By Nora Sullivan
November 9, 2026
For many couples, the journey to the altar is a long, winding road of coordination, guest lists, and venue tours. But for Taylah and Jason, whose love story spans across continents, the destination was always going to be something out of the ordinary. In a breathtaking celebration that blended old-world Italian romance with deeply personal touches, the couple tied the knot surrounded by just 12 of their nearest and dearest. Traveling all the way from Australia and New Zealand, their small circle of family and friends gathered at the magical Villa Montanare in Cortona, Tuscany, for a wedding that felt less like a traditional large-scale production and more like an intimate retreat into a shared dream.
The path to this sun-drenched Tuscan hillside began in August 2024, when Jason orchestrated a proposal that turned an already sentimental milestone into a cinematic memory. Jason carefully planned an entire evening centered around The Westin Hotel, the exact location of the couple’s very first date. Upon checking in, the couple was greeted with chilled champagne. Unbeknownst to Taylah, a more profound surprise awaited behind the door of their hotel room. When she turned the handle, she stepped into a space decorated with cascading roses, gourmet chocolates, and another bottle of champagne.
While taking in the romantic setup, Taylah turned around to find Jason down on one knee. Overwhelmed by sheer surprise, the first words out of her mouth were a bewildered, “Are you doing it now?”—a lighthearted moment the couple still laughs about. Jason then looked at her and delivered a heartfelt promise: “Taylah, you are the person I want to spend the rest of the life with, to laugh and cry with. Will you marry me?” Despite the initial shock, tears, happiness, and excitement, Taylah eagerly said yes. The newly engaged pair spent the rest of the afternoon basking in their own private bubble, celebrating the promise of forever before heading downstairs for a celebratory dinner and drinks. Reflecting on the day, Taylah noted it was the most perfect setting with her favorite person, one she would choose over and over again.
When it came time to plan the wedding itself, the aesthetic vision was clear: romantic, elegant, and intimate. Yet, translating that vision into a physical reality brought its own set of surprises, particularly when it came to the bridal fashion. Taylah had long harbored a specific dress style in mind and even mapped out a boutique known for carrying similar designs. However, after trying on that initial concept, she quickly realized it simply did not suit her. Walking out of the store, she felt a momentary wave of confusion regarding what she actually wanted.
Fortunately, her mother spotted another bridal boutique just down the road and suggested they pop in for a look. As luck would have it, the store had a last-minute cancellation, opening up a slot for Taylah to try on gowns. Rushing through the racks, they pulled out every style that caught their eye until Taylah spotted a dress that immediately commanded her attention. Before even stepping into it, she knew it was the one, drawn immediately to the unique texture of the fabric, the lace-up back, and the drop waist.
As the seamstress laced her into the gown, Taylah caught small, fleeting glimpses of herself in the mirror. When she finally turned around to face her full reflection, she felt a wave of emotions—beautiful, elegant, graceful, and, above all, more like herself than ever before. When the fitting room curtain finally opened, there were no words spoken by her mother and sisters; instead, the room was filled with silent sobbing, a universal sign that the search was finally over. The gown was none other than The Alby Lace Up Jacquard Dress by Pronovias.
On the wedding day itself, the enchanting grounds of Villa Montanare provided a historic backdrop for every phase of the celebration. The day began with deeply emotional moments shared before the ceremony even commenced. As Taylah prepared to walk out, her father came up for a first look. Turning the corner of the stairs, a man typically of very few words could only manage a quiet, heartfelt “wow.” At the exact same time, Taylah’s mother was on FaceTime with another sister who was unable to make the long journey from Oceania, ensuring she could still be an active part of the monumental morning.
The ceremony unfolded in the romantic olive garden of Villa Montanare, soundtracked by a carefully curated playlist that underscored the emotional weight of the day. As Taylah made her entrance, the garden echoed with the gentle strains of Stephen Sanchez’s “Until I Found You.” During the box ritual, Billie Eilish’s “Birds of a Feather” played softly, while Ed Sheeran’s “Best Part of Me” accompanied the formal signing of the papers. As the newly married couple recessed back up the aisle, Alex Warren’s “Carry You Home” signaled the joyous start of their married life.
Following the ceremony, guests moved to the poolside for a rich cocktail hour featuring an extensive array of finger foods. Providing the auditory backdrop for the afternoon, musician Salvo Falcone serenaded the group with acoustic guitar and vocals, elevating the unreal Tuscan scenery into something truly unforgettable.
One of the most touching unscripted moments of the cocktail hour involved the wedding’s photographer, Linda. Choosing to spend her birthday behind the lens to capture Taylah and Jason’s big day, the couple decided to turn the tables on her. They brought her up from behind the camera and onto the dance floor, leading the small group of guests in a heartfelt rendition of “Happy Birthday” to celebrate her dedication and artistry.
As evening descended over the hills of Cortona, the reception transitioned to a romantic dinner held underneath the dreamy wine pergola of Villa Montanare. The tablescape was anchored by stunning floral centerpieces arranged inside ceramic vases, while floor arrangements greeted guests at the gift station. The floral design throughout the day was anchored by loose, organic arrangements featuring white dahlias, white roses, white delphinium, white lisianthus, white cosmos, clematis, alstroemeria, and sweet pea. Jason wore a complementary boutonniere of white blooms and greens, while the ceremony space was framed by two large floral urns alongside delicate arrangements lining the aisle and marking the chairs.
The culinary experience for the 12 guests was an authentic exploration of Italian flavors. The multi-course menu featured ravioli stuffed with Pecorino di Pienza, followed by tagliolini tossed with confit cherry tomatoes, burrata, and crystallized basil. For the main course, guests enjoyed Chianina fillet paired with Syrah and rosemary-infused potatoes.
To conclude the meal, the couple opted for a classic Italian wedding tradition: a live, show-stopping preparation of a Chantilly cream Mille Feuille, assembled directly in front of the guests.
As a parting token of appreciation, Taylah and Jason treated their guests to custom wedding favors that leaned heavily into the local terroir. Each guest received a bottle of homemade, organic Limoncello crafted exclusively from lemons grown at Villa Montanare. To display the bottles, Weddings by Silke utilized an antique wooden bread bowl, presenting the homemade gifts alongside the candlelit dinner table in a manner that honored local craftsmanship.
Looking back on the weekend, the couple expressed profound gratitude for the seamless coordination and warm atmosphere provided by their planning team, led by Silke and Andreas. In a note echoing the sentiments of many destination wedding couples still caught up in the magic of their memories, Taylah and Jason shared that they are still dreaming of their perfect day, wishing they could return to the rolling hills of Tuscany for just a little longer.
