⛵ Already booked

Find the cruise you already booked

We hold every sailing. Your line, roughly when, and where you’re headed — that’s enough. We’ll hand back the whole trip: the one unmissable thing at every port you call at, who runs it, and what it costs booked direct instead of through the ship.

  1. 1 · Line: Windstar
  2. 2 · When: November 2026
  3. 3 · Where: Caribbean
  4. 4 · Your sailing

← All Windstar regions in November 2026

Which sailing is yours?

4 Windstar Caribbean sailings leaving in November 2026. Yours is one of these.

Sun 8 Nov Star Pride · 7 nights from San Juan San Juan · St. Georges · Bequia · Mayreau · Les Saintes · +1 more Plan my ports → Sun 15 Nov Star Pride · 7 nights from San Juan San Juan · Cruz Bay · Port of Basseterre · Gustavia · Philipsburg · +1 more Plan my ports → Tue 24 Nov Wind Star · 11 nights from Bridgetown Bridgetown · Bequia · St. Georges · KRALENDIJK · Willemstad · +4 more Plan my ports → Sun 29 Nov Star Pride · 7 nights from San Juan San Juan · Cruz Bay · Gustavia · Port of Basseterre · Philipsburg · +1 more Plan my ports →

Not booked yet? Plan a whole trip from scratch — flights, the sailing, hotels and the bucket list, priced in one place.