Jessica Carroccio and Sam Millham met at a wedding in Montecito in September 2021. She was a guest of the bride, he of the groom—both college friends. “Despite the hundreds in attendance, the unattached pool was rather small and—fortunately—not placed at the same table,” Jessica recalls. It was her best friend who gave her a push—literally—toward Sam on the dance floor. “He asked me to dance,” she adds. Sam had already asked to be introduced.
Two years later, on a quiet walk through Tribeca, Sam proposed beneath the Staple Street skywalk. “It was completely unexpected,” Jessica recalls. The moment was casual but orchestrated—complete with a surprise photographer and a post-massage family celebration at home. “My friends were shocked when I told them I still went to the massage afterward,” she laughs.
For their wedding, Jessica envisioned a setting that felt lush and timeless—“like The Secret Garden,” she explains. She also wanted a view of the ocean. Through Over The Moon Editor’s Pick Planner Exclusive Italy Weddings, they were introduced to Villa Cimbrone. With one Saturday left in their desired timeframe, it felt meant to be. “We fell in love with the breathtaking views and fascinating history of the property and promptly locked it down.” Over The Moon The List Illustrator Ceci New York created a custom invitation suite, and the couple enlisted Rosita Lipari to photograph.
On September 21, 2024, the couple welcomed guests to the historic villa in Ravello, perched high above the Amalfi Coast. Jessica approached the weekend’s aesthetic with a sharp editorial eye. “I focused on feeling and looking my best from the inside out,” she notes. “I wanted my dress to complement rather than overpower me.” She landed on a nearly perfect Oscar de la Renta dress—altered to remove the back completely—and paired it with diamond earrings and a sleek bun courtesy of Alessandro Mancino.
Sam wore a navy shawl-collar tuxedo by J. Meuser. “He researched and interviewed tailors for so long he nearly ran out of time to have one made,” Jessica laughs.
On the day-of, guests followed a winding path to the tea room, then down a grassy aisle framed by Flower Addicted arrangements, cypress trees, and ocean views. “We were so giddy,” the bride remembers. “During the ceremony, we could see our closest friends sitting in the foreground…[it] was extraordinary.” A close family friend of Jessica’s father officiated, and the music—ranging from Radiohead’s “Creep” to Miley Cyrus’s “Flowers”—was played on harp and violin.
Later, everyone gathered in the villa’s crypt for a candlelit dinner and musical accompaniment by Jazz Around Italy. The newlyweds made a point to sit and enjoy each course. “The food was so good that, despite it being our own wedding, we ate every course,” Jessica says. On the menu: cuttlefish pasta, carnaroli risotto with red shrimp, and herb-crusted sea bass.
Toasts were delivered throughout the evening, beginning with the bride’s father, followed by her brother and Sam’s best man, Max.
After dinner, guests were led back through the villa’s grounds to the cliffside lawn, which had been transformed with a dance floor and club lighting. A buffet of Italian pastries and the couple’s wedding fruitcake awaited, though most guests opted to stay on the dance floor until midnight.
The couple danced their first dance to “Volare” by the Gipsy Kings, the result of months of salsa lessons. “The minutes flew by so quickly,” Jessica recalls. The night concluded with a walk through the gardens to the after-party, where the music and dancing stretched into the early hours.
