How We Pulled It Off: A Monastery Wedding With Drag Queens in Sintra, Portugal

Two grooms explain how they found a fado performer, flamenco dancers, and drag queens for their 100-guest celebration in the magical Portuguese town.Hugo CoelhoAs a couple, Taylor Rains and Carter Joyce have a shared sense of romance, particularly as it relates to travel. “Exploring the world has just helped to deepen our relationship,” says Carter. Since meeting online in 2016, they’ve spent their holiday seasons in Belgium hopping around Christmas markets. It was during their 2022 trip that they became engaged. “We got our mulled wine and got on the Ferris wheel in the main market in Brussels, and Carter proposed,” says Taylor. “It took two full rotations of the Ferris wheel for me to pick my jaw up off the ground.”Carter Joyce (left) and Taylor Rains met online in 2016, became engaged on a trip to Belgium in 2022, and knew their wedding had to incorporate their love of travel. Hugo CoelhoIt makes sense, then, that they’d want to have their wedding in a storied venue or a gorgeous destination—or both. Their early research found the Charleston-based duo looking into opulent venues, such as the Biltmore Estate in North Carolina, chateaux in France, and villas in Italy. They realized that plotting a destination wedding would allow them to curate a gorgeous experience for their loved ones.“One of our favorite things to do is share recommendations—these are the restaurants, this is the little cafe, this is the person to ask for—and we saw this as an opportunity to do that on a grander scale,” says Taylor. “We could curate all these vignettes and experiences that you, as our guests, could then enjoy and experience.” Once they viewed their wedding that way, going international was an easy decision.The ceremony was set within the stone walls of a 16th-century monastery in Sintra. Hugo CoelhoAhead, the grooms explain how and why they pulled off their unique 100-guest Portugal destination wedding—which featured a fado performer, drag queens, flamenco dancers, and a ceremony set within the crumbling stone walls of a 16th-century garden—in the magical town of Sintra.Find a planner who feels like a friendWhen they began their planning process, Carter and Taylor weren’t sure about which country they wanted to marry in—yet they knew who they wanted to oversee the wedding. In Taylor’s research of wedding planners who specialized in European destination celebrations, he found the London-based firm Matthew Oliver Weddings, and adored their Instagram feed. “One of our criteria when we were examining portfolios was that every event and every wedding had a unique identity and felt like an extension of the couple,” says Carter. Living in Charleston, the couple are accustomed to seeing cookie-cutter weddings with an established echoing the city, and they wanted theirs to be more reflective of who they are. Matthew Oliver’s events fit that bill. “That alone made them top contenders,” he says.In their first conversation with staff planner Georgia Haldenby, about a year and a half out from their wedding, they knew she was the one. “We all clicked, and she understood us very well,” says Taylor. “We didn’t want it to be a strictly transactional relationship, like ‘Here’s the final invoice, it’s been lovely seeing you.’ We wanted it to feel a friendship.”The grooms enjoy a calm moment with a loved one amidst the busy weekend. Hugo CoelhoA small snag came when the couple had to pause planning due to one of their parent’s health issues. When they came back to Georgia, they were heartbroken to learn she’d booked up the rest of the year. They reluctantly started chatting with her recommendations for another planner—and then they got a happy text “She said, ‘I don't know what voodoo you worked, but one of my couples has canceled and you guys are back on,’” Carter laughs.Check every single possible boxGeorgia’s first order of business was a big one: helping the grooms determine which destination they should choose in the first place. In the months they’d paused their planning, the pricing on venues in France and Italy for their desired time frame had shot up. “Prices had doubled or tripled since we’d started looking at chateaux and villas,” says Carter. “So Georgia sat us down and we had an honest conversation about budget, as well as where we’d been in the world and what places we really liked.”She then encouraged them to imagine, in a dream world, what qualities their perfect destination wedding could include. Their list was: a place they’d visited together, with historical significance, that was architecturally stimulating and beautiful, with a modern (and wheelchair-accessible) resort for guests within walking distance, and an international airport 30 minutes away that offered nonstop flights from New York, Atlanta, and DC.Guests gather in a courtyard of Penha Longa Resort for cocktail hour. Hugo CoelhoThe grooms lean on each other on a grassy stretch of resort. Hugo CoelhoBetter than any AI generator, their planner immediately suggested Sintra, a town in Portugal 20 miles from Lisbon known for its whimsical castles—but which also had a sprawling Ritz-Carlton property, the Penha Longa Resort, that included all contemporary conveniences as well as multiple event spaces on site.“We both lit up,” Taylor remembers. “We loved Sintra. The castles are beautiful. The Portuguese people are so nice. The food is great. It’s super accommodating. We were surprised it had not entered our minds prior, to be honest.”The welcome dinner was set at a charming pink mansion on the Penha Longha Resort's property. Hugo CoelhoGuests made their way to the mansion across the historic cobblestones. Hugo CoelhoChoose venues for their flowDuring the planning process, Carter and Taylor made two trips to Portugal: one for a gut-check visit to the venues, on which they’d already put down deposits, and one for menu tastings and other final vendor conversations. They did book the Penha Longa Resort, the place that had made their planner think of Sintra in the first place, and held all of their events within the property.While the convenience and historical significance of the venues were paramount, the spaces offered additional benefits. “They were beautiful—that much is a given,” says Taylor. “But the layout of the spaces could not have worked better for the vision we had of ushering people throughout the afternoon and evening, keeping them surprised and entertained.”Their welcome dinner was held at the charming pink mansion, Casa Dos Penedos, while the wedding day was held around a monastery. The ceremony itself—which was officiated by a friend—was set within the crumbling, 16th-century, stone-walled Nuncio Gardens, built near the monastery and featuring ivy-covered stone walls, archways, and a shallow reservoir at the center. A cocktail hour following in the monastery courtyard and dinner in the Sala Dos Arcos, a dramatic space with a ceiling comprised entirely of archways. Dancing occurred in the Salão Nobre, a soaring salon with wall-to-wall carvings and a stunning carved-wood fireplace.The reception dinner decor was kept simple to let the ornate details of the setting shine. Hugo CoelhoAnother view of the courtyard ceremony, which was set around a small pool of water. Hugo CoelhoKeep the aesthetic simpleWhile their wedding venues were stunning in their ornate details, from the peacocks painted on the ceiling of the Casa Dos Penedos to the blue and white tiles along the courtyard, the couple wanted to go slightly cleaner and more masculine with the wedding decor they’d be bringing in. “The brief was Ralph Lauren, late ‘90s, equestrian,” says Carter.“We didn’t want to compete with the setting and the property itself,” says Taylor. “We wanted that to be more of a flourish in the last five to 10% of the design, and really let the spaces breathe.”Floral arrangements for the ceremony were placed in a portico before which the grooms stood. Hugo CoelhoFor their welcome dinner, they brought the formality down a bit with light linens, bamboo chairs, potted herb plants on the tables, and no assigned seats. Their ceremony was spare, with only a few urns filled with dusty pink and peach roses, while dinner featured loads of thin white candles set in bronzed candelabra at staggered heights. Their florist was Atelier Decorelle, while tableware and furniture came from Rental Co.The welcome dinner was held beneath the dramatic archways of Sala Dos Arcos. Hugo CoelhoPurge your people-pleasing tendenciesAs Carter and Taylor put it, giving people recommendations is their love language, so they were eager to help their guests plot their trips to Portugal—whether they were coming for just the wedding weekend or expanding their vacations to visit major cities like Lisbon, Porto, and beyond. They created a wedding website that included the pertinent wedding info, like hotels and schedules, but also offered their favorite spots in all the aforementioned cities.The couple was interested in helping their guests even more—”I would have rented a bus and driven [guests] from the airport to Sintra if anybody had asked me,” cracks Taylor—but Georgia gently stopped them.“She recognized our innate people-pleasing and how it could really hurt us in the long run,” says Carter. So while they did help their immediate families book their flights and accommodations, they simply listed their planner’s own contact information so she could field all questions about transportation, timing, and other logistics. “She served as a travel agent as much as a wedding planner,” says Carter.Flamenco dancers twirled around the garden path as guests walked to the welcome dinner. Hugo CoelhoLive musicians accompanied the dancers, who were brought in as a nod to Taylor's Spanish heritage. Hugo CoelhoStart the weekend with a bang.To properly welcome their loved ones to Portugal, the couple threw a Portuguese barbecue dinner on Friday night. “It was an indoor-outdoor experience, with a bar overlooking the cityscape, the mountains, and the sea,” Taylor says. “We had our guests dropped off and they walked through the forest up to the venue. When they entered, we had flamenco dancers and live musicians playing.”Flamenco dancers from Rueda Flamenca lined the garden path while guests walked in, as a nod to Taylor’s mother who is Spanish. During dinner, a musician named Manel Ferreira performed fado, the Portuguese folk music, playing guitar and serenading guests.The grooms created welcome bags that included a hand-drawn map of the area. Hugo CoelhoTile details at the resort, where there was always something beautiful underfoot. Hugo CoelhoFront load the cultural elementsThe fado performer wasn’t the only hit of Portuguese culture the guests received upon arrival. In their hotel rooms, guests found welcome bags offering a hand-drawn map of the area, as well as the beloved pastry pastel de nata (egg tarts) and a fan printed with the designs of azulejos, the instantly recognizable blue-and-white ceramic tiles the country is known for.Plates of Portuguese food were served throughout the weekend, with appetizers particularly traditional. Hugo CoelhoFood was another major way of integrating the local culture into their wedding. Aside from the Portuguese barbecue foods at their welcome dinner, their wedding meal featured several traditional flavors, such as cod fritters and sausage, while the mains were more continental. “We tried to balance it and make the appetizers very Portuguese, and the principal plates were a fish and a meat—turbot, a very flaky white fish, and a version of beef Wellington—still with Portuguese flavors, but identifiable for all the guests,” says Carter.Consider some cultural complicationsThe elephant in the room of their wedding planning, says Carter, was that they were a same-sex couple trying to marry in a majority-Catholic country. “Even though we know that [most of] Europe is exceptionally accommodating and supportive, there’s always that tinge of concern, like ‘How’s this going to work?’” he says. Happily, they found that their vendors went beyond accepting; they actually were “amplifying,” as he put it, noting that they actually felt more comfortable being “loud” in their affection in Portugal than they did at home in the southern United States.Although the couple was worried about damaging the tiles underfoot with such footwear as high heels, the Penha Longa Resort events team assured them that all surfaces were meant to be walked on. Hugo CoelhoDon’t be too precious in the pretty spacesThe couple were thrilled to work within the lavish rooms in their chosen venues, but worried aloud about the possibility of damaging the details. But the events team at the Penha Longa Resort were particularly befuddled, for example, when they fretted about high-heeled shoes damaging or scuffing the gorgeous mosaic tile on the floor of one courtyard. “‘No, the tile’s meant to be walked on. You’re meant to experience it that way,” Taylor remembers as the response.Similarly, they were concerned about the Salão Nobre, which they used for the dancing portion of the evening. What if someone spilled a drink on the wood floors, or bumped against the plaster molding? The event manager responded that “This place has been around for 600 years with people having parties and carrying on, and it will be around far longer,” Taylor recalls. “It’s meant to be lived in and enjoyed and experienced.”The grooms share a dance beneath the high ceilings of the Salão Nobre. Hugo CoelhoFind a glamorous way to stay awakeThe dancing portion of the evening was powered by a DJ from Your Jukebox. But the couple knew that weddings in Portugal (and much of Europe) typically last until sunrise; their own rental of the space gave them free rein until 6 a.m. “We talked to Georgia about how to keep the momentum up, other than just pumping people with espresso martinis, which we also did,” says Taylor. “But how do we usher in a new element for the last three hours without shifting locations again?”Drag queens were brought in toward the end of the night to keep the party going. ? 2026 Hugo Coelho, all rights reserved.In the end, dancing lasted until about 3 a.m. Hugo CoelhoThe solution was drag queens. The newlyweds surprised their guests with midnight performances from three drag performers, via Pride Talent: one who was shockingly tall (at 7’8”), one who was playing the saxophone, and one who could breathe fire (though wasn’t permitted to do so within the historic venue, which understandably did have some limits). Starchy late-night snacks came out, too, including Belgian waffles and Spanish croquettes.“The arrival of the drag performers will live forever in my mind as the most fun reaction shot of the night,” says Taylor. “Their bringing in all the guests as part of their show, to walk the catwalk or dance, really propelled the party forward for another three hours.” The glamorous event finally wound down around 3:00 a.m.Kaitlin Menza is a writer and former editor at Teen Vogue, Glamour, and Seventeen. She covers food, travel, health, pop culture, and everything else wonderful the world has to offer. She lives in New York City. You can find her work at kaitlinmenza.com. ... Read More