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Windstar Cruises to Caribbean

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8-night caribbean cruise
$3,747
Windstar Cruises – Star Pride
4.5 (95)
Departs Oct 20, 2026 from Boston, Massachusetts
Up to 2 deals including an Avoya Exclusive
11-night caribbean cruise
$4,568
Windstar Cruises – Star Pride
4.5 (95)
Departs Oct 28, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,426
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 08, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$6,136
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 08, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$4,158
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 15, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,976
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 15, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,866
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 22, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,496
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 22, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
11-night caribbean cruise
$6,851
Windstar Cruises – Wind Star
4.6 (89)
Departs Nov 24, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,419
Windstar Cruises – Star Legend
4.5 (86)
Departs Nov 27, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
15-night caribbean cruise
$5,757
Windstar Cruises – Star Legend
4.5 (86)
Departs Nov 27, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,073
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 29, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,496
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 29, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
8-night caribbean cruise
$2,700
Windstar Cruises – Star Legend
4.5 (86)
Departs Dec 04, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
16-night caribbean cruise
$6,281
Windstar Cruises – Star Legend
4.5 (86)
Departs Dec 04, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,621
Windstar Cruises – Star Pride
4.5 (95)
Departs Dec 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,496
Windstar Cruises – Star Pride
4.5 (95)
Departs Dec 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,373
Windstar Cruises – Star Pride
4.5 (95)
Departs Dec 13, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,416
Windstar Cruises – Star Pride
4.5 (95)
Departs Dec 13, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,693
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 19, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,887
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 19, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,621
Windstar Cruises – Star Pride
4.5 (95)
Departs Dec 20, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$6,296
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
$2,817
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 26, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,811
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 26, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
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