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Windstar Cruises to Caribbean

Showing 76-100 of 124 results
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7-night caribbean cruise
$2,656
Windstar Cruises – Star Legend
4.5 (86)
Departs Dec 27, 2027 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
13-night caribbean cruise
$3,760
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 27, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,434
Windstar Cruises – Star Legend
4.5 (86)
Departs Dec 27, 2027 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
6-night caribbean cruise
$2,108
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 03, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,443
Windstar Cruises – Star Legend
4.5 (86)
Departs Jan 03, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
13-night caribbean cruise
$3,955
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 03, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,014
Windstar Cruises – Star Legend
4.5 (86)
Departs Jan 03, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,432
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 09, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,250
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 09, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,411
Windstar Cruises – Star Legend
4.5 (86)
Departs Jan 10, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,014
Windstar Cruises – Star Legend
4.5 (86)
Departs Jan 10, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,448
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 16, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$3,970
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 16, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,443
Windstar Cruises – Star Legend
4.5 (86)
Departs Jan 17, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,014
Windstar Cruises – Star Legend
4.5 (86)
Departs Jan 17, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,971
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 23, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$3,830
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 23, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,411
Windstar Cruises – Star Legend
4.5 (86)
Departs Jan 24, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,014
Windstar Cruises – Star Legend
4.5 (86)
Departs Jan 24, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,273
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 30, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$3,970
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 30, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,443
Windstar Cruises – Star Legend
4.5 (86)
Departs Jan 31, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,014
Windstar Cruises – Star Legend
4.5 (86)
Departs Jan 31, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,537
Windstar Cruises – Wind Surf
4.7 (148)
Departs Feb 06, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,320
Windstar Cruises – Wind Surf
4.7 (148)
Departs Feb 06, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
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