When Sean Coghlan and Spencer Schrage began planning their wedding, they weren’t simply searching for a beautiful venue. “Our number one goal,” Sean explains, “was to find a place to create community and connection.” They found exactly that at Il Borro, the Ferragamo-owned estate tucked deep within the Tuscan countryside, where the couple hosted a multi-day wedding event from June 4–8, 2025, that blurred the line between destination wedding and immersive house party.
The pair first met on a dating app in 2018 but didn’t reconnect in person until Labor Day weekend in Provincetown in 2021, where a chance encounter at Victor’s restaurant turned into dinner plans back in New York—and eventually, engagement. Provincetown would later become the setting for Spencer’s proposal, complete with a jazz duo performing on the dunes, a surprise family gathering at The Red Inn, and a plane flying over Cape Cod with a proposal banner that read, “Sean, I love you. Will you marry me?” trailing behind it.
That sense of theatricality—and emotional detail—carried seamlessly into Tuscany.
Working closely with Over The Moon Planner Design Anarchy Studio for more than a year, Sean and Spencer approached each evening as its own fully realized world. “We were focused on setting a unique aesthetic for each of the three evenings,” Spencer explains, “from the location through the design, florals, food, drinks, and fashion.”
The celebrations began in Florence with cocktails at Collegio alla Querce before guests transitioned to the Tuscan countryside for night one— an “Italian Countryside Chic” welcome dinner awash in terracotta tones. Guests found seating assignments at a pasta-market-inspired installation, while linen pasta bibs invited everyone to embrace their “saucy side.” Music by London-based DJ Carly Foxx and a surprise performance by local Italian boy band Boys4Road transformed the medieval Borgo into what guests affectionately nicknamed the “Gay Village.”
If the first evening introduced the energy of the weekend, night two became its visual crescendo. Hosted as a maximalist garden party, the rehearsal dinner centered around a single imperial table for 172 guests layered with custom textiles by Design Anarchy Collection, lush arrangements by White Pepper Studio, and handwritten notes placed at every setting. “The table was drenched with prints, colors, florals, and lamps,” Sean shares. As the sun set, a Sienese flag performance by Quartiere di Canneti marched guests into dinner before The Three Tenors surprised attendees with an operatic finale beneath the Tuscan sky.
By the wedding evening on June 7, however, the mood shifted entirely. The ceremony unfolded along Il Borro’s iconic cypress-lined driveway beneath a custom fabric chuppah softened with elegant florals. The couple worked with Rabbi Barbara Aiello—the only female Reform rabbi in Italy—to incorporate Italian and Jewish traditions into the ceremony, including Spencer’s bar mitzvah tallit gifted decades earlier by his grandmother.
Music played an especially significant role throughout the evening. After months of searching, Sean and Spencer discovered Australian duo Tobi Tobi, who performed renditions of songs by Coldplay, Troye Sivan, and Kygo as guests gathered beneath the Tuscan hills. “The ceremony was intentionally intimate and emotional,” Spencer shares. “This moment was the most important for us, and we wanted it to feel raw and real.”
Fashion throughout the weekend reflected the same level of intention. Sean and Spencer collaborated with Loro Piana and Brunello Cucinelli for the first two evenings before changing into Tom Ford made-to-measure ivory dinner jackets for the wedding ceremony. Later, they surprised guests with black tuxedos for dinner and dancing, accented by green floral brooches by New York pin designer Andrew Werner.
Dinner revealed itself like a cinematic jazz club hidden in the Tuscan countryside. Green became the defining visual motif of the evening, from the velvet chairs, custom lampshades, Ginori Oriente Italiano plates, and layered arches wrapped in foliage to the emerald-checkered dance floor. London vocalist Celeste opened the evening with soulful renditions of “Bad Romance” and “Purple Rain” while guests dined on spinach ricotta gnudi, paccheri pasta, and millefoglie prepared live by Galateo Ricevimenti.
Photography by Over The Moon Directory Photographer David Bastianoni Studio captured the layered atmosphere of the weekend with painterly softness, while Waterfall Visuals documented everything on film. Invitations and paper goods by Stationery Stories and Letter Ink introduced guests to the weekend’s evolving visual world long before they arrived in Tuscany.
But perhaps the most memorable moment came after the reception ended. Guests descended into Bar Buttero, a nightclub built within Il Borro’s wine caves and reimagined for the evening as a playful homage to Tuscan cowboys and downtown nightlife.
Leather masks appeared on silver trays, instrumentalists joined DJ Carly Foxx on the dance floor, and the energy shifted from elegant dinner party to something far more uninhibited. “It was beyond our expectations,” Sean says of the celebration. “A night for the ages.”
