8-night caribbean cruise
Inside From
$2,426
Windstar Cruises – Star Pride
4.595 Reviews
Departs Oct 20, 2026 from Boston, Massachusetts
Up to 2 deals including an Avoya ExclusiveView Expanded Details
Windstar Cruises to Caribbean
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Up to 2 deals including an Avoya Exclusive
11-night caribbean cruise
Oceanview From
$3,930
Windstar Cruises – Star Pride
4.595 Reviews
Departs Oct 28, 2026 from San Juan, Puerto Rico
Up to 3 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$2,968
Windstar Cruises – Star Pride
4.595 Reviews
Departs Nov 15, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$4,294
Windstar Cruises – Star Pride
4.595 Reviews
Departs Nov 15, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$2,411
Windstar Cruises – Star Pride
4.595 Reviews
Departs Nov 22, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$3,902
Windstar Cruises – Star Pride
4.595 Reviews
Departs Nov 22, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
11-night caribbean cruise
Oceanview From
$8,446
Windstar Cruises – Wind Star
4.689 Reviews
Departs Nov 24, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$2,419
Windstar Cruises – Star Legend
4.586 Reviews
Departs Nov 27, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya ExclusiveView Expanded Details
15-night caribbean cruise
Oceanview From
$4,139
Windstar Cruises – Star Legend
4.586 Reviews
Departs Nov 27, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$2,443
Windstar Cruises – Star Pride
4.595 Reviews
Departs Nov 29, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$4,462
Windstar Cruises – Star Pride
4.595 Reviews
Departs Nov 29, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
8-night caribbean cruise
Oceanview From
$2,740
Windstar Cruises – Star Legend
4.586 Reviews
Departs Dec 04, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya ExclusiveView Expanded Details
16-night caribbean cruise
Oceanview From
$4,542
Windstar Cruises – Star Legend
4.586 Reviews
Departs Dec 04, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$3,811
Windstar Cruises – Star Pride
4.595 Reviews
Departs Dec 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$4,518
Windstar Cruises – Star Pride
4.595 Reviews
Departs Dec 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$2,618
Windstar Cruises – Star Pride
4.595 Reviews
Departs Dec 13, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$3,428
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Dec 19, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$5,524
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Dec 19, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Inside From
$3,811
Windstar Cruises – Star Pride
4.595 Reviews
Departs Dec 20, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$3,377
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Dec 26, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$5,440
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Dec 26, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$3,288
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Jan 02, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$5,636
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Jan 02, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$4,231
Windstar Cruises – Star Pride
4.595 Reviews
Departs Jan 03, 2027 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$8,270
Windstar Cruises – Star Pride
4.595 Reviews
Departs Jan 03, 2027 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
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