Between the two of us, my husband and I have made the trip to the Southernmost point of the United States — The Keys, Florida — fourteen times. And while we probably know people who have attended Grateful Dead shows with greater frequency, I figure making the long trek more than a handful times says something. From where we live in Nashville, we’ve taken just about every mode of transportation our budget will allow. We’ve flown on tiny prop planes from Miami. We’ve taken the four-hour ferry from Fort Myers. But our favorite way is to drive.
On my first drive—years before meeting my husband—I rode down in a fifteen-passenger van with college friends for spring break. I was 20. Drunk on the myths of Hemingway (and rum) I made the ill-fated decision to enter Sloppy Joe’s—the bar he made famous—with a borrowed ID. I spent the next day in community service picking up trash on a sliver of beach in an orange vest that said “inmate” on the back. You’d think the experience would sully the place for me. But oh no, I returned the next year for redemption and entered Sloppy Joe’s legally.
FAST FORWARD: The Keys Today
Fifteen years later, my husband asked me out for the first time from Key West via a Facebook message. He was standing on a parade float wearing a grass skirt and a bra. “Don’t look at any of my photos while I’m down here,” he wrote, knowing I was back in Tennessee. Of course, I looked at all of them. It was love at first sight.
We’re older now—pushing 50—and only slightly wiser, but definitely more subdued. We have our favorite haunts in the Keys. Nostalgic spots that we visit on repeat. But the stretch of about 180 miles never gets old along with us. We always learn something or meet someone new or find a quirky stone unturned. These days, we still might go to Sloppy Joe’s but just for one piña colada. They never even card me anymore.
THE BEAUTY OF THE KEYS
As Pulitzer Prize finalist and novelist Joy Williams says, “the best way to enjoy the Keys is still to seek out their simplicity and their eccentricity.” Indeed, the drive down can help ease a person into this frame of mind. It often takes longer than you think it should, and sometimes a traffic accident or road work will make it even longer. But the old adage about journeys versus destinations remains true.
While taking a break from fiction, Williams wrote The Florida Keys: A History & Guide (Random House Trade Paperbacks), which I consider the greatest guidebook of all time. Though the last version printed in 2003, it remains timeless in many ways—honest and humorous and expertly written. The book also serves as a reminder to respect the ecology of this region by traveling with a light footprint and considering the damage unchecked development and strain on the environment can cause. She writes about the complicated nature of the Keys and the road as a means to witness all that this scraggly collection of lands offers along the way through natural beauty and manmade kitsch:
“The Keys sparkle downward, warm and bright, full of light and air and a bit of intrigue. The Keys are relaxed, a little reckless. The Keys are water and sky, horizon, daybreak, spectacular sunsets, the up of night. The least interesting thing about them is the road, but the road, as is its nature, allows entrance. The road is the beginning.” — Joy Williams
BEGINNING THE DRIVE
We like to start our drive, officially, at a fruit stand south of Miami in Homestead, Florida, called Robert is Here. The story of the place begins in 1959 when 6-year old Robert Moehling set up a roadside fruit stand to help his family sell produce for their farm. In an attempt to draw traffic, his father painted “Robert is Here” on the back of a hurricane shutter.
Now more than sixty years later, Robert is still here in his apron arranging fruits and greeting guests. Giant ceiling fans stir muggy air over piles of pomegranate, passion fruits, guanábana, sapodilla, tamarindo, guavas, avocados, and key limes. Coolers stock quarts of fresh coconut water and sliced fruits for the road, like mango or papaya. There’s a petting zoo and live music on weekends. Don’t miss the beloved milkshakes—just fresh fruit, milk, and ice.
Though Homestead is technically pre-Keys, it’s a fitting place to begin. By 1904 the Florida East Coast Railway reached Homestead from St. Augustine. When the United States announced construction of the Panama Canal, oil magnate Henry Flagler decided to extend his railway to Key West for trade possibilities. The project dubbed Flagler’s Folly by some at the time, operated from 1912 to 1935. This extension laid the groundwork for the road that would replace it after a Labor Day hurricane washed large parts of the railroad away.
From Homestead, you can take the quicker and more traveled US Highway 1. We recommend the slower and more rustic scenery of Card Sound Road. While it adds about 6 miles to the trip, you can stop at Alabama Jack’s, a roadside biker-type bar situated along the mangroves. Open air with plastic chairs and buoy decor, it draws families, travelers, and regulars. A honky tonk band often plays from 2 pm on weekends against the clang of empty beer bottles hitting the trash cans. It’s a rough-hewn little respite from the road. But a cold beer, plate of conch fritters, and steamed shrimp will fortify your travels.
EATING WELL IN THE KEYS
For something a bit fancier, drive farther south hooking up with US 1 to Key Largo for a place called Snook’s Bayside Restaurant and Grand Tiki Bar. The Keys has its share of old-school dinner spots decorated with shells and fish nets and captain’s chairs. But at Snook’s the decor is mostly breathtaking pink sunsets to the sound of steel drum bands. Guests dine outdoors sipping cocktails under white umbrellas over plates of mahi mahi meuniere in lemon butter with tomato and capers.
Lest you think it too fancy, I recall the first time I phoned to make a reservation. The man who took my name ended our exchange with an exuberant “Rock on!” before hanging up. How could it not be a good time?
Our next stop, especially if we’ve stayed overnight, doesn’t sit on the water, though you’re never far from it on this road. Harriette’s Restaurant has been serving travelers and locals for forty years. Many folks stop for breakfast plates piled with pancakes, bacon, and eggs, or for burgers, fish sandwiches, or fried seafood platters.
But the restaurant also is known for its muffins, which we take to go. Check the dizzying menu ahead of time as you’ll have up to twenty-six choices. The oversized hunks of breakfast cake come in variations of key lime as well as toasted coconut, guava cream cheese, and mango to the more traditional chocolate chip or blueberry.
Heading farther down to Islamorada, we never miss an opportunity to stop at the Lorelei Restaurant & Cabana Bar. Years ago, our friend Pat Martin of Martin’s Bar-B-Que Joint in Nashville recommended it, and he knows far too much about food and fun to ignore. Parked at this fishing marina restaurant, we order the fresh catch sandwich and feel the breeze coming off the water. For dessert, try the frozen key lime pie—a slice of pie in beverage form with a graham cracker crust rim.
Since it wouldn’t be feasible to simply eat your way to Key West, we suggest taking in the natural world, too. Driving along the Overseas Highway, you’ll notice 42 bridges connecting the lilypad Keys. It’s impossible not to marvel at tiny communities set against the expanse of Atlantic Ocean, Florida Bay, and the Gulf of Mexico in their many shades of blue. The Turtle Hospital at Marathon Key offers tours to travelers and an education on the magnificent creatures. Also special to the area, it’s worth learning about the endangered Key Deer at the National Key Deer Refuge at Big Pine Key.
WHEN HUNGER STRIKES
Once you’ve traveled long enough to have your appetite back, you’ll ideally be passing through Stock Island. This area used to have a reputation as a service island and home to most of the remaining shrimp fleet. It has since undergone a hip renaissance in the last several years with a spotlight on hotels, restaurants, and artist studios as a respite from rowdier Key West. Consider Matt’s Stock Island Kitchen and Barat the Perry Hotel where guests can taste black bean empanadas or grouper gnudi made with cornbread.
Arriving in Key West proper, I like to start with Cuban food. My favorite Cuban sandwiches come from a corner bodega called 5 Brothers Grocery and Sandwich Shop. Family run since 1978, it’s an ideal spot to pack provisions for a picnic. Consider Fort Zachary Taylor Historic State Park, where you can walk through the shade of pines to a natural beach.
For a Cuban meal in a seated but no-frills dining room, the mom-and-pop El Siboneyis worth the venture for plates of picadillo or roast pork. We like to begin each morning with Cuban coffee. Our favorite, Sandy’s Cafe, serves big styrofoam cups of strong coffee from the back of a working laundromat. But we’ll also hit the closest on any given trip, such as the Cuban Coffee Queen, which has several locations.
TAKING IN THE ARTS
Between meals, you might find yourself lured by the ghosts of the Keys’ deep literary past as well as its thriving present. Tourists flock to see Hemingway’s house, naturally, but along the way you’ll maybe even spot poetry etched into the streets across town. The annual Key West Literary Seminar also offers a walking tour that begins at the Monroe County Public Library and ventures past the “former homes and favorite haunts of Tennessee Williams, Shel Silverstein, Elizabeth Bishop, and Robert Frost.”
A visit to Key West wouldn’t be complete without a stop at Books & Books, the shop by author Judy Blume. It’s part of the nonprofit Studios of Key West, a site for visual art, classes, performances, and residences for writers and artists.
At dinner time, there are always newer restaurants to dazzle, such as Little Pearl. But we can’t help making our way to a classic, Blue Heaven. Choose an outdoor table where live music often plays and Key West chickens peck near your feet. The menu includes seafood as well as Southern American and Caribbean influences. You’ll find Caribbean “BBQ” Key West shrimp deglazed with Red Stripe beer as well as an island plate with portobello mushroom, black beans, skillet corn, plantains, and cornbread with curry butter.
If you’re too full for dessert, you can always order the key lime pie with its outrageous pillow of meringue for lunch another day at Salute! on the Beach. (Another location, Salute serves the same slices of the pie, and it will transport you to a different vibe and part of the island with a beach view.)
SAYING BYE TO THE KEYS
To stay, Key West has its share of large hotel chains, but we prefer the smaller (and often more eccentric) family-run operations. We have visited many over the years and found favorites such as Key West Hospitality Inns. We also like the Angelina Guesthouse, a simple place with grounds laced in bougain-villea. You can even wake to the crow of the infamous Key West roosters and the smell of hot, fresh cinnamon rolls baked by staff for breakfast.
There’s nightlife at the bars along Duval Street, which draw plenty of tourists. We recommend venturing deeper, though, and off the path to places like the Green Parrot. With a history dating back to the 1890s, it’s a funky mix of live music, pool, or even the regular meet-up of the local ukulele club.
I remember one visit when we pulled into town late. Well past dinnertime, we walked around the corner from our hotel to the Parrot for a nightcap. I’d hardly taken a sip of beer when a fellow patron placed an actual green parrot on my shoulder. My husband snapped a picture, and I posted it with a caption to commemorate the ending—some might say beginning—of our journey: “Welp, we made it to Key West.”
What’s the Code?
We partnered with Road.Travel to offer curated itineraries as part of our Special Travel Issue! Through the QR codes, you can download the itineraries from our pages directly to your device. Follow along the next time you get behind the wheel.
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