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Windstar Cruises to Caribbean
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7-night caribbean cruise
$6,062
Windstar Cruises –
Star Seeker
Departs
Mar 06, 2026
from
San Juan, Puerto Rico
Up to 1 deal
14-night caribbean cruise
$11,296
Windstar Cruises –
Star Seeker
Departs
Mar 06, 2026
from
San Juan, Puerto Rico
49-night caribbean cruise
$35,393
Windstar Cruises –
Star Seeker
Departs
Mar 27, 2026
from
San Juan, Puerto Rico
Up to 2 deals
including an Avoya Exclusive
10-night caribbean cruise
$3,026
Windstar Cruises –
Star Pride
Departs
Oct 22, 2027
from
Boston, Massachusetts
7-night caribbean cruise
$2,862
Windstar Cruises –
Star Pride
Departs
Nov 01, 2027
from
San Juan, Puerto Rico
14-night caribbean cruise
$4,593
Windstar Cruises –
Star Pride
Departs
Nov 01, 2027
from
San Juan, Puerto Rico
7-night caribbean cruise
$2,930
Windstar Cruises –
Star Pride
Departs
Nov 08, 2027
from
San Juan, Puerto Rico
14-night caribbean cruise
$4,593
Windstar Cruises –
Star Pride
Departs
Nov 08, 2027
from
San Juan, Puerto Rico
7-night caribbean cruise
$2,862
Windstar Cruises –
Star Pride
Departs
Nov 15, 2027
from
San Juan, Puerto Rico
14-night caribbean cruise
$4,593
Windstar Cruises –
Star Pride
Departs
Nov 15, 2027
from
San Juan, Puerto Rico
8-night caribbean cruise
$3,067
Windstar Cruises –
Wind Surf
Departs
Nov 20, 2027
from
Saint Maarten (Phillipsburg), Netherlands Antilles
15-night caribbean cruise
$4,719
Windstar Cruises –
Wind Surf
Departs
Nov 20, 2027
from
Saint Maarten (Phillipsburg), Netherlands Antilles
7-night caribbean cruise
$2,930
Windstar Cruises –
Star Pride
Departs
Nov 22, 2027
from
San Juan, Puerto Rico
7-night caribbean cruise
$2,851
Windstar Cruises –
Wind Surf
Departs
Nov 28, 2027
from
Saint Maarten (Phillipsburg), Netherlands Antilles
14-night caribbean cruise
$4,519
Windstar Cruises –
Wind Surf
Departs
Nov 28, 2027
from
Saint Maarten (Phillipsburg), Netherlands Antilles
7-night caribbean cruise
$2,835
Windstar Cruises –
Star Pride
Departs
Nov 29, 2027
from
San Juan, Puerto Rico
14-night caribbean cruise
$4,993
Windstar Cruises –
Star Pride
Departs
Nov 29, 2027
from
San Juan, Puerto Rico
7-night caribbean cruise
$2,867
Windstar Cruises –
Wind Surf
Departs
Dec 05, 2027
from
Saint Maarten (Phillipsburg), Netherlands Antilles
14-night caribbean cruise
$4,519
Windstar Cruises –
Wind Surf
Departs
Dec 05, 2027
from
Saint Maarten (Phillipsburg), Netherlands Antilles
7-night caribbean cruise
$2,851
Windstar Cruises –
Wind Surf
Departs
Dec 12, 2027
from
Saint Maarten (Phillipsburg), Netherlands Antilles
15-night caribbean cruise
$4,919
Windstar Cruises –
Wind Surf
Departs
Dec 12, 2027
from
Saint Maarten (Phillipsburg), Netherlands Antilles
8-night caribbean cruise
$3,267
Windstar Cruises –
Wind Surf
Departs
Dec 19, 2027
from
Saint Maarten (Phillipsburg), Netherlands Antilles
15-night caribbean cruise
$5,219
Windstar Cruises –
Wind Surf
Departs
Dec 19, 2027
from
Saint Maarten (Phillipsburg), Netherlands Antilles
7-night caribbean cruise
$3,262
Windstar Cruises –
Star Legend
Departs
Dec 20, 2027
from
San Juan, Puerto Rico
14-night caribbean cruise
$5,193
Windstar Cruises –
Star Legend
Departs
Dec 20, 2027
from
San Juan, Puerto Rico