A Week-Long Destination Celebration in Anguilla


After Sarah Jesup Hershey and Brett Hershey got engaged on a beach in Anguilla in April 2017, it was a no-brainer that the couple would convert this special spot (and their favorite island!) into their wedding venue. However, Hurricane Irma threw the pair's planning for a loop, completely destroying the private villa where Sarah and Brett had chosen to tie the knot. In the end, they had to postpone the ceremony by two months. "That was an unexpected road block that made things stressful!" the bride admits.

Regardless, the duo's week-long destination celebration (featuring a beach party to start!) went off without a hitch. "Every day was unique and different while still keeping the island vibe," says Sarah. With the help of Stefanie Cove and Co., the couple's dream venue was restored to its former glory thanks to a bit of added greenery and a custom open-air dancing space. For the ceremony and reception, Sarah and Brett stayed within a neutral white and ivory color palette, paired with muted mauve accents. "Our wedding day was the perfect mix between relaxed island, New England prep, and modern chic," adds Sarah.

You have to see this idyllic island ceremony (and the bride's three gorgeous outfit changes!) so keep reading for all the photos by Lauren and Abby Ross.

The couple stuck to their island theme by hosting a beach party for their guests. The bride wore a swimsuit by Bamba Swim for the occasion. Also, note: The groom's customized towel, which was personalized with illustrations of the couple's dogs!

Sarah and Brett wanted their rehearsal dinner to feel festive and fun. They booked Picante, a casual taco restaurant, and decorated the outside seating area with custom Papel Picado banners.

On the big day, Sarah wore a pink slip (by Are Your Am I) to get ready at the private villa.

The ceremony itself took place on Friday, during which Sarah sported the first of her three bridal ensembles—a beaded tulle Marchesa ball gown. Brett gifted her diamond studs, and she paired them with a simple tulle veil and white Gianvito Rossi sandals.

Keeping in line with the wedding's soft, subdued color palette, the bride carried a delicate blend of textured ivory, mauve, and blush florals in hand.

Sarah and Brett converted a preexisting trellis (overlooking a fountain, no less!) into their ceremony altar. Hurricane Irma had ravaged the vegetation formerly growing on the property, but the couple's florist stepped in with plenty of local blooms and greenery to create a completely natural look. Clusters of delphinium, lilac, and spirea lined the aisle.

The bride and groom weren't the only noteworthy guests—the couple's three dogs, escorted by the bridal party, also made an appearance at the wedding, which was officiated by one of their best friends. "My husband and I wrote our own vows and read them in private after our ceremony," says Sarah.

Brett's look featured a navy linen-and-silk-blend Tom Ford suit with a Patek Philippe 5170P watch and a white garden rose boutonniere.

"Food was really important for us, so we flew three chefs from the U.S.," says Sarah of the reception. "During cocktail hour, we had a large raw bar, a caviar station, and light passed apps." The couple also served two signature cocktails, the Skinny Margarita and Classic Daiquiri.

Escort cards were placed atop a glass table filled with tropical plants.

The newlyweds and their 49 guests all dined at one long, narrow table beneath a seaside tent. Low floral centerpieces ran the entire length of the tablescape. The original flora intended for the tent ceiling unfortunately arrived dead, so the duo's florist saved the day yet again, foraging local plants to accent the custom rattan lanterns overhead. "It ended up looking even more amazing than the original greenery," says the bride.

Sarah and Brett's family-style menu hit on a few of their favorite local foods, like Anguillan grilled crawfish, jerk chicken, whole grilled red snapper, plantains, pigeon peas and rice, jonnycakes, and hearts of palm salad.

As the night wore on, dancing took place in a custom open-air space made from striped, sheer panels. "The guests could enjoy the natural beauty of the ocean backdrop, yet still have the essence of a true structure to block strong sea winds and create an intimate afterparty space," says the couple's wedding planner, Stefanie Cove. Lanterns also contributed to the area's understated elegance, adding an extra focal point.

After dinner, Sarah changed into another beaded Marchesa number, this one slightly more fitted. She and Brett opted for not one but two simple sponge cakes, complete with a handmade topper depicting their dogs.

For the bride's third and final look, she sported a white Olivia von Halle slip dress with Manolo Blahnik sandals during the after-party. DJ Sam French helped kick the celebration into high gear, along with mini versions of Brett's favorite drink, piña coladas. The next day, the couple wrapped up the week-long destination celebration with one last hoorah at Blanchards Beach Shack, a picturesque local food joint on the island.

All in all, despite the natural disaster setback, Sarah largely attributes their wonderful experience to their planner. Her advice for couples who are planning? "Hire a wedding planner who you absolutely love and have complete faith in—it makes the process so incredibly easy and enjoyable," she says.

Wedding Team

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