Rachel Sargent & Brad Gregory
June 11, 2022

It started with a pool party.

In the summer of 2018, Rachel Sargent was poolside with friends when she ran into a familiar face. Though she’d never met him before, she recognized the handsome stranger as “Brad from ComparePower,” the founder of an energy-provider comparison site she’d used when moving into her first apartment weeks earlier. “He thought I was just trying to flirt with him,” she laughs about telling him she was a customer. She wasn’t—but she didn’t mind that the flirtation continued from his direction over the next few months when they’d run into one another with mutual friends. A kiss on her birthday made them official, and two years later, a proposal on his made it forever.

After waiting out the second wave of the pandemic to start planning, Rachel found the available venue selection less than inspiring. They started their search in Brad’s home state of California, but nothing clicked. “It got to the point where we were looking in Georgia, in Boston…,” Rachel remembers. “Finally we just said, ‘This isn’t us.’ ” After they half-jokingly mentioned Italy, their planner, Julian Leaver of Julian Leaver Events, produced a viable venue within a day: Villa Cimbrone in the coastal town of Ravello. Rachel and Brad booked it sight unseen.

Julian recruited the creative minds at GRO Designs to orchestrate the look and feel, and together with the bride and groom, the team planned a four-day-long celebration for the ages. Each event was as painstakingly put together as the next, from the kickoff yacht excursion and intimate rehearsal dinner to the over-the-top ceremony and reception. And before sending guests back home, the celebration ended—how else?—with a pool party.

DAY 1: Thursday

Yacht Party

LOCATION: Patrizia Napoli

Rachel and Brad wanted to kick off their celebration in a big way—with an epic yacht party. But sometimes big dreams beget big problems. In this case: missing bridal attire (trapped in lost luggage), hard-to-obtain Italian military clearance, and uncooperative weather.

Yet when the boat departed, no one would’ve suspected anything had been amiss, thanks to a team of seasoned pros who made the difficult look easy. The clouds parted, the Aperol flowed, the oysters were plentiful, and guests were treated to an unforgettable outing that included a surprise set by Brad’s favorite EDM artist, Above and Beyond’s Paavo Siljamäki. Rachel marvels at how their team pulled it off. “I’m still finding out about things I didn’t know Julian and his team just took care of very silently,” she says.

But for all their meticulous planning, the couple learned that sometimes the unscripted moments end up making the best memories. After outrunning the rain for much of the afternoon, the skies finally opened and began to downpour. Rather than let it dampen the festivities, Rachel remembers, “We just started dancing in the rain, and it was the most beautiful experience.”

Lady in Red

Rachel donned this off-the-shoulder Berta dress for the Italian-inspired portrait shoot, and again at the pool party. The color was echoed in the checkered tablecloths used at the rehearsal dinner.

DAY 2: Friday

Rehearsal Dinner

LOCATION: Trattoria da Lorenzo

After the euphoric high of the boat party, the rehearsal dinner was an intentional decrescendo—and an intimate chance to connect. “Almost like a Sunday supper,” says Julian.

The event was held in Scala at Trattoria de Lorenzo—a family-run eatery overlooking the Amalfi Coast. To keep the experience authentic, the restaurant’s existing decor was used, down to the red-and-white checkered tablecloths. Small arrangements and potted herbs were brought in to run the length of the tables. Guests shared heartwarming speeches over a dinner of Italian dishes served family style.

Though the result looks simple, Nathan stresses that “effortless” is often anything but. By purposefully pacing the evening—having guests enjoy cocktails in the restaurant’s front garden, then guiding them into the cozy interior before revealing the terrace view—the team told a story through tempo and spaces. “Of course it’s beautiful—that’s the obvious part about what we do,” Nathan says. “But we want a different type of experience, where people walk away and almost can’t understand why it was so amazing. That’s all in the design.”

Golden Girls

“The theme was sparkles, beading, glam, and warm golden tones that embodied the location,” says Rachel, who let her attendants choose their own dresses. “During they ceremony, they were all glowing and shining in the sun.”

DAY 3: Saturday

Wedding Day

LOCATION: Villa Cimbrone

To no one’s surprise, the most awe-inspiring moments were reserved for the most momentous day of the long weekend. “The wedding day was all about surprise and delight,” says Julian.

Given the mountainous location of Brad and Rachel’s venue, the portion of the garden used for helicopter landings would prove an integral part of the proceedings—not only because a great deal of the materials had to be brought in by air but also because this expanse of grass was transformed into a lush locale for the ceremony. Says GRO’s Sidney Stitle, “We brought in hundreds of plants—natural growing greenery—and made it an overgrown enchanted garden.”

Every moment of the day was carefully choreographed, starting with Rachel’s procession, which was timed—to the second—to “Finder” by Cyrus Reynolds. Performers dressed as eagles escorted her and her stepfather down the aisle, parting at a dramatic moment in the song to unveil the beautiful bride.

Those performers were also critical in keeping guests entertained on walks to and from the cocktail hour, which took place on a majestic cliffside terrace, and during the three-hour dinner in the delphinium-dripping crypt. “I was worried our guests were going to be so bored,” Rachel remembers of the prolonged meal service. But with the help of the performers, a band, and the cake-cutting, she says, “Three hours went by so fast.”

Once dinner was over, guests were guided to the otherworldly dance party, where DJ Paavo once again performed a set, desserts were served en masse, and lights illuminated the Amalfi Coast until the wee hours of the morning. It was the culmination, Brad says, of months of hard work. “Seeing all of my friends and family together in the most beautiful place I’ve ever experienced made everything so worth it,” he says.

DAY 4: Sunday

Pool Party

LOCATION: Villa Cimbrone

In their signature style, Brad and Rachel took the traditional day-after brunch up a level, hosting a pool party at Villa Cimbrone before guests departed.

“We wanted to take people back to the Dolce Vita ’60s,” says Nathan. Vintage-inspired changing booths, Vespas, a gelato cart, and a fruit market helped set the scene. A traditional millefoglie was prepared tableside by chefs and cut under a canopy of bougainvillea and lemons (which were, naturally, brought in for the occasion) by the newly minted Mr. and Mrs. Gregory.

In keeping with the experiential theme of the weekend, the event wouldn’t have been complete without some live entertainment, which came in the form of synchronized swimmers and—Brad’s idea—a hunky lifeguard. “For me, it was all about experience,” Brad says. “I wanted to bring my best friends and family together for a moment to remember and to create new memories as a united family. That, and of course, really great food and wine.”

Against the musical backdrop of one final Paavo set, guests enjoyed five hours of food, gelato, and fun in the sun.

Guests: 100

First Dance: “Baby It’s You” by London Grammar

Honeymoon: Switzerland, Kenya, Rwanda, England