Family, Food, and Good Wine Were the Focus at This Intimate Wedding in Tuscany

Jen and Matt, who met on a dating app in 2019, share a love of hosting their family and friends and a passion for diving into even the smallest details of an event. When Matt proposed, he popped the question in private—before surprising Jen with a festive engagement dinner that included their closest family and friends (“Some of which traveled internationally for this special day!” says the couple). “The proposal and celebration with family and friends was an absolute surprise to Jen—she thought they were going out to dinner to celebrate a friend’s birthday,” says the couple. “And in true Matt fashion, he had been planning every little detail of this day for over two months.”

That same attention to detail and fondness for celebrating inspired their wedding weekend in Tuscany in October 2022. With 40 guests traveling to celebrate for three days, including at an outdoor wedding ceremony and dinner on October 8, Jen and Matt pulled out all the stops. “From the onset, we wanted to create a wedding weekend that was an intimate celebration while also feeling like a vacation with our closest family and friends,” says the couple, who worked with Laura Bravi Events. “We were really focused on prioritizing our guests’ experience and included elements of surprise throughout each event, on top of the amazing food and wine. Our favorite memories with family and friends always involve good food and wine and entertainment, and we wanted to continue on with the tradition for our wedding weekend.”

The couple and their guests started the weekend with a private tour, wine tasting, and lunch at Fattoria Le Pupille Winery, and then hosted a Tuscan-barbecue-themed welcome party that night; the day after their ceremony, they hosted a brunch and pool party before guests departed. “The easiest part was that we had a very clear vision of what we wanted our wedding weekend to look and feel like, for us and our guests,” they say.

The couple and their guests stayed at the wedding site, La Pescaia Resort. “Originally a farm belonging to Florentine royals—the Tolomei family—La Pescaia has this natural, organic beauty, and, being a little off the beaten path, has an authentic, old-world and intimate feel we wanted,” says the couple. “Having our family stay onsite with us at the venue was the best part. Being able to walk down and hang out with everyone at any moment of the weekend made for a relaxing and fun atmosphere.”

Ahead, see all the details of their big day, which was photographed by Molly Carr Photography.

The invitation suite from Michaela McBride Calligraphy included torn-edge paper, an embossed monogram, gold leaf-adorned wax seals, and illustrations of the Tuscan countryside. The couple describes their color scheme as “soft light shades that resemble a late summer sunset: cream, dusty pink, pale tangerine, and rosewood, with a touch of French blue and sage to complement the lush greenery throughout La Pescaia, for a refined, fresh, and romantic feel.”

Custom canvas welcome bags waited for the guests upon their arrival to the resort. Jen and Matt filled each bag with “the essentials:” Acqua Panna bottled water, a small bottle of Fattoria Le Pupille Poggio Valente Sangioves, powdered electrolytes, and snacks. “We wanted our guests to feel at ease after their travels to Italy,” says the couple.

Jen chose a Monique Lhuillier ball gown covered in hand-appliquéd floral lace, Jimmy Choo heels, and sentimental jewelry. “I wore a set of pearl earrings and a bracelet made by my late aunt, paired with a gold David Yurman bracelet with blue topaz gemstones—Matt’s birthstone—that he gifted me; this also served as my 'something blue,'” she says.

Hair and makeup artist Giulia Cresci of Guilia Makeup created a subtle look that elevated Jen’s typical beauty routine. “I wanted to feel and look natural,” says the bride. “I’m very minimal when it comes to makeup—typically just eyeliner, mascara, and maybe blush."

For his wedding attire, Matt ordered a bespoke tuxedo made by Ascot Chang and custom J. FitzPatrick shoes. Finishing touches included a Nomos Glashutte Tangomat GMT Ref. 635 watch and two of his favorite scents: Clive Christian 1872 Geranium, and Maison Francis Kurkdjian Baccarat Rouge 540 Eau de Parfum. “Jen is very particular with fragrances, and she also happens to love these two,” he says. 

While the couple chose to have a first look partly for practical reasons—relieving some of the stress of the photography timeline—they also looked forward to some time alone before the ceremony. “It gave us a special moment to ourselves and allowed us to check in with each other and share how we were feeling on such a whirlwind day,” says Jen. “Since we opted not to read personal vows during the ceremony, this moment also allowed us to privately connect, be in the moment, and share what the day meant to us.”

Jen and Matt kept their bridal party family-only, with Matt’s younger brother, Nick, serving as the best man, and Jen’s younger sister, Alice, taking on the maid of honor role. Jen’s niece, Josephine, donned a green and white floral crown as the flower girl. 

Jen carried a textural bouquet of roses, cosmos, dahlias, abelia, and wild fennel—”many of which were grown and harvested from the flower farm on property,” she says—from Siloh Floral Artistry. Deeper rust tones throughout Alice’s bouquet complemented the peach, pink, and ivory blooms Jen carried. 

For the outdoor ceremony, which took place in front of a greenery-covered stone wall, the couple wanted “a refined, fresh, and painterly feel with natural elegance and organic textures,” says Jen. “We created a growing meadow of flowers coming up from the ground starting at the back row of chairs, lining each side of the aisle and eventually encircling [us] at the altar.”

A string quartet from Assya Live Music performed classics from The Beatles and Elvis Presley as the bride and groom each walked down the aisle with their parents. Jo Bertolino of Tuscan Pledges guided the couple through their “I dos” in a ceremony customized for Jen and Matt. “We didn’t share personal vows during the ceremony; however, our officiant perfectly captured the essence of our relationship,” they say. As the couple left as husband and wife, the musicians played Stevie Wonder’s “Signed, Sealed, Delivered.”

Jen and Matt chose to have all their guests sit at a single long table for the al fresco dinner reception. A canopy of vines and roses wound around sparkling chandeliers. “We wanted to maintain a natural, effortless look with textural centerpieces, organic movement, soft candlelight, and pops of bright coral and orange in both the floral and patterned charger plates,” says Jen. 

One of Matt’s key wedding visions included driving a vintage Italian Fiat along the winding Tuscan roads before arriving at the reception. “We loved the idea—aside from the fact that Matt has never driven a stick shift,” says Jen. “He failed to disclose this bit of information to me and instead brushed it off, insisting it had been a while but he knew what he was doing. When it came time to take the car out for a drive before making our grand entrance, Matt kept his cool and was able to successfully execute the drive and entrance—albeit staying in first gear the entire time. It wasn’t until we were all relaxing by the pool the next day that he told me the truth about his manual driving experience, or lack thereof, and I realized it was a big potential crisis averted!”

After hosting a barbecue at the welcome party, Jen and Matt kept their reception menu on the lighter side: asparagus and foie gras soup, stuffed pappa al pomodoro cappellacci, tonnarelli pasta topped with pecorino and Italian truffle, and scallop-and-pumpkin risotto. 

“The overall reception dinner was our favorite part of the wedding,” says the couple. “All the nerves and stresses of the day were lifted, and we were able to enjoy a slow, lengthy dinner party filled with great food, wine, and special guests. The ambience, from the table setup to being outside as the sun was setting, and all the little details around the dinner made for such a relaxing and unforgettable moment.”

Before the couple’s band filled the dance floor, Jen and Matt hired an Italian tenor to serenade guests during the meal with three songs: “The Prayer,” “Nessun Dorma,” and “Funiculi Funicula.” “With the whirlwind day and all the emotions, we had actually genuinely forgotten that a tenor would be showing up during dinner, and were equally as surprised as our guests!” says the couple. “It ended up being the highlight of dinner and a memory we’ll never forget.”

After sharing their first dance to “Conversations in the Dark," the pair helped prepare a traditional millefoglie cake for their loved ones.

Later in the evening, Jen and Matt joined their guests on the dance floor. Their attention to detail paid off as they celebrated with their friends and family. “In the end you really want to be proud of your day and what you spent so much time planning and putting effort into,” they say. “For us, despite it being ‘our day,’ we really wanted our guests to feel like they were part of it, as well."