Alex and Carlo’s Romantic Destination Wedding in the Hills of Chianti

For Chicago couple Alexandra (“Alex”) and Carlo, a traditional hometown celebration simply wouldn’t do. Instead, they decided to exchange vows in a place that had long held a piece of their hearts: the Chianti region in the rolling hills of Tuscany.

CHOOSING CHIANTI

Carlo comes from a large Italian family still deeply connected to their roots, with some relatives living just outside Florence. With family ties and countless visits to the region over the years, the couple dreamed of hosting a destination wedding in the heart of the Chianti region. “We always knew how special it would be to create a reason for Carlo’s Italian family to reunite in a place so important to us,” Alexandra shared. With guests traveling from across the globe, the couple set out to create an authentic Tuscan experience that was truly worth the trip.

TUSCAN SCENERY

After a Wednesday welcome party at the Grand Baglioni Hotel in Florence, the Thursday ceremony was hosted at Villa Medicea di Lilliano. Nestled among olive groves and sweeping Tuscan hills, this historic Medici estate-turned-vineyard was the dreamiest backdrop. The black-tie optional affair unfolded amid grand architecture and a storybook landscape, and the couple’s love for Italy was reflected throughout.

TI SPOSERÓ

The ceremony itself took place in the villa’s courtyard, centered around a historic stone fountain. The couple exchanged self-written vows, with celebrant Janneke from Tuscan Pledges delivering part of the service in Italian to honor Carlo’s family. Music played a powerful role throughout the day, especially when a guitarist performed

“Ti Sposeró” during the ceremony. The sweet lyrics — “Tra tutti quei colori… ogni giorno che vivrò, Ti sposerò” /“Among all these colors, every day that I live, I’ll marry you” — brought the couple (and guests!) to tears.

GOOD LUCK RAIN

Although their day turned out to be a rainy one, it became part of the celebration’s charm. “There’s an Italian saying that our family kept reminding us of all day: ‘Sposi bagnati, sposi fortunati!’,” said Alexandra. Loosely translated, it means “Wet bride, lucky bride.” And lucky is exactly how the couple felt. “Despite the rain, we truly felt like the luckiest people in the world. To celebrate our love in the most magical setting and see our vision come to life.”

To contrast the villa’s warm neutrals and lush greenery, the couple chose a vibrant palette of red, coral, orange and white for their florals and decor details. Luckily, the bright blooms popped even more when a pre-ceremony rain shower blanketed the hills in mist and gave the scene an ethereal glow.

CIN CIN!

A terrace cocktail hour set the scene for the rest of the night, as guests sipped Aperol spritzes and Negronis while catching glimpses of Florence’s Duomo in the distance. The dinner that followed was a feast of classic Tuscan fare, curated with Carlo’s culinary sensibilities in mind. As the owner of Chicago’s Offset BBQ, he made sure every bite, like handmade pasta with wild boar ragù and pecorino-pear tortelli, was unforgettable.

For dessert, the couple skipped a traditional cake in favor of a beloved Italian tradition: assembling their own millefoglie. In front of their guests, Alexandra and Carlo constructed this delicate dessert, layering crisp pastry layers, fresh cream and berries.

FULL OF PERSONALITY

With over 30 guests staying in private villas adjacent to the venue and many of Carlo’s relatives nearby, the weekend felt more like an intimate getaway than a single-day event. While the couple may have been far from home, personal touches made the celebration feel uniquely theirs. Cocktail coasters from The Lodge — the bar where Alex and Carlo first met — were used at the bars, while custom napkins featuring hand-drawn illustrations of their beloved dachshund, Henry, added a playful nod to their life together in Chicago. The most sentimental detail of all? Alexandra’s veil, lovingly hand-sewn by her mother over the course of several months.

From heartfelt vows and misty Chianti hills to Aperol spritzes and millefoglie made by hand, Alex and Carlo’s wedding beautifully captured the romance of Italy and the soul of a Chicago love story.

Vendors

PHOTOGRAPHY Marissa Kelly Photography
VENUE Villa Medicea di Lilliano
OFFICIANT Tuscan Pledges
PLANNER Wedding Italy
FLORAL Lilla Florals
HAIR & MAKEUP Valeriya Beauty
BRIDE’S GOWN Ines Di Santo from Ultimate Bride Chicago
GROOM’S FORMALWEAR SuitShop
STATIONERY Jolly Edition
CATERING Guidi Lenci Catering
ENTERTAINMENT & LIGHTING Wedding Music & Lights

Inspired to marry away from home? Check out more stunning destination weddings here!