A multi-generational vacation enjoyed at Georgia’s fabled Sea Island by Members Bob and Pat Henry—and their 12 children and grandchildren—is an annual celebration rich in both tradition and memories-in-the-making.
It is only 9 a.m., but the cloudless day has already surrendered to welcomed heat as I pad my way along the powdery Atlantic shoreline. The sand—chalky and fine like warm flour—tingles my feet, urging me into a brisk walk toward the water. Splashing into the ocean, I wade deeper and deeper before I turn around to face the magnificent structure behind me. The Sea Island Beach Club, The Cloister’s iconic Mediterranean landmark, seems to shine in the early morning sun, its Spanish tiles glowing a fiery red and its slender archways casting deep dark shadows on the halls behind them.
This particular morning, the hotel is abuzz with activity. Exclusive Resorts Members Pat and Bob Henry—and their clan of 14 that spans three generations—is already holding court by the swimming pool, with the children whizzing down the water slide and the adults soaking up some much needed R&R. The Henrys arrived only yesterday from their respective homes in Pennsylvania, New Jersey, and Florida, but judging from the ease with which they have fallen into their holiday routine, it is clear that this annual family reunion offers some much-needed refreshment.
According to Pat Henry—the family matriarch who, along with her husband Bob and the couple’s three children and six grandchildren aged 4 to 15, reserve two Exclusive Resorts Sea Island homes for one week every summer—the trip is a treat that the Henrys look forward to year after year. “Sea Island is our ulimate family vacation because it’s just perfect for all ages,” she says. “Every year we ask the kids if they want to go someplace else, but they always want to come right back here. It’s just wonderful for our big family.”
The Henry clan falls into a long line of families that have visited Sea Island since its debut nearly a century ago. Soon after the hotel opened in 1928, a Christmas visit by Calvin Coolidge garnered the property accolades as America’s most high end retreat. Gazing past the Henry family toward The Cloister, I picture the palm trees that welcomed Coolidge and his wife to the refined resort. I envision him zipping away in Howard Coffin’s stately yacht with his beloved chow, Tiny Tim, to explore neighboring St. Simons Island. Of course, Coolidge was only the first of many prominent figures to fall for Sea Island. Dwight D. Eisenhower (who visited after the end of World War II) may have swum along the exact same stretch of ocean I am floating in now.
Despite Sea Island’s illustrious past, the 88-year-old luxury resort maintains a laid-back and utterly unpretentious air. Purchased in 2016 by Denver’s Anschutz family—another clan of regular visitors— the five-mile-long isle, with its massive arched oak trees and perfectly manicured lawns, possesses the sort of ease and authenticity that comes only from decades of distinction. This understated provenance is exactly what brought the Exclusive Resorts executive team to the island nearly a decade ago. Blending heritage and honor, adventure and leisure, exclusivity and elegance, Sea Island embodies the vital spirit of the quintessential Exclusive Resorts family holiday.
A Flagship is Born
Though Coolidge and Eisenhower weren’t quite lucky enough to experience the Sea Island of today, it’s clear that the statesmen’s values—family and sportsmanship among them—remain at the property’s core. Nowhere are these values more obvious than at Exclusive Resorts’ development, located just north of The Cloister. Nestled behind majestic oak trees in two secluded cul-de-sacs, the 24 residences form a charming enclave—and one of the only private communities behind Sea Island’s gates— where guests can find peace, quiet, and a true sense of community. It’s no wonder the flagship remains a perennial favorite among Members and their families since joining the Club’s portfolio in 2009.
“We really wanted to capture what Sea Island is all about,” says Exclusive Resorts’ CEO Cathy Ross, who spearheaded the two-year, approximately $60 million development of the Club’s private Sea Island community. “It’s the definition of Southern charm, and it’s all about family. We wanted this to be a place our Members would return to generation after generation.”
To bring this vision to life—and tap into Sea Island’s historic Southern style—Ross turned to Exclusive Resorts’ then Vice President of Architecture and Design, David Oswold. In turn, Oswold looked to The Cloister for inspiration. The famed hotel, originally designed by legendary architect Addison Mizner in the late 1920s, had been demolished only a few years prior and reinstated with a new building bearing the same Spanish- Mediterranean style. “Sea Island did an amazingly beautiful job, because they weren’t trying to copy the original,” says Oswold. “They continued the Cloister’s tradition in terms of style but they were honest about it and gave it something new and fresh and relevant for today. That was a benchmark that we wanted to maintain in designing our residences.”
At 3,700-square-feet, these homes are indeed a convergence of history and modernity, blending traditional elements such as rough-hewn wood beams, Spanish-Mediterranean roof tiles, and wrought-iron staircases with more contemporary concepts like gas fireplaces, private plunge pools, screened-in porches, oversized windows, and family-friendly floor plans. Interiors are also reminiscent of Sea Island’s values: All materials and furnishings are American made.
Perhaps most significant, Oswold’s plan for the homes ensured that families would enjoy a good mix of public and personal areas, with private zones—two master suites and two additional bedrooms—radiating off a grand central space with 20-foot ceilings. For Ross, the open-air kitchen and expansive living areas including the screened-in porch with a summer kitchen are indeed the heart of the homes. “We designed these spaces knowing Sea Island is a resort packed with family activities,” she explains. “The question was, ‘how do you come back after a long day outdoors and get everyone together?’ These larger spaces flow together so there is plenty of room for families to gather for meals and game nights.”
Ensuring everything runs smoothly at Exclusive Resorts’ Sea Island community are Macy Barrett and John Tate. Both have been with the property for eight years each, and they are devoted to keeping Members fed, entertained, and blissfully looked after, catering each trip to what will create the most memorable experiences for families. They have even helped arrange special moments such as proposals and weddings. “One couple, the Johnsons, was engaged and subsequently married at Sea Island,” Tate recalls. “They now have two young children, so there is yet another generation of Johnsons that we look forward to seeing every time they come.” Tate and Barrett have been equally integral in orchestrating the Henry family’s annual stays, arranging everything from rounds of golf and visits to the spa to special chef-prepared dinners in their cottage.
Low Country, High Spirits
“I don’t actually like seafood,” Pat tells me over cocktails in her cottage. The Henry residence is teeming with activity this evening: granddaughters taking selfies, sons recapping their morning on the golf course, grandsons lacing up their sneakers for a pre-dinner bike ride around the neighborhood. But it’s the aromatic stew in the kitchen, tended by a team of Sea Island’s private chefs and stewards that has prompted Pat’s culinary confession. Still, the lowcountry boil—a Southern delicacy consisting of shrimp, clams, potatoes, and corn all prepared in one big, steaming pot—has brought the entire Henry clan together after a day of activities on the island. And for that, Pat is more than happy to dine on a bit of seafood.
Whether for seafood or not, it seems inevitable that the Henrys would be famished this evening. The day started in earnest with the men on the green and the women at the spa. The former was a sweltering affair with temperatures climbing fast by 9 a.m.; the latter was a mellow moment of peace for mothers and daughters alike. By noon it was off to the horse stables for a family ride on the beach, followed by fishing on the dock in the shadows of The Cloister. The catches were small—nothing more than a pound or two—but ice cream sandwiches and plenty of shade proved reason enough to cast line after line. Now, just before sunset, the first signs of sunburn are beginning to show, and it is clear that the parents and grandparents are pleased to gather around the living room with drinks in hand.
“They take such great care of us, and they are so good with the kids,” says Jennifer Henry, Pat and Bob’s daughter-in-law, nodding toward the kitchen where Chef Santoria Axson has recruited several of the children to help prepare the family feast. Donning junior chef ’s caps, they mix coleslaw, spear vegetables, and chatter with their newfound culinary hero. It’s a charming end to a long day—one that will surely be repeated tomorrow with skeet shooting, swimming, and a s’mores bonfire at The Lodge. And though I’m tempted to accept Pat’s invitation to join the family for a genuine Southern spread, I have evening plans of my own at the cottage.
The Finer Things
For all of its down-home country allure, Sea Island has a refined side too—and I’m about to explore it for myself. After changing out of my shorts and T-shirt, I head first to The Georgian Room Lounge, a sultry little bar tucked behind a gold satin curtain just off The Cloister lobby. Dark wood paneling and burgundy capitonné benches lend a slightly speakeasy-style vibe. The cocktail list, however, is far more imaginative than any Prohibition pub would offer. I order the Tiki Time—house-made vanilla vodka, punch, and pineapple juice served in a copper pineapple-shaped goblet—and settle onto a bar stool.
But it’s quickly bottoms up as my 8:30 dinner reservation calls. Tonight, Macy has booked me the chef ’s table, a special treat (enjoyed frequently by Exclusive Resorts Members) beyond the usual extravagances of The Georgian Room, the only Forbes Five-Star restaurant in Georgia. For a second, I feel like a celebrity bypassing the velvet ropes of a Hollywood premiere as the maître d’ walks me past the restaurant’s candlelit tables and through the double swinging doors that lead to the kitchen. Once inside, I score a small table in the middle of it all—a front-row seat to the action of the night. I quickly spot Sea Island’s Chef de Cuisine Julian Schiebel—a young culinary prodigy who hails from Germany—carefully laying delicate gold foil over his signature chocolate dessert. My mouth instantly begins to water.
Course after course soon arrives. There’s the seared diver scallop topped with caviar; the Wagyu beef tenderloin soaked in sweet port; and the divine dairy cart from which I suppress the urge to sample each and every cheese. At last, the chocolate dessert comes, and with it, Schiebel, who regales me with tales of his fabled kitchen. It’s a surprise that someone so young would helm a restaurant so established, yet Schiebel says this is all par t of the Sea Island ethos. “There is a real progressive approach here,” he explains. “It’s not about doing things the way they’ve always been done at Sea Island. It’s about taking that foundation and building something new with it.”
At the end of my six-course meal, I am fully stuffed and utterly satisfied—yet I ponder a nightcap. I have no doubt that Coolidge almost certainly ended their nights in such a manner, but alas, I decide I am not quite stately enough to manage anymore turpitude for tonight. Instead, I slowly make my way back to my cottage, winding past the slender palms and iconic structures that seem to be on every Sea Island postcard from both the past and present. Passing by the Henry family’s home, I hear that the party is still going strong, with the sounds of children splashing in the pool and joyful chatter drifting through the night. Indeed, I realize that Sea Island, both old and new, is, more than anything, home.