Atop the Sina Bernini Bristol hotel in Rome, with terracotta domes and ancient ruins stretching in every direction, Sarah Leonard and Adrian Wyland marveled as more than 100 of their favorite people gathered on the other side of the world — for them. After months of planning anxiety, a calm washed over Sarah. “I saw my friends and family together and thought, This is why we’re here,” she says.
That communal spirit shaped their three-day celebration, as guests traveled from the Eternal City to the Umbrian countryside. The weekend felt less like a forma fête and more like being welcomed into an Italian family home — if, say, that home were a medieval castle built in the 14th century.
Early Days
The couple’s story began in a considerably less cinematic setting, at a college charity dance competition. Sarah, then a senior, was paired with Adrian, a shy sophomore with what he describes as “two left feet,” simply because they were the tallest participants. “I had no business doing a dance competition,” Adrian says.
Though they didn’t take home the prize — some of Adrian’s fraternity brothers got a little too festive before the performance, disqualifying their team — they left with something better. Friendship slowly evolved into a relationship, carrying them from Chicago to business school in London to New York, where they now live. When the topic of engagement arose, Sarah insisted on a couple of conditions: the proposal had to be a surprise, and ideally while her nails looked good. Adrian succeeded on one count.
In the private basement dining room of a London restaurant, a server handed Sarah what appeared to be a cocktail menu. Instead, it was a custom illustrated booklet Adrian had commissioned from a Chicago artist, tracing their relationship through drawings. On the opening page, a ginger-haired man stood beside a brunette woman, followed by the pair standing outside of their Chicago home, address included. Sarah flipped through the pages distractedly, searching for the champagne list, until Adrian nudged her. “Sarah, pay attention,” he said. Her nails were four weeks grown out and she was dressed head-to-toe in black — “like a funeral,” Sarah laughs — but that no longer mattered, especially since both of their families had flown in for the surprise.
Following the Feeling
A destination wedding wasn’t the original plan. After the engagement, the couple spent a couple of weeks traveling through Italy and found themselves enchanted by its unhurried pace and sense of community. “It was calm and comfortable, and we felt very at home there,” Sarah says.
Back in Chicago, they toured more than 20 venues trying to recreate that warmth. Nowhere came close. Eventually, they stopped resisting the obvious, and to their surprise, their parents enthusiastically embraced an Italian wedding.
Their planner, Lisa Jaroscak Chin of Elegante Weddings and Events, who had studied opera in Perugia, Umbria’s capital, steered them toward the region. It’s Tuscany’s quieter, more authentic counterpart, she told them. The venue she recommended, Castello Di Petrata, was built in 1340, making it one of Umbria’s oldest working estates, surrounded by olive groves and orchards. It’s run by a father and his two sons — one the chef, the other managing the business — while the patriarch tended the gardens himself every day. “We wanted something very local and mom-and-pop,” Sarah says. “Like a grandma making pasta.” They signed the contract before ever visiting.
Days to Remember
The celebrations began with rooftop welcome drinks in Rome before guests boarded buses together for Umbria the next morning. (Sarah and Adrian arranged transportation so no one would have to navigate winding roads in a rental car.) Once at Castello Di Petrata, guests indulged in la dolce vita via a pizza-and-pasta party with a gelato cart, live Italian music, and dancing that stretche unexpectedly late after one of the venue owners casually stepped behind the DJ booth himsel.
On the wedding day, Sarah got ready beneath a pergola overlooking the countryside in a tulle KYHA gown — not the sleek silhouette she once imagined, but the dress that felt right after stressful shopping experiences elsewhere. “Completely unexpected,” she says, “but it fit the venue.” She change twice more before the night ended: into a satin slip dress for the hora and cake cutting, then into a minidress for the dance floor.
The ceremony, officiated by Sarah’s cousin, wove personal storytelling with Jewish tradition as family members each delivered one of the Seven Blessings. Cocktail hour followed on the garden bluff, a jazz band playing beneath the open sky. “It was the perfect post ceremony setting,” Adrian says. “It was a relaxed atmosphere, with all of our friends in a single place mingling with our families, listening to amazing music.”
Dinner, a feast of truffle pasta and short rib, unfolded al fresco across long serpentine tables. Between then, the couple shared their first dance as Mr. and Mrs. to Aretha Franklin’s “You Send Me,” carefully choreographed, though no one accounted for Sarah’s heel to briefly get caught in the cobblestones.
Later came a champagne tower and a millefoglie, the traditional Italian “thousand-layer” pastry, assembled by the couple in front of their loved ones, its delicate layers symbolizing the many layers of a life built together. Then a saxophone player led guests toward a hidden space behind the villa, where they were met with disco lights and fog machines to pack the dance floor until nearly sunrise.
By 5:00 a.m., guests jumped in the pool. “The whole point of a destination wedding for us was having everyone together,” Adrian says. “Not just for one night, but for days. Watching our friends become close with our families — that’s what I’ll remember forever.”
After the wedding, the couple slipped away for a mini-moon in Puglia at Masseria Calderisi, then months later enjoyed a formal honeymoon in Japan. In Tokyo they stayed at the Okura, then retreated to Beniya Mukayu, a secluded ryokan tucked deep in the woods. There they spent several days wearing kimonos, soaking in onse baths, and embracing the same sense of calm and connection that defined their wedding weekend.
Vendors
Planner: Elegante Weddings and Events // Venue: Castello Di Petrata // Photography: Audra Wrisley // Video: Diego Perrini Video // // Beauty: Sara Onori // Florals: Bird and Bumble // Entertainment: Blue Moon Italian // Jazz Band // Stationery: Mite Print // Rentals: Preludio Divisione Noleggio // Gown: KYHA // Tuxedo: P Johnson Tailors
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