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Windstar Cruises to Caribbean

Showing 101-124 of 124 results
7-night caribbean cruise
Oceanview From
$2,411
Windstar Cruises – Star Legend
4.586 Reviews
Departs Feb 07, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
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14-night caribbean cruise
Oceanview From
$4,014
Windstar Cruises – Star Legend
4.586 Reviews
Departs Feb 07, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
View Expanded Details
7-night caribbean cruise
Oceanview From
$2,448
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Feb 13, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
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14-night caribbean cruise
Oceanview From
$4,250
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Feb 13, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
View Expanded Details
7-night caribbean cruise
Oceanview From
$2,443
Windstar Cruises – Star Legend
4.586 Reviews
Departs Feb 14, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
View Expanded Details
14-night caribbean cruise
Oceanview From
$4,154
Windstar Cruises – Star Legend
4.586 Reviews
Departs Feb 14, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
View Expanded Details
7-night caribbean cruise
Oceanview From
$2,432
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Feb 20, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
View Expanded Details
14-night caribbean cruise
Oceanview From
$4,180
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Feb 20, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
View Expanded Details
7-night caribbean cruise
Oceanview From
$2,551
Windstar Cruises – Star Legend
4.586 Reviews
Departs Feb 21, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
View Expanded Details
21-night caribbean cruise
Oceanview From
$4,271
Windstar Cruises – Star Legend
4.586 Reviews
Departs Feb 21, 2028 from San Juan, Puerto Rico
Up to 1 deal including an Avoya Exclusive
View Expanded Details
7-night caribbean cruise
Oceanview From
$2,623
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Feb 27, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
View Expanded Details
14-night caribbean cruise
Oceanview From
$4,320
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Feb 27, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
View Expanded Details
7-night caribbean cruise
Inside From
$2,677
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Mar 05, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
View Expanded Details
14-night caribbean cruise
Oceanview From
$4,320
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Mar 05, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
View Expanded Details
7-night caribbean cruise
Inside From
$2,894
Windstar Cruises – Star Pride
4.595 Reviews
Departs Mar 06, 2028 from Oranjestad, Aruba
Up to 2 deals including an Avoya Exclusive
View Expanded Details
14-night caribbean cruise
Inside From
$4,640
Windstar Cruises – Star Pride
4.595 Reviews
Departs Mar 06, 2028 from Oranjestad, Aruba
Up to 2 deals including an Avoya Exclusive
View Expanded Details
21-night caribbean cruise
Inside From
$6,768
Windstar Cruises – Star Pride
4.595 Reviews
Departs Mar 06, 2028 from Oranjestad, Aruba
Up to 2 deals including an Avoya Exclusive
View Expanded Details
7-night caribbean cruise
Oceanview From
$2,518
Windstar Cruises – Wind Surf
4.7148 Reviews
Departs Mar 12, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
View Expanded Details
7-night caribbean cruise
Oceanview From
$2,411
Windstar Cruises – Star Pride
4.595 Reviews
Departs Mar 13, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
View Expanded Details
14-night caribbean cruise
Oceanview From
$4,014
Windstar Cruises – Star Pride
4.595 Reviews
Departs Mar 13, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
View Expanded Details
7-night caribbean cruise
Oceanview From
$2,443
Windstar Cruises – Star Pride
4.595 Reviews
Departs Mar 20, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
View Expanded Details
14-night caribbean cruise
Oceanview From
$4,014
Windstar Cruises – Star Pride
4.595 Reviews
Departs Mar 20, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
View Expanded Details
7-night caribbean cruise
Oceanview From
$2,411
Windstar Cruises – Star Pride
4.595 Reviews
Departs Mar 27, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
View Expanded Details
23-night caribbean cruise
Inside From
$4,211
Windstar Cruises – Star Pride
4.595 Reviews
Departs Mar 27, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
View Expanded Details
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