It all began over a coffee. In the shivering heart of early 2021, Chicago was locked in the grip of a pandemic “second wave.” Indoor dining was a memory, and the wind off Lake Michigan was biting. But for Stephanie and Adam, this was the setting of a first date from Hinge that morphed into a marathon. They walked for hours, bundled in heavy coats, talking so incessantly that the frost on the pavement seemed to melt beneath their boots.

That winter walk was the first step on a path that would eventually lead them 4,800 miles away to the rolling hills of Tuscany. In September of 2024, the couple stood on the grounds of Tenuta di Artimino, proving that the best adventures are those shared with the person who makes you forget the weather.

The Vision: Why Italy?

For Stephanie, an Italian wedding was a childhood dream held close to the vest. But for Adam, the destination represented something more profound: growth. Before meeting Stephanie, Adam had never left the United States. Their first international trip together was to Italy, a journey that shifted his perspective and became the cornerstone of their partnership.

“Travel has been meaningful for us ever since,” the couple explains. “Celebrating our wedding in Italy felt natural, but we also wanted to share that sense of discovery with our families. Many of Adam’s relatives had never been to Europe, so we viewed the wedding not just as a day, but as a week of togetherness and shared adventure.”

To ensure their loved ones could maximize their time abroad without exhausting their vacation days, Stephanie and Adam made a strategic move: they chose a Tuesday. A mid-week celebration allowed guests to spend the preceding weekend exploring Florence or Rome and the following days winding down, creating a vacation-wedding hybrid that felt intentional and unhurried.

The Venue: The Villa of a Hundred Chimneys

The search for the perfect backdrop led them to Tenuta di Artimino, a UNESCO World Heritage site also known as the Villa La Ferdinanda. Built in 1596 as a hunting lodge for the Medici family, the estate is famous for its distinctive chimneys and sprawling olive groves.

Finding the venue was a stroke of serendipity. Two close friends, John and Julia, had visited the estate previously and insisted it was the only place that could match the couple’s vision. “We needed a location large enough for our group but flexible in case plans changed,” says Stephanie. “The venue worked wonderfully, though its historic layout created one of our only logistical hurdles.”

Upon arrival, the couple realized that while the Villa provided a regal check-in point, half of their guests were staying in the Paggeria Medicea, the charming village apartments across an olive grove. With only one golf cart ferrying luggage back and forth, the process slowed to a Tuscan crawl. Their advice to future couples? “Plan your check-in logistics carefully, especially if guests arrive all at once by bus. Rent an extra vehicle if you have to; it’s the first impression of the entire experience.”

The Details: Understated Elegance

When the big day arrived, the aesthetic was one of “refined restraint.” Working with Lilla Florals, the couple chose to let the Renaissance architecture and the silver-green leaves of the olive trees do the heavy lifting.

Personalization, however, was woven into every corner. Adam’s sister, Amanda, hand-crafted custom welcome bags for every guest, stocked with local snacks, water, and essential “hangover-recovery” kits. During the cocktail hour, guests admired a custom portrait of the venue painted by a family friend, a piece of art that now hangs in the couple’s home as a permanent window back to Tuscany.

The fashion was equally timeless. Adam donned a sharp Giorgio Armani suit, while the bridal party looked effortless in Azazie and Macy’s, blending a touch of American style with the high-fashion atmosphere of Italy.

The Vows: A Family Affair

The ceremony was an intimate production led by those who knew them best. Adam’s brother-in-law, Ryan, stood at the altar as the officiant, while nieces Brooklyn and Emersyn served as flower girls, their laughter echoing against the ancient stone walls.

The most poignant moment came when Stephanie and Adam exchanged their self-written vows. “We initially considered exchanging them privately,” they admit. “But ultimately, we chose to share them with the loved ones who had traveled from around the world to be there. It felt right to let them into that private world we’ve built since that first walk in Chicago.”

The Secret Moment: A Balcony and Prosecco

While the reception, catered by Delizia Ricevimenti, was a whirlwind of music, lights, and celebration, the couple’s favorite memory happened in the quiet gaps of the schedule.

“As natural introverts, we knew we needed a second to breathe,” Adam recalls. After the formal photos were finished, the two slipped away to their room. They sat on a private balcony overlooking the valley, glasses of prosecco in hand, and took thirty minutes of absolute silence to soak in the fact that they were finally husband and wife.

Reflections from the Hills

Looking back, the couple credits their seamless experience to their planning team, Lisa and Lucy with Elegante Weddings & Events. While Lisa managed the local vendors with a calm energy that the couple found infectious, Lucy navigated the labyrinthine process of the Italian marriage license, making the legalities feel like a minor footnote rather than a stressor.

Stephanie’s parting wisdom for destination brides? “Having the venue and guest accommodations in the same place changed everything. No transportation to coordinate, no rushing. If a guest needed to freshen up or grab a jacket, their room was right there. It made the whole day feel like a relaxed house party in a palace.”

As the sun set over the Tuscan hills on that Tuesday in September, Stephanie and Adam sealed the start of a lifelong journey that began with a cold walk and ended in the warmth of the Italian sun.