Sydney and Shane weren’t always on each other’s radar—at least not when they attended high school together. But when Sydney couldn’t resist teasing Shane on social media years later about his tragic-looking COVID-era meal prep, something clicked. “It looked awful…and I told him so,” Sydney laughs. From that cheeky exchange to exchanging vows under the southern Italian sun, the couple’s journey brought them—and about 60 of their favorite people—to Masseria Moroseta, a chic whitewashed bed and breakfast nestled in the olive groves near Ostuni in Puglia, Italy.

Why Puglia?

“I had always envisioned a European wedding,” Sydney shares. But it wasn’t until she followed the Masseria Moroseta’s chef, Giorgia Eugenia Goggi, on Instagram and cooked up one of her meatball recipes (a Shane favorite!) that the venue cemented itself as the one. “Food was a top priority for me…and the venue is stunning in its simplicity and natural beauty.”

When they discovered the cost was far more reasonable than comparable U.S. venues, the deal was sealed. Planning from afar came with the usual “Italy-is-on-its-own-time” quirks. “We tried to discuss our welcome dinner during an October visit and the restaurant told us to just email them a month before. Classic!”

The Vibe

Sydney and Shane opted for a relaxed, minimalist design that let the setting shine. Wild local greenery, hand-assembled by their planner Santa Vigante, set the tone at the ceremony. “Because the venue and region is already so stunning, we wanted to let it shine naturally,” Sydney says.

Dinner tables were decorated with moody fruits and candlelight, but the real charm was in the personal details. Each guest received a handwritten note from the couple. “It was my idea to give hand-written notes to each of our guests…acknowledging their part in our journey as a couple and their importance to us as individuals,” Sydney explains.

Shane, ever the game-lover, added another personal touch: “He included custom crosswords in the dinner packets he made,” Sydney says, “and even a mocktail option on our drinks list for friends and family who don’t drink.”

Ceremony with Personality

No cookie-cutter traditions here. “We didn’t have a wedding party,” Sydney says. Instead, Shane walked down the aisle with his mom to The Pointer Sisters’ “I’m So Excited” (yes, really), while Sydney and her dad followed to Sister Sledge’s “Thinking of You.” They were married by a longtime family friend of Shane’s, who struck the perfect balance between heartfelt and hilarious.

And the vows? A cinematic moment. “Shane aligned his vows with quotes from his favorite movies—we all laughed when he declared to me, ‘I’ll always love you, Paul Atreides.’” Their first kiss sealed the deal to The Drifters’ “This Magic Moment,” nodding to The Sandlot’s legendary Squints and Wendy Peffercorn smooch.

Eat, Dance, Mozzarella

Guests were treated to a multi-sensory Italian feast: Aperitivo accompanied by the swingin’ sounds of Past e Fasul, cocktails by Quanto Basto from Lecce, and a jaw-dropping dinner under the stars. “We wouldn’t have had a mozzarella man pulling cheese during aperitivo if we’d gotten married back home!” Sydney says. DJ Cherry Pie (yes, that’s her name) flew in from San Francisco and brought the perfect party energy.

And while the couple skipped traditional dances during dinner, they surprised everyone by hitting the dance floor with their parents once the real party started—because when in Italy, you make the rules.

Advice from the Newlyweds

Sydney has two big takeaways for couples planning their day:

“Weddings are expensive, and you are the ones getting married. Don’t feel like you have to do everything ‘because that’s what you do at a wedding.’ Think about what actually aligns with you as a couple.”

And don’t forget your guests:

“Try not to have side events that are only for some guests. Think about everyone’s comfort—maybe don’t ask people to wear black tie at noon in a humid climate. Little details make a big difference.”

Even without a videographer, the couple captured candid moments thanks to phone footage from friends and a front-row ceremony video shot by Sydney’s best friend. “We really are grateful for those recorded moments.”

Their best tip? Take quiet time together, alone, throughout the day.

“Make sure you have a few minutes to just yourselves during cocktail hour… The day really does pass by so fast, so take the time to appreciate what you’ve planned coming together!”

Vendors: Venue & Cake: Masseria Moroseta; Wedding Planner: Santa Vigante of Italian Boutique Weddings; Photography: Sarah Lord; Florals: Local greenery arranged by Santa; Stationery: Aerialist Press; Gown: KYHA Studios; Groom’s Suit: Ralph Lauren; Music: DJ Cherry Pie and Past e Fasul; Welcome Dinner: Impasto Napoletano; Desserts: La Bottega del Pasticciere; Cocktails: Quanto Basto