An Intimate Destination Wedding in Tuscany with Just 36 Guests

In 2016, photographer Leila Brewster was on the Caribbean island of Antigua documenting a wedding. Singer/songwriter Joel Cross was hired to play during the ceremony, and so the two met while working. It was love at first sight, Leila says, and the pair began dating right away.

Months later, Leila and Joel were in Cabo, Mexico, where Leila was photographing another event. Joel asked if she wanted to walk on the beach before dinner. "I had absolutely no idea Joel was going to propose to me," she says. After about 100 yards, Leila realized what was happening. "I said yes, and immediately tackled him!"

On July 19, 2017, six months after they got engaged, Leila and Joel traveled from their home in New York City to Italy, for a Tuscan-chic wedding. Thirty-six of their nearest and dearest joined the couple at Dimora Buonriposo Farmhouse for an intimate, relaxed celebration. "We just wanted an elevated backyard wedding under the natural light of the sun and the moon—something that was super laid-back and chill," Leila says.

Just like at the wedding at which they first crossed paths, Joel performed—but this time it was an original song he wrote for Leila during their vows. The couple rode into the sunset in an old Fiat, making for a fairytale-esque Tuscan wedding.

Leila says she let her friend Emily Hostetler of Paper Moss, have free rein with the invitations. The stationery featured a light green font, and had a custom motif at the top with an intertwined "L" and "J" for the couple's first initials. "She nailed it," the bride says. Guests were prompted to respond via an Italian "Sì or No?" at the bottom of the card.

Leila and Joel decided to tie the knot in the hills of Pienza, a city in Tuscany, Italy, because they felt an incredible connection to the area. "We also knew we wanted a small destination wedding, and Italy has everything—great people, great sights, ease of travel, and the best food," Leila says.

The couple loved the overall feel of Dimora Buonriposo Farmhouse. "It was perfectly placed between Rome and Florence, so guests had options," Leila says of traveling for the destination affair. She and Joel stayed at the venue, along with Joel's parents, sister, and several of the couple's friends.

"In all honesty, I am not a dress-wearer, so I knew I wanted something that was effortless—something flirty, that fit the backdrop of the Tuscan hills," Leila says, who ended up in the first dress she tried on. Even after going through several other options, the bride returned to this Elizabeth Fillmore number. Leila loved the appliqués on it and that the fabric was made in Italy. In New York, Leila worked closely with Elizabeth to customize the frock, adding pockets, a tea-length hemline, and a cinched waistline. The bride wore Gianvito Rossi shoes and says they were "the most comfortable shoe I have ever worn with a heel."

Joel sported a dark-blue, custom suit from Suitsupply, because he loved the color and breathable fabric for their summer celebration. His shoes were from Saks Fifth Avenue.

"I wear a braid pretty much every day of my life, so I thought that it would be the perfect fit to resemble me in daily life, and to be able to just not have to worry about it during the wedding day," Leila says. Adrienne Aereboe styled the laid-back look. Leila also stuck with her daily fresh face, just adding some mascara to her lashes.

Leila's bouquet, created by Le Petit Jardin, featured olive branches, eucalyptus, and white flowers such as roses, veronica, and peonies.

Joel had both of Leila's rings made by Bella Bijou Fine Jewelry in his home state of Texas. "He knew I wanted something untraditional, gold, and simple," the bride says. "It is perfect!" Joel's brushed white gold band came from APS Jewellery, an Australian jeweler.

Leila and Joel's late afternoon ceremony took place overlooking the rolling hills of Tuscany. "I loved that view—it was just so classically Tuscan," the bride says. "I wanted the whole event to be simple, and wanted the surroundings to really shine."

The parasols were a last-minute addition. "The sun is really hot in Tuscany that time of year, and we didn't want our friends and family to burn," Leila says.

Leila and Joel's ceremony was nonreligious, but had a spiritual feel. "We totally believe we knew each other in a past life, and are just carrying on our love in this lifetime," Leila says. One of Joel's longtime friends officiated, adding an intimate and personal touch. The bride says she and Joel are constantly joking and making each other laugh, as they did in this photo.

Exchanging vows was a particularly special moment for the couple. The groom also sang a song he wrote for Leila, and there wasn't a dry eye at the ceremony. "I couldn't keep it together, and neither could any of our family and friends," Leila says. "I was so excited to play the song I'd been working on for months for my bride, and seeing her reaction was my most memorable moment of the day," says Joel.

After the couple said, "I do," guests tossed lavender as they recessed up the aisle.

Cocktail hour took place on the patio of the villa, where guests snacked on cheese and other traditional Tuscan bites, courtesy of Roland's Social & Business Catering.

Appetizers were passed during cocktail hour, including in fried vegetables served in wood veneer cones.

Leila, Joel, and their 36 guests sat at one long table for the reception. "A long table was, in my opinion, the only option—like one giant picnic table," the bride says.

The place settings were simple, yet elegant—classic white plates, silver cutlery, and dark green napkins tied with a soft white ribbon. Leila wanted to reuse everything, she says, so the garlands from the ceremony doubled as the table runner. For dinner, guests ate chicken filets in a pistachio crust with yoghurt dressing, and timbale of eggplant with mozzarella, tomatoes, and basil.

Leila and Joel had a good laugh during Joel's mother's toast—she talked about the groom "having tons of game when he was in high school," Leila says. The bride's mother also gave an entertaining speech.

Leila and Joel shared a romantic first dance to another song written by the groom, called "Candlelight." "It's an incredible love song, and he chose it for our first dance," Leila says.

The couple was all smiles as they cut their semi-naked carrot cake—the best one Leila has ever had!

Leila and Joel shared a smooch in the sunroof of the black Fiat Cinquecento that they (quite literally) drove off into the sunset in. After the ceremony, the florists draped the garland over the front of the car to add to the Italian ambience. "The little Cinquecento is an all-time favorite," the bride says.

At the conclusion of their intimate nuptials in Italy, Leila and Joel were off to Portugal for a two-week honeymoon.

Photography, Erich McVey

Location, Dimora Buonriposo Farmhouse

Catering, Cake, and Rentals, Roland's Social & Business Catering

Flowers, Le Petit Jardin

Videography, Elysium Productions

Stationery, Paper Moss

Bride's gown, Elizabeth Fillmore Bridal 

Bride's shoes, Gianvito Rossi

Hair & makeup, Adrienne Aereboe

Groom's suit, Suitsupply

Groom's shoes, Saks Fifth Avenue

Wedding bands, APS Jewellery; Bella Bijou Fine Jewelry