Eight years ago, during a December babymoon for our first born, we checked into The Cloister at Sea Island and were instantly smitten. Maybe it was the twinkling Christmas lights, the scent of pine mingling in the halls, or the quiet pace of the marshlands, but something about Sea Island wrapped us up and stayed with us. That first stay marked the beginning of what would become a cherished family tradition: returning every December to experience the magic of the holidays in a place that feels more like home each year.
This summer, we decided to see Sea Island in a new light and stayed for the week of the 4th of July. And let me tell you, it was Americana at its finest. Where Christmas at The Cloister is cozy and elegant, the 4th of July was vibrant, nostalgic, and bursting with patriotic fun. Two seasons, two completely different experiences and we’re officially hooked on both.
Whether you’re planning your first trip or returning as a longtime guest, here’s a little guide to what makes Sea Island so special through every season.
Where to Stay
From the moment you pull through the grand oak-lined drive, The Cloister welcomes you with timeless architecture, Southern hospitality, and the kind of comfort that feels both luxurious and lived-in. Whether you’re tucked away in a river view suite or enjoying the family-friendly Beach Club rooms, every corner of the property is warm, peaceful, and beautifully done. It’s our home base for beach days, holiday magic, and everything in between.
Where to Eat
Tavola – for breakfast
This Italian-inspired spot in The Cloister courtyard serves the most delicious morning spread. Fresh pastries, creamy cappuccinos, and eggs your way – always a favorite start to the day.
Snack Shack – for lunch
Steps from the pool, this casual spot is perfect for grabbing a burger, smoothie, or soft-serve cone between swims. The kids can’t get enough – and honestly, neither can we.
Southern Tide – for a kid-friendly lunch or dinner
Southern Tide is one of our favorite spots for an easy lunch, especially with kids. It’s right by the pool and water, and there’s a playground just next to it, which makes waiting for food feel completely stress-free. We love how relaxed it is – one of those simple Sea Island lunches that always ends up on repeat for us.
Sea Strike – for a kid-friendly dinner
A family go-to, this bowling alley-meets-restaurant is equal parts fun and relaxed. Pizza, sliders, and strikes, it’s the ultimate low-key night out.
Georgian Rooms – for date night
The Georgian Room feels like such a treat, especially if you love interiors! The room itself is beautiful and timeless, and dining there feels like stepping into another era of Sea Island. It’s one of those places where you find yourself lingering over every detail as much as the meal, and always leaves me inspired.
Colt & Alison – for date night
Colt & Alison is always one of our favorite dinners on Sea Island. Tucked inside The Lodge, it has a classic, old-school feel and overlooks the Plantation Golf Course, which is especially beautiful at sunset. We usually plan our reservation for after the sunset and bagpiper — it’s the perfect way to ease into the evening. The food is always wonderful and comforting, and it’s a dinner we look forward to every year.
What to Do
Sea Island is best explored by bike. There’s something so nostalgic about pedaling beneath moss-draped oaks and along the quiet marsh paths. It’s our favorite way to start the day.
The Pool (summer)
With water slides, frozen drinks, and poolside service, the Beach Club pool is where we lived all week during our summer stay. Some winters, if the weather is mild, my kids will get in the pool!
Heaven on earth. Whether you go for a massage, facial, or just some quiet steam room time, the spa is a serene escape you won’t want to miss.
World-class options for both, with programs for all ages. My husband loves the golf course, and the kids are starting to enjoy tennis clinics too.
In-Shore Fishing Trip
We loved taking an in-shore fishing trip during our summer visit – calm waters, beautiful views, and such a fun way for the whole family to connect with the coastal setting. Captain Brandon was so kind and knowledgeable, making it an experience we’ll never forget.
Bagpiper at The Lodge + S’mores
Every evening at 4 p.m., a bagpiper plays overlooking the water at The Lodge. It’s the perfect pre-dinner tradition – and don’t miss the complimentary s’mores by the fire pits afterward!
Holidays vs. Summer
Christmas at Sea Island
Think crackling fires in the lobby, gingerbread house displays, breakfast with Santa, and children’s Christmas parties. Everything is wrapped in magic and tradition. It’s peaceful, cozy, and full of wonder.
4th of July Week
Pure, old-fashioned fun. Parades, fireworks, live music, beach parties, and red-white-and-blue everything. It’s busy, playful, and full of joy in the best way.
Both seasons offer something truly unique – and now, we can’t imagine choosing just one.
What to Pack
Elevated Athleisure
Think polished sets and comfy sneakers for morning strolls and bike rides.
Summer Style
Sundresses are the way to go. Easy, breezy, and perfect for both beachside lunch and dinner under the stars.
Winter Style
For December visits, pack cozy knits, tailored coats, and dressy layers for dinners and holiday events – chic, festive, and still comfortable.
Coordinated Kids Outfits
Nothing cuter than matching swimwear for the beach or Christmas jammies for cocoa by the fire. It’s the little touches that make the memories sweeter.
Winter Wonderland
Summer Fun
Sea Island has become the backdrop of some of our family’s most treasured moments. It’s where we slow down, reconnect, and soak in the seasons – whether it’s by a roaring fireplace in December or with sandy toes in July. If you’re looking for a place to create lasting traditions, I can’t recommend it enough.
Here’s to years of returning and always finding something new to fall in love with.
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