As winter approaches the Northern Hemisphere, sun-starved travelers are increasingly turning to multi-destination getaways to make the most of their time off, and few regions cater better to island-hopping dreams than the Caribbean. Boasting more than 30 distinct nations and territories, the Caribbean stretches from volcanic mountain peaks draped in dense rainforest to flat, powdery coral cays ringed by turquoise waters, with a layered cultural tapestry shaped by centuries of British, French, Dutch and Spanish colonial influence. It is little surprise, then, that demand for twin- and multi-island holidays is surging: industry data from regional travel specialist ITC shows twin-centre bookings have jumped 20% compared to 2025, with popular pairings including Grenada and St Lucia, and Antigua and St Kitts. Most neighbouring islands are connected by short ferry rides or quick connecting flights, and major tour operators offer all-inclusive packages that simplify inter-island travel as much as sipping a cold rum punch on the beach. To help travelers plan their perfect winter escape, travel expert Nigel Tisdall has curated 12 handpicked twin- and multi-island breaks to suit every budget, interest and group type, detailed below.