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A Vibrant Retro Wedding in a Charming Portugese Castle

A Vibrant Retro Wedding in a Charming Portugese Castle

Where effortless love, nostalgic style, and pure joy collide

A Vibrant and Playful Wedding Under the Portuguese Sun

Caitie and Andrew celebrated a love story as unique as they are in the mesmerising surroundings of Portuguese nature and atmosphere. The ceremony itself was a breath of fresh air: lighthearted and engaging, it struck the perfect balance between sentiment and playfulness. The reception that followed was less about grandeur and more about connection – an elevated dinner party where family and friends felt truly at home. Caitie radiated elegance in her delicate off-shoulder dress and chic Jacquemus pumps, while Andrew turned heads in a bold ochre yellow suit. Together, they were the embodiment of effortless style and charm, setting the tone for a celebration that was as relaxed as it was unforgettable. Delight in a heartfelt interview with the bride and marvel at the exquisite floral arrangements crafted by the talented hands of our member, Oh, Maria Flores.

A Vibrant and Playful Wedding Under the Portuguese Sun

Our Love Story

^{The Day We Met}

We met in late 2016 through Bumble and on a crisp fall Sunday in Brooklyn, Andrew took it offline for drinks at Goldie’s, a cozy bar with quirky vintage Vegas charm—velvet paintings of Dolly Parton and the Rat Pack, a horseshoe bar strung with gold tinsel, and cozy tufted booths. Unbeknownst to each other, we both lived within five minutes of the bar, and our date quickly turned into bonding over our shared love for our Greenpoint neighborhood. We have been attached at the hip ever since.

^{The Proposal}

In 2022, Andrew planned a surprise long-weekend trip masked as a birthday celebration to keep me off the scent of a long-awaited proposal. The getaway to Portugal spared no detail—staying at a Douro Valley retreat by designer Pierre Yovanovitch, a private boat excursion, wine tastings, and a mountain top picnic. Despite a weekend full of romantic moments, Andrew waited, leaving Caitie sure the proposal wouldn’t come. Back in Porto the night before their return home, Andrew took Caitie to her favorite restaurant, Mistu. After dinner, Caitie was ready to call it a night, which torpedoed Andrew’s plan to pop the question on the picturesque banks of the Douro. Improvising and with Caitie’s guard fully down, he proposed back in the hotel room, where sparkling wine and flowers awaited.

^{The Engagement Ring}

Andrew collaborated with Caitie's best friend, jeweler Mariah Thornton, to custom design her original engagement ring. It featured a vintage tapered baguette diamond paired with a green-blue sapphire. Unfortunately, the ring was stolen just a few months later. Determined to create a meaningful replacement, Andrew, Caitie, and Mariah collaborated again to design a new ring, paying tribute to the original with another vintage tapered baguette diamond. The custom wedding bands were designed to nest with the engagement ring while having negative space around it. The bands feature heirloom diamonds and a green sapphire.

Our Wedding

^{The Vision}

We envisioned a wedding that celebrated the unique spirit of our love, spread across multiple days to create a seamless blend of connection and joy. From the welcome party to the main event and a laid-back pool party the following day, each moment was crafted to be memorable yet effortlessly enjoyable. Avoiding the trappings of formality, we aimed for experiences that felt distinctly ours, inviting friends and family into a weekend where the focus was on warmth, fun, and relaxed togetherness.

^{Our Team of Vendors}

Guided by our desire for a celebration that was fun, authentic, and true to us, we chose vendors who shared our vision and connected with us easily. We wanted not only our guests to revel in the experience but our team to feel inspired and fulfilled as they brought our dream to life. Ramone’s photography, with its vibrant, non-traditional style, was an instant match. As an interior designer, for Caitie, amazing floral design was essential, and Maria (Oh, Maria Flores) understood her vision seamlessly. Marta and Antonio from TwoPack elevated the dining experience with local flavors and open-fire cooking. When it came to music, Benga from Your Jukebox navigated our particular tastes and kept us dancing until dawn. Fernanda, our wedding planner, easily grasped our desired vibe and seamlessly brought all the component parts together into a cohesive, well-oiled production.

^{The Location}

Portugal had been the backdrop for so many cherished memories that choosing it for our celebration felt natural. Andrew discovered Castelo Ventoso on a Dutch luxury rental site, and we were fortunate they agreed to host their first-ever wedding. We sought a venue that was relaxed, offered on-site accommodation for a number of guests, and featured varied spaces to guide the day’s flow. Most importantly, the property harmoniously fused history and modernity, with restored elements from its time as a Jesuit monastery complemented by contemporary comforts.

^{The Ceremony}

We wanted our ceremony to feel anything but conventional—lighthearted and engaging, with our guests as participants rather than mere observers. To create that atmosphere, we arranged the seating in-the-round and greeted everyone with sparkling wine and our own quirky take on waiting room music. Lauryn, Caitie’s sister, kicked things off with a soulful acoustic cover of the Talking Heads' This Must Be the Place.

Our very dear friend Jake Szymanski officiated, delivering a warm and whimsical ceremony. In one delightful twist, he placed ribbons on three random chairs, inviting those guests to step forward and help create a wedding cocktail—each contributing a symbolic ingredient to our cups, offering a bit of liquid courage before the vows. It was a perfect balance of sentiment and playfulness, setting the tone for a joyful celebration and a seamless transition into cocktail hour.

^{The Reception}

Our cocktail hour took place by the pool, with sweeping views of the cork trees and the sun setting softly in the distance. Dinner was set up just behind the house, nestled in front of the dance floor. We wanted the evening to feel like an elevated dinner party—relaxed and intimate—so we opted for a long communal-style table and family-style service. TwoPack truly impressed us, expertly blending innovative techniques with the rich flavors of traditional Portuguese ingredients. To this day, we're still dreaming of that wood-fired roasted pork belly!

^{The Special Touches}

With a smaller guest list, we wanted our invitations to be unique and evocative of Portugal. Instead of traditional stationery, we sent hand-poured candles in sardine tins. Our talented friend and artist, Shane McClatchey, collaborated on the graphics for the wrapper and tin tops, subtly incorporating elements from Castelo Ventoso. Along with the candles, we included custom matchbooks, hoping our guests were the first to burn their invitations—for all the right reasons.

Andrew's mom has a legendary talent for crafting outlandish Halloween costumes, and one of her most memorable creations from his childhood was a magic chicken, complete with a pickle-on-a-stick wand. Inspired by Andrew’s ochre yellow wedding suit, she surprised us (and embarrassed Andrew) by recreating the iconic pickle wand for the occasion. It served as an impromptu symbol of blessing during the ceremony—and, as the night wore on, became a makeshift limbo stick on the dance floor.

^{Our Favorite Moment}

It's a tie between watching the wide-eyed confusion and nervous hands of our three unsuspecting ceremony bartenders as they crafted our symbolic Negronis, and witnessing Andrew’s 90-year-old grandmother steal the show on the dance floor, putting everyone else to shame. Both had us grinning from ear to ear.

A Vibrant and Playful Wedding Under the Portuguese Sun

Our Style

^{The Bridal Looks}

Finding the perfect wedding dress was more challenging than expected. I didn’t have a clear vision, but I knew I wanted something unique, timeless, and comfortable—without too much fuss. After months of searching, I came across The Brooklyn Dress from NewWhite. When I tried it on, it fit like a glove, was incredibly comfortable, and in that moment, I knew I had found exactly what I didn’t know I was looking for. Rather than a traditional veil, I opted for a long organza empire skirt—something I could easily remove to stay comfortable throughout the day but still adds some additional texture and layer. My best friend and jeweler made all of my jewelry with the exception of vintage pearl earrings from Andrews mom she got in Japan almost 40 years prior!

Though I hadn’t initially planned for an after-party dress, meeting Alice changed everything. I knew I had to work with her. We dove right into exploring the Garment District in NYC, spending hours poring over incredible textiles. After much deliberation, we chose a striking chainlink sequin fabric—remarkably heavy, with just the right amount of bounce. I felt like a human disco ball as we draped the very last bit of fabric they had left. It was just enough! Alice’s talent blew me away. She took my measurements, created a 3D model of my body, and applied the fabric digitally so we could see exactly how it would fall before she went to town with her scissors. The result was pure magic– it literally lit me up! I couldn't wait to slip into the dress and race back to the dance floor, ready to keep the party going. It was a hit–and quite the workout!

^{The Groom Looks}

Andrew curated his welcome party outfit around a custom "seed packet" shirt by kpc., an independent designer known for crafting garments from carefully sourced deadstock fabrics. He paired it with tailored trousers from Knickerbocker and fisherman sandals by Jacques Solovière. Avoiding tradition and formality, Andrew sought a wedding suit that was playful yet refined. He found it in the bold color and dramatic lapels of his Giuliva Heritage ensemble. Paired with a breezy silk shirt from Post Romantic Co. and Carmina loafers, the outfit exuded laid-back sophistication. A vintage Longines watch, a gift from his late father, added sentimental flair, while all custom jewelry by Mariah Thornton completed the look.

Our Advice

^{For The Planning Process}

Choose a planner you truly vibe with. We were fortunate to collaborate with Fern, whose understanding of our vision from the start was invaluable. She played a key role in keeping our stress at bay while ensuring everything ran smoothly. Above all, remember to have fun and make choices that reflect your style, rather than feeling bound by tradition. We loved bending a few wedding conventions, surprising our guests, and infusing personal touches that made the day feel like a genuine reflection of who we are.

^{For On The Day}

First piece of advice: if writing your own vows don’t leave them until the last minute! We both wrote ours, but somehow procrastinated until the morning of. While the context helped inspire the right words, it did steal a bit of the opportunity to ease into the day. Beyond that, just try to relax and stay present. Time really does fly—before you know it, the day is over in the blink of an eye. It doesn’t have to be flawless to be unforgettable, so let go of the pressure and just enjoy the moment.

^{For Post-Wedding}

We didn’t want the magic to end the moment the wedding did, so we invited our guests to unwind with us at a relaxed recovery party by the pool. We then extended the celebration with a weeklong “buddymoon” at Casa da Volta, a stunning villa nearer to the coast, surrounded by 10 of our closest friends. It was the perfect blend of relaxation and continued good vibes, allowing us to savor the warmth and excitement of our wedding long after it ended.

A Vibrant and Playful Wedding Under the Portuguese Sun