Cayman Islands Grand Slam

December 5, 2006

Standing in the bow of Mark Phillips’s 14-foot skiff, I squint into the dreamy dappled water off Little Cayman. The sun is at my back. The wind is blowing stiff from the east. And the moment of truth is fast approaching.

“You are about to catch a bonefish,” Mark Phillips says.

“Yeah, right,” I reply.


But I might as well humor Phillips. The 24-year-old Oklahoma native is, after all, a well-meaning young man. He spends part of each year working as a fishing guide at the Southern Cross Club, a legendary haunt of outdoors folk – divers and anglers, mostly – and the oldest resort on Little Cayman. Passionate and accomplished in his craft, Phillips sincerely wants me to succeed in the mission at hand. To increase my chances, he has even equipped me with one of his hand-tied flies. It resembles a tiny, fuzzy albino shrimp. Phillips refers to it as the “Hugh Hefner.”

“Because it has nailed so many bonefish,” he says.

I remind Phillips that while the Hugh Hefner might be every bit as potent as he claims, my own fly-fishing skills are, shall we say, substantially lower on the performance ladder.


My conquests have been few and far between. I cast badly. And bonefish spook easily. Besides that, did I mention that the wind is blowing really, really stiff from the east?

Phillips ignores me, persisting in his upbeat forecast.

“You are about to catch a bonefish,” he repeats. “Heck, who knows, you might just get yourself a grand slam.”


So preposterous is this last remark that I don’t even bother dignifying it with a reply. In the parlance of hard-core anglers who visit here, a grand slam is a rare and heady accomplishment. It means catching three wily piscatorial prey – a bonefish, a permit, and a tarpon – in a single day. At the Southern Cross, only a couple of people do it every year. I don’t have a chance in hell.

Besides, I’ve already claimed my own personal “Cayman slam,” and I am feeling pretty cocky about it. In a week of travel, I have bagged all three of the Cayman Islands – Grand Cayman, Cayman Brac, and Little Cayman – each as different from the other as, well, a bonefish is from a permit. I have strolled Seven Mile Beach, snorkeled in the governor’s backyard, and played a game of down ‘n’ dirty dominoes so fierce it actually drew blood. I have scaled the “heights” of one of the oddest geological formations in the lower latitudes and sipped rum late into the night with a clan of Caribbean Celts. I have witnessed red-footed boobies engaged in mortal midair combat with pirating frigate birds and have dropped down over the 6,000-foot underwater ledge known as Bloody Bay Wall. I have eaten spicy whelk stew with sea pie and not cried out for a bicarbonate afterward.

Yes, it has been a great week. Catching a bonefish would be gravy on a plate heaped high with goodies.


“Get ready,” whispers Phillips. “Here they come.”

I twitch my fly rod and Hugh Hefner wiggles, anxious to do his thing…

Maybe it’s because they are so far removed from any neighbors – Jamaica to the southeast and Cuba to the north are the closest landfalls, and both are more than 125 miles away. Maybe it’s because they lacked the indigenous cultures of other Caribbean islands – no Tainos, no Arawaks, no Caribs – and weren’t settled until relatively late in the colonial scheme of things. Or maybe it’s because, girdled by reefs that earned them the name “Graveyard of the Caribbean,” they were never more than navigational markers on the major shipping routes. Not even Christopher Columbus, who sighted them in 1503 while sailing from Panama, saw fit to stop on these low-slung limestone outcroppings, emergent specks on an underwater ridge that runs all the way to Cuba’s southeast coast. Columbus, that most prolific of all Caribbean nomenclators, called them Las Tortugas, or the tortoises, for the vast number of sea turtles his crew spotted nesting on the beaches. They took their later name from all the crocodiles – “caim¿ns” to the Caribs – that once slithered about in the lagoons but whose stocks have long since been depleted.

For any variety of reasons – isolation, inertia, take your pick – the Cayman Islands are largely a modern contrivance, late-bloomers that came of age and began luring substantial legions of foreign suitors only in the past 40 years or so. Even now, of the three islands that make up this British dependency, only Grand Cayman, with 95 percent of the population (about 37,000 residents out of a total of 40,000) has given itself wholly to the pursuit of international commerce. But it has done so in major fashion.

The 22-mile-long sickle-shaped island, referred to as the “mainland” by the residents of Little Cayman and Cayman Brac, not only boasts a welloiled tourism infrastructure – big airport, big hotels, big duty-free shopping district – capable of handling more than 1.5 million visitors a year but has also positioned itself as one of the world capitals of offshore banking. At most recent count, nearly 600 banks and trusts were doing business there, and nearly 60,000 corporations were listed in the Cayman Islands Registry of Companies, taking advantage of altogether benign Caymanian laws that allow virtually no direct taxation – no taxes on income, property, capital gains, or inheritance.

It all makes for a curious mix of sun-drenched hedonism and hard-core capitalism. Only on Grand Cayman can you snorkel along a beach lined with tiki bars and bikiniclad babes sipping umbrella drinks, then walk a couple of blocks downtown to find yourself in the shadow of glistening high-rises emblazoned with corporate logos – Bank of Nova Scotia, Bank of Lichtenstein, Bank of China – and harboring spreadsheet mystics in three-piece suits.

But it was the wet-suited crowd that kindled the flames of Grand Cayman’s tourism industry. Back in 1957, an entrepreneurial-minded scuba enthusiast by the name of Bob Soto opened the island’s first dive shop. It grew into a marine empire that spawned dozens of competitors – there are now more than 30 dive outfitters on Grand Cayman alone and at least 160 official dive sites, many of them just 100 yards or so offshore. With no heavy industry to pollute the waters and no runoff from big rivers, the visibility, in balmy weather, is about as close to ideal as it gets.

The big draw is Stingray City, a shallow sandbar that lies off the northern end of the island and is home to a resident population of some 30 to 40 southern stingrays. The sociable two- to three-foot-long creatures – there’s no danger of being jabbed by their barbed tails unless you step directly on them while they are feeding in the sand – love nothing more than to let themselves be stroked on their bellies by gleeful tourists.

For those who prefer to avoid the stingray cattle calls, it’s easy enough just to walk along the shore and dip in at any number of likely spots. Setting out one afternoon from my hotel with mask, snorkel, and fins in hand, I have only to stroll a few paces north on Seven Mile Beach before I spy a promising patch of coral about 50 yards offshore. While I am taking off my T-shirt and preparing to dive in, I notice a small white sign nailed to a casuarina tree. It says: “Please respect the governor’s privacy.”

A dozen or so casuarina trees line the beach, each about ten yards apart and each sporting an identical sign. Were the signs not there, I wouldn’t be tempted to investigate further, wouldn’t even notice the sprawling one-story home hidden behind podocarpus hedges. But the signs are there, and I hear music. Drawing closer, I see a string quartet tuning up on a patio. Bottles of champagne are icing down; silver-domed platters are keeping the munchies warm. The governor, it appears, is getting ready to have himself a good ol’ time. Tuxedo-clad waiters chat idly, waiting for guests to arrive. Since I lack an invitation, not to mention a shirt, when one of the waiters spots me, I take it as my cue to head back toward the water.

It turns out to be a delightful little shore dive with thick schools of reef fish – grunts and snappers and brilliant blue tangs that are obviously conditioned to expect handouts – trailing me everywhere I go. Afterward, I sit in the sand dunes under the casuarina trees, as close to the governor’s home as propriety allows. The sun is going down. There is the happy chatter of well-lubricated guests. The string quartet plays something that sounds like Haydn. Or maybe it’s Liszt. Doesn’t matter. Purloined music sounds all the sweeter.

Much of the time I spend on Grand Cayman is marked by a feeling that I am really elsewhere. Some moments, when the sea is a brilliant mirror and the horizon stretches into the blue forever, it seems that I am far to the south, on some other flat-as-a-pita island, say Aruba or Bonaire. Other times, when at a market where vendors are serving up ackee and saltfish or giant plates of jerked pork and chicken, I get the feeling of being in Jamaica. That’s fitting, since Grand Cayman’s first settlers are thought to have been Cromwell’s British troops fleeing royalist soldiers in Jamaica, from which much of Grand Cayman’s workforce still hails. Most of the time, however, I feel as if I haven’t strayed far from my home in Florida. The strip malls that buffer West Bay Road along Seven Mile Beach are home to all the familiar fast-food franchises. And everywhere there are realestate signs for Century 21, RE/MAX, Coldwell Banker, and the other usual suspects. There is so much buying and selling going on – milliondollar high-rise condos, giant Mediterranean-style mansions on half-acre beachfront lots – that one can sympathize with the home owner who, in one West Bay community I pass through, has erected a sign in his yard that plainly states: “This house is NOT for sale!”

The quest for a sense of Caymanian place has me heading east to the Mastic Trail. On the dirt road leading to the trailhead, I must get out of my car and open a rusty wire gate latched with frayed rope. A plaintive, hand-scrawled note on the gate says: “Please close gate so cows not roam¿very please.” Sure enough, a half-dozen tawny cows are eyeing me from the other side of the gate, intent on making a quick escape. I swing the gate open and shoo back the cows, but as soon as I am in the car, the cows turn and gallop through the gate. They have pulled this trick before. I get out of my car and yell at the cows. There are, I suppose, few sights more ridiculous than a grown man yelling at cows, especially when the cows are so blithely ignoring him. So I hop in my little Korean rental sedan and circle back, thinking I might round them up on four wheels and herd them to where they belong. For the record, this is one of the few sights more ridiculous than watching a grown man yell at cows. If cows are capable of sneering, then these cows sneered at the would-be cowboy pursuing them in his Hyundai. For their sake and their owner’s, I hope they did not roam far.

Blazed in the mid-19th century so that Caymanians could haul goods and timber from one side of the island to the other, the Mastic Trail fell into disuse before being restored by the National Trust for the Cayman Islands in 1994. It’s the closest thing there is to an outback on Grand Cayman, a two-mile trek through a surprisingly diverse range of terrain. I follow it into a soggy black mangrove swamp (a plank path keeps hikers dry) then into an old-growth forest lush with bromeliads, orchids, and other flora made all the more interesting by the local names – “duppy bush,” used to brew a potion said to scare away the dead; and the “shake-hand tree,” with leaves that resemble a friendly outstretched palm. The trail eventually leads to “The Mountain,” a very slight bump in the terrain that, at 60 feet above sea level, is the highest point on Grand Cayman.

With the rigors of trail and wayward beasts behind me, I find my way to the town of East End. Thought to be the oldest settlement on Grand Cayman, it’s the perfect antidote to the hustle and bustle of George Town. At Pirate’s Cove, a pint-size bar nestled in a palm grove along the roaring windward coast, I sip a Guinness with my fish-and-chips while watching a game of dominoes on the bar’s back porch. It’s a typical Caribbean version of the game, meaning it is blazingly fast and highly percussive. The players slap their dominoes on the table with such force and fury that it sounds like rifle shots.

When one of the players exits, the others invite me to join the game. I take a seat next to a mountain of a man who tells me his name is Chester. He weighs every bit of 300 pounds, and he wears a red T-shirt emblazoned with the slogan: “I’m big all over, momma.”

“Loser buys Guinness,” says Chester.

I wish I could accurately report on what happens next – the subtle intricacies of the game, the plotting, the strategy. Mostly, though, I don’t understand a bit of it, except when Chester or one of his buddies turns to me and says, with politely masked impatience, “It’s your turn” or, less politely masked, “Play your piece, man, play your piece.”

At one point, Chester slaps down his piece with such ferocity that it splits the tabletop, leaving Chester with a gash on his forearm. He wipes the blood on his red shirt, and we move the game to another table.

Cut to the chase: I lose, OK? Over the next hour or so, I lose several times.

Another round of Guinness, please.

Being a rather huge fan of interisland boat travel (one way of saying that I am none too fond of flying in small interisland planes), I was disappointed to learn that there isn’t a ferry service connecting the three Cayman islands. Then again, it is a healthy haul from Grand Cayman to Cayman Brac – about 80 miles – and the seas quite often pick up without much warning. The flight, in an eight-seat, twin-engine Piper Navajo, is not nearly as awful as I have suffered in puddle-jumpers elsewhere; it takes 50 minutes and transports me back at least 50 years.

Cayman Brac is, well¿it is one of the most peculiar islands I have ever visited. The people are nice, the accommodations comfy, the food and drink quite satisfying. It is the Brac itself – ” brac ” is the Gaelic word for bluff – that gives the island such singular weirdness. Dominating almost the entire 12-mile length of the island, the bluff – a product of eons-old seismic upheaval on the sea bottom – resembles a monstrous fossilized gray whale sloping upward from its tail in the west to form in the east a looming bulbous head that’s nearly two miles across and rises 140 feet above the sea. It is omnipresent and monolithic. It is also riddled with dozens of caves, which over the years have provided residents of the Brac shelter from hurricanes.

Before setting out to explore the bluff, I stop in for lunch at the G&M Diner, where owner Grant Geddes considers me with skepticism when I tell him I have come to research a magazine article about the Brac.

“You writers never get it right about the Brac,” says Geddes, 66, who was a captain of oil freighters before retiring to open his restaurant. “You make it out like there is nothing here, like it is just a tiny deserted island. Hell, we’re as big as Long Island, New York [he exaggerates] – only about four million people short is all. And there are plenty of beauteous things here that the world needs to know about.”

One of those beauteous things – whelk stew with sea pie – is served up by Geddes himself. In Geddes’ recipe, the whelk is boiled out of its shell, ground like hamburger, and then cooked slowly in coconut milk with lots of pepper. Sea pie is the local name for dumplings, simple flour-and-water concoctions that are pressed flat like noodles and tossed into the stew just before it is served.

“It eats good, doesn’t it?” says Geddes, who, like many of the island’s 1,200 or so residents, can trace his heritage to 18th-century settlers. He goes on to tell me, in the island’s particular Scottish-like brogue, that my visit to the Brac comes at a perfect time, since the “shamrock are a blomin,” counterpointing the bluff’s craggy gray face with bright yellow blossoms.

So immense is the bluff that it essentially separates the north side of the island from the south, with only one torturous road to connect them. But the bluff is easily accessible from a dirt road that runs its length, with numerous hiking trails splitting off from it. I set out on the Lighthouse Trail, trekking through terrain where cactus and agave sprout from limestone craters and silver thatch palms rustle their bushy heads. I walk for two hours, seeing no one and hearing nothing but the relentless wind.

Only five miles separates Cayman Brac fron Little Cayman, but again, unless you hitch a ride with a fisherman or on a dive boat, the only way to shuttle between the two is by plane. From takeoff to touchdown on Little Cayman’s grass and limestone runway, the flight takes eight minutes.

Even with a flurry of homebuilding in recent years, primarily by well-heeled North Americans, fewer than 200 people live on Little Cayman. Over the course of a couple of days, a visitor is practically guaranteed of at least seeing, if not actively engaging, most all of them.

A wiry fellow by the name of Fidel Castro Christian unloads my baggage at the little airport. The next day, I stop to chat with him while he helps some friends sink pilings for a dock. That evening, Christian and his pals are holding down stools at the Southern Cross Club, debating everything from the excesses of religion to the merits of modern cinema. They greet me like an old friend.

Christian is also on hand when I am introduced to Little Cayman’s most numerous inhabitant – the odd but compelling redfooted booby. The more than 5,000 pairs of boobies on the island make up one of the world’s largest congregations of the birds. They are players in a daily spectacle capable of galvanizing even the most hardened nonbirder, and my sunset flight from Cayman Brac delivers me just in time to witness it. Having set out early in the morning, incoming flocks of boobies now vector toward their nesting grounds at Booby Pond, a brackish lagoon that lies just east of the runway. The birds are on their way to feed their young by regurgitating fish they have scooped up during a day at sea. But first the boobies must make it past a gauntlet of magnificent frigate birds, their eternal enemies. Not nearly as accomplished at fishing as the boobies – their talent lies in performing electrifying aerial acrobatics – the frigate birds instead play the role of highwaymen.

“Look there,” shouts Christian, pointing high in the sky. “Bastard’s split him off one.”

Like a wolf stalking a herd of caribou, one of the frigate birds has succeeded in separating a booby from its protective squadron, and they now engage in an avian dogfight, spiraling down toward the ground. Suddenly, the booby pulls out of the death-plunge and, as it does, disgorges its hard-earned catch. The marauding frigate bird intercepts its meal in midair as other frigates swoop down to feast on what it misses.

Things are much more civilized for human diners on the island. I myself take a seat in the chummy dining room of the Southern Cross Club, where I enjoy grilled wahoo with a roasted-red-pepper sauce, and a crisp Italian white wine to wash it down. Founded in 1958 by a North Carolina doctor and several of his sports-minded friends, the Southern Cross operated as a private club until 1980, when it was bought by a group of 30 investors who opened it to the public while managing to keep the clubby atmosphere. In 1995, it was purchased by Peter Hillenbrand, a son of one of the investors, who was in college working toward a degree in marine biology when this opportunity came along.

“Not a tough choice,” says Hillenbrand, 39, as we smoke cigars at the club’s open-air bar. “Here I’m surrounded by more marine biology than I could ever hope to study.”

There are only five resorts on Little Cayman, with a total of just 80 rooms. Southern Cross, with its six cottages – painted in pinks and greens and yellows and strung along a precious sliver of impossibly white sand – can handle a maximum of only 24 guests, the majority of whom have been coming here for years. It couldn’t get much more relaxed or low-key. The chef clangs a bell to call guests for meals. And if the bartender is not around, you pour your drinks on the honor system.

Hillenbrand tells me it’s unfortunate that I’m not visiting between January and June. He points toward the water and the club’s dock. “That’s when you can see the real thing, the Southern Cross, rising just above the horizon, right off the end of the dock,” he says.

Early the next morning I am on the dock to board the Southern Cross dive boat for the ten minute trip to the island’s windward side and Bloody Bay Wall. Despite its grim moniker, Bloody Bay Wall is benign and diver-friendly. At most wall dives, you must descend to at least 70 or 80 feet before reaching the ledge. But throughout the Caymans, the wall is significantly shallower, and at the site known as Mixing Bowl, we drop down to just 30 feet and there we are, peering down into the fathomless inky blue beyond.

Our divemaster Huw Evans is a wry fellow who hails from Wales (“That’s Huw with a ¿w’ and Wales without the ¿h,’” he says.) He leads our party of six down to 60 feet and into a swim-through – a snaky coral-encrusted tube that transects the wall – and after dazzling us plenty, pops us out at a depth of about 100 feet; from there we make a slow, easy ascent along the face of the wall. Our second dive is just a five-minute ride east at Great Wall. Here we are met by broad coral pastures abounding with critters: Hawksbill turtles scoot in front of us, fat lobsters goggle out from hidey-holes, stingrays hover, then arc and skedaddle as we draw near.

After lunch back at Southern Cross, I accept Peter Hillenbrand’s offer to take me on a “grand tour” of Little Cayman in his pickup truck. Even dawdling – stopping at Tarpon Lake to watch its huge eponymous inhabitants roll in the flats, checking out the blissfully deserted beaches at Charles Bay and Point of Sand, then scaring up several big iguanas, the island’s official pets – the whole tour lasts barely an hour.

“You’ve seen it all,” says Hillenbrand as he parks his pickup. “The only thing left is for you to catch a bonefish.”

“Do you see the mud?” Mark Phillips asks, his voice still a whisper. “There, at 2 o’clock.” He points off our starboard bow, and finally I spot it: In the otherwise turquoise water, I see a milky white cloud drifting our way. Somewhere in the cloud is a school of bonefish, nosing down in the sandy bottom, munching on shrimp and tiny crabs, their silvery tail fins occasionally breaking the surface.

I cast, but my fly falls short of the school. Another cast; off the mark again. Amazingly, my ineptitude has not spooked the fish. By sheer luck, my third cast reaches the edge of the mud. I begin stripping line, trying to remember what Phillips told me to do should a bonefish actually strike. And then – bam! – in an instant my line is taut, the reel is screaming, and the supple rod is bending forward against itself.

I wish I could accurately report what happens next – the ecstatic dance of man versus prey, the delicate interplay, the subtle strategy. But all I can do is hold on.

Cut to the chase: I land the bonefish, OK? Over the next hour or so, I land several of them.

Another round of Cayman Islands, please.


More Close to Home