Benjamin Di'Costa

Windjammer Landing Resort & Residences

Vice President, Marketing & Communications

Benjamin Di’Costa is redefining the global perception of Saint Lucia through visionary marketing leadership that merges luxury, culture, and influence. As Vice President of Marketing at Windjammer Landing Resort & Residences, he has transformed the property into a magnet for global icons—from GRAMMY winners Chloe and Halle Bailey and Hollywood A-lister Taraji P. Henson to Burna Boy, Babyface, and the cast of The Real Housewives of Beverly Hills. His strategy extends beyond celebrity partnerships: he has made Windjammer a trusted haven for world leaders, including the President of Nigeria, strengthening the resort’s reputation for privacy and prestige. Benjamin has also championed inclusive tourism across the Caribbean through partnerships with local LGBTQ+ organizations and cultural events. By combining cultural diplomacy, celebrity storytelling, and community impact, he has elevated Saint Lucia from a luxury escape to a global stage for creativity and connection—proving how hospitality marketing can shape the narrative of an entire nation.

Career Highlights: 

• Transformed Windjammer Landing Resort & Residences into a globally recognized destination, generating over 6.3 billion media impressions in one year.

• Drove record revenue growth through campaigns such as “September to Remember,” which surpassed booking goals. 

• Recognized with multiple Junior Design Awards, including the 2025 Gold Award for Best Family Hotel, for balancing high-end appeal with multi-generational inclusivity.