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Windstar Cruises to Caribbean

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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
49-night caribbean cruise
$35,393
Windstar Cruises – Star Seeker
Departs Mar 27, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
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
14-night caribbean cruise
$4,593
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 08, 2027 from San Juan, Puerto Rico
7-night caribbean cruise
$2,862
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 15, 2027 from San Juan, Puerto Rico
14-night caribbean cruise
$4,593
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 15, 2027 from San Juan, Puerto Rico
8-night caribbean cruise
$3,067
Windstar Cruises – Wind Surf
4.7 (148)
Departs Nov 20, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
15-night caribbean cruise
$4,719
Windstar Cruises – Wind Surf
4.7 (148)
Departs Nov 20, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
7-night caribbean cruise
$2,930
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 22, 2027 from San Juan, Puerto Rico
7-night caribbean cruise
$2,851
Windstar Cruises – Wind Surf
4.7 (148)
Departs Nov 28, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
14-night caribbean cruise
$4,519
Windstar Cruises – Wind Surf
4.7 (148)
Departs Nov 28, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
7-night caribbean cruise
$2,835
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 29, 2027 from San Juan, Puerto Rico
14-night caribbean cruise
$4,993
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 29, 2027 from San Juan, Puerto Rico
7-night caribbean cruise
$2,867
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 05, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
14-night caribbean cruise
$4,519
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 05, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
7-night caribbean cruise
$2,851
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 12, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
15-night caribbean cruise
$4,919
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 12, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
8-night caribbean cruise
$3,267
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 19, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
15-night caribbean cruise
$5,219
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 19, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
7-night caribbean cruise
$3,262
Windstar Cruises – Star Legend
4.5 (86)
Departs Dec 20, 2027 from San Juan, Puerto Rico
14-night caribbean cruise
$5,193
Windstar Cruises – Star Legend
4.5 (86)
Departs Dec 20, 2027 from San Juan, Puerto Rico
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