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Windstar Cruises to Caribbean

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7-night caribbean cruise
$3,062
Windstar Cruises – Star Legend
4.5 (86)
Departs Jan 31, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,893
Windstar Cruises – Star Legend
4.5 (86)
Departs Jan 31, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,051
Windstar Cruises – Wind Surf
4.7 (148)
Departs Feb 06, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,819
Windstar Cruises – Wind Surf
4.7 (148)
Departs Feb 06, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,030
Windstar Cruises – Star Legend
4.5 (86)
Departs Feb 07, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,893
Windstar Cruises – Star Legend
4.5 (86)
Departs Feb 07, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,967
Windstar Cruises – Wind Surf
4.7 (148)
Departs Feb 13, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,819
Windstar Cruises – Wind Surf
4.7 (148)
Departs Feb 13, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,062
Windstar Cruises – Star Legend
4.5 (86)
Departs Feb 14, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,893
Windstar Cruises – Star Legend
4.5 (86)
Departs Feb 14, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,051
Windstar Cruises – Wind Surf
4.7 (148)
Departs Feb 20, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,819
Windstar Cruises – Wind Surf
4.7 (148)
Departs Feb 20, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,967
Windstar Cruises – Wind Surf
4.7 (148)
Departs Feb 27, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,819
Windstar Cruises – Wind Surf
4.7 (148)
Departs Feb 27, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,051
Windstar Cruises – Wind Surf
4.7 (148)
Departs Mar 05, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,819
Windstar Cruises – Wind Surf
4.7 (148)
Departs Mar 05, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,967
Windstar Cruises – Wind Surf
4.7 (148)
Departs Mar 12, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,030
Windstar Cruises – Star Pride
4.5 (95)
Departs Mar 13, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,062
Windstar Cruises – Star Pride
4.5 (95)
Departs Mar 20, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
15-night caribbean cruise
$5,658
Windstar Cruises – Star Legend
4.5 (86)
Departs Nov 27, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
8-night caribbean cruise
$4,019
Windstar Cruises – Star Legend
4.5 (86)
Departs Feb 22, 2027 from Oranjestad, Aruba
17-night caribbean cruise
$4,689
Windstar Cruises – Star Pride
4.5 (95)
Departs Oct 22, 2027 from Boston, Massachusetts
14-night caribbean cruise
$4,566
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 22, 2027 from San Juan, Puerto Rico
21-night caribbean cruise
$7,324
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 22, 2027 from San Juan, Puerto Rico
14-night caribbean cruise
$4,627
Windstar Cruises – Star Pride
4.5 (95)
Departs Feb 21, 2028 from Puerto Caldera (Puntarenas), Costa Rica
Up to 1 deal including an Avoya Exclusive
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