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Windstar Cruises to Caribbean

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8-night caribbean cruise
$3,348
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 19, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
15-night caribbean cruise
$5,816
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 19, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,548
Windstar Cruises – Star Legend
4.5 (86)
Departs Dec 20, 2027 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,896
Windstar Cruises – Star Legend
4.5 (86)
Departs Dec 20, 2027 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,516
Windstar Cruises – Star Legend
4.5 (86)
Departs Dec 27, 2027 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,852
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
13-night caribbean cruise
$5,420
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
$5,739
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
$2,168
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
$2,373
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
$5,263
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
$5,582
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
$2,362
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
$5,423
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
$2,341
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
$5,582
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
$2,273
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
$5,423
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
$2,373
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
$5,582
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
$2,362
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
$5,423
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
$2,341
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
$5,582
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
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