This Nantucket Celebration Is the Ultimate Preppy-Wedding Inspiration

Kristen and Jonathan

Millie Holloman

Back in the summer 2009, a newly-introduced Kristen and Jonny spent time getting to know each other on the island of Nantucket. They had first met in July in Boston, before she departed for a trip. The relationship developed, and come early fall, the pair was dating long-distance, with Kristen living in Connecticut and Jonny still in Massachusetts. Less than half a year later, Kristen relocated and the two were finally in the same city at the same time.

Six years from that move, and not too far away from the spot where it all started, on September 6, 2014, the couple became husband and wife. It was a natural choice; the spot has felt like a sanctuary for the couple over the years, and it was made even more special because the bride's family lives there. Barbeques, yard games, the beach, and the brews all symbolize their ideal retreat, and the pair wanted to show all of their loved ones the things that make the island so special to them when they tied the knot during a destination wedding weekend in early fall. A welcome party at a brewery, rehearsal dinner on the beach, and tournament of champions all led up to a ceremony in a quaint chapel on the island followed by a reception at a private home that lasted until the wee hours.

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The Stationery Suite

Millie Holloman

The invitations needed to include a lot of information for guests, and to keep it all neat and easy-to-read, it was bound into a booklet, which was tucked into a muslin bag stamped with the shape of the island and finished off with a tag. The assorted pieces were sent in a kraft paper box with addresses calligraphed by Southern Bee Designs.

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The Invitation

Millie Holloman

The invite combined letterpress printing and offset printing and three fonts (Cash Outline, Gotham, and Carpel), with a reply card designed as a postcard that could be torn out of the booklet and mailed.

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The Style

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Jonny wore a gray Suitsupply suit with a navy tie, and Kristen chose a silk chiffon dress which she paired with a crystalline beaded sash, both from J.Crew. Her chandelier pearl earrings were from Bhldn.

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The Welcome Basket

Millie Holloman

Nantucket Bike Basket Company baskets were stuffed with goodies from the couple, most of which were customized for the occasion—a t-shirt, playing cards, Frisbees, a "do not disturb" sign, koozies, and "I survived Jonny and Kristen's wedding" stickers, as well as Nantucket Nectars lemonade and Cape Cod potato chips to snack on, and a welcome booklet and map of the island to help with enjoying the weekend.

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An Emotional Moment

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"Kristen is not always as sentimental as me, and when I read her card and her words that so beautifully articulated what our relationship means to her, I couldn't help but break down in tears," Jonny recalls. "I was so moved by her honesty and the way she perfectly captured the reasons we are so great. It was that, combined with the gravity of the moment—about to leave for the church—and the freedom of knowing I would never again be alone, that from that day forward, I would share everything with the one true love of my life."

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The First Look

Millie Holloman

"I was so thankful we both decided to make time to have a first look before the ceremony," Kristen recalls. "Our family wasn't crazy about the idea at all, but seeing Jonny in the garden outside of the chapel before the ceremony calmed me down and reminded me why we were doing this, what the day was all about."

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Added Charm

Millie Holloman

Jonny's mom, Susan, said that Kristen's bouquet wouldn't be complete without a silver Nantucket charm, which was pinned to the ribbons around the flowers' stems.

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A Gift for the Guys

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Jonny gave both best men a pair of monogrammed cufflinks from Shreve, Crump & Low—an iconic jeweler in the couple's meeting place of Boston—and a bottle of Cleveland Whiskey, an award-winning distillery near the couple's home. Jonny wanted them to have something special from both of the places where he has lived and spent time with the guys. The "confidence cards" were Jonny's idea as he wanted to let both of his groomsmen know what he has appreciated most about their friendship with him over the years, especially because both (jokingly) compete for who is actually his best friend and "the better best man."

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A White Boutonniere

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White ranunculus, olive leaves, and tiny blue berries found growing on the island were wrapped with blue-and-white striped ribbon for the boutonnieres.

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The Kids

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Kristen's 7-year-old twin cousins served as ring bearer and flower girl. Jack wore an Appaman suit with a bow tie, and Ella donned a J.Crew dress.

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Taking the Bus

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Many guests stayed at the Nantucket Hotel (others rented houses), and took their vintage green bus to the ceremony.

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The Church

Millie Holloman

Kristen and Jonny loved that the Siasconset Chapel has always been a welcoming place for people of all faiths—it currently serves as a joint place of worship for both the Catholic and Protestant communities on the island. It's also within the same parish Kristen's parents were married in 1983.

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Ready to Enter

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Before the bride's entrance, the groom's mother, Susan, sang "Ave Maria." Then Kristen walked down the aisle with her father, Tom, to the sounds of Pachelbel's "Canon in D."

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The Ceremony

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The bride and groom's sisters each gave a reading during the service, which was led by a priest Jonny was close with from his college days.

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Jingle Bells

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"We both love biking around Nantucket and wanted to include as many nods to this as we could," Kristen says. "We were planning on giving bike bells with custom labels in the welcome baskets, but Jonny thought it might be fun to have everyone ring them as we came out of the church. It was perfect."

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The Bridal Party

Millie Holloman

The bridal party was kept small, with just Kristen's two sisters, and Jonny's two closest friends serving as bridesmaids (in J.Crew) and groomsmen (in Suitsupply). The group of six swung by Siasconset Beach for photos following the ceremony.

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Cocktail Hour

Millie Holloman

Though it threatened to storm all day, everyone lucked out: The rain didn't come until after the after-party, so the outdoor cocktail hour went on as planned.

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The Food

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With bikes being so important, a vintage two-wheeler was borrowed from the local shop and suspended over the cheese table in the gardens, complete with a basket full of flowers.

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The Cocktails

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Cocktail hour was held at the greenhouse and gardens of the private home. Guests chose between a his cocktail (the Jack Rose, made with Jack Daniels and lemonade with a splash of cherry) and her cocktail (the Blue Lemurade, made with blueberry mint Triple 8 vodka, lemonade, and a splash of soda).

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Stir Sticks

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The bride's parents still have drink stirrers from their wedding and love doing custom stirrers for parties and events that they host. In addition to "his" and "hers" numbers for the signature cocktails, an illustration of lemurs on a tandem bike (harkening back to an inside joke between the couple) were used in other beverages.

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A Frame to Sign

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Jonny's dad made a frame from reclaimed wood for guests to sign as they entered the reception tent. It surrounded a print outlining all of the places Kristen and Jonny's families have lived from their grandparents on. "Place was and is a super important element to the couple," says event planner and designer Jennifer Rose of Salt Harbor Designs says. "We added this as a little surprise."

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The Table Décor

Millie Holloman

Pillar candles and floral boxes filled with ranunculus, garden roses, astilbe, lisianthus, bay leaves, and olive leaves ran down the center of the long tables. "The couple wanted the night to feel like a huge family dinner," Jennifer Rose notes. "The result was exactly that, as guests passed the salad, poured each other wine, and shared stories and laughter."

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Setting the Table

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"It was very important to us that there be food and wine on the table when everyone was seated," Kristen says of the cheese, meats, and wine bottles set on the tables. "Family and friends' speeches were up first and we're not known for our brevity."

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The Place Setting

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Menus were printed on dinner napkins and topped with fresh bread and a sprig of herbs that held each guest's place card.

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The First Dance

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The newlyweds chose Johnny Cash's "Rose of My Heart" as their first dance song.

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The Cake

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Family friend Pam Goddard, of A Piece of Cake, made the two-tier confection of red velvet cake with cream cheese frosting, and vanilla cake with raspberry cream filling and cream cheese frosting.

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Local Sweets

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What Nantucket celebration is complete without little chocolate whales? These, from Nantucket Candy Company, were one of the sweets on offer for dessert.

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The Getaway

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Jonny and Kristen rode vintage cruiser bikes while their guests surrounded them with sparklers. It ended with a jump in the pool—a quick relief from the evening's humidity. "One of my favorite moments from the wedding was jumping in after we rode away," Jonny recalls. "It felt like we were escaping, just the two of us, to be mischievous and light-hearted like little kids, but now with the responsibility of our newly-minted bond. I was so strangely moved by the seemingly-cliché symbolism of us taking the plunge. I think it had to do with the intimacy of the moment, since we were alone for the first time since the ceremony."

They scurried off to the guest house to change before heading to the party barn next door for a pizza party and late-night drinks.

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Millie Holloman

Photography: Millie Holloman Photography

Ceremony Location: Siasconset Union Chapel

Event Planning, Stationery, and Flowers: Salt Harbor Designs

Catering: The SeaGrille Restaurant

Videography: Brighter Lights Media

Calligraphy: Southern Bee Designs

Officiant: Father Donald MacMillan

Cake: A Piece of Cake (508-228-6184)

Reception Music: Encore

Rentals: New England Country Rentals

Hair and Makeup: Darya Salon & Spa

Transportation: Cranberry Transportation Service

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