10 Cheapest Caribbean Destinations to Visit This Winter

"The Dominican Republic is having a moment this winter, with three destinations making our list, thanks in part to new and expanded flight routes."

"a great moment to show affordable spots like Kingston and Montego Bay some love and support the island's recovery while soaking up their sun, culture, and hospitality."

Winter is the Caribbean's busiest and most expensive season, but pockets of value remain for strategic travelers. Kayak analyzed flight searches to the Caribbean between Sept. 1 and Dec. 4, 2025, for travel from Dec. 21, 2025, through Feb. 28, 2026. Rankings are based on average round-trip economy airfare and nightly hotel rates for standard double-occupancy rooms. The Dominican Republic has three destinations showing affordability due in part to new and expanded flight routes. Jamaica's reopening has made Kingston and Montego Bay more affordable opportunities to support recovery while enjoying sun, culture, and hospitality. Travelers can find relative value despite peak-season demand.

Read at Travel + Leisure