A 3-Day wedding weekend in tuscany that started with a pool party

Megan and Douglas met at a work training in 2018, later reconnecting by chance at a Nebraska-Iowa football game. A lighthearted bet (and a 4.5-hour drive) turned into something more, and within months, they were planning a three-week trip through Europe. That journey not only confirmed their chemistry but also led to a cross-country move and the start of their life together in Chicago. Nearly six years later, Douglas proposed during a sunset date night in the city, followed by a surprise celebration with their closest friends.

Their wedding in Tuscany was intimate, intentional, and full of personal meaning. Planned and designed by Eventi Gaia Weddings & Events and hosted over three days at Villa La Selva, the celebration included a sunset welcome party with Italian street food, a poolside DJ dance party, and a candlelit rehearsal dinner under twinkling lights.

The ceremony took place beneath towering cypress trees overlooking the hills, followed by dinner under arched brick ceilings surrounded by flowers by Deep Flowers and chandeliers after a last-minute weather shift. Guests ended the night dancing in the wine cellar to a live DJ and saxophone.

Megan’s looks included several outfit changes, including a custom Viero Bridal gown and a pearl-detailed pool party dress, while Douglas kept it timeless in black-tie.

Every detail—from a tiramisu tower to a classic Italian-style wedding cake—reflected the couple’s thoughtfulness and love for travel, family, and each other.