The unveiling of the ‘4 Island – One Escape’ island-hopping experience marks a significant milestone for regional tourism in the Northeast Caribbean. This innovative initiative promises to deliver a seamless, multi-island adventure, highlighting the unique diversity and charm of interconnected destinations. While this development is being celebrated as a fresh approach, it is, in fact, a revival of a visionary concept introduced over three decades ago. The original idea, spearheaded by Brian Meade and the Northeast Caribbean Tourism Alliance (NECTA), aimed to promote the region’s offerings globally, positioning airlines as catalysts for tourism development rather than mere carriers. However, the momentum was tragically halted by Hurricane Luis in 1995, which devastated infrastructure and led to the alliance’s dissolution. Despite this setback, the dream of regional unity and multi-island travel endured. Today, as the ‘4 Island – One Escape’ initiative takes flight, it pays homage to the legacy of NECTA and Meade’s foresight. This new chapter in Caribbean tourism stands on the shoulders of a dream that envisioned the region not as a collection of competitors but as a family of destinations with a shared narrative. The architects of this initiative are encouraged to draw inspiration from the past, as sometimes, the best way forward is to remember where the journey began.