Windstar Cruises Cruises

Explore upcoming cruising options with Windstar Cruises. With 8 departures currently available, this cruise line offers travel across 4 itineraries and 14 destination ports, giving travelers meaningful choice on route shape and departure timing.
The 7 ships in the fleet currently spotlight routes in Eastern Caribbean, Southern Caribbean. In the coming season, popular sailing activity tends to be grouped around flagship itineraries and repeat demand corridors, with standout ports including San Juan, Saint George's, Terre-de-Haut (Les Saintes) and more.
Fleet coverage is built around ships such as Star Pride, Wind Surf, Star Breeze, which gives different options for cabin mix and onboard experience depending on timing and length.
This page focuses on practical browsing: you can compare upcoming sailings, filter by itinerary popularity, and quickly move to ship-level details or destination deep dives to plan the trip.
It is ideal for quickly building a shortlist: compare route frequency, check what ports are repeated, then jump into a departure window with a price snapshot and deck-level expectations.
Whether you want a short escape or a longer seasonal sequence, the current departures here are a useful starting point for price tracking and route discovery.