All Caribbean Cruises on Windstar Cruises

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7 Night Caribbean Cruise from San Juan, Puerto Rico
7 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
DepartingInteriorOceanviewBalconySuite
Jan 17, 2028-$1,951$3,246$5,311
7 Night Caribbean Cruise from San Juan, Puerto Rico
7 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
DepartingInteriorOceanviewBalconySuite
Jan 10, 2028-$1,951$3,246$5,311
Jan 24, 2028-$1,951$3,246$5,311
7 Night Caribbean Cruise from San Juan, Puerto Rico
7 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
DepartingInteriorOceanviewBalconySuite
Dec 13, 2026-$1,951$3,067$3,977
7 Night Caribbean Cruise from San Juan, Puerto Rico
7 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
DepartingInteriorOceanviewBalconySuite
Nov 15, 2026-$3,739$4,649$5,909
Jan 10, 2027-$1,951$3,067$3,977
Mar 20, 2028-$1,951$3,211$5,276
7 Night Caribbean Cruise from San Juan, Puerto Rico
7 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
DepartingInteriorOceanviewBalconySuite
Dec 6, 2026-$2,262$3,067$3,977
Dec 20, 2026-$2,262$3,137$4,362
Jan 3, 2027-$3,417$4,117$6,252
7 Night Caribbean Cruise from San Juan, Puerto Rico
7 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
DepartingInteriorOceanviewBalconySuite
Nov 8, 2026-$1,951$3,067$3,977
Nov 22, 2026-$1,951$3,067$3,977
Mar 13, 2028-$1,951$3,067$3,977
8 Night Caribbean Cruise from Boston, MA
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
DepartingInteriorOceanviewBalconySuite
Oct 20, 2026Contact cruise line for pricing & availability
8 Night Caribbean Cruise from Bridgetown, Barbados
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
DepartingInteriorOceanviewBalconySuite
Dec 4, 2026-$2,327$3,607$5,967
8 Night Caribbean Cruise from Philipsburg, St Maarten, St Martin/St Maarten
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
DepartingInteriorOceanviewBalconySuite
Dec 19, 2027-$2,996-$3,956
10 Night Caribbean Cruise from Boston, MA
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
DepartingInteriorOceanviewBalconySuite
Oct 22, 2027Contact cruise line for pricing & availability
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