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A Poolside Wedding at the Windsor Club in Vero Beach, Florida

By Shayna Seid | Photography by 

KV Photography

Caroline Benedetto, who works in publishing and digital advertising (previously at Town & Country and Elle), and Max Stein met during the first week of her freshman and his sophomore year at Roanoke College. Once they had both graduated and ended up in New York, their college sweetheart relationship solidified into something more official. After dating for four years, but knowing each other for 10, Max proposed at The Carlyle hotel.

When it came time to pick a wedding destination, the two didn’t even think of anywhere other than the Windsor Club in Vero Beach, Florida. “Both of our families have planted roots in Vero Beach over the years. It’s a special place for us, and our families, and not to mention stunning in every single way,” says Caroline. To help with planning, they hired Lauren Melillo from the club and Lara Andrew of Lara’s Theme

For her dress, Caroline knew she wanted something sleeveless for a spring Florida wedding. She ended up choosing Sareh Nouri’s sophisticated Naomi gown with a bow in the back. “My mom, a former NYC fashion retailer in the 80s, always knows best and picks the perfect clothes, and once she found this dress, the search was over!!” Caroline says. She completed the look with white, leather Stuart Weitzman sandals. Her “something borrowed” was her mother’s pave diamond bracelet and her neighbor’s veil, her “something old” was the Stein family gold ring and a four-generation old diamond watch that’s been worn by every bride on her mother’s side, and her “something blue” was a sapphire and diamond ring. Her wedding day beauty look was kept very minimal. “I am not a makeup girl—never do my hair—and I wince at the thought of hairspray,” the bride admits. 

The groom wore a Brooks Brothers tuxedo with a Ralph Lauren shirt and Stubbs & Wooten velvet slippers. His bowtie and cummerbund were from Drake’s, and he also wore his late grandfather’s Rolex, which had been gifted to him on his recent 30th birthday from his father. Groomsmen wore black tuxedos with black grosgrain bow ties and cummerbunds, while bridesmaids were in blush THEIA Couture dresses.

Carrying a bouquet of tropical greens, orchids, and white sweet peas, Caroline walked down the aisle to meet her future husband. The ceremony was officiated by the maid of honor’s father. “It was truly special to have him up there with us and my best friend Sophie, his daughter, at my side,” says the bride. The 20 minute wedding was pretty traditional with a prayer reading, the Corinthians, and notes from Sophie’s dad. “We both tried so hard to keep stoic and composed, but with all the excitement and adrenaline, we both were struggling not to uncontrollably smile the entire time!” Once they said, “I do,” the two exited the chapel and jetted off in a golf cart, with a special-edition, Belle Epoque hand-painted bottle of Perrier Jouet on ice, for a moment alone. 

Meanwhile guests gathered at the Windsor Club’s Beach Club under a big, white tent by the pool for the reception. At the tables, dark brown rattan chargers, crisp white linens, candles, and tall vases with tropical greens were tastefully arranged. Dark wooden ballroom chairs and the mahogany dance floor contrasted with bright white touches, and the tent was draped in an airy fabric and warm string lights for a subtle glow during dinner. 

During the meal, Caroline’s father kicked off the toasts by welcoming everyone, and then the best man, William, and the maid of honor, Sophie, also made heartwarming speeches. After that, The Rivertown Band led everyone to the dance floor.

The new Mr. and Mrs. had their first dance to “Beyond the Sea” by Bobby Caldwell, and then the party was back in full swing. “We have a notoriously wild bunch of friends, and the dance floor was filled the entire time . . . multiple tuxedo pants split,” Caroline jokes. At the end of the evening, she changed into her second party dress by Rochas. And the newlyweds made sure to grab a second to themselves too. “Max and I took a bottle of champagne, two plates of cake, and a few minutes of quiet, alone up on the beach club steps, looking down at everyone in the tent.”

Once the night ended, Caroline and Max exited through sparklers, and after briefly cruising back to their suite, they rejoined everyone for a pool party!