A Storied Getaway on Florida's Atlantic Coast Ushers in a New Era of Luxury

Halfway through cocktails, I have my we're-not-in-Kansas-anymore moment. I'd come to Windsor, Florida, a New Urbanism-style members-only hamlet on the central coast, to see freshly unveiled guest suites redesigned by Chicago-based decorator Alessandra Branca.

In the courtyard of the Village Suites, a small private hotel in Windsor's town center, a Jamb lantern is hung with multiple chains in the Roman style to keep it from swinging in subtropical winds. Cock-tail table and chair and sofa in a Perennials fabric, Heveningham Collection. Round table, Stone Yard. Mirror, Ballard Designs. Beams and ceilings in Gibraltar Cliffs, Benjamin Moore.

The setup, I'd thought, was clear: a tony planned community in an elevated, but essentially country club, vein. Yet here I stand in the clubhouse's gallery, clutching my negroni sbagliato, confronted with etchings, ceramics, and tapestries by Grayson Perry, a Turner Prize-winning, cross-dressing Londoner who mines his subconscious in intricate, idiosyncratic, and oft-explicit works of art.

A vintage bird print establishes the blue-and-white scheme in the Goodwood Suite. Custom sofa in Anna French and Brunschwig & Fils fabrics. Spindle armchair with cushions in a Kravet fabric, Century. Vintage side chair with cushion in a Schumacher fabric. Vintage armchair in a Brunschwig & Fils fabric. Lamps, Circa Lighting. Wallcovering, Phillip Jeffries.

It's fabulous. And this delicious dollop of culture was designed precisely to upend the kind of expectations I'd packed along with my monk straps. “We have all the classic things: golf, croquet, tennis, the beach,” says entrepreneur Hilary Weston, who-with her husband, Canadian retail magnate W. Galen Weston-developed Windsor in 1989. “But it was the cultural dimension that was the real point of difference.”

A sweet Casa Branca tile backsplash counteracts a sleek lacquered SieMatic island. Palecek stools in a Kravet fabric with Samuel & Sons trim. Fittings, Kohler. Pendants, Circa Lighting.

Originally in partnership with London's Whitechapel Gallery, the Westons now work with the Royal Academy of Arts and bring notable exhibitions-Alex Katz, Jasper Johns, and Ed Ruscha, among others-to their subtropical paradise.

Whitewashed beadboard paneling creates a unifying backdrop for contemporary and African touches in the Doncaster Suite. Custom sectional. Pair of Oly armchairs in a Lee Jofa fabric. Wing chair, Selamat. Floor lamp, Circa Lighting. Bowls (on wall), Global Views. Rug, Jaipur Living. Walls in Steam, Benjamin Moore.

The blue-chip collaboration is telling. The Westons do nothing by halves. When planning Windsor, they turned to Andrés Duany and Elizabeth Plater-Zyberk, the cofounders of New Urbanism, a movement toward densely designed, walkable communities. The duo plotted out a vaguely Southern, Anglo Caribbean-style village organized around public spaces that encourage strolls to the post office or the café for a morning cup of coffee.

Vintage pendants. Stools, Palecek. Island, SieMatic.

The Westons' connoisseurship extends to Windsor's interiors, too. John Stefanidis decorated their home here, and the late Naomi Leff did the beach club (later freshened by Rod Mickley). Branca was tapped to redo the Village Suites, a mini hotel for guests of members or prospective residents. For would-be Windsorites, it provides a taste of life in this subtly gilded enclave.

Four-poster bed, Oly. Bed linens, Casa Branca for Sferra. Vintage chair with cushion in a Dedar fabric. Vintage desk. Walls in a Brunschwig & Fils cotton.

Branca shows up for our walk-through fresh from the airport in brightly printed Prada pajamas and beige leather ballet flats. It's her ethos in an outfit: classic yet freethinking, stylish but adapted to the rigors of real life.

Pendants, Circa Lighting; fittings, Kallista; baskets, Crate & Barrel.

We start in my suite, where the rooms are paneled in whitewashed beadboard, the ceilings soar, and the vibe is contemporary and global: There is a beaded African helmet on the mantel, mud cloth-covered throw pillows, and plenty of wicker.

Custom sofas, armchairs, and curtains in Casa Branca fabrics; cocktail table, Serena & Lily; sconce, Arteriors; wallpaper, Donghia; photograph, Massimo Listri.

“I wanted a neutral palette,” Branca says. “This is beachy and loose.” She'd opened up the kitchen to the living room and amped up the sense of luxury in the bathroom with limestone floors and Kallista fittings. “The kitchen counter doubles as a bar; you have friends over, and they congregate. And bathrooms are an experience these days-we live in them.”

Designer Alessandra Branca

Across the loggia, the Ascot Suite channels another mood entirely: A Coromandel screen mingles with a toile-covered sofa and 1940s French rattan; headboards are backed by blue-and-white ticking that hangs languorously from finials (“My little ode to Potsdam!” Branca exclaims). “Every suite is different,” she says. “Nothing is the same.”

Vintage bamboo étagère; walls in a Casa Branca grass cloth.

But really, she's not being truthful. A thread of crisp elegance and comfort runs through every space. It feels as if a hostess offstage has arranged each detail for your delight: Orchids flutter above tables, shells and coral spill across shelves, coffee-table books are stacked for perusal.

A courtyard view.

Later that night, as I drift off, cocooned in embroidered Italian sheets, I look around and sigh. I'm scheduled to leave in the morning, but I pull out my phone and ponder sending Branca a text: When can I move in?

This issue originally appeared in the May/June 2018 issue of Veranda.