Palm Beach Winter Season : Events, Escapism, and Iconic Glamour
Back this week, Palm Royale, Apple TV’s deliciously dark comedy starring Kristen Wiig and Ricky Martin, returns with its satirical lens on Palm Beach society just in time for the season’s grand reopening. As Thanksgiving nears, the town’s iconic homes unlock their gilded gates, Worth Avenue begins to hum, and Palm Beach reclaims its role as winter’s most glamorous escape.
While the rest of the world braces for cold fronts and grey skies, Palm Beach offers a radiant reprieve: a sun-drenched sanctuary where glamour never hibernates and fantasy is a daily ritual.
Kristen Wiig and Ricky Martin in “Palm Royale”
The Season Awakens
November marks the unofficial start of Palm Beach’s social season. The air is warm, the light golden, and the rhythm unmistakably leisurely. Vintage convertibles glide past manicured hedges, and the scent of gardenia mingles with espresso from Sant Ambroeus. It’s a place where time slows, and style accelerates.
The homes oh, the homes. Facing the Atlantic with unapologetic grandeur, these architectural marvels are more than residences; they’re symbols of legacy and taste. From Addison Mizner’s Mediterranean Revival masterpieces to the Kennedy family’s storied estate, Palm Beach’s oceanfront mansions are as much a part of its mythology as the people who inhabit them. It’s here that Cecilia Guest was photographed in iconic fashion editorials, her elegance forever etched into the town’s visual memory.
Worth Avenue: The Riviera of Retail
No visit is complete without a stroll down Worth Avenue. Palm-lined and polished, it’s a retail reverie where Chanel, Gucci, and Pucci share real estate with local gems like CJ Laing and Marissa Collections. The arcades and courtyards offer quiet glamour, perfect for discovering vintage brooches or resort-ready caftans.
And then there’s Lilly Pulitzer. You cannot miss it. The brand’s Palm Beach roots run deep—born from a juice stand and a need for washable prints, Lilly’s kaleidoscopic dresses became the unofficial uniform of the island’s elite. Today, stepping into the flagship store feels like entering a Technicolor dream: citrus hues, playful patterns, and a spirit of carefree sophistication.
Social Rituals and Sunset Affairs
Palm Beach’s social calendar is a masterclass in curated indulgence. From charity galas at The Breakers to intimate garden soirées in El Cid, the town pulses with events that blend philanthropy and flair. The Colony Hotel hosts poolside brunches that feel lifted from a Slim Aarons photograph, while Mar-a-Lago remains a backdrop for political and social intrigue.
Evenings begin with aperitivo at Buccan or cocktails at Café Boulud, and end with moonlit walks along the Lake Trail, where banyan trees frame the Intracoastal like a living sculpture garden.
C.Z. Guest in Palm Beach was the embodiment of effortless elegance
With her signature white shirts, garden gloves, and sun-kissed poise, she turned simplicity into high style. At her oceanfront estate, she entertained with grace, rode horseback along manicured trails, and cultivated orchids with the same precision she brought to fashion. Palm Beach was her canvas where social rituals met natural beauty, and where her presence became part of the town’s mythology. Photographed by Slim Aarons and adored by Truman Capote, C.Z. was more than a muse she was Palm Beach’s perennial icon, blending American aristocracy with breezy, barefoot charm.
Culture, Colour, and Quiet Moments
Beyond the glamour, Palm Beach offers quiet sophistication. The Norton Museum of Art, the Society of the Four Arts, and the Flagler Museum provide cultural depth, while antique shops and galleries offer curated escapes into design and history.
For those seeking serenity, the Lake Trail invites morning jogs and golden-hour strolls. Paddleboarding along the Intracoastal reveals a different view of the island one of stillness, light, and reflection.
Palm Beach isn’t just a break from winter it’s a return to fantasy. With Palm Royale reigniting our obsession and the season in full swing, there’s no better time to indulge in its sunlit drama. Whether you’re chasing vintage glamour, modern serenity, or a glimpse of the past through Cecilia Guest’s lens, Palm Beach promises a story worth telling.
