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Windstar Cruises to Caribbean
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7-night caribbean cruise
$2,957
Windstar Cruises –
Wind Surf
Departs
Mar 20, 2027
from
Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals
including an Avoya Exclusive
10-night caribbean cruise
$3,827
Windstar Cruises –
Star Pride
Departs
Oct 22, 2027
from
Boston, Massachusetts
Up to 2 deals
including an Avoya Exclusive
17-night caribbean cruise
$6,649
Windstar Cruises –
Star Pride
Departs
Oct 22, 2027
from
Boston, Massachusetts
Up to 2 deals
including an Avoya Exclusive
7-night caribbean cruise
$2,688
Windstar Cruises –
Star Pride
Departs
Nov 01, 2027
from
San Juan, Puerto Rico
Up to 3 deals
including Avoya Exclusives
14-night caribbean cruise
$4,504
Windstar Cruises –
Star Pride
Departs
Nov 01, 2027
from
San Juan, Puerto Rico
Up to 2 deals
including an Avoya Exclusive
7-night caribbean cruise
$2,551
Windstar Cruises –
Star Pride
Departs
Nov 08, 2027
from
San Juan, Puerto Rico
Up to 2 deals
including an Avoya Exclusive
14-night caribbean cruise
$4,364
Windstar Cruises –
Star Pride
Departs
Nov 08, 2027
from
San Juan, Puerto Rico
Up to 2 deals
including an Avoya Exclusive
7-night caribbean cruise
$2,443
Windstar Cruises –
Star Pride
Departs
Nov 15, 2027
from
San Juan, Puerto Rico
Up to 2 deals
including an Avoya Exclusive
14-night caribbean cruise
$4,224
Windstar Cruises –
Star Pride
Departs
Nov 15, 2027
from
San Juan, Puerto Rico
Up to 2 deals
including an Avoya Exclusive
8-night caribbean cruise
$3,028
Windstar Cruises –
Wind Surf
Departs
Nov 20, 2027
from
Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals
including an Avoya Exclusive
15-night caribbean cruise
$4,845
Windstar Cruises –
Wind Surf
Departs
Nov 20, 2027
from
Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals
including an Avoya Exclusive
7-night caribbean cruise
$2,411
Windstar Cruises –
Star Pride
Departs
Nov 22, 2027
from
San Juan, Puerto Rico
Up to 2 deals
including an Avoya Exclusive
14-night caribbean cruise
$4,197
Windstar Cruises –
Star Pride
Departs
Nov 22, 2027
from
San Juan, Puerto Rico
Up to 2 deals
including an Avoya Exclusive
21-night caribbean cruise
$7,460
Windstar Cruises –
Star Pride
Departs
Nov 22, 2027
from
San Juan, Puerto Rico
Up to 2 deals
including an Avoya Exclusive
7-night caribbean cruise
$2,572
Windstar Cruises –
Wind Surf
Departs
Nov 28, 2027
from
Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals
including an Avoya Exclusive
14-night caribbean cruise
$4,600
Windstar Cruises –
Wind Surf
Departs
Nov 28, 2027
from
Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals
including an Avoya Exclusive
7-night caribbean cruise
$2,658
Windstar Cruises –
Wind Surf
Departs
Dec 05, 2027
from
Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals
including an Avoya Exclusive
14-night caribbean cruise
$4,320
Windstar Cruises –
Wind Surf
Departs
Dec 05, 2027
from
Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals
including an Avoya Exclusive
7-night caribbean cruise
$2,642
Windstar Cruises –
Wind Surf
Departs
Dec 12, 2027
from
Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals
including an Avoya Exclusive
15-night caribbean cruise
$4,845
Windstar Cruises –
Wind Surf
Departs
Dec 12, 2027
from
Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals
including an Avoya Exclusive
8-night caribbean cruise
$3,308
Windstar Cruises –
Wind Surf
Departs
Dec 19, 2027
from
Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals
including an Avoya Exclusive
15-night caribbean cruise
$4,620
Windstar Cruises –
Wind Surf
Departs
Dec 19, 2027
from
Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals
including an Avoya Exclusive
7-night caribbean cruise
$3,052
Windstar Cruises –
Star Legend
Departs
Dec 20, 2027
from
San Juan, Puerto Rico
Up to 2 deals
including an Avoya Exclusive
14-night caribbean cruise
$4,434
Windstar Cruises –
Star Legend
Departs
Dec 20, 2027
from
San Juan, Puerto Rico
Up to 2 deals
including an Avoya Exclusive
7-night caribbean cruise
$2,432
Windstar Cruises –
Wind Surf
Departs
Dec 27, 2027
from
Saint Maarten (Phillipsburg), Netherlands Antilles
Up to 2 deals
including an Avoya Exclusive