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An Elegant Caribbean Wedding Weekend That Highlighted the Spirit of Anguilla

By Cathleen Freedman | Photography by 

Jessa Schifilliti

|Planning by 

Events at Malliouhana

While Rachel Greenberg and Christian Mark attended the same high school on Philadelphia’s Main Line, it wasn’t until one fateful Thanksgiving Eve that they met. The two were both visiting from New York City, began chatting, and realized they had even more in common than their hometown.

They dated and moved into their Greenwich Village apartment together in 2017. Two years later, on October 17, 2019, Christian proposed to Rachel at home. He thoughtfully chose the date to coincide with his parents’ wedding anniversary.

The couple knew they wanted a destination wedding, and Anguilla was an early frontrunner. Christian’s family has frequented Anguilla since he was three years old, and Rachel fell in love with the island after joining his family vacations. They loved the idea of guests discovering the island’s beauty for themselves.

A quick tour of the Malliouhana Resort in January 2020 checked off every box for their venue. “The hotel and grounds are impeccably designed to capture the spirit of the island; there are bright splashes of color and every shade of blue to accentuate the natural surroundings, which does a lot of the heavy lifting,” the couple asserts. Beautiful artwork from Caribbean artists decorates the walls. The hotel was everything they wanted.

The couple turned to Malliouhana’s Khondah Hazell for guidance. “She was born and raised in Anguilla and has a great sense for just about every aspect of the planning process,” Rachel shares. Their friend, designer Lara Glaister, painted the tropical-inspired invitation suite. Because of the spread of COVID-19, the couple postponed their wedding twice. “We sent out three save the dates!”

The island of Anguilla took extreme precautions to create a COVID-free “bubble.” The borders were shut off and closed from the outside world, and guests visiting the island underwent rigorous testing and application process to enter. Finally, come December 2021, the couple could celebrate their nuptials. The wedding weekend kicked off Thursday evening with cocktails and hors d’oeuvres poolside. The following night, guests walked along the beach to Blanchard’s Restaurant on Meads Bay for the welcome party. They were greeted by local reggae band, Vere Musiq, and a tiki bar in the sand. The evening progressed with plenty of barefoot dancing, grilled crayfish, and heartfelt speeches.

For the Friday night welcome dinner, Rachel slipped into De Castro‘s handmade Orquidea dress, Loeffler Randall heels, and pearl Lele Sadoughi earrings, which were engagement gifts from friends. Christian wore a tan Boglioli blazer, a custom white shirt, olive pants, a needlepoint belt from Smathers & Branson, and light brown Sabah shoes.

After trying on nearly 100 dresses, Rachel found “the one” at Saks Bridal Salon in New York City. She paired her Isabelle Armstrong “Amalfi” gown with Amelie George earrings, pearl pins in her hair, and Cult Gaia heels. The Malliouhana spa applied her effervescent wedding day makeup. The groom sported a custom navy dinner jacket and cream pants from Munro Atelier, a natural-colored shantung tie from Drake’s, and brown linen Belgian Shoes loafers.

The groomsmen all donned their own blue suits and white dress shirts, which were designed by the bride’s company, David Donahue. Rachel let her bridesmaids pick out their own dresses in a blue and white color palette. While getting ready, the bridesmaids donned breezy Hill House Home dresses.

On December 4, 2021, guests gathered on the property’s bluff overlooking the ocean. A live acoustic trio played while they found their seats. Rachel’s father, Howard Greenberg, officiated the ceremony and set the lively tone for the day. Black Orchid Florists & Events created the floral arrangements at the altar. The bride and groom gathered with their siblings on either side of them. At the end of the ceremony, Christian partook in the Jewish tradition of the breaking of the glass to honor Rachel’s paternal grandparents.

The newlyweds joined guests for cocktail hour, just as the sun set on the horizon. Local steel drum legend Michael “Dumpa” Martin and his keyboardist played, and island cocktails with passed canapés were offered.

The reception began when the bride and groom entered Cafe Celeste, while the Omalie360 band serenaded the crowd with “Jamming” by Bob Marley. The restaurant’s dramatic terrace on a cliff overlooking Meads Bay functioned as the evening’s dance floor. Christian’s best man, Scott Baldasare, and Rachel’s maid of honor, Meredith Gerland, delivered touching speeches. Dinner of local tuna carpaccio, blackened mahi, and rack of lamb was served. The newlyweds cut into a chocolate semifreddo with pecan crumble, raspberry crémeux, and salted caramel and shared their first dance. “This is actually a funny story,” Rachel laughs. “Christian and I decided before we were even engaged [that] our first dance would be to Neil Young’s ‘Harvest Moon.’ It is our song; we play it at home all the time. Luckily, we didn’t have a choreographed dance. After being introduced, the band started playing Lauv’s ‘I Like Me Better,’ and we both just went with it.”

Tiki torches lit the path to the after-party at Leon’s. Guests grabbed glowsticks and pushed their luck at limbo while DJ Sugar played tunes that kept everyone on the dance floor all night long. With the exception of photographer Jessa Schifilliti, Christian and Rachel’s vendors were all Anguilla locals. “We can’t thank each of them enough for working with us through the multiple date changes,” Rachel shares. “They really made an uncertain situation much more manageable.”