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Windstar Cruises to Caribbean

Showing 26-50 of 58 results
Roundtrip
14-Night Caribbean Cruise
$4,599
Windstar Cruises – Star Pride
90 Reviews
Departs Nov 02, 2025 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$2,599
Windstar Cruises – Star Pride
90 Reviews
Departs Nov 09, 2025 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$2,299
Windstar Cruises – Wind Surf
145 Reviews
Departs Dec 07, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$2,599
Windstar Cruises – Wind Surf
145 Reviews
Departs Jan 04, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
8-Night Caribbean Cruise
$5,399
Windstar Cruises – Star Seeker
Departs Jan 15, 2026 from Miami, Florida
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$3,299
Windstar Cruises – Star Seeker
Departs Jan 23, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
Roundtrip
14-Night Caribbean Cruise
$5,599
Windstar Cruises – Star Seeker
Departs Jan 23, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$3,299
Windstar Cruises – Star Seeker
Departs Jan 30, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
Roundtrip
14-Night Caribbean Cruise
$5,299
Windstar Cruises – Star Seeker
Departs Jan 30, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$2,999
Windstar Cruises – Star Seeker
Departs Feb 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
Roundtrip
14-Night Caribbean Cruise
$5,299
Windstar Cruises – Star Seeker
Departs Feb 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$3,299
Windstar Cruises – Star Seeker
Departs Feb 13, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
Roundtrip
14-Night Caribbean Cruise
$5,399
Windstar Cruises – Star Seeker
Departs Feb 13, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
18-Night Caribbean Cruise
$5,399
Windstar Cruises – Wind Surf
145 Reviews
Departs Feb 17, 2026 from Cozumel, Mexico
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$3,099
Windstar Cruises – Star Seeker
Departs Feb 20, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
Roundtrip
14-Night Caribbean Cruise
$5,199
Windstar Cruises – Star Seeker
Departs Feb 20, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$3,099
Windstar Cruises – Star Seeker
Departs Feb 27, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
Roundtrip
14-Night Caribbean Cruise
$7,299
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
$2,499
Windstar Cruises – Wind Spirit
98 Reviews
Departs Feb 28, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$4,299
Windstar Cruises – Star Seeker
Departs Mar 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
Roundtrip
14-Night Caribbean Cruise
$7,199
Windstar Cruises – Star Seeker
Departs Mar 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
Roundtrip
7-Night Caribbean Cruise
$2,699
Windstar Cruises – Wind Spirit
98 Reviews
Departs Mar 07, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
Roundtrip
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
Roundtrip
14-Night Caribbean Cruise
$3,699
Windstar Cruises – Wind Surf
145 Reviews
Departs Mar 21, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
Roundtrip
10-Night Caribbean Cruise
$3,999
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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