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7-night caribbean cruise
$2,222
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 16, 2025 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$7,193
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 16, 2025 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,189
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 23, 2025 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,862
Windstar Cruises – Star Pride
4.5 (95)
Departs Nov 30, 2025 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
5-night caribbean cruise
$1,969
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 02, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
12-night caribbean cruise
$3,416
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 02, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,051
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 07, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$3,239
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 07, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,066
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 14, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$4,623
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 14, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,771
Windstar Cruises – Wind Surf
4.7 (148)
Departs Dec 21, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$4,016
Windstar Cruises – Wind Spirit
4.8 (100)
Departs Dec 28, 2025 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,649
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 04, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$6,547
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 04, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$2,676
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 11, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals including an Avoya Exclusive
8-night caribbean cruise
$6,796
Windstar Cruises – Star Seeker
Departs Jan 15, 2026 from Miami, Florida
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,422
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 18, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
14-night caribbean cruise
$6,747
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 18, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,624
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 25, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
15-night caribbean cruise
$6,766
Windstar Cruises – Wind Surf
4.7 (148)
Departs Jan 25, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$5,127
Windstar Cruises – Star Seeker
Departs Jan 30, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$5,127
Windstar Cruises – Star Seeker
Departs Feb 13, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
11-night caribbean cruise
$4,463
Windstar Cruises – Wind Surf
4.7 (148)
Departs Feb 17, 2026 from Cozumel, Mexico
Up to 2 deals including an Avoya Exclusive
18-night caribbean cruise
$6,915
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
$9,262
Windstar Cruises – Star Seeker
Departs Feb 20, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
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