For generations, The Cloister at Sea Island has been the crown jewel of summer getaways in the South. It’s not just a resort; it’s an institution. A place where tradition meets luxury, where kids run barefoot on the sand while their parents sip cocktails under the shade of live oaks. It’s where families return year after year, building memories that weave into the fabric of who they are.
We were able to steal a long weekend at the beginning of Fall, and I’m so glad we did. We got a suite at the Cloister, which featured a king bedroom and a den with a pull-out couch. We’ve been down to Sea Island before, but this was the first time with the boys staying at the Cloister. And they LOVED it. We arrived on Friday at lunch, and left on Monday afternoon… just the right amount of time to stretch our legs and enjoy a lot of what the Cloister and its tremendous staff have to offer.
I’ve always said that Red Clay Soul is about culture, pastimes, and style wrapped in a Southern Dutch oven, and Sea Island fits that bill perfectly. It’s timeless but not stale, luxurious but not pretentious, refined but still family-first. It’s the kind of place where you can golf in the morning, fish in the afternoon, and dress for dinner at night — and everyone in your crew will find their groove.
Some History…
The Cloister first opened in 1928, built in the Mediterranean style by Addison Mizner, the same visionary behind Palm Beach’s iconic look. From the very beginning, it wasn’t just a hotel; it was a statement. A retreat for families who valued tradition, privacy, and Southern hospitality at the highest level.
What makes Sea Island special is that it has never tried to be trendy. It doesn’t have to. The Spanish Revival arches, the terra-cotta roofs, the marsh views at sunset — they’ve been enchanting visitors for nearly a century. You can feel the history as you walk the halls. Presidents, royalty, and captains of industry have all stayed here, but what’s more important is how many families have built generational traditions under its roofs.
Grandparents who came in the 1950s are now bringing their grandchildren, passing down stories of catching their first fish in the brackish backwaters or learning to play tennis on the red clay courts. That sense of continuity makes The Cloister more than just a hotel, it almost feels like a living scrapbook.
I first experienced Sea Island in college, when I worked Junior Staff for a few weeks in the Spring. It was during that experience that I promised myself that I’d bring my family down to the Island someday, for many reasons…
The Setting
The Cloister sits on Sea Island, Georgia, a barrier island just east of St. Simons. It’s a stretch of coast that feels both tucked away and wide open at the same time. For those who have been down…that drive over the marsh to Sea Island is like a portal to another place. There’s nothing like it. The beaches are pristine, framed by dunes and sea oats, while the marshlands feature some of the best sunsets you’ll ever see.
When you step onto the property, you’re greeted not just by the architecture, but by the landscape. Moss-draped live oaks shade the pathways. Bright hydrangeas and manicured lawns give way to wide stretches of sand. And everywhere you look, there’s water: the Atlantic on one side, the Black Banks River on the other. For kids, it’s a natural playground. For adults, it’s instant relaxation.
Something for Everyone
The genius of Sea Island lies in how activities are curated to suit any age and stage of life. This isn’t one of those resorts where the adults are happy but the kids are bored, or where the kids have fun but the parents feel like they’re running a daycare. Sea Island gets it right. The kids go to a camp (there are a TON of options – just call your concierge), Mrs. RCS goes to the spa, and I get to play golf. Then we all meet at the Beach Club and kick into ‘family’ gear.
We typically start our day with coffee and a few muffins in the Cloister lobby… me reading and catching up on work and the boys would enjoy their iPads for a bit, all while we let mom get an extra hour of sleep. We’d then get dressed and go for a long bike ride – we’re at that age where bikes are life, and there are plenty of trails and sidewalks to explore. We’d head over to the beach club for a couple of hours, and set up camp in a couple of chairs, going from the pool to the beach then into the arcade, and to the snack bar…over and over again. It was wonderful.
We took advantage of Camp for the boys – they were gone for the a little more than half the day doing all sorts of fun stuff: kayaking, sailing, wildlife watching, beach action, and games… Enough time for Mrs. RCS and me to play 18 and have lunch. It was nice to get some adult time during our quick trip. It filled our tanks, and the boys were worn out when we picked them up.
Tools of the trade
Fast friends…we called them ‘The Tribe’
Why It’s Worth It
Let’s be honest: Sea Island isn’t cheap. It’s an investment. But what you’re buying isn’t just a hotel room. You’re buying tradition, service, and peace of mind. You’re buying a place where you know your kids are safe, where every detail has been thought through, where you can step away from the grind and focus on the people who matter most.
There’s also something to be said for the exclusivity of it. Sea Island has managed to maintain a sense of privacy that feels increasingly rare. You don’t have to fight the chaos of more commercial beach destinations. You’re not shoulder-to-shoulder with strangers blasting Bluetooth speakers. You’re in a place that values quiet luxury, where the biggest sound at night is the ocean rolling in.
The boys and I took Mrs. RCS on a date to the River Bar
From the Red Clay Soul perspective, that’s what makes Sea Island special. It’s not about showing off. It’s not about being seen. It’s about investing in our family, building our own traditions and these experiences that last long after our tans fade.
The Takeaway
Summer comes and goes in a flash. School, work, and obligations will always be waiting. That’s why it matters where you choose to spend those precious weeks of freedom with your family. The Cloister at Sea Island has been the choice for generations of Southerners because it gets everything right: the setting, the service, the style, the substance. It’s magic for our family, and I’d bet it would be magic for yours, too.
For families looking to give their kids memories that stick and to invest in something bigger than just a week at the beach, The Cloister at Sea Island is as good as it gets.
Long beach walks…the goods
Pack the polos, sundresses, flip-flops, and loafers. Load up the car, load up the kids, roll the windows down as you cross the causeway, and let the salt air hit your face.
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Thanks for this. One of my favorite posts this year!