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Windstar Cruises to Caribbean

Showing 76-96 of 96 results
7-night caribbean cruise
$3,462
Windstar Cruises – Star Pride
4.5 (95)
Departs Jan 10, 2027 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,867
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
14-night caribbean cruise
$4,419
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
$2,651
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
$4,219
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
$2,667
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
$4,219
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
$2,651
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
$4,319
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
$2,767
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
$4,419
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
$2,751
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
$4,519
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
$2,867
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
$4,408
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
$2,651
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
$4,219
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
$2,667
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
$4,219
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
$2,651
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
24-night caribbean cruise
$14,138
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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