Set against the sun-drenched hills of Tuscany, this three-day wedding at Il Borro unfolded like a dream — filled with pizza under string lights, a floral-filled secret garden ceremony, gelato carts rolling into parties, a choreographed first dance under candlelight, and a vintage Fiat getaway. Every detail, from the Millefoglie cake to the surprise fireworks, was carefully planned by Brenda Babcock Celebrations to immerse guests in a celebration of beauty, joy, and la dolce vita.
Location: Tuscany, Italy
Style: Romantic, classy, whimsical
Time of planning: 1 year
Number of guests: 120
Setting: Villa
Season: Summer
Hailey and Alex first crossed paths while studying at MIT, introduced briefly through a mutual friend, but it wasn’t until a spontaneous ski trip that their story truly began. Despite Hailey being a non-skier, she enthusiastically joined the trip, and Alex found himself teaching her how to ski — a weekend that sparked their connection. Over the next eight years, they built a life together exploring New York City’s food and wine scene, traveling, cooking, and skiing. On the eve of Hailey’s 30th birthday, Alex proposed in his candlelit apartment filled with white rose petals. After nearly a decade of growing together, they envisioned a wedding that would celebrate not only their love, but also the people who shaped their lives and relationship.
Bridal Morning
Hailey began the wedding day with an intimate breakfast alongside Alex and their families at the villa — a quiet moment shared before the excitement unfolded. As preparations began, she got ready surrounded by her closest friends on one floor of the villa, while Alex prepared on another. With the late summer Tuscan light streaming in through the windows, Orazio Image Consultant worked on her hair and makeup, keeping the look soft and romantic to match the setting. Her fragrance for the day, Quelques Fleurs l’Original by Houbigant Paris, was a subtle tribute to Princess Diana, adding a personal and timeless touch.
For the ceremony, Hailey chose a strapless Reem Acra dress with 3D floral embellishments that shimmered delicately in the light, combining elegance with a touch of whimsy — the exact blend she hoped to find. She paired the dress with classic white Manolo Blahnik flats, prioritizing comfort without compromising style.
Her bouquet by Nina e I Fiori was a dreamy arrangement in pastel tones, designed to feel romantic, natural, and a little bit wild, perfectly matching the secret garden aesthetic of the ceremony. For jewelry, she wore a cherished pair of Van Cleef & Arpels earrings borrowed from her mother-in-law — delicate floral clusters from the Socrates collection that mirrored the soft, ethereal spirit of her overall look.
Groom's Fashion
Alex wore a custom tuxedo by Sartoria Corcos, handcrafted in Florence by tailor Kotaro Miyahira, whose soft-shouldered, classic style brought both structure and comfort. He paired it with shoes from Baudoin & Lange and a sentimental FP Journe watch gifted by his parents — refined details that reflected his lifelong love of tailoring and thoughtful design.
Ceremony
Hidden within the medieval stone paths of Il Borro, the ceremony space was originally a modest courtyard — but with the vision of planner Brenda Babcock Celebrations and the floral artistry of Nina e I Fiori, it transformed into a secret garden brought to life. Inspired by a wisteria-covered walkway Hailey had seen during an earlier visit, the ceremony design featured soft lavender, pink, blue, and white blooms woven into natural arrangements and overhead florals cascading from the trees above. The space felt secluded and intimate, filled with delicate textures and colors that reflected the romantic, whimsical mood of the day, while still embracing the rustic character of the ancient stone village.
The ceremony itself was deeply personal and intentionally non-religious, officiated by one of Alex’s oldest friends, who invited the couple to pause, turn toward their guests, and soak in the overwhelming support surrounding them. Hailey’s brother-in-law and a childhood friend read excerpts from Captain Corelli’s Mandolin and a quote from Einstein — a mix of romance and lighthearted nerdiness that suited them perfectly.
"The whole thing went by in a happy blur, but celebrating each other’s love, in front of essentially everyone we love, will remain one of the greatest moments of our lives."
The couple shared emotional, handwritten vows, with Alex holding back tears through his speech. Afterward, they recessed to “How Long Will I Love You” from About Time, walked through a path lined with cheering guests tossing olive leaves, and hopped into a vintage pastel blue Alfa Romeo for a celebratory drive — a joyful, cinematic moment that felt entirely their own.
"We walked down the path lined with our friends & family who were throwing olive leaves, with an Italian Folk Duo playing music following closely behind. We couldn’t stop laughing in joy!"
Private Moment
Just after the ceremony and again before joining their guests at the reception, Hailey and Alex took two quiet moments alone — short but meaningful pauses to reconnect, reflect, and take in the day together. These in-between moments, filled with laughter, hugs, and whispered conversations, were captured with natural intimacy by David Bastianoni Studio, whose digital photography brought softness and depth to even the most fleeting glances.
"Starting the car and driving off with an old manual transmission was nerve-wracking, but the showmanship of it all was really fun."
Decor & Setting
As guests made their way from the cocktail hour through the gardens, they arrived at the reception space — a gravel terrace beside the villa that Brenda Babcock had completely transformed. The setting unfolded like a hidden scene: long tables framed by floral structures and hanging lights, soft pastel blooms in pink, peach, cream, and lavender, and hundreds of glowing candles layered between delicate glassware and custom place settings.
The dusky pink of the villa façade became part of the palette, echoing the romantic, feminine atmosphere. “We were speechless when we walked up to it,” they said, “the candlelight, the colors, the flowers — it was even more beautiful than we had imagined.”
"We wanted a specific feel for the wedding day, consistent with our invitation suite — romantic, feminine, natural, ethereal, with a touch of whimsical — and Roberta & Brenda executed perfectly."
Reception
Dinner was served beneath strings of glowing lights as guests found their seats at tables named after the ski trails at Stratton Mountain — a nod to where Hailey and Alex’s story began. The menu, curated by Tuscan Excelsia, featured a refined take on traditional Tuscan fare: Pear and Pecorino Cheese Tortelli, Risotto with Chianti Grape Must, Pancetta and Shallots, followed by a choice of Sea Bass or Steak. Each dish was paired with wine produced on-site at the Il Borro winery, making the experience even more rooted in the place they had come to love. Between courses, speeches from co-maids of honor, co-best men, and the couple’s parents brought emotion and laughter, adding layers of meaning to an already unforgettable evening.
For dessert, Hailey’s vision of the perfect wedding cake came to life. Roses Cakes created a delicate, pressed-flower masterpiece layered with Fior di Latte for Alex and Gianduja for Hailey. As they sliced into the cake, glasses clinked — and in that moment, a surprise fireworks display lit up the sky. Hailey and Alex had kept it a secret from everyone, even their families. “We didn’t realize we were in for a surprise too — the length and quality of the fireworks was unreal!” they shared. The burst of color and light over the Tuscan hills was a surreal high point, leaving everyone in awe.
The party moved to the estate’s amphitheatre, where guests formed a sparkling tunnel with sparklers in hand as Hailey and Alex led the way into the celebration. The energy soared the moment Fully Funktional took the stage, opening with “Shut Up and Dance.” Hailey slipped into a playful, shorter Alexia Maria dress, ready to take over the dance floor with friends and family. The band kept everyone on their feet with a mix of favorites, making the amphitheatre feel electric under the Tuscan night sky.
As the night deepened, the energy never dropped. DJ Leonardo and DJ Lorenzo took over after the band, keeping the crowd going with beats that carried into the early morning. At 3:30 a.m., guests were still dancing — thanks in part to the perfectly timed trays of spaghetti alla puttanesca that made their way around the amphitheatre. Between the music, the food, and the electric mood of being together in such a magical setting, the night felt endless in the best possible way.
"We keep saying it, but being in Tuscany, at Il Borro, surrounded by all our loved ones, declaring our love for each other, was a dream come true for both of us."
Advice from the couple:
• Align on why you want to have a wedding and remember it. For us, our goal really was to share our love with everyone we love, which dictated our attitude towards planning and ended up influencing the structure and vibe of the 3 nights. The process was also undoubtedly stressful, and there were times when we would get caught up in details, pulling back and remembering our ultimate goal for the entire event helped keep things in perspective.
• Lastly, a practical piece of advice for brides: if you’re planning on wanting your eyelashes curled or extended for your wedding day, try to get them done in advance if you can! I didn’t think to look into an eyelash lift and perm or semi-permanent eyelash extensions, but felt like that could have saved a lot of time during the wedding events!
PLANNER Brenda Babcock Celebrations | VENUE Il Borro | PHOTOGRAPHER David Bastianoni Studio | VIDEOGRAPHER Alessandro Pardi | FLORALS Nina e I Fiori | MUAH Orazio Image Consultant | DRESS & VEIL Reem Acra | HEELS Manolo Blahnik | EARRINGS Van Cleef & Arpels | RECEPTION DRESS Alexia Maria | SUIT Sartoria Corcos | SHOES Baudoin & Lange | WATCH FP Journe | RINGS Ashley Zhang Jewelry, Fully Funktional | CATERING Tuscan Excelsia | CAKE Roses Cakes | RENTALS Preludio Noleggio, Brenda Babcock Celebrations | STATIONERY Shhh My Darling | BRIDE Hailey | GROOM Alex
