Margaritaville at SeaMargaritaville Paradise
Destination
Caribbean
Islands, beaches, and three routes
From $149 per person · 3,215 itineraries available · (9,600 sailings)
Caribbean cruises offer warm water and the widest ship choice from U.S. homeports. Fares follow the calendar: winter dry season costs most; late spring and early fall often mean better value.
Caribbean sailings
3,215 itineraries match — showing 8 starting at the lowest fares.
Best time to cruise the Caribbean
December through April is dry-season peak: reliable beach weather, busiest ships, and the highest fares (especially around holidays and spring break). Late April through early June is a common shoulder window — still warm, fewer crowds, and often meaningfully lower prices before the heaviest storm months.
Atlantic hurricane season runs June 1 through November 30, with the highest activity in August through October. Cruises still sail; lines may swap or skip ports. September and October often show the deepest discounts. Southern Caribbean (ABC islands) sits south of the main hurricane belt — a useful option if you are booking late summer or fall.
What you'll find
- Year-round warmth from dozens of weekly Florida and Gulf departures
- Eastern, Western, and Southern loops — beaches, ruins, or ABC culture
- 5–7 night sailings are the sweet spot; longer trips suit Southern routes
- Clear seasonal pricing: peak winter, shoulder spring, bargain fall
- Drive-to or short-flight homeports cut total trip cost vs. fare alone