14-night caribbean cruise
Oceanview From
$5,090
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
Windstar Cruises to Caribbean
Showing 26-50 of 124 results
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
Oceanview From
$3,251
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
$5,764
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
7-night caribbean cruise
Oceanview From
$3,202
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Jan 09, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$5,930
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Jan 09, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$2,758
Windstar Cruises – Star Pride
4.595 Reviews
Departs Jan 10, 2027 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$3,008
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Jan 16, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$6,210
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Jan 16, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$4,182
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Jan 23, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$6,630
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Jan 23, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$2,728
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Jan 30, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$5,860
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Jan 30, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$3,517
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Feb 06, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$6,770
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Feb 06, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$4,373
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Feb 13, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$8,030
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Feb 13, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$3,727
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Feb 20, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 3 deals including Avoya ExclusivesView Expanded Details
14-night caribbean cruise
Oceanview From
$7,680
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Feb 20, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
8-night caribbean cruise
Oceanview From
$4,340
Windstar Cruises – Star Legend
4.586 Reviews
Departs Feb 22, 2027 from Oranjestad, Aruba
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$3,988
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Feb 27, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$6,420
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Feb 27, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Inside From
$3,097
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Mar 06, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$5,930
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Mar 06, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$3,393
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Mar 13, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$5,790
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Mar 13, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
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