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All Caribbean Cruises on Windstar Cruises
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Showing 21 - 30 of 40 Cruises
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8 Night Caribbean Cruise from Boston, MA
Windstar Cruises Star Pride
Departure Port:
Boston, MA
OCG Class
Luxury
Cruises to: HAMILTON; HAMILTON; ST GEORGE'S BERMUDA; ST GEORGE'S BERMUDA; SAN JUAN; SAN JUAN
Departing
Interior
Oceanview
Balcony
Suite
Oct 20, 2026
Contact cruise line for pricing & availability
Add to Compare
8 Night Caribbean Cruise from Bridgetown, Barbados
Windstar Cruises 3tar Legend
Departure Port:
Bridgetown, Barbados
OCG Class
Luxury
Cruises to: RODNEY BAY; BEQUIA; ST. GEORGE'S, GRENADA; WILLEMSTAD, CURACAO; ORANJESTAD, ARUBA; ORANJESTAD, ARUBA
Departing
Interior
Oceanview
Balcony
Suite
Dec 4, 2026
-
$2,327
$3,607
$5,967
Add to Compare
8 Night Caribbean Cruise from Philipsburg, St Maarten, St Martin/St Maarten
Windstar Cruises Wind Surf
Departure Port:
Philipsburg, St Maarten, St Martin/St Maarten
OCG Class
Luxury
Cruises to: ST. JOHN'S, ANTIGUA; GUSTAVIA, ST. BARTHELEMY; SOPER'S HOLE, TORTOLA, BVI; PHILIPSBURG, ST. MAARTEN; PHILIPSBURG, ST. MAARTEN
Departing
Interior
Oceanview
Balcony
Suite
Dec 19, 2027
-
$2,996
-
$3,956
Add to Compare
10 Night Caribbean Cruise from Boston, MA
Windstar Cruises Star Pride
Departure Port:
Boston, MA
OCG Class
Luxury
Cruises to: HAMILTON; HAMILTON; ST GEORGE'S BERMUDA; ST GEORGE'S BERMUDA; GUSTAVIA, ST. BARTHELEMY; SAN JUAN; SAN JUAN
Departing
Interior
Oceanview
Balcony
Suite
Oct 22, 2027
Contact cruise line for pricing & availability
Add to Compare
13 Night Caribbean Cruise from Aruba
Windstar Cruises Star Pride
Departure Port:
Aruba
OCG Class
Luxury
Cruises to: WILLEMSTAD, CURACAO; GUSTAVIA, ST. BARTHELEMY; SAN JUAN; SAN JUAN; ST. GEORGE'S, GRENADA; BEQUIA; MARIGOT BAY
more ...
Departing
Interior
Oceanview
Balcony
Suite
Mar 6, 2028
Contact cruise line for pricing & availability
Add to Compare
13 Night Caribbean Cruise from Philipsburg, St Maarten, St Martin/St Maarten
Windstar Cruises Wind Surf
Departure Port:
Philipsburg, St Maarten, St Martin/St Maarten
OCG Class
Luxury
Cruises to: GUSTAVIA, ST. BARTHELEMY; SOPER'S HOLE, TORTOLA, BVI; PHILIPSBURG, ST. MAARTEN; PHILIPSBURG, ST. MAARTEN; ROSEAU, DOMINICA; BASSETERRE, ST. KITTS; GUSTAVIA, ST. BARTHELEMY
more ...
Departing
Interior
Oceanview
Balcony
Suite
Jan 3, 2028
Contact cruise line for pricing & availability
Add to Compare
14 Night Caribbean Cruise from San Juan, Puerto Rico
Windstar Cruises 3tar Legend
Departure Port:
San Juan, Puerto Rico
OCG Class
Luxury
Cruises to: ST. GEORGE'S, GRENADA; BEQUIA; MARIGOT BAY; SAN JUAN; SAN JUAN; PHILIPSBURG, ST. MAARTEN; GUSTAVIA, ST. BARTHELEMY
more ...
Departing
Interior
Oceanview
Balcony
Suite
Jan 10, 2028
Contact cruise line for pricing & availability
Add to Compare
14 Night Caribbean Cruise from San Juan, Puerto Rico
Windstar Cruises 3tar Legend
Departure Port:
San Juan, Puerto Rico
OCG Class
Luxury
Cruises to: GUSTAVIA, ST. BARTHELEMY; BASSETERRE, ST. KITTS; PHILIPSBURG, ST. MAARTEN; SAN JUAN; SAN JUAN; ST. GEORGE'S, GRENADA; BEQUIA
more ...
Departing
Interior
Oceanview
Balcony
Suite
Jan 3, 2028
Contact cruise line for pricing & availability
Add to Compare
14 Night Caribbean Cruise from San Juan, Puerto Rico
Windstar Cruises 3tar Legend
Departure Port:
San Juan, Puerto Rico
OCG Class
Luxury
Cruises to: PHILIPSBURG, ST. MAARTEN; GUSTAVIA, ST. BARTHELEMY; BASSETERRE, ST. KITTS; SAN JUAN; SAN JUAN; ST. GEORGE'S, GRENADA; BEQUIA
more ...
Departing
Interior
Oceanview
Balcony
Suite
Jan 17, 2028
Contact cruise line for pricing & availability
Add to Compare
14 Night Caribbean Cruise from San Juan, Puerto Rico
Windstar Cruises Star Pride
Departure Port:
San Juan, Puerto Rico
OCG Class
Luxury
Cruises to: ST. GEORGE'S, GRENADA; BEQUIA; MARIGOT BAY; SAN JUAN; SAN JUAN; GUSTAVIA, ST. BARTHELEMY; BASSETERRE, ST. KITTS
more ...
Departing
Interior
Oceanview
Balcony
Suite
Dec 6, 2026
Contact cruise line for pricing & availability
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