Inside Thomas J. Henry and Dr. Elena Alvarez-Westwood’s Engagement Celebration in Puerto Rico

A celebration rooted in intention, scale, and cultural resonance set the tone for the new year as Thomas J. Henry marked his engagement to Dr. Elena Alvarez-Westwood with a sweeping evening at the Fairmont El San Juan Hotel in Isla Verde. Drawing hundreds of guests to San Juan, the gathering unfolded as a carefully orchestrated tribute to music, place, and shared values, transforming the historic oceanfront property into a stage for one of the Caribbean’s most talked-about private events of 2025.

From the moment guests arrived, the experience signaled that this would be no ordinary engagement celebration. An outdoor performance by the Earth Harp greeted attendees, its strings suspended across the hotel’s entrance as projected imagery moved across the building’s façade in sync with the music. The effect was immersive and ceremonial, setting a reflective tone before the evening’s momentum began to build.

Inside the Fairmont’s iconic lobby, a cocktail reception unfolded amid intricate ice sculptures and live music performed by 35 musicians from the Philharmonic Orchestra of Puerto Rico. Familiar compositions were reinterpreted with Latin inflections, creating a sense of continuity between classical form and regional expression.

The couple requested an unplugged experience for the night, encouraging guests to remain present rather than document the moment through screens. The decision underscored the event’s emphasis on shared experience, inviting connection and conversation within a setting designed to be savored rather than captured.

As the evening progressed, the celebration shifted into a new register with surprise performances by Marc Anthony, Ricky Martin, and other Latin superstars. The energy quickly moved beyond that of a traditional engagement party, taking on the feel of a private concert where guests remained on their feet through each set. The performances bridged generations and genres, reflecting the couple’s ties to Latin culture while elevating the night into a rare, collective moment.

Following the musical performances, attention turned skyward. A choreographed drone show illuminated the Caribbean night above Isla Verde, tracing celebratory patterns set to music. As the drones faded, a full fireworks display erupted above the resort, drawing cheers across the property and creating a natural crescendo for the evening.

The spectacle gave way to a more personal moment with the presentation of a birthday cake honoring Dr. Alvarez-Westwood, seamlessly folding celebration into celebration and reinforcing the night’s layered meaning.

After formalities concluded, the celebration transitioned into an open-ended dance party. Two DJs guided the energy well into the early hours, with the final performance delivered by Robby Elias from Miami. Guests flowed between indoor and outdoor spaces, taking in views of palm-lined pools and the shoreline while enjoying signature cocktails and late-night bites. The atmosphere balanced glamour with ease, allowing the night to unfold organically as conversations, music, and movement carried on.

Dr. Alvarez-Westwood’s styling reflected the event’s international scope. Her hair was styled by Eddy Scudo, with makeup by Hung Vanngo. She wore designs by Paris fashion designer Zuhair Murad alongside pieces by Puerto Rico–based designer Gustavo Arango, pairing global couture with regional creativity.

As guests departed, they received parting gifts that tied the celebration back to the island. Bottles of Don Q Gran Reserva Añejo Rum from Dr. Alvarez-Westwood’s hometown of Ponce and chocolates from Montadero offered a final, thoughtful connection to Puerto Rico’s craftsmanship.

Beyond the spectacle, the engagement marks a shared commitment to philanthropy. Together, Thomas J. Henry and Dr. Elena Alvarez-Westwood are building on recent charitable efforts on the island, including support for post-earthquake recovery of education services in Guayanilla and their role as title sponsors of the American Cancer Society Puerto Rico Gala.