Destination

Eastern Caribbean

USVI, St. Maarten, and classic eastern loops

From $281 per person · 537 itineraries available · (1,465 sailings)

Eastern Caribbean itineraries lean island-dense beach-and-shop days — St. Thomas, St. Maarten, San Juan, and private-island stops from Florida homeports.

Eastern Caribbean sailings

537 itineraries match — showing 8 starting at the lowest fares.

Best time for Eastern Caribbean

Winter dry season (December–April) is peak demand. Late spring shoulder weeks often cut fares before the busiest storm months.

What you'll find

  • Island-hopping 5–8 night loops from Miami and Port Canaveral
  • Private-island days mixed with classic port calls
  • Shorter flights for East Coast and Florida drive-to guests
  • Beach time first; culture and shopping vary by stop
  • Compare eastern vs western by the actual port list

Popular departure ports

FAQ