Destination
Eastern Caribbean
USVI, St. Maarten, and classic eastern loops
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
No live sailings match this region right now. Browse all sailings or ask us to watch for new sailings.
Search all sailingsBest 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