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Jessica Costantino and Michael Syslo’s Magical Destination Wedding at Villa Cimbrone

By Shayna Seid | Photography by 

Adovasio Studio

|Planning by 

Exclusive Italy Weddings

When Michael Syslo’s sporting goods store was deemed an essential business during the pandemic, he was understaffed. Menemsha House Founder Jessica Costantino, who was a family friend of his, started helping out in the office. A workplace romance quickly blossomed.

Just shy of their three-year anniversary, Mike proposed on top of the mountain at Belle’s Camp, Vail’s farthest outpost. And after she said yes, Jessica started planning the wedding at her dream venue, Villa Cimbrone, in Ravello.

The pair wed in a legal and religious ceremony on June 7, 2024, and their larger celebration and blessing was set for August 10, 2024. For the latter, Over The Moon Editor’s Pick Planner Exclusive Italy Weddings brought the multi-day destination affair to life, and Kathryn Green set the tone with a beautiful invitation suite. Photographer Adovasio Studio and videographer Giulio Cantarella captured every moment.

The welcome party was rooted in tradition and focused on authentic Italian food and family gatherings. To this, Jessica wore a vintage-inspired Lace Made dress.

The next night’s rehearsal dinner was set at a castle on the sea, fully embracing the Amalfi Coast with delicious seafood. To enhance the scene, Jessica wore Kim Kassas’s “Agnes” ballerina-esque dress.

Originally, Jessica chose Kim Kassas’s “Giovanna” from the Oh Romeo Collection for the ceremony, but as the planning continued, she realized she wanted to wear something more dramatic. “I went back, this time with Mike. It was untraditional to include him, but he’s truly my best friend, and I valued his opinion,” the bride shares. “I showed him ‘Giovanna,’ and together we chose ‘Ruth’ for the ceremony from the Your Majesty Collection, and ‘Giovanna’ for the reception. . .‘Giovanna’ was the perfect transitional dress. I added draped shoulders and wore it as I had my dance with my father and first dance with my husband. After cake cutting, we removed the detachable skirt, so I could dance all night!”

In the Garden of Two Fountains, bridesmaids in butter yellow looks from Shona Joy preceded before Jessica walked down the floral-lined aisle by Armando Malafronte. “Hydrangeas, my favorite flower, played a central role in the design, adding volume and softness to the scene,” she shares.

Once with Mike, their priest from back home, who flew to Italy to bless the marriage, made the ceremony more personal and sacred. “As I stood there, taking it all in—the beauty of the setting, the emotion in the air, and a year’s worth of planning come to life—I kept thinking, this doesn’t even feel real,” Jessica shares. “It was truly a dream.”

In the crypt, the reception began, as a jazz band softly set the mood. After a delicious seated dinner, everyone moved back to the re-set ceremony space for dancing under the stars with a DJ and a saxophonist.

The newlyweds shared a first dance to “Let The Light In” by Lana Del Rey. “The dance with my husband was intimate, moving, and gave us a chance to take in the day for a moment amidst all of the energy,” Jessica remembers. A short walk away, the after-party began and didn’t end until the early hours of the morning.

As it was Mike’s first time in Italy, the couple honeymooned around the Amalfi Coast and Rome to celebrate their marriage with plenty of pasta, romantic views, and gelato by the sea.