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Windstar Cruises to Caribbean

Showing 76-100 of 106 results
14-night caribbean cruise
$4,099
Windstar Cruises – Star Pride
4.5 (91)
Departs Dec 13, 2026 from San Juan, Puerto Rico
Up to 1 deal including an Avoya Exclusive
7-night caribbean cruise
$2,699
Windstar Cruises – Star Pride
4.5 (91)
Departs Dec 20, 2026 from San Juan, Puerto Rico
Up to 1 deal including an Avoya Exclusive
14-night caribbean cruise
$4,299
Windstar Cruises – Star Pride
4.5 (91)
Departs Dec 20, 2026 from San Juan, Puerto Rico
Up to 1 deal including an Avoya Exclusive
7-night caribbean cruise
$2,699
Windstar Cruises – Star Pride
4.5 (91)
Departs Dec 27, 2026 from San Juan, Puerto Rico
Up to 1 deal including an Avoya Exclusive
14-night caribbean cruise
$4,099
Windstar Cruises – Star Pride
4.5 (91)
Departs Dec 27, 2026 from San Juan, Puerto Rico
Up to 1 deal including an Avoya Exclusive
7-night caribbean cruise
$2,499
Windstar Cruises – Star Pride
4.5 (91)
Departs Jan 03, 2027 from San Juan, Puerto Rico
Up to 1 deal including an Avoya Exclusive
14-night caribbean cruise
$3,999
Windstar Cruises – Star Pride
4.5 (93)
Departs Jan 03, 2027 from San Juan, Puerto Rico
Up to 1 deal including an Avoya Exclusive
7-night caribbean cruise
$2,499
Windstar Cruises – Star Pride
4.5 (93)
Departs Jan 10, 2027 from San Juan, Puerto Rico
Up to 1 deal including an Avoya Exclusive
7-night caribbean cruise
$2,599
Windstar Cruises – Star Pride
4.5 (92)
Departs Nov 09, 2025 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,599
Windstar Cruises – Star Pride
4.5 (92)
Departs Nov 23, 2025 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
8-night caribbean cruise
$5,899
Windstar Cruises – Star Seeker
Departs Jan 15, 2026 from Miami, Florida
Up to 1 deal
7-night caribbean cruise
$3,699
Windstar Cruises – Star Seeker
Departs Jan 23, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$6,399
Windstar Cruises – Star Seeker
Departs Jan 23, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,399
Windstar Cruises – Star Seeker
Departs Jan 30, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$7,499
Windstar Cruises – Star Seeker
Departs Jan 30, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,899
Windstar Cruises – Star Seeker
Departs Feb 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$6,499
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
$3,399
Windstar Cruises – Star Seeker
Departs Feb 13, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,799
Windstar Cruises – Star Seeker
Departs Feb 13, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,399
Windstar Cruises – Star Seeker
Departs Feb 20, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,699
Windstar Cruises – Star Seeker
Departs Feb 20, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,399
Windstar Cruises – Star Seeker
Departs Feb 27, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$13,599
Windstar Cruises – Star Seeker
Departs Mar 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,999
Windstar Cruises – Star Seeker
Departs Mar 13, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
10-night caribbean cruise
$4,099
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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