When Molly and Shawn began envisioning their wedding day, their priorities were refreshingly simple: they wanted the food to be delicious, they wanted plenty of it, and, above all, they wanted their guests to feel entirely pampered. Set against the breathtaking backdrop of the Italian countryside at Villa Montanare in Cortona, Tuscany, their multi-day wedding celebration unfolded like a movie, blending effortless elegance with the warmth of a traditional Italian family dinner.
Designed, styled, and planned by Weddings by Silke—the creative force that also owns the enchanting Villa Montanare—the weekend-long festivities felt like an immersive destination experience rather than a single afternoon event. From personalized welcome notes and curated wine tastings to a vibrant pizza party and a deeply emotional cliffside ceremony, Molly and Shawn crafted a celebration that prioritized connection, comfort, and culinary excellence.
A Warm Tuscan Welcome and Pre-Wedding Festivities
The celebration began long before the official wedding day. Molly and Shawn welcomed their guests to Italy days in advance, greeting them with meticulously assembled welcome bags and handwritten love notes awaiting them in their hotel rooms. The thoughtful hospitality set the tone for a weekend where guests were pampered from beginning to end.
The pre-wedding itinerary immersed attendees in the rich culture and charm of Tuscany. On Wednesday, guests enjoyed a fun-filled wine-tasting tour complete with a traditional lunch. By Thursday, the group gathered for an informal welcome dinner on the dreamy terrace of La Loggetta restaurant in Cortona.
The official wedding weekend kicked off on Friday with a vibrant Welcome Pizza Party at Villa Montanare. The evening featured a striking all-white dress code, bold flowers in shades of pink, magenta, yellow, orange, and white, and decorative lemons that instantly signaled a warm Tuscan welcome. Cream-and-sage striped tablecloths, sage-colored napkins, woven bistro chairs, charger plates, candleholders, napkin rings, table lamps, antique silver cutlery, and Provence glassware created a rustic yet refined aesthetic tailored for the occasion.
A Feast to Remember: Food and Drink in Italy
Food was central to the couple’s vision for the wedding. Rather than opting for a complicated or overly curated menu, Molly and Shawn sought to capture the feeling of an authentic Italian meal—where the dishes keep coming, the wine flows freely, and conversations deepen as the night wears on.
The culinary journey began at the welcome area, where guests were treated to fresh skewers of watermelon and feta, as well as peach and mozzarella, accompanied by Aperol Spritz, Prosecco, and infused water.
This transitioned into a rich cocktail hour featuring classic Tuscan specialties. Guests enjoyed hand-cut ham, Caprese finger food, Parmigiana bowls with salad, salsiccia, focaccia, a cheese board, grissini, salmon, and panzanella, all supported by an open bar.
At the dinner table, guests were served a carefully crafted menu that included tagliolini with lemon and pink pepper, handmade pici pasta with Tuscan ragù, and “Marry Me” chicken breast served with a dried tomato sauce. For dessert, an assortment of sweets and fresh fruits accompanied a two-tier white strawberry Mascarpone wedding cake.
Beverages flowed continuously from an open bar, featuring signature cocktails tailored to the couple: an Aperol Spritz chosen by Molly, and a Gin and Tonic chosen by Shawn.
Florals, Decor, and Romantic Elegance
The flowers and decor across both event days showcased distinct color palettes while maintaining a cohesive, highly intentional design where every detail was thoughtfully chosen.
For the wedding day itself, the couple envisioned a romantic soft pastel palette featuring light blue, blush, yellow, lilac, and white. The arrival welcomed guests with a simple golden stand featuring a floral garden rattan vase underneath and elegant centerpieces.
The ceremony took place on the highest shaded terrace of Villa Montanare, offering open, panoramic views of the Tuscan landscape. An asymmetrical layered arch was designed to frame the view without obstructing the scenery. Flower compositions lined the aisle and were placed behind the chairs, completing an intimate and serene setting. As a touching personal detail, a sash was placed on the chair next to Shawn’s mom during the ceremony to reserve a seat honoring Shawn’s deceased father.
The cocktail hour continued the aesthetic with stunning views, a fancy golden mirrored bar corner complete with bar menus, personalized drink stirrers, and copper bar accessories. Timeless Toile de Jouy tablecloths added a refined design touch. An impressive Prosecco tower stood as a picturesque centerpiece, surrounded by a ground floral garden against the backdrop of Villa Montanare.
As a playful nod to vintage elegance, the couple departed in a rare white vintage Autobianchi Stellina, which doubled as a charming prop for photos during the cocktail hour.
Dinner and dancing took place in the dreamy olive garden, "Giardino Paradiso." Guests were guided by a charming seating chart set within a rattan flower garden. The dining tables featured Toile de Jouy linens, elegant ‘800 wooden-accented chairs, and glass vases of varying sizes holding centerpieces. Romantic, delicate glassware and light blue calligraphed rolled place cards lent an airy, light quality to the setting.
As a parting gift, guests received bottles of handmade, biological Villa Montanare olive oil placed on cream porcelain charger plates with golden accents, matching the golden cutlery. As night fell, fairy lights strung through the olive trees cast a romantic, heavenly glow over the reception area.
An Emotional Ceremony and Personal Touches
The ceremony was anchored by the celebrant, who beautifully narrated the couple’s love story and spoke on the meaning of marriage. Among the deeply personal elements was a ring warming ceremony—a tradition new to many in attendance.
Before reaching the bride and groom, the wedding bands were passed individually among the guests. Each person held the rings for a brief moment to offer a blessing, a prayer, or a well-wish for the couple’s future. By the time the rings reached Molly and Shawn, they had been physically held and blessed by every guest present, adding profound emotional weight to the intimate gathering.
Music played a vital role in setting the tone. All ceremony selections were performed live on harp and violin. Molly walked down the aisle with her father to a timeless and emotional rendition of "Canon in D." Following the ceremony, the newly married couple exited to Bruno Mars’s upbeat track "Marry You," transitioning smoothly from the emotional weight of the vows to a joyful celebration.
Reflecting on the wedding weekend, Molly noted that while the setting, food, and design details were extraordinary, the true magic lay in the people. The evening featured heartfelt speeches and toasts from lifelong friends and family members who reflected the couple’s journey back to them.
Sharing their gratitude after returning home, Molly and Shawn expressed their appreciation to Weddings by Silke, noting that friends and family continued to describe the celebration as feeling like something straight out of a movie.
