In a professional and transactional setting, Stephanie and Taro’s introduction to one another was seemingly mundane in the moment. But, of course, this is a story about a dreamy, fairytale-like destination wedding uniting two wonderful souls in none other than Tuscany, Italy. As a result, one can assume this meeting was, in hindsight, quite serendipitous. “We actually met on a transaction; I was a lawyer advising [a company] on a transaction where my now wife worked on the private equity investment team,” the groom explains.

From the beginning of Steph and Taro’s journey to the altar, all signs pointed to Italy as the ideal place to tie the knot. Not only did the couple celebrate five years of dating in this wine-lover’s paradise, but the groom had developed a fondness for the Italian countryside through his father’s work in the hospitality industry.

The choice to wed at Castello del Nero came out of Taro and Steph’s desire to honor their shared Singaporean origins. “The Castello del Nero is owned by COMO Hotels, a Singaporean hospitality group,” Taro tells us.

Inspired by the soft colors that paint Tuscany’s hillsides, the design of this wedding weekend featured “blush, dusty peach, butter yellow, sage, and a whisper of sky blue, all layered over natural textures,” Steph explains. Long wooden tables were set with stonewashed linen runners, terracotta details, and clusters of taper candles rising at varied heights. The florals captured the romance of an Italian garden just before sunset: “airy arrangements of garden roses, ranunculus, sweet peas, and lisianthus, threaded with olive branches and rosemary for that subtle Mediterranean scent.”

Personalization played a starring role, woven into the tactile details their loved ones would interact with throughout the weekend. “We designed a watercolor crest with cypress and olive sprigs and carried it through the invitation suite, bar menus, and welcome notes,” the couple says. Their escort display doubled as a heartfelt favor, mini bottles of extra-virgin olive oil topped with wax-sealed, hand-calligraphed tags, nestled into vintage wine crates. Even the smallest details were made with love: “At each place, we DIY’d hand-painted ceramic ‘tile’ place cards in pastels to echo Tuscan floors.”

The ceremony itself offered an inspirational blend of tradition, heritage, and personal significance. “We incorporated a traditional tea ceremony that honored elements of our Singaporean Chinese heritage,” the couple shares. This grounding moment of cultural reverence stood alongside a unique family tradition: Ferraris. “To celebrate the family’s love and collection of Ferrari, we arranged a Ferrari tour; my father and groomsmen drove to and from Castello del Nero to Brioli Castle through the hills of Chianti.”

And, of course, the wine choices carried meaning too. Guests were served Rinaldi’s Barolo 2019, selected not only for its pedigree but also for its symbolism. “This wine is special because 2019 was the year we met, and the wine is from a top producer from the Piedmont region, where we celebrated our 5th anniversary,” Taro explains. They even procured the wine directly from a cherished restaurant in Langhe, Trattoria La Coccinella, another nod to the chapters of their love story written across Italy.

One of the most sought-after regions for destination weddings, Tuscany certainly came with planning challenges, but Steph and Taro found two key decisions that transformed the process completely. “Planning from afar, two things changed everything: partnering with a local planner and doing a pre-wedding site visit with an overnight stay,” they say. That single trip brought clarity to decisions that once felt abstract. “Being on the property let us walk the exact ceremony route, feel the light at the hour we’d be saying our vows, listen for evening noise, and time the shuttle from our host hotel.”

Their visit became a catalyst for efficiency. They met vendors face-to-face, refined expectations, conducted a mini walk-through, and “finalized the floor plan, menu priorities, rain plan, and portrait locations, all in a single visit.” They even used the stay as a quality-control test for their guests’ experience, evaluating everything from check-in to breakfast. “That short trip saved months of back-and-forth and replaced stress with clarity.”

Looking back, the couple’s biggest insight is one every destination-wedding couple should hear: logistics matter just as much as aesthetics. “Our biggest lesson: treat logistics as hospitality,” they share. Their goal was to make every moment, from arrival to the walk down the aisle, feel seamless. And, as Taro so beautifully puts it, “When guests cross borders for you, every friction you remove becomes a love note.” We couldn’t agree more.

In line with this goal, the bride and groom created a simple “Trip One-Pager” that housed shuttle schedules, dress codes by event, and a custom map. They tracked guest arrivals so their planner could adjust transportation in real time and designated a single point person (not themselves) for guest questions. Their pre-ceremony site visit also taught them the value of planning for real-world conditions: sun direction, shade, wind, ambient noise, power access, and local curfews.

To elevate the celebration even further, the couple found thoughtful ways to weave in joyful surprises and personal passions. A rainbow smoke show punctuated the festivities, followed by an unforgettable ride in a vintage Alfa Romeo Spider. The night closed with a bang, literally, as a shimmering firework display lit the sky above the sprawling estate.

When all was said and done, Castello del Nero became more than a venue in Taro and Steph’s eyes; it became the setting where their past and future intertwined, surrounded by loved ones who had journeyed across the world to celebrate their union. It was elegant, intentional, culturally rich, and deeply personal, everything a destination wedding should be, if you ask us.