Jenna Hershey, a fashion publicist, and JP Coviello, a hedge fund trader, met the good old-fashioned way—at a bar in the West Village, Wilfie and Nell to be exact. After two and a half years of dating, JP proposed on Shelter Island. “It was the last weekend in September,” remembers Jenna. “JP had chartered a boat ride for us and two friends—or so I thought. When we were ready to go, I asked where our friends were and he said they had actually gotten a flat tire on the way and didn’t think they could make it. At that moment, I felt a little suspicious, but convinced myself nothing was happening. We boarded this beautiful old, wooden boat and cruised around Ram Island for an hour before anchoring in Coecles Harbor for sunset. JP said he had a present for me and pulled out a book he had made of photos from the past two and a half years of our relationship. He read all of the captions page by page and before turning over the last page, said he had one more present for me. He pulled out a ring box, turned to the last page, and asked me to marry him. I was—somehow—completely shocked! The captain and his wife were hiding on the bow taking photos the whole time, so we have the sweetest photos from that moment.” Afterwards, they called all of their friends and family to share the news and then went to dinner at their favorite restaurant, Vine Street Cafe.
The two always knew they wanted to get married on Shelter Island. “It’s our favorite place and means so much to both of us and our families,” explains Jenna. “It’s where we went on our first trip together, where we said ‘I love you’ for the first time, and where we got engaged.” Jenna’s family also has a summer home there, so it made perfect sense.
For the venue, they landed on The Ram’s Head Inn. “It was built in 1929 and is classic Shelter Island, sitting atop a hill overlooking Coecles Harbor,” says Jenna. “It completely embodies the relaxed elegance that we wanted for our wedding. We wanted the aesthetic to be simple and natural, as if we were hosting an al fresco dinner at home.”
Jenna chose an ivory Chantilly lace Monique Lhuillier wedding dress and paired it with white laser cut Tabitha Simmons sandals. “I wanted to feel comfortable and like myself—the dress was so light and the low block heel was perfect for walking in the grass,” she says. She kept her jewelry simple, and in addition to her engagement ring, wore her mother’s diamond earrings as her something borrowed, her grandmother’s gold bracelet as her something old, and tiny diamond flower necklace that JP had given her for her birthday. She carried a natural straw Kayu clutch embroidered with blue and green leaves and her new initials. Her hair was worn down in beachy waves, and she kept her makeup natural and glowing.
The ceremony took place at the bottom of the hill at Ram’s Head, overlooking the water. Even though it wasn’t a religious service, Jenna was raised Jewish and has always loved the look and symbolism of a Chuppah, so the couple stood underneath a Chuppah of sorts made of white birch and silver dollar eucalyptus. An acoustic guitarist played “Yellow” by Coldplay, “Forever” by Ben Harper and “Here Comes the Sun” by the Beatles. The bride and groom walked down the aisle with both of her parents, and a close friend and wife of one of JP’s two best men married them. “We wrote our vows, but together, as it was important for us to make the same promises to each other,” says Jenna. “JP’s sister Jaimie did a reading, the only one. We kept the ceremony short and sweet.”
At the reception, they used cream and flax striped linens for cocktail hour and La Tavola gray linen tablecloths and white linen hemstitch napkins for dinner. They also created lots of beautiful, ambient light from candles, bistro lights, and vine ball lights over the dance floor. “The florals were really important to me,” says Jenna. “We kept the palette neutral, with white and cream flowers—ranunculus, dahlias, garden roses, Queen Anne’s lace, snowberries—and lots of greenery using silver dollar eucalyptus and seeded eucalyptus. The bouquets and arrangements were loose, garden gathered, a bit bohemian, and we did garlands around doorways and down the length of the long dinner tables.”
Cocktails took place outside on the lawn. Aperol Spritzes and Spiked Watermelon Agua Frescas were served with lots of little bites like mini lobster rolls, fish tacos, gazpacho, and a big table of antipasti. Dinner was in a Sperry tent further down on the lawn. For dinner, there were assorted breads from Blue Duck Bakery on the North Fork, local tomato and goat cheese salad, Montauk striped bass with corn succotash, crispy kale, and salsa verde, and braised short rib with potato puree and sauteed kale. And then, a coconut cake from Sag Harbor Baking Co and assorted Briermere Farms pies was served for dessert.
At the end of the night, JP made an impromptu toast, right as it started to pour. After some dancing in the tent, everyone ran up the hill huddled under umbrellas for more dancing to a DJ in the Inn’s bar. “Aftewards, we went with our closest friends to my family’s house down the road,” says Jenna. “There, we ate late-night food and swam in the rain.”