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Windstar Cruises to Caribbean

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22-night caribbean cruise
$4,870
Windstar Cruises – Star Legend
4.5 (86)
Departs Feb 21, 2028 from San Juan, Puerto Rico
21-night caribbean cruise
$6,686
Windstar Cruises – Star Pride
4.5 (95)
Departs Feb 21, 2028 from Puerto Caldera (Puntarenas), Costa Rica
14-night caribbean cruise
$4,824
Windstar Cruises – Star Pride
4.5 (95)
Departs Feb 28, 2028 from Balboa, Panama
7-night caribbean cruise
$2,558
Windstar Cruises – Star Pride
4.5 (95)
Departs Mar 06, 2028 from Oranjestad, Aruba
Up to 1 deal including an Avoya Exclusive
14-night caribbean cruise
$4,489
Windstar Cruises – Star Pride
4.5 (95)
Departs Mar 06, 2028 from Oranjestad, Aruba
21-night caribbean cruise
$6,952
Windstar Cruises – Star Pride
4.5 (95)
Departs Mar 06, 2028 from Oranjestad, Aruba
17-night caribbean cruise
$17,784
Windstar Cruises – Star Seeker
Departs Mar 27, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
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