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Windstar Cruises to Caribbean

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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
7-night caribbean cruise
$3,267
Windstar Cruises – Wind Surf
4.7 (148)
Departs Mar 28, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 3 deals including Avoya Exclusives
7-night caribbean cruise
$3,545
Windstar Cruises – Star Seeker
Departs Apr 06, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
11-night caribbean cruise
$4,257
Windstar Cruises – Star Pride
4.5 (95)
Departs Oct 28, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$5,893
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
$3,562
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
$5,893
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 15, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
11-night caribbean cruise
$5,730
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
$3,162
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
$5,393
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
$3,519
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
$5,911
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
$3,230
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
$5,493
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
$3,262
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
$5,593
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
$3,667
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
$6,219
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
$3,330
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
$6,793
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
$3,551
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
$5,819
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
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
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