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Windstar Cruises to Caribbean

Showing 76-100 of 102 results
14-night caribbean cruise
$5,419
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 16, 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 Jan 23, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,919
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
$3,067
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
$4,919
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
$3,051
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
$4,919
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
$3,167
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
$5,019
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
7-night caribbean cruise
$3,151
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
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
$4,919
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
$3,067
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
$4,919
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
$3,051
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
$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
$4,360
Windstar Cruises – Wind Spirit
4.8 (100)
Departs Feb 14, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
24-night caribbean cruise
$15,438
Windstar Cruises – Star Seeker
Departs Mar 27, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
49-night caribbean cruise
$28,243
Windstar Cruises – Star Seeker
Departs Mar 27, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
28-night caribbean cruise
$15,895
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 04, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
55-night caribbean cruise
$27,646
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 04, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$8,247
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 18, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
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