Road trips are as much a beloved touchstone of American culture as is apple pie. But if you’re wheeling down the pretty necklace of islands that string together the Florida Keys, Key lime pie is on the menu and good-natured boasting is the side dish at restaurant after restaurant that heralds its citrus dessert as best.
Driven straight, U.S. 1, called the Overseas Highway—from laid-back Key Largo to party-hearty Key West—zips end-to-end in just two-and-a-half hours. But depending on traffic, this colorful journey is worth slowing down to better savor. Spend a night or two here and there, tying a week of days into an indelible memory, in places as posh or as no-fuss as you like, working your way to the southernmost point in the continental United States, all the while sampling funky and flavorful sites, sounds, and sensations.
1. LOOSEN UP AT THE FIRST OF MANY HAPPY STOPS
Leaving Miami, jumpstart your vacay vibe at Alabama Jack’s, in Homestead, on Card Sound Road, a toll-way through mangrove swamps. This honky-tonk, perched on two barges over the bayou, has been around more than 50 years—weathered to be sure, yet still desired. Celebs, like Today’s Kathie Lee Gifford, sing its praises, but you’re as likely to gobble up the legendary conch fritters and sweet potato fries while sitting next to bikers, families, CEOs, mechanics, smitten couples, and those looking for love. In other words, everybody grooves at AJ. It doesn’t have a website (try calling 305-248-8741), and doesn’t appear to need advertising to fill its open-air room. Starting at 2 p.m., musicians cover songs by Jimmy Buffett, The Beach Boys, and a coterie of country-celebrating songwriters; by 7 p.m. this joint closes, because the mosquitoes are hungry, too.
2. INDULGE YOUR COCOA LOCO LONGINGS
For a box of sweet treats, pull over next at Key Largo Chocolates, the only chocolatier in the Florida Keys. Owners Kristie and Bob Thomas craft delectable nibbles in whimsical shapes, such as starfish, turtles, crocodiles, and flip-flops. Best sellers include truffles in flavors as palate-invigorating as champagne, tiramisu, mango, cherry, coconut, tequila, banana daiquiri, creme de menthe, and, of course, Key lime.
3. RIDE A MOVING MOVIE HISTORY ICON
In Key Largo, fans of John Huston’s iconic 1951 film The African Queen swoon over the very vessel on which Humphrey Bogart and Katharine Hepburn starred in the pulse-rapids drama. Ah, love! Registered now as a National Historic Site, African Queen—first built in 1912 in Africa for use by the East Africa British Railways Company to transport cargo, hunters, and missionaries across the Victoria Nile and Lake Albert—has been newly restored and now cruises the placid canals here. Captain Lance Holmquist and his wife Suzanne Holmquist signed a lease with The African Queen Trust to refurbish and run the famed boat. As I sat at its bow (remembering Bogey’s character saying, “Nobody in Africa but yours truly can get a good head of steam on the old African Queen!”), I asked Lance Holmquist whether I could try my hand at the steam gear and whistle. Toot! Toot! Swoosh! Whoosh! At the end of the film, Hepburn’s character exclaims that her experience on board was “so stimulating!” I just had a whole lot of fun.
4. SETTLE INTO YOUR FIRST NIGHT WITH A SOOTHING SUNSET
A painterly end-of-day sky-scene is Mother Nature’s almost daily ritual here. In Key Largo, eyeball a comfy chair and raise your glass in a toast. One of the best views to philosophize the sun down is at Kona Kai Resort Gallery, a small boutique inn owned by Joe and Veronica Harris, former New Yorkers who felt the Keys calling their names. The lodging’s sandy beach, impressive works for sale by international artists, and botanic gardens round out this intimate escape.
5. BE PAMPERED AT AN EXPANSIVE RESORT…
Live it up in luxury at Cheeca Lodge, an Islamorada oasis since 1946, where big game fishing and society ooh-la-la put it on the must-do map. With 27 acres of lush gardens and two pools, this resort attracts honeymooners and families, kayakers, and tennis pros. For spa-goers, Cheeca Spa incorporates Tiger Clam shells right from the sea into its Signature Hot Lava Shell Massage. At its Atlantic Edge restaurant, relish the locally caught seafood, such as hogfish and grouper; or catch your own fish on an excursion and bring it back for the chef to cook any way you please. An on-property cemetery pays respect to early Keys pioneers, called Conchs.
6. …OR TWO
At secluded, swanky Hawks Cay Resort in Duck Key—which harbors a beachfront and a marina—fishing, diving, snorkeling, kite-boarding, and stand-up paddling woo water-sport adventurers. Yet the best water-devoted moments for many guests are at its on-site Dolphin Connection, where you can swim with (and be kissed by) bottlenose beauties in an ocean-fed saltwater lagoon. Recharged yet? At the Calm Waters Spa, a skin-smoothing Key Lime Mojito Signature Scrub puts the famous fruit to new use; breathe deeply afterward in its eucalyptus steam room. For kids four to 17 years old, age-group divided activities and club haunts are well designed, with supervised nature hikes, treasure hunts, athletic games, and more. After dusk, you’ll likely see romantics holding hands in a banquette at Alma, where executive chef Sandor Matyi melds bold Latin cuisine with refined European techniques.
7. …OR GET CASUAL AT A MELLOW BUNGALOW
In Islamorada, Pines Palms corrals a dozen cottages, each in different décor; there is a heated freshwater pool and tiki bar, too. Wake up to sky as turquoise as the sea and stretch your legs on its pier (photo above); then take a walk on the mild side up the road to cute Midway Café Coffee Bar (305-664-2622), which whips up tropical espresso macchiatos, fresh fruit smoothies, and cream-swirled waffles. Its friendly owner, Nicole Lindholm, originally from Chicago, moved here years ago for, as she says, “the beautiful weather and beautiful people.”
8. DISCOVER ART WITH HEART CHILL IN A SURFER-INSPIRED SPOT
In Islamorada, you can’t miss the Rain Barrel Artisans’ Village, because its entrance is towered over by a 30-foot lobster statue dubbed Betsey (photo above). Amble the leafy path to multiple shops chock full of sculpture, pottery, paintings, glass designs, jewelry, and knickknacks. And then drive further to Islamorada’s Morada Way Arts Cultural District to shop fancy galleries and peek in artists’ studios. Nearby, also in Islamorada, amid an abundance of tropical flowers, surfboard-decorated Morada Bay Café plops its Beach Café tables on white sand, so you can merrily bury your toes in softness while supping on conch salad and Keys stone crab. Indoor and outdoor bars, live entertainment (oh, those hip-swaying hula dancers!), Adirondack chairs, and monthly full-moon parties make this a laid-back-fun-forward scene anytime.
9. GET UP TO DATE ABOUT TURTLE LOWDOWN
In Marathon, enjoy a guided educational session at the Turtle Hospital, which has been rehabbing injured sea turtles, researching their healthcare, and returning them to their natural habitat since 1986. You’ll tour the surgical suite and watch Greens, Loggerheads, and Kemp’s Ridleys recuperate in their holding tanks, while boning up on info about boat injuries, viral tumors, and life behaviors.
10. BE CHARMED BY KEY WEST’S SMALL HOTELS
When you finallly arrive at this southernmost of U.S. cities, you’ll find the BBs here are among the most beguiling anywhere. Island City House, my favorite, is the oldest-operating guesthouse in Key West and encompasses three buildings—Island City House, Carriage House, and Cigar House, which was a former cigar-rolling factory, all of which surround an ambrosial garden, where you breakfast under trees.
11. SCOPE OUT A KEY WEST SEND-OFF
On Mallory Square Dock, overlooking the Gulf of Mexico, hundreds of people gather every evening for the Sunset Celebration, Musicians, psychics, acrobats, and jugglers entertain an ebullient crowd. As the firey ball slips beneath the horizon, join in the oohs-and-aahs.
12. EAT UP KEY WEST BOUNTY
There is so much good food, so little time! El Meson de Pepe, a Cuban-inspired restaurant run by chef Pepe Diaz and his family since 1986, is housed in the brick building Cayo Hueso y Habana, now an emporium on Mallory Square, but where, in the 19th century, thousands of Cuban refugees once disembarked. Order Pepe’s rabirubia frita entera (fried whole yellowtail) and camarones al ajillo (shrimp sauteed in olive oil, white wine, garlic, and lemon), then take a spin on the dance floor to the tune of a lively band.
On Duval Street in Old Town Key West, Jimmy Buffett parrot-heads make their trek to mecca Margaritaville for cheeseburgers in paradise and booze in the blender; bands perform nightly, except Mondays. Nearby, Smokin’ Tuna Saloon keeps its guests applauding with a busy roster of mood-elevating musicians and a raw bar. Another raw bar revelation—with towering platters of crabs, oysters, clams, Key West pink shrimp, and Royal Red shrimp—is at Conch Republic Seafood Company, by the Historic Seaport.
And thank heavens there is Blue Heaven, on Thomas Street in a century-old building, where decades ago a bordello, cockfighting den, and boxing ring (with some matches refereed by Ernest Hemingway) carved out niches. Today, this quirky and adorable haven allows roosters to roam the outside grounds as you eat on brightly painted tables under an almond tree. Married owners Suanne Kilchar and Richard Hatch, along with Richard’s chef brother, Dan Hatch, got this dream soaring 20-some years ago with recipes from their mother, Betty Hatch. Now kitchen-led by executive chef Guillaume Pailloux, the restaurant offers yummy day-long menus that never fail to rustle up lines of customers, though I covet most its breakfast reverie, especially specialty lobster eggs benedict.
Suanne and Richard also own Salute! On The Beach, on Higgs Beach, where Dan is currently lending an expert culinary hand; it focuses on Italian classics, such as linguini with mussels, lasagna, and Tuscan bean soup.
Then, aim your headlights over Cow Key Channel Bridge, nosing around nearby Stock Island, Key West’s less-wild wee neighbor, for a locals-cherished hangout, Hogfish Bar Grill, next to Safe Harbour Marina. Sit outdoors on rustic picnic tables or indoors under a soaring thatched roof to ravish delish fish tacos, blackened mahi mahi, hogfish sandwiches, and coconut shrimp. You’ll also find a jukebox, bandstand, full bar, pool table, and waiters who smile like you’re family.
13. FLOAT ON A BOAT NEAR WHERE DOLPHINS HANG OUT
Captain Victoria Impallomeni-Spencer, a native wilderness guide for 38 years with an environmental marine science degree, has many skills, perhaps the most spell-binding of which is her dolphin-whispering talent. Sign up for an endearing, soul-enriching afternoon through her Dancing Dolphins Spirits Charters to observe dolphins living freely. Aboard her 25-foot powerboat, she blows her dolphin-sensitive whistle and those who recognize her sound swim alongside. She plays a concert of songs for them, too—from Leonard Cohen melodies to classical pieces. On the serene afternoon that I searched for dolphins with Victoria, they were initially evasive. Then an energetic handful appeared, bobbing around our ship. I stared at their faces, the blue sky, the clear sea, and, oh wow, my joyful tears fell.
14. FEEL THE FLUTTER AND WONDER
At the Key West Butterfly and Nature Conservatory on Duval Street, there are butterflies galore—hundreds of them in myriad colors. They dart among blooming plants and waterfalls. If you’re very still, they might alight upon your head and shoulders. Don’t miss the Key West Garden Club at the West Martello Tower (a Civil War fort and National Historic Site) where White Street meets the Atlantic Ocean. Brick pathways and arched courtyards outdoors lead you among a rare collection of native and exotic trees and plants. Orchids perfume the air.
15. COMMUNE WITH AN OLD MAN AND THE SEA
No visit to Key West would be complete without a peek at the Hemingway Home, on Whitehead Street, where Ernest lived and wrote. There is a museum to explore, and lots of historical lore to brush up on, as well as the six-toed cats to spy, but the most exciting part for visitors is his study, where his typewriter still tops a table.
16. AHOY YOUR MATEYS AT THE END OF THE LINE
Channel your inner pirate or first-mate fantasies aboard the 80-foot, square-rigged, topsail Schooner Jolly II Rover with its distinctive red sails. Directed by personable owner Bill Malone and his crew, you can help hoist the sails, steer the wheel, fire the cannon, or just veg with your bev. There are afternoon trips, but, once again, the Florida Keys’ sunsets are a powerful elixir, and its night-time stargazing voyages offer up many opportunities for wishes.
For more info, go to: The Florida Keys Key West and Visit Florida.
What has inspired you about the Florida Keys? Do you have a favorite hideaway here? Where have you most enjoyed traveling? We’d love to know!
Frequent globetrotter Laura Manske has visited most U.S. states, explored 70+ countries, and cruised 60+ ships. She loves to wander the world, unearthing travel joy, beauty, adventure, and humor through her camera lens and articles. Now, she’s sharing pictures and memories of her favorite spots on Parade.com.