Now, this is island hopping: a 126-mile drive that skips across an archipelago of 1,700-plus keys, islets and islands; vistas of ahh-inspiring blue water from more than 40 bridges; an osprey’s-eye view of coral reefs and tidal flats. Toss in kayaks, conch fritters, quirky diners and opulent hotels, and we can only be in one place—the Florida Keys.
For many Florida Keys road-trippers, there’s a question that surfaces again and again: Where’s the beach? Mangroves, margaritas, aquamarine waters—somewhere in all that green and blue there have to be a few slices of heavenly sand.
There are, of course. And just like the Keys themselves, these unconventional beaches are one of a kind. Most are made of coral cobble, so pack your water shoes. Some are serene outposts of solitude, shaded by coconut palms. Some are thronged with snorkelers and windsurfers. A few are long enough for a serious stroll, while others are pocket-sized slivers of sand begging for a beach towel.
Most of the Keys’ beaches are hidden from the road and tucked away under coconut palms and bay cedars, which makes it fun to take on the challenge of hunting down the perfect one. Skipping from islet to island, ducking into roadside souvenir shops and open-air diners, keeping a sharp eye out for tiny Key Deer—a drive down this island chain is the quintessential road trip. It all starts where Florida’s mainland ends: at Mile Marker 126 on historic U.S. 1. From there, you’ll count down to Mile Marker 0, where funky Key West clings to the southernmost sands of the “Conch Republic.”
ISLAND TIME: The Upper Keys
Slow down your inner clock by taking the scenic route. Just south of Florida City, skip the tacky entrance to the Keys down the first part of U.S. 1 and hang a left onto Card Sound Road. A $1 toll will buy you a trip through soothing miles of green woods and mangrove flats in Crocodile Lake National Wildlife Refuge. You’ll intersect back with the main drag smack in the middle of Key Largo. The largest of the Keys, this 33-mile-long island has a pair of beaches you don’t want to miss—for very different reasons.
Granted, most folks don’t show up at John Pennekamp Coral Reef State Park with sand buckets. The park is famous for its glass-bottom-boat tours of the sprawling, 119-square-mile Key Largo National Marine Sanctuary. But afterward you can head to the park’s Canon Beach, where coconut palms shade the coral sand. From there it’s just a 100-foot swim to snorkel around the remnants of an early Spanish shipwreck.
Most days you’ll share Canon Beach with fellow tourists, but there’s an intriguing alternative. Just down the highway, south of Tavernier, check out Harry Harris Park Beach. This man-made beach lies on a small, protected lagoon where the kids can perfect their snorkeling technique. It’s a lesser-known spot where locals come to picnic, and Spanish conversation and laughter season the breeze.
FISH AND SHIPS: Islamorada & the Middle Keys
For most folks, Islamorada (pronounced “Isle-uh-muh-RAH-duh”) means fishing, and hundreds of charter boats and guides crowd the marinas. Even if baiting a hook isn’t in your plans, it’s still a blast to hang out near the docks in late afternoon, watching boats return with catches of shimmering dorado or tales of elusive bonefish.
For some live action, head to Robbie’s Marina (877-664-8498; robbies.com) off Mile Marker 77.5. More than two decades ago an injured tarpon showed up here, and the marina owner called in a local doctor who sewed up the fish with a mattress needle and twine. After six months of careful feeding, “Scarface” was released, but he soon returned for more handouts—and brought some friends. These days, dozens of the huge “silver kings” cruise the dock. Visitors pay a dollar to watch the more intrepid hand-feed the leviathans from a bucket of baitfish ($3). It’s a don’t-miss show, no matter what your age.
Heed the beach call on Lower Matecumbe Key. That’s where you’ll find Anne’s Beach, a tranquil Atlantic-side spot with thatched picnic pavilions and an elevated boardwalk. Start your day here with a gorgeous sunrise and an enormous cinnamon roll from nearby Bob’s Bunz (305-664-8363).
BEST FOR BEACHES: The Lower Keys
As you cross the Seven Mile Bridge from Marathon to Big Pine Key, your beach alarm should start blaring. Here, U.S. 1 hops, skips and jumps along the most undeveloped portions of the Keys, anchored by the famous beaches of Bahia Honda State Park.
Most folks head for Calusa and Loggerhead, two beaches near park headquarters. Instead, turn left after the park entrance and wind your way through the mangroves toward Sandspur Beach, a two-mile-long crescent of the Keys’ softest sands. Nearshore snorkeling turns up sea biscuits and sightings of the Caribbean spiny lobster—a clawless crustacean with bright blue and orange spots.
In fact, reveling in subtropical nature is the best thing about the Lower Keys. Here you’ll find some of the archipelago’s most pristine habitats. At the National Key Deer Refuge, kayak guides (305-872-7474; bigpinekayak.com) take paddlers into the secluded 84,000-acre park that’s home to hundreds of Key Deer, a two-foot-tall subspecies of the common white-tailed deer. About six miles south of Big Pine Key is Looe Key National Marine Sanctuary. You might try a snorkel tour at Looe Key Dive Center (800-942-5397; diveflakeys.com), and make like an eagle ray as you skim above elkhorn and brain coral.
PARTY CENTRAL: Key West
After spending a few days hunting for hidden beaches, it’s time to let your hair down and embrace the outrageousness of the Conch Republic’s capital. For most folks, Key West means Old Town’s Duval Street, crowded with shopping and big-name bars like Sloppy Joe’s, the Bull & Whistle and Jimmy Buffett’s Margaritaville.
Just three blocks from the “Duval Crawl,” respite comes in the form of Fort Zachary Taylor Historic State Park. Its beach is fronted by a rock breakwater that calms the ocean enough for even the smallest swimmers. For a bit more excitement, check out Smathers Beach, where you can rent a sailboard, small sailboat or snorkel gear and work off that giant slice of key lime pie.
One show you don’t want to miss is the nightly sunset celebration on the Key West waterfront. As the sun dips low over the Gulf of Mexico, crowds fill Mallory Square, once the anchorage of Keys’ pirates. Today the wharf is a melee of vendors, jugglers, escape artists, gymnasts, psychics and magicians, each holding their own spellbound audiences.
Here, you’re really at the end of the road. But for Florida Keys road-trippers, that’s not a bad place to be. After all, you get to experience it all over again on the way back.
PADDLE THE MANGROVES: Streams wind under canopies of mangroves in Dusenberry Creek, where manatee spend the winter. Three-hour kayak tour, $50. Key Largo; 305-451-3018; kayakfloridakeys.com
DAY-TRIP THE DRY TORTUGAS: Really get away from it all on these seven islands, 70 miles west of Key West. Snorkel the coral reefs and check out an historic fort. Day trips from Key West, $140 per adult. 800-634-0939; keyambassador.com; doubles from $199
This beachfront beauty gets raves for service, a deep wine list and a menu that blends Asian flavors, French style and Florida seafood. Reservations recommended. Mile Marker 81.5, Islamorada; 305-664-3225; dinner for two, $100*
Think “posh dive” on the water, with very fresh seafood. Mile Marker 47.5, Marathon; 305-743-6247; dinner for two, $64
No Name Pub
Famous for pizza and fried grouper, plus the best key lime pie. Mile Marker 30, Big Pine Key; 305-872-9115; dinner for two, $30
An intimate 50-seater crafting seafood worthy of a splurge. 600 Fleming St., Key West; 305-292-1244; dinner for two, $90
Ricky’s Blue Heaven
An artist, a writer and a renowned chef team up in a house where Hemingway once refereed boxing fights. 729 Thomas St., Key West; 305-296-8666; dinner for two, $80
Conch Republic Seafood Co.
Huge bar for adults, huge fish tank for kids, huge views of the harbor. 631 Greene St., Key West; 305-294-4403; dinner for two, $65
*Prices cover a three-course meal for two, not including drinks, tax or tip.