7-night caribbean cruise
Oceanview From
$2,957
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Mar 20, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
Windstar Cruises to Caribbean
Showing 51-75 of 124 results
Up to 2 deals including an Avoya Exclusive
10-night caribbean cruise
Inside From
$3,827
Windstar Cruises – Star Pride
4.595 Reviews
Departs Oct 22, 2027 from Boston, Massachusetts
Up to 2 deals including an Avoya ExclusiveView Expanded Details
17-night caribbean cruise
Inside From
$6,649
Windstar Cruises – Star Pride
4.595 Reviews
Departs Oct 22, 2027 from Boston, Massachusetts
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Inside From
$2,688
Windstar Cruises – Star Pride
4.595 Reviews
Departs Nov 01, 2027 from San Juan, Puerto Rico
Up to 3 deals including Avoya ExclusivesView Expanded Details
14-night caribbean cruise
Oceanview From
$4,504
Windstar Cruises – Star Pride
4.595 Reviews
Departs Nov 01, 2027 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Oceanview From
$2,551
Windstar Cruises – Star Pride
4.595 Reviews
Departs Nov 08, 2027 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$4,364
Windstar Cruises – Star Pride
4.595 Reviews
Departs Nov 08, 2027 from San Juan, Puerto Rico
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 15, 2027 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$4,224
Windstar Cruises – Star Pride
4.595 Reviews
Departs Nov 15, 2027 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
8-night caribbean cruise
Oceanview From
$3,028
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Nov 20, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
15-night caribbean cruise
Oceanview From
$4,845
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Nov 20, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
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, 2027 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$4,197
Windstar Cruises – Star Pride
4.595 Reviews
Departs Nov 22, 2027 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
21-night caribbean cruise
Oceanview From
$7,460
Windstar Cruises – Star Pride
4.595 Reviews
Departs Nov 22, 2027 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Inside From
$2,572
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Nov 28, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Inside From
$4,600
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Nov 28, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Inside From
$2,658
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Dec 05, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$4,320
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Dec 05, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Inside From
$2,642
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Dec 12, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
15-night caribbean cruise
Inside From
$4,845
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Dec 12, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
8-night caribbean cruise
Inside From
$3,308
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Dec 19, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
15-night caribbean cruise
Inside From
$4,620
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Dec 19, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Inside From
$3,052
Windstar Cruises – Star Legend
4.586 Reviews
Departs Dec 20, 2027 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
14-night caribbean cruise
Oceanview From
$4,434
Windstar Cruises – Star Legend
4.586 Reviews
Departs Dec 20, 2027 from San Juan, Puerto Rico
Up to 2 deals including an Avoya ExclusiveView Expanded Details
7-night caribbean cruise
Inside From
$2,432
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Dec 27, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya ExclusiveView Expanded Details
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