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All Caribbean Cruises on Windstar Cruises
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Showing 31 - 40 of 40 Cruises
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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; BASSETERRE, ST. KITTS; GUSTAVIA, ST. BARTHELEMY
more ...
Departing
Interior
Oceanview
Balcony
Suite
Nov 8, 2026
Contact cruise line for pricing & availability
Mar 13, 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; BASSETERRE, ST. KITTS; GUSTAVIA, ST. BARTHELEMY
more ...
Departing
Interior
Oceanview
Balcony
Suite
Nov 8, 2026
Contact cruise line for pricing & availability
Mar 13, 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; BASSETERRE, ST. KITTS; GUSTAVIA, ST. BARTHELEMY
more ...
Departing
Interior
Oceanview
Balcony
Suite
Nov 8, 2026
Contact cruise line for pricing & availability
Mar 13, 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; BASSETERRE, ST. KITTS; GUSTAVIA, ST. BARTHELEMY
more ...
Departing
Interior
Oceanview
Balcony
Suite
Nov 8, 2026
Contact cruise line for pricing & availability
Mar 13, 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: GUSTAVIA, ST. BARTHELEMY; BASSETERRE, ST. KITTS; PHILIPSBURG, ST. MAARTEN; SAN JUAN; SAN JUAN; ST. GEORGE'S, GRENADA; BEQUIA
more ...
Departing
Interior
Oceanview
Balcony
Suite
Dec 13, 2026
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; BASSETERRE, ST. KITTS; GUSTAVIA, ST. BARTHELEMY
more ...
Departing
Interior
Oceanview
Balcony
Suite
Jan 3, 2027
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: BASSETERRE, ST. KITTS; GUSTAVIA, ST. BARTHELEMY; PHILIPSBURG, ST. MAARTEN; SAN JUAN; SAN JUAN; ST. GEORGE'S, GRENADA; BEQUIA
more ...
Departing
Interior
Oceanview
Balcony
Suite
Nov 15, 2026
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15 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: ROSEAU, DOMINICA; BASSETERRE, ST. KITTS; GUSTAVIA, ST. BARTHELEMY; PHILIPSBURG, ST. MAARTEN; PHILIPSBURG, ST. MAARTEN; ST. JOHN'S, ANTIGUA; GUSTAVIA, ST. BARTHELEMY
more ...
Departing
Interior
Oceanview
Balcony
Suite
Dec 12, 2027
Contact cruise line for pricing & availability
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16 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; CARTAGENA, COLOMBIA
more ...
Departing
Interior
Oceanview
Balcony
Suite
Dec 4, 2026
Contact cruise line for pricing & availability
Add to Compare
20 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
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