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Windstar Cruises to Caribbean

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11-night caribbean cruise
$3,182
Windstar Cruises – Wind Surf
4.7 (148)
Departs Feb 17, 2026 from Cozumel, Mexico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$4,351
Windstar Cruises – Wind Surf
4.7 (148)
Departs Feb 28, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,727
Windstar Cruises – Wind Surf
4.7 (148)
Departs Mar 07, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$5,162
Windstar Cruises – Star Seeker
Departs Mar 13, 2026 from San Juan, Puerto Rico
Up to 3 deals including an Avoya Exclusive
7-night caribbean cruise
$2,657
Windstar Cruises – Wind Surf
4.7 (148)
Departs Mar 14, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$6,519
Windstar Cruises – Wind Surf
4.7 (148)
Departs Mar 14, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,399
Windstar Cruises – Star Pride
4.5 (95)
Departs Mar 15, 2026 from Oranjestad, Aruba
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,711
Windstar Cruises – Wind Surf
4.7 (148)
Departs Mar 21, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
10-night caribbean cruise
$6,757
Windstar Cruises – Star Seeker
Departs Mar 27, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
17-night caribbean cruise
$12,244
Windstar Cruises – Star Seeker
Departs Mar 27, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
24-night caribbean cruise
$18,728
Windstar Cruises – Star Seeker
Departs Mar 27, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$4,367
Windstar Cruises – Wind Surf
4.7 (148)
Departs Mar 28, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 3 deals including Avoya Exclusives
21-night caribbean cruise
$6,494
Windstar Cruises – Wind Surf
4.7 (148)
Departs Mar 28, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$4,726
Windstar Cruises – Star Seeker
Departs Apr 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$11,440
Windstar Cruises – Star Seeker
Departs Apr 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
22-night caribbean cruise
$16,895
Windstar Cruises – Star Seeker
Departs Apr 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
8-night caribbean cruise
$2,926
Windstar Cruises – Star Pride
4.5 (95)
Departs Oct 20, 2026 from Boston, Massachusetts
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$6,793
Windstar Cruises – Star Pride
4.5 (95)
Departs Dec 20, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$4,262
Windstar Cruises – Star Pride
4.5 (95)
Departs Dec 27, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$7,393
Windstar Cruises – Star Pride
4.5 (95)
Departs Dec 27, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$4,030
Windstar Cruises – Star Pride
4.5 (95)
Departs Jan 03, 2027 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$7,293
Windstar Cruises – Star Pride
4.5 (95)
Departs Jan 03, 2027 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,719
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 16, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,893
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
$3,062
Windstar Cruises – Star Legend
4.5 (86)
Departs Jan 31, 2028 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
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