Windstar Cruises Cruises

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7 Night Caribbean Cruise from Philipsburg, St Maarten, St Martin/St Maarten
7 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; FALMOUTH HARBOUR, ANTIGUA; SOPER'S HOLE, TORTOLA, BVI; PHILIPSBURG, ST. MAARTEN; PHILIPSBURG, ST. MAARTEN
DepartingInteriorOceanviewBalconySuite
Dec 19, 2026-$2,450-$3,290
7 Night Caribbean Cruise from Philipsburg, St Maarten, St Martin/St Maarten
7 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
DepartingInteriorOceanviewBalconySuite
Jan 23, 2027-$3,766-$4,431
Mar 6, 2027-$2,086-$2,926
Mar 20, 2027-$2,191-$3,031
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-$2,301$3,246$5,311
Jan 24, 2028-$2,399$3,274$5,374
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-$2,301$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: GUSTAVIA, ST. BARTHELEMY; BASSETERRE, ST. KITTS; PHILIPSBURG, ST. MAARTEN; SAN JUAN
DepartingInteriorOceanviewBalconySuite
Jan 3, 2028-$2,301$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: BASSETERRE, ST. KITTS; GUSTAVIA, ST. BARTHELEMY; PHILIPSBURG, ST. MAARTEN; SAN JUAN
DepartingInteriorOceanviewBalconySuite
Dec 20, 2027-$2,724$3,424$5,524
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-$2,126$2,857$4,152
Nov 22, 2026-$2,857$3,592$5,027
Mar 13, 2028-$2,154$3,624$5,724
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-$2,654$3,809$4,299
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-$2,126$2,857$4,152
Dec 20, 2026-$2,157$2,857$4,152
Jan 3, 2027-$4,117$4,817$7,652
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-$2,126$2,857$4,152
Mar 20, 2028-$2,126$3,386$5,451

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