A “Pretty in Pink”–Themed Party Kicked Off This Wedding Weekend Overlooking the Tuscan Hills
Gabrielle Hackman always had a good feeling about John Beebe, a former farmer turned real estate broker and a classmate of Hackman’s older brother. When they first met she thought he was “the nicest guy—and so grounded.” There was just one catch: He lived in Massachusetts, and she was on the West Coast. “Then I moved to New York, and out of the blue he called to ask me out,” Gabrielle, the director of immersive media initiatives at a real estate firm, remembers. “We had the best time together, exploring the city. I always felt like myself around him. Even with a two-hour drive apart, we immediately became a couple and have been together ever since.”
After six years of dating, the couple, who both now work for her family’s real estate company, purchased their first home—and then the sellers, according to John, invited them over for a celebratory round of drinks. “But when we arrived, something felt off,” Gabrielle recalls. “For one thing, the sellers weren’t there, and John seemed nervous.” They walked around to the backyard to wait, and then John said he had a gift for her.
“There really was no preamble; he just handed me a big red box,” she remembers. “I gasped. It was a Cartier love bracelet—and when I looked closely, I saw that it was engraved with the inscription ‘marry me’ in French, which my family speaks at home. He then dropped to one knee and officially proposed. I was in shock.” Minutes later, just as he had planned it, their families and close friends arrived. They cheered. Gabrielle and John hugged, laughed, and cried—and then, they all caravanned to Gabrielle’s parents’ house, where a beautiful engagement dinner was waiting.
Their wedding was held one year later in Montalcino, Italy, at the Rosewood Castiglion del Bosco. “John and I love Italy,” the bride explains. “It was our go-to destination when we traveled during our dating years, and the venue was a perfect combination of romantic Tuscan charm, Italian heritage and history, simple luxury, and breathtaking, natural beauty.”
The couple worked with Emily Park and Esther Oh at Studio Komorebi and the staff at Castiglion del Bosco to plan their dream wedding weekend. “Everyone listened carefully to understand our creative vision, but also thought outside the box,” Gabrielle says. “Of course, because of the distance, we had to rely on FaceTime and Zoom calls to sort out many details with multiple vendors, but the vendors were easy to work with and incredibly well organized.” They did, however, make one trip to Italy in April to finalize everything.
In addition to the wedding itself on Saturday, they also planned other weekend events: a party on Thursday (which happened to be Gabrielle’s 30th birthday) with lunch and games, a rehearsal dinner on Friday, and a brunch on Sunday. It was important to both the bride and the groom, as they planned the weekend, that each event offered guests a unique experience, so every party needed to have its own distinct personality.
“When we chose the wedding date, we knew the weekend would overlap with my 30th birthday,” Gabrielle says. “I’ve always loved themed parties, so we settled on ‘pretty in pink’ for Thursday’s birthday party, which made for incredible photos and a very girly vibe.”
The rehearsal dinner the following evening felt like a classic Italian family dinner. Guests were surrounded by bountiful charcuterie stations, and the casual elegance of the evening took inspiration from the land and its lush greenery, countryside wildflowers, and freshly grown vegetables. To keep things lively, everyone was led into dinner parade-style by a traditional Italian five-piece band.
While the programming of the weekend was incredibly important to Gabrielle, the fashion lineup was her own personal Super Bowl. Before moving into real estate, she spent years working for stylists and at clothing brands, so she felt like she had a lot to live up to. To that end, she visited countless designers and bridal salons and tried endless options. Ultimately, though, she had the same goal for everything she chose: It had to be classic, yet unique—and it had to strike the right balance between the two.
For Thursday night’s birthday party, she selected a soft-pink, silk taffeta Carolina Herrera mini dress with dramatic, puffy sleeves and a long flowy train. “It was the first night of the weekend, and I wanted to wow,” she says. “It was my 30th, and I knew I could get away with something over the top.”
The following night, at the rehearsal, she wore a short white Oscar de la Renta dress with a fully flouncy skirt, and for a playful twist, she paired it with bright orange Valentino platforms and a mini orange Jacquemus bag. “I didn’t want my outfit to look predictable,” Gabrielle says. “And the accessories were the perfect addition.”
For the wedding, she wanted a dress that had a traditional shape, but with differentiating details. She chose a Monique Lhuillier strapless gown with a more contemporary-feeling slit up the side. “It stood out to me because of its unique light silk brocade fabric,” Gabrielle explains. “And the wow for me: a stunning and versatile, ultra-feminine bolero that was removable, of course. I had never seen a bride wear a jacket before, and that sold me.”
Eventually, she changed into a bedazzled Oscar de la Renta mini halter dress. “It was a sparkly number, perfect for dancing,” she says.
At 5:30 p.m., on a sunny Saturday in June, guests gathered in their festive black tie, and the bride walked down the aisle, escorted by her parents, to James Taylor’s “Sweet Baby James.” The couple then said their vows on a platform overlooking Tuscany’s rolling hills and vineyards. “We wanted the ceremony to be romantic and dramatic, and it was,” Gabrielle says. “We were elated, felt lucky, and in love.”
Afterwards, everyone was transported by bus to one of the countryside villas on the property, a restored 18th-century Tuscan farmhouse, for a cocktail reception, followed by an elegant sit-down dinner, served al fresco while the sun set and speeches were given. Post-dinner, guests moved to another side of the house for a traditional Italian millefoglie wedding cake that the pastry chef assembled right in front of the guests, building each layer like a work of art. “Just as we were cutting the cake, we surprised our guests with an incredible fireworks show,” Gabrielle says. “We then moved into a glass greenhouse—which we staged like a Gucci nightclub—for nonstop dancing, wild photo booth shenanigans, gelato, late-night pizza, and endless memory-making.”
Photo: Alex Bramall1/81We got married at Rosewood Castiglion del Bosco, which is situated within a 900-year-old, 5,000-acre estate, one of the oldest and best-preserved in Tuscany. Here’s the ceremony site, a breathtaking view overlooking the Brunello vineyards. When we first saw it, we knew it was where we had to say “I do.”
Photo: Alex Bramall2/81Time alone at our villa, the day before guests arrived. John and I always have so much fun together.
