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Windstar Cruises to Caribbean

Showing 26-50 of 96 results
8-night caribbean cruise
$3,516
Windstar Cruises – Wind Spirit
4.8 (100)
Departs Mar 07, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$5,033
Windstar Cruises – Star Seeker
Departs Mar 13, 2026 from San Juan, Puerto Rico
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,367
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
$6,119
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
$3,119
Windstar Cruises – Star Pride
4.5 (95)
Departs Mar 15, 2026 from Oranjestad, Aruba
Up to 2 deals including an Avoya Exclusive
6-night caribbean cruise
$4,016
Windstar Cruises – Wind Spirit
4.8 (100)
Departs Mar 15, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,416
Windstar Cruises – Wind Spirit
4.8 (100)
Departs Mar 21, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
7-night caribbean cruise
$3,651
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
14-night caribbean cruise
$6,619
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
$5,857
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
$8,584
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
$3,867
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
21-night caribbean cruise
$5,544
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
$3,726
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
$8,480
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
$12,405
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
$2,426
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
$3,757
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
$2,730
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
$4,693
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
$2,962
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
$4,693
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
$2,930
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
$4,593
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
$4,630
Windstar Cruises – Wind Star
4.6 (89)
Departs Nov 24, 2026 from Bridgetown, Barbados
Up to 2 deals including an Avoya Exclusive
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