of the “Fuck-You” Lizard
Later in the evening, C.W. was storytelling, when out of the thatch of surrounding palm trees we heard a resounding and curt, “FUCK YOU!”
C.W. smiled and said, “Oh, you think you can do better?”
“Fuck you!” said the unseen verbal assailant. The crowd was visibly uncomfortable as they glanced around the yard in an attempt to locate the nasty music critic.
C.W. continued, “Maybe you’d like to come up here and do a song?”
Another resounding “Fuck you!” rang out from the palm trees. We thought it was an escaped house parrot. But the answer was much more unexpected.
As it turns out, the heckler is a lizard. The ‘Fuck-You Lizard’ — aka the tokay gecko — was imported to Key West from Viet Nam. Fantasticly, the mating call of this animal sounds amazingly similar to the all-too-familiar lewd insult.
Who would have known?
Southernmost Point and Duval Street
The next day I ventured out on my own while Rick worked. I made my way to the south end of Duval Street just a few blocks from the house. The aptly named Southernmost Point is marked by a massive brightly painted buoy. The writing on the buoy explains that it sits at the lowest latitude in the contiguous United States. It was the furthest south either of us had been on the North American continent.
Duval St., in the heart of Key West, was named in honor of William Pope Duval, Florida’s first territorial governor. Landmark buildings in eye-popping shades with gingerbread trims, enchanting courtyards, a variety of museum-type attractions, gift shops wine bars and cigar shops, clothing boutiques, and incredible art galleries offer a vast palette of sights, sounds, scents, and textures.
Duval runs north to south from the Gulf of Mexico to the Atlantic Ocean. Duval is the epicenter of a neverending party. You’ll find non-stop music and entertainment available morning, noon, and night. There are 43 bars on Duval St. and it’s only about a mile long! There are just as many bars within a block of Duval. There are also scores of restaurants ranging from fresh juice stands and takeout windows to fine patio and roof-top dining. The aroma changes constantly as you walk the length of Duval.
Key West hosts big events on an almost weekly basis — when there’s not a raging pandemic. World-famous fetes such as Fantasy Fest, Superboat Races, the Key West Music Festival, and one of our favorites, the Parrot Heads in Paradise Meeting of the Minds, a weeklong celebration of “trop rock” music inspired by Jimmy Buffet.
Key West sunset cruises
No trip to Key West could be complete without a sunset cruise. When I woke up from my siesta, Rick surprised me with tickets on a charter boat, complete with free drinks and a tropical-themed buffet. It didn’t take me long to don my most colorful dress, slip on my sandals, and be cruise-ready.
It was a gorgeous night to view an ocean sunset. The parameters of the deck were jammed with cellphone-wielding landlubbers all trying to snap pictures of the same red-gold horizon. One of Rick’s passions is sunset photography, so we knew the best was yet to come.
Boat drinks and beer flowed freely at the bar while a DJ/musician friend of Rick’s who goes by the name of “Frankendred” spun some high-energy rap and reggae.
Sangria in hand, we wandered below to the impressive tropical buffet. There was savory coconut shrimp, delicate salmon steaks, cheeseburgers, pork ribs, and a massive Caesar salad, as well as a fine selection of desserts. We enjoyed a leisurely, quiet nosh, far from the madding crowd on the upper deck.
We timed our photo session perfectly. Just as we finished eating, the crowd dispersed to the lower deck. With the upper deck pretty much to ourselves we snapped tons of pictures
Before we knew it, the two-hour cruise was almost over. The sky was black and starfilled when we pulled back into the harbor. We disembarked with full bellies, a slight buzz, and scores of sunset photos. This cruise was worth every penny!
There are several party cruise companies on the island to choose from but the regularly sell out, so advanced reservattions are advised.
The Key West Butterfly Museum
The next morning I was eager to do some more exploring. Rick had a few hours of work, so I thought I would check out the Key West Butterfly Museum. I had passed by the museum the day before on my way to Duval St and was intrigued.
When I entered this otherworldly domain, every bit of stress dissipated instantly. I was utterly smitten by the sweet pungent aromas of the exquisite flowering plants, the cascading waterfalls, and of course, the hundreds of jewel-toned butterflies and resplendent tropical birds.
At least 50 to 60 varieties of butterfly species from around the globe thrive in this amazing, glass-enclosed, climate-controlled habitat. I thought my heart would burst with child-like glee as a luminous, metallic-blue sky-flower landed delicately on my wrist. I stood breathlessly still for a while before she took flight. It was one of the most satisfying moments of my life, and I was honored to be her perch for a few seconds.
A hefty Germanic-sounding gentleman looked at me in awe and told me he’d been stalking this particular butterfly for an hour. He was a serious photography buff with a Nikon the size of a microwave slung around his neck. I hope he got his shot of the elusive creature, as well as a good chiropractor!
This stunning facility has an onsite Learning Center, where you can brush up on butterfly anatomy, physiology, lifecycle, feeding, and migratory patterns of the Monarch. In another section, you can get up close and personal with some live caterpillars working toward earning their wings.
There is also a charming little Gift Shop with an assortment of butterfly and nature-related items. Wings of Imagination is a butterfly-oriented art gallery featuring the amazing acrylic shadow boxes created by artist Sam Trophia.
The Hemingway House
I told Rick that I was interested in seeing the Hemingway House before I left the island, so we ventured out on a blazing hot Sunday afternoon.
This historical house was the residence of the esteemed American novelist Ernest Hemingway. Ernest wrote some of his greatest works here, including “The Snows of Kilimanjaro,” “To Have and Have Not,” and “Islands in the Stream.”
The Hemingway mansion was originally constructed in 1851 by Asa Tift, a wealthy marine architect. It was inhabited by Hemingway and his wife Pauline from 1931 to 1939. On November 24, 1968, Hemingway’s home was designated a National Historic Landmark.
The Hemingway House is one of the biggest tourist draws in Key West. It’s situated across from the Key West Lighthouse, at 90 Whitehead Street. A main attraction is the numerous polydactyl felines (six-toed cats) that freely roam the estate. I encountered a few of these elegant creatures, and I counted their toes. They were indeed polydactylpusses!
The house is impeccably maintained and every room tells a story of this fascinating era. I was thrilled to peer into one room and see an ancient typewriter on display. I was transported to another time as I envisioned him maniacally clacking away at the keyboard in between sips of single malt whiskey or bourbon.
The grounds are stunning, with towering ferns fringing the parameters of the house, charming little wooden bridges spanning serene lily ponds, and the piece de resistance — a giant, saltwater swimming pool. You can practically taste the profound literary relevance in the surrounding, exotic historical atmosphere.
Fort Zachary Taylor State Park and Beach
Fort Zachary Taylor was originally built in conjunction with a series of coastal forts after the war of 1812. It was constructed as part of the mid-19th century defense strategy to protect the southeast coast.
The foundation of the fort is made of New England granite and oolitic limestone and boasts walls rising fifty feet above mean sea level with an impenetrable thickness of five feet. This impressive fort contained a large barracks with an 800-man capacity.
During the 1898 Spanish-American War, WW I & II, Fort Zachary Taylor was heavily in use. It was also manned during the Cuban Missile Crisis in 1962.
The park offers daily, narrated tours. Tourists can peruse Civil war artifacts while learning about the construction and history of this amazing structure.
For decades the site hosted mostly tourists and history buffs. However, the Florida State Parks Service has converted the surrounding 87 acres of land into a world-class historical park.
Aside from live music, dining, and drinking, Fort Zachary Taylor’s beach remains the main attraction for most sun-worshipers and swimmers who flock to Key West in the winter months. This dreamy stretch of sandy beach is the best on the island in our humble opinion.
Snorkelers can enjoy an enchanting underwater oasis brimming with coral, parrotfish, yellowtail snapper, and lobster. Many tourists bring fishing rods to catch their dinner off the west rock jetty along the Key West Shipping Channel.
Others will fancy birdwatching along the wooded nature trails while discovering the many varieties of native plant life. The park also offers lush, shaded biking paths alongside the fort and the Shipping Channel.
After a day of biking, hiking and swimming, tourists flock to the Cayo Hueso Cafe for exquisite seafood delights.
And remember to stick around after your hearty meal to experience the most incredible sunsets in Key West where the Gulf meets the Atlantic. Key West sunsets rarely disappoint!
Fort Zachary Taylor can also be booked for Key West weddings and private events.
Dining in Key West
CW’s place lies directly across the street from the famous Louie’s Backyard restaurant, one of the most popular restaurants on the island, offering fantastic Caribbean fare, friendly service, and unparalleled ocean views.
When Louie’s Backyard first opened in 1971, there was only seating for twelve people and only one waiter! It was purchased in 1983 by Phil Tenney and was lovingly renovated with great attention to detail. This diligence earned Louie’s Backyard an esteemed place in the National Register of Historic Places.
Louie’s Backyard has received iconic, beloved status over the years and is a must-visit establishment for those visiting Key West for the first time. In addition to the gourmet Caribbean fare, the seaward-facing deck offers spectacular ocean vistas and glorious sunsets.
For over three decades, chef Doug Shook has delighted many discerning palates with his mouth-watering culinary skills. He likes to keep the menu fresh, and this tendency results in four or five menu revisions annually. Every entre is lovingly prepared, primarily dedicated to the local daily catch, such as snapper, swordfish, grouper, hogfish, lobster, and delectable Key West “pinks” (shrimp.)
There are also innovative, outrageously delicious recipes specially prepared by chef Shook, like conch fritters spiced with hot pepper jelly.
For those with landlubber tastebuds, Louie’s offers free-range chicken, fine steaks, lamb chop, and heirloom pork dishes all prepared with the freshest of ingredients.
Louie’s was immortalized by Jimmy Buffet in one of his songs. In fact, rumor has it that the King of the Parrotheads actually resided in the house at one point. He has even been known to show up and perform there on special occasions. Other local musicians including C.W. Colt often showcase their talents at the venue from time to time.
Louie’s also has a waterside lower deck with a charming bar that also offers mesmerizing ocean views of the Atlantic. Enjoy the gorgeous setting while sipping a selection of fine wines, handcrafted cocktails, and martinis.
Louie’s is a favorite spot for locals, visiting celebrities, tourists, and dog-loving hipsters. That’s right — this bar is dog-friendly and located right next to Dog Beach.
You will not be disappointed with a visit to Louie’s Backyard! However, this restaurant is extremely popular. Make sure you book your table well in advance if you don’t want to miss out!
Check out Rick’s rockin’ instrumental, “Super Boat,” featuring scenes from Key West’s annual boat racing event, the Offshore World Championships.
Do we recommend visiting Key West and the Florida Keys?
Key West is one of our most favorite winter vacation stays. You won’t find a more Caribbean/tropical vibe without leaving the mainland. We highly recommend adding this to your to-do list.
Although lodging and dining on the island can be pricey, there’s plenty of free entertainment and beaches. Public transportation around the island is also free. Parking can be challenging during peak season.
Tips for traveling to Key West
- You don’t have to drive to Key West. You can also fly into the Key West International Airport. And the Key West Express ferry comes in from Fort Myers, Fla. — a three-hour tour.
- To get an overview of what Key West has to offer, start your trip out with a narrated hop-on-hop-off excursion with the Old Town Trolley Tour.
- Mallory Square is the place to be in the early evening with a myriad of street performers, vendors, and spectacular sunset views.
- In late fall and early winter, seaweed tends to clog the shoreline on western beaches. If you’re a swimmer you might want to wait until late winter/early spring.
- Bring at least one windbreaker or sweatshirt if you’re going to Key West in the winter months. I can get chilly on occasion, especially if you’re on a tour boat.
- The summer months can also be fun if you can tolerate the tropical heat and humidity.
- We don’t recommend bringing children on a walk down Duval Street unless you’re willing to expose them to a bit of debauchery.
