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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: December 2026
  3. 3 · Where: Caribbean
  4. 4 · Your sailing

← All Windstar regions in December 2026

Which sailing is yours?

5 Windstar Caribbean sailings leaving in December 2026. Yours is one of these.

Fri 4 Dec Star Legend · 8 nights from Bridgetown Bridgetown · Rodney Bay · Sunset Cruising Pitons · Sca · Bequia · +2 more Plan my ports → Sun 6 Dec Star Pride · 7 nights from San Juan San Juan · St. Georges · Bequia · Mayreau · Deshaies · +1 more Plan my ports → Sat 12 Dec Star Legend · 8 nights from Port of Oranjestad Port of Oranjestad · Cartagena · Bocas Del Toro · San Blas Islands · Panama Canal · +1 more Plan my ports → Sun 13 Dec Star Pride · 7 nights from San Juan San Juan · Cruz Bay · Gustavia · Port of Basseterre · Philipsburg · +1 more Plan my ports → Sun 27 Dec 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.