A Couple and Their 50 Guests Celebrated Their Wedding at a Villa in Tuscany Surrounded by Cypress Trees

Sherry and James might have met at a crowded, loud club in New York City in 2015, but they managed to ascertain that they had several things in common right off the bat; they grew up in the same area, both attended New York University, and even shared a few mutual friends. “It was truly a serendipitous relationship,” Sherry says. “My hometown was also only 10 minutes from his parent’s place, so we had frequented so many of the same restaurants growing up.” Six years in, James’ work relocated the pair to Texas. A few months after their move, they planned a trip back to New York City, and a simple picnic in Central Park with friends turned into one of the most memorable moments of Sherry’s life when James popped the question. “I knew something was up when he started confidently leading me through Central Park, which he usually can’t navigate without Google Maps,” Sherry says. 

When Sherry and James stumbled upon Villa Cetinale in Siena, Italy, on Pinterest, they fell in love with the Tuscan venue’s cypress trees. They asked 50 of their loved ones to join them at the estate for their destination wedding on October 13, 2022. “It was important for us to create a weekend celebrating our love with the closest people to us,” Sherry says. “We wanted to keep it intimate and special.” The couple had to skip traditional food and drink tastings, but they trusted their planners at Weddings in Tuscany to help them pull off an elegant celebration complete with a live cake decorating ceremony and late-night McDonalds. You won’t want to miss the details of Sherry and James’ European nuptials in these photos by Matteo Coltro.

Sherry studied abroad in Florence and had always dreamt of bringing James to Italy, so Villa Cetinale was a dream venue for their wedding day. “Being able to give our guests a unique experience was important and the villa was like none other,” Sherry says. “Every corner of the estate was truly magical.” The pair invited their small group of guests to their nuptials via timeless black and white invitations finished with custom wax seals and envelope liners that Sherry made herself.

On the couple’s wedding day, James wore a classic black tuxedo with a black bow tie from Suit Supply. His boutonnière featured a white flower with sprigs of foliage and greenery, finished with a blush ribbon. Groomsmen matched the man of the hour in classic black; together, the group kicked off the celebrations with a big bottle bubbly and a few toasts.

When Sherry went shopping for her wedding dress, she had a specific vision in mind—but when she tried the gown that matched it on, it didn’t flow the way she envisioned. She tried on a few other options, including a nude glittered tulle gown with a floral lace corset top by Tom Sebastien. “The gown itself was absolutely stunning, but there was one thing missing,” Sherry says. “The sleeves from the original dress that added something unique.” The designer customized the gown and added the sleeves to create Sherry’s dream dress. The bride kept her hair and makeup simple and reflective of her daily style. “I wanted most of my look to be centered around my dress,” she notes.

Sherry shared the wedding's color palette, which included neutrals and blush, with her bridesmaids and asked them to choose dresses they felt great in. Her maid of honor decided on a solid blush gown and the rest of the bridal party wore floral ensembles.

The bride's wedding bouquet included moments of blush and greenery. “I wanted the florals to pop against the colors of our dresses, so I chose mainly blush for mine and white for the bridesmaids,” she explains.

Sherry and James are both introverts, so they knew a first look would help ease their nerves before the ceremony. “It gave us time to ourselves,” Sherry says. “We didn’t get any moments alone throughout the day to appreciate each other, so we were both looking forward to this time.” The couple decided to write a different set of private vows to share with each other during this moment. “It was intimate and special,” the bride says.

As guests entered the garden for the ceremony, they were greeted by a welcome sign that Sherry made. “I would’ve loved to have DIY’d so much more, but having to carry everything across the world restricted me,” she says.

The ceremony took place in the estate’s world-famous garden, where two oversized statues and rows of cypress trees created a feeling of grandeur. An asymmetrical open arch and aisle flower arrangements were all the scenic space needed.

Sherry and James asked their friend, Chris, to officiate their nuptials. “He has always been so supportive of our relationship, so it felt natural to pick him,” the bride says. “He also has a great speaking voice, so that helped in the decision!” Sherry walked down the aisle with both her mom and dad by her side to Haley Reinhart’s “Can’t Help Falling in Love.” When the couple exchanged their vows, Sherry made sure to include a quote from their first dance song.

They newlyweds snapped a selfie with all of their guests before celebrating back down the aisle to “This Will Be (An Everlasting Love)”—a nod to one of Sherry’s favorite childhood movies, The Parent Trap.

At the cocktail hour, guests enjoyed “his” and “hers” signature drinks and grazing tables filled with Italian favorites, including crusty bread, fresh herb crackers, sun dried tomatoes, and olives.

For Sherry and James' reception, one long dinner table was set up on the lawn. The table was covered in a floor-length ivory tablecloth and decorated with a variety of candles, bud vases, and low floral arrangements; flowers that decorated the ceremony aisle were repurposed as floor décor at the base of the table.

Each place setting featured a gold rimmed white plate, white linen napkin, and a sprig of greenery. The couple’s planner added two arched chandeliers and covered the posts in greenery, which ended up being one of the bride’s favorite touches.

Sherry and James made their grand entrance to the reception to Tiesto’s “Split” with their wedding party. Then, James took the spotlight with a solo dance moment as guests cheered him on. “It really got the party started and I could feel everyone getting amped,” Sherry says. “The vibe was everything!”

The couple served a traditional Italian dinner, with two pastas and a steak dish as highlights of their menu. “Different wine was served to complement each course, which was fantastic,” Sherry says. For dessert, they chose a traditional Italian millefoglie wedding cake. “We decorated the cake in front of our guests, filling it with fruits and cream,” the bride says.

Sherry and James took the floor to share their first dance as a married couple to Kygo’s “Firestone.” Then, they danced with their parents to Celine Dion’s “Because You Loved Me.”

The couple hired a sax player to entertain guests during the reception. “One of our core memories was when James took me to a music event where a sax player made a guest appearance,” Sherry says. “It was such a nice touch that we never forgot, so we wanted to share it with our guests.”

A few other reception highlights? Sherry surprised James with smoke guns during the party, which added a whole other layer of fun. The couple's late-night menu was also a hit: When they lived in New York, James would buy Sherry a McDonald’s cheeseburger after every late night out, so they offered guests their go-to fast food as an end-of-night treat. “It was a mission to get it delivered to the middle of nowhere, but our planner made it happen,” Sherry says.

To couples who are in the middle of the planning process, Sherry recommends creating a day that feels special to who you are as a couple. “We had a lot of details that we incorporated that meant something to both of us, whether the guests noticed or not!” the bride shares.