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.
