For a two-week Caribbean itinerary in 2026, the key is breathable, high-volume fabrics and "reef-safe" protection. Pack about 5–7 lightweight tops, 3 pairs of shorts, 2 bathing suits, and 2 "resort casual" outfits for dinners. Since many islands have implemented strict environmental laws, it is a peer-to-peer requirement to bring reef-safe sunscreen (zinc or titanium-based) to protect the coral. Essential gear includes a dry bag for boat excursions, a wide-brimmed sun hat, and high-quality polarized sunglasses. Footwear should be minimal: one pair of sturdy walking sneakers for hiking, one pair of waterproof sandals (like Tevas), and one pair of dressier flip-flops. Don't forget a lightweight rain shell or poncho for sudden tropical downpours. To save space, skip the heavy toiletries and hair dryer, as almost all resorts provide them. A "pro-tip" for 2026 is to pack a portable power bank and an eSIM (like Airalo) to avoid massive roaming charges while navigating between different island territories.