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Windstar Cruises to Caribbean

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7-night caribbean cruise
$3,151
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 23, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,119
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 23, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,267
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 30, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,219
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 30, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,251
Windstar Cruises – Wind Surf
4.7 (148)
Departs Feb 06, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,219
Windstar Cruises – Wind Surf
4.7 (148)
Departs Feb 06, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,267
Windstar Cruises – Wind Surf
4.7 (148)
Departs Feb 13, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,119
Windstar Cruises – Wind Surf
4.7 (148)
Departs Feb 13, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,119
Windstar Cruises – Wind Surf
4.7 (148)
Departs Feb 20, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,267
Windstar Cruises – Wind Surf
4.7 (148)
Departs Feb 27, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,019
Windstar Cruises – Wind Surf
4.7 (148)
Departs Feb 27, 2027 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 06, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,019
Windstar Cruises – Wind Surf
4.7 (148)
Departs Mar 06, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,267
Windstar Cruises – Wind Surf
4.7 (148)
Departs Mar 13, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,119
Windstar Cruises – Wind Surf
4.7 (148)
Departs Mar 13, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,151
Windstar Cruises – Wind Surf
4.7 (148)
Departs Mar 20, 2027 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
7-night caribbean cruise
$7,312
Windstar Cruises – Star Seeker
Departs Feb 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$5,836
Windstar Cruises – Star Seeker
Departs Feb 27, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$6,062
Windstar Cruises – Star Seeker
Departs Mar 06, 2026 from San Juan, Puerto Rico
Up to 1 deal
14-night caribbean cruise
$11,296
Windstar Cruises – Star Seeker
Departs Mar 06, 2026 from San Juan, Puerto Rico
10-night caribbean cruise
$3,026
Windstar Cruises – Star Pride
4.5 (95)
Departs Oct 22, 2027 from Boston, Massachusetts
7-night caribbean cruise
$2,862
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 01, 2027 from San Juan, Puerto Rico
14-night caribbean cruise
$4,593
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 01, 2027 from San Juan, Puerto Rico
7-night caribbean cruise
$2,930
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 08, 2027 from San Juan, Puerto Rico
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