An Unforgettable Destination Wedding at Montestigliano Estate

Set amidst the rolling hills of Tuscany, Simona and Jim’s wedding at MONTESTIGLIANO was a breathtaking celebration of love, culture, and timeless romance. With deep ties to Italy and a shared love for adventure, the couple crafted a multi-day experience that seamlessly blended elegance with warmth, ensuring every guest felt part of their story. Stunningly captured by ADRIAN PHOTOGRAPHERS, they had this to share with us, “It was as though we stepped right into a magical Tuscan movie. We started with private vows on Gambier Island, off the coast of Vancouver, and ended with a three-day Italian celebration on the hilltop of Montestigliano in Tuscany, Italy. When talking with Simona and Jim about their Italian destination wedding, they wanted a natural Italian experience, which made Montestigliano the perfect fit. The preserved villas, natural farm property, and magnificent rolling hills overlooking breathtaking Tuscany were the perfect backdrop for such an occasion. The talents of The Knights Club kept a great flow to the wedding day and gathered everyone together effortlessly, regardless of the language barrier between their family and friends. The combination of location, florals, and good company made for a quintessential “pinch me” experience that gave Simona and Jim a wedding most dreams are made of.”

The wedding day began in the most relaxed and sentimental way. Simona and Jim shared a slow morning together, enjoying coffee and pastries on the patio while taking in the countryside. As the preparations began, Jim gathered with his father and closest friends for celebratory drinks before getting dressed. Meanwhile, Simona joined her mother, maid of honor, and closest girlfriends at another villa. She shared heartfelt thank-you cards, and the group shed a few happy tears while reminiscing about their journey together.

Dressed in an elegant and airy ANNA KARA gown, Simona radiated timeless beauty. Jim looked effortlessly stylish in a linen suit—perfectly suited for the warm Italian summer evening. The couple opted for a first look beneath the venue’s grand maritime pines, creating a truly intimate moment before the festivities began.

Simona and Jim’s journey began in early 2020, when, after a few socially distanced dates, they quickly became inseparable. “We spent so much quality time together that it quickly became clear we were meant to be from the start,” Simona shares. Their proposal story is just as special—so much so that it happened twice.

The first, an impromptu moment on a mountain peak facing Mt. Assiniboine in British Columbia, Canada, was where the couple had fallen in love years before. Without a ring but caught in the perfect moment, Jim proposed with a delicate flower, making for an unforgettable and intimate experience. The second proposal, more traditional yet equally magical, took place on a rugged beach in Tofino, BC, with a beautiful ring in hand as the waves crashed along the shore.

The ceremony was held outdoors, overlooking the breathtaking olive groves and rolling hills of Tuscany. Wanting to ensure all guests felt included, the couple had a bilingual celebrant officiate in both Italian and English. Close friends and family shared readings, adding personal touches to the heartfelt vows.

As the warm Tuscan sun filtered through the clouds, the setting was picture-perfect—a true reflection of the love and connection shared between Simona, Jim, and their loved ones.

Choosing MONTESTIGLIANO as their venue was deeply personal. With Simona’s entire family living in Italy, the couple wanted a wedding that felt like an authentic Italian experience for their guests. The 18th-century Tuscan estate, with its olive groves, vineyards, and breathtaking views, provided the perfect backdrop for their dream celebration.

Accommodating all 70 of their guests, the hilltop hamlet allowed for an immersive, multi-day wedding experience, where friends and family could soak in the beauty of Tuscany while celebrating love.

Following the ceremony, the newlyweds joined their guests for a lively aperitivo in the lush gardens, where an incredible spread of Italian delicacies awaited. A chef carved fresh prosciutto, while guests sipped on fine wines from the property and the Piedmont region, where Simona grew up.

The reception, set in the charming stone plaza of Montestigliano, was nothing short of a fairy tale. Long tables adorned with creamy peach-hued florals and candlelit ambiance created a romantic atmosphere, as guests indulged in a multi-course traditional Italian feast.

One of the highlights of the evening was the entertainment. The live band, THE KNIGHTS CLUB, set the tone for an unforgettable night, alternating between Italian and English songs. “When they played ‘Nel Blu Dipinto di Blu’ in the middle of dinner, every guest stood up, formed a circle, and sang along—it was a moment we’ll never forget,” Simona recalls. The energy carried on into the night, with a DJ keeping the dance floor alive well into the early hours of the morning.

The celebrations didn’t end there. The following day, the couple hosted a relaxed poolside party, complete with a charming gelato cart serving artisanal Italian gelato—one of the best the newlyweds had ever tasted.

After their dream wedding, Simona and Jim embarked on an extraordinary four-month honeymoon, traveling from the sun-drenched beaches of Sardinia to the breathtaking landscapes of New Zealand. Highlights included the island of Madeira, an overwater bungalow experience in Bora Bora, and exploring both islands of New Zealand, making for an adventure of a lifetime.

Their wedding at Montestigliano was more than just a single day—it was a deeply meaningful experience that brought together loved ones from across the globe to celebrate in true Italian style. From the heartfelt ceremony to the unforgettable music and exquisite cuisine, Simona and Jim created a wedding that perfectly reflected their love story—a blend of adventure, romance, and the beauty of Italian culture.