How We Pulled It Off: A Jamaica Wedding Nodding to the Island’s Hollywood Heyday
Naomi Goggin
Growing up in San Francisco, Caitlin de Lisser-Ellen visited her mother’s native Jamaica annually—and it was on the Caribbean island that, as a child, she had one of her first experiences of how magical a wedding could really be: At an aunt’s nuptials at Frenchman’s Cove, “a resort that was really popular in the 1950s with Hollywood people like Errol Flynn, we partied until 4:00 am,” she says. “I couldn’t tell if [it was that] I was just a child, or this was actually the coolest wedding I would ever go to. That stuck in my head as the type of wedding where people can let loose and enjoy.”
Years later, Caitlin grew up to be a film and TV producer. She got engaged to John G. Santoro—now a criminal defense attorney with the public defender's office—who she met in college in New York City. And the vision of Jamaica loomed large for the now Oakland, California-based couple: The island means a lot to the bride’s family, and is a significantly more affordable place to get married than big US cities in the Northeast (John is from Connecticut) and California where the couple have friends and family.
So they opted for the bride’s ancestral Jamaica, marrying in Ocho Rios in February 2024. Ahead, how the couple planned an Old Hollywood-themed celebration complete with a pig roast, a pool party, and a plenty of martinis.
Be patient for the right property
While Caitlin’s Jamaican family members are based around the northeastern city of Port Antonio, the couple worried that it was too far from the country’s major airports—and thus inconvenient for most of their guests. “The places I’d grown up going to were ultimately not going to make sense, so we looked at estates and hotels that were within a two-hour range from the airport, and could give us the bespoke experience we were looking for,” she says. Resorts around Negril were vetoed for being a bit too small and public; some towns also had noise ordinances the couple didn’t want to worry about. Most properties in that area offered standardized event packages, which the couple felt were too cookie-cutter.
The couple found the right area in Ocho Rios, a smaller port town on the north coast within their desired distance of the airport, and packed with beautiful, historic estates. They chose one of those estates, Frankfort Villa, as both the wedding venue and their home base. “It could [fit] the most people, and we could have the most privacy and the most free reign,” John says. The white-washed, 17th-century fort-turned-villa still had historical details throughout the property, including a cannon and a former schoolhouse on the grounds with six bedrooms, plus a pool and a small private beach. “It feels like you’re on this deserted island, and we were able to have the run of the place,” says John.
Tap an expert (or three) from your arsenal
To help in their venue research, the couple relied on Caitlin’s mother, Margaret de Lisser, for her knowledge of the country and network of contacts; they ultimately found Frankfort Villa via word of mouth. Mother and daughter also took several planning trips to Jamaica together, and hired helpers in the form of Katie Donahoe of KCD Event Co., a Los Angeles-based event producer and planner, and a local Jamaican planner Chalene Roye-Myrie of Krafted by Design.
Two planners were necessary, Caitlin reasoned, because as a filmmaker the visuals of the wedding were high priority for her: From the stationery and textiles to the florals and food, she had a vision. Katie was “instrumental” in bringing it into being, and Chalene assisted with all the details on the ground, like local vendors and set-up in the days leading up to the celebration.
Keep the theme subtle
The look Caitlin was going for? Not the barefoot, beachy tropes, but a “retro tropical maximalism” inspired by Jamaica’s Hollywood-elite heyday in the 1950s: Marilyn Monroe and Arthur Miller had honeymooned in Ocho Rios, while Ian Fleming wrote all of his James Bond novels here in the same decade. The couple’s own style choices reflected this era, and the champagne tower, martinis, and cigar-rolling at the reception tied it all together.
Caitlin and her American planner Katie sourced all the textiles in the US, and flew with them to Jamaica for the wedding: “Many people [warned] me that linens are incredibly heavy, and that is indeed true,” the bride laughs now, “but it felt like it was all worth it in terms of bringing the vision to life.”
Switch to island time—and expect transportation snafus
Even with two planners, and a bride adept at project management, there was one logistical hurdle that was tough to cross: local transportation. With winding country roads, guests staying at multiple villas across the area, and no Uber equivalent on the island, the couple struggled with scheduling pickups and making sure everyone arrived at their various events on time. “It was like running a subway train: once you have a delay at the first stop, it’s going to have ripple effects,” Caitlin says. And with just one road into and out of the estate, any traffic jams could set them back. One branch of the bride’s family was staying an hour away, and missed the beginning of the ceremony when their bus got lost en route. Additionally, the Wi-Fi connection went down at a crucial moment, making it difficult to keep people updated about the schedule or answer any questions.
“There were hiccups for sure,” John says, but the couple learned throughout the planning process that they needed to turn off their type-A, American mindsets whenever possible and adopt a more relaxed approach. “The thing I really like about Jamaica is that no one is that pressed,” Caitlin says.
When schedule changes occur, pivot to pool party as needed
The couple arrived to Jamaica on the Tuesday before their Saturday wedding and settled in at GoldenEye, Sir Ian Fleming’s former home-turned-luxury-hotel. Come Thursday, they had the run of their ceremony location, and had planned a boat cruise followed by an offsite rehearsal dinner for an intimate group of family and friends. Unfortunately, the weather on Thursday proved to be too windy for the catamaran excursion, so they pivoted to a pre-rehearsal pool party back at the villa instead, embracing the turn of events for a more relaxed setting. “It felt like a house party where we had everyone over for the day to hang out and catch up, or get to know each other if they didn’t already,” John says.
A welcome party was hosted on Friday at the Great House, another historic property under the same ownership as Frankfort Villa. Saturday’s ceremony was held at Our Lady of Fatima Roman Catholic Church, and the cocktail hour and reception back at the Frankfort Villa. And as the home base of the couple and their immediate friends and bridal parties, the villa wound up hosting after-parties as well as “recuperation and relaxation days,” particularly the day after the wedding.
Immerse guests into the culture
At the welcome party on Friday night, guests were served fresh coconuts as they walked into the Great House, which offered a view over the cliffs to the Caribbean sea. A group of local musicians, through ShowJam Entertainment, played mento music—a type of Jamaican folk music that was especially popular in the 1940s and ‘50s and relies on African rhythmic traditions—to set the relaxed vibe. Dinner was a buffet of classic Jamaican fare catered by a nearby restaurant Miss T’s Kitchen, so that newcomers could enjoy the local cuisine. The centerpiece was a pig roast, a tradition from Caitlin’s family celebrations that she knew had to be included.
While the wedding itself was a bit more formal, Jamaican flavors and ingredients were still front and center—oxtail bites during cocktail hour, and jerk pork and langoustine as main courses at dinner. “We made sure to focus as much as we could on utilizing local vendors so we could keep things really in touch with the island,” Caitlin says.
Nod to home and your own story
Amid the palm trees and bottles of Red Stripe beer, the couple created two moments that spoke to their love story and family: At the wedding, the bar area was inspired by the legendary Bemelmans Bar in New York, the city where they’d met. The cocktail bar’s whimsical children’s book illustrations inspired the bar area’s menus, napkins, and matchbooks.
And because the bride’s mother—the native Jamaican herself—sits on the board of the Salvador Dalí Museum in Florida, Surrealists elements were thrown into the mix on the reception dance floor: guests were handed neon wigs, masks, flamingo hats, and funny glasses with the aim of kicking the party up a notch. “It was this descent into chaos and surrealism as the night stretched on,” Caitlin says.
Embrace the unexpected
While the couple and their planning team carefully considered every detail, there was one happy accident that sticks out in the groom’s memories. “We had a checkered dance floor installed right on the beach, maybe 30 feet from the water, and by the end of the night, people were going swimming in the warm water, then coming back to the dance floor, and vice versa,” he laughs.
His loved ones had the time of their lives in such a gorgeous setting, which made all the hiccups worth it: “There's nothing to be underestimated about having an incredible view and a beautiful sky as the background to the happiest weekend of your life,” he says.
Originally Appeared on Condé Nast Traveler
Trending Travel Destinations
Want to be the first to know? Sign up to our newsletters for travel inspiration and tips
The 20 Best Things to Do in Bangkok
The 13 Best Places to Travel in January, From Mexico to Manila
