December 2026 Windstar Cruises Cruises

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6 Night Oceania & South Pacific Cruise from Moorea, Society Islands, French Polynesia
6 Night Oceania & South Pacific Cruise from Moorea, Society Islands, French Polynesia
Windstar Cruises Star Breeze
Departure Port: Moorea, Society Islands, French Polynesia
OCG Class
Luxury
Cruises to: RAIATEA; RAIATEA; MOTU MAHAEA, NEAR TAHA'A; BORA BORA; BORA BORA; HUAHINE; PAPEETE, TAHITI more ...
DepartingInteriorOceanviewBalconySuite
Dec 11, 2026Contact cruise line for pricing & availability
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-$2,345-$3,185
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 9, 2027-$2,121-$2,961
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-$2,121-$2,961
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: SOPER'S HOLE, TORTOLA, BVI; GUSTAVIA, ST. BARTHELEMY; FALMOUTH HARBOUR, ANTIGUA; PHILIPSBURG, ST. MAARTEN; PHILIPSBURG, ST. MAARTEN
DepartingInteriorOceanviewBalconySuite
Jan 16, 2027-$2,121-$2,961
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: FALMOUTH HARBOUR, ANTIGUA; SOPER'S HOLE, TORTOLA, BVI; GUSTAVIA, ST. BARTHELEMY; PHILIPSBURG, ST. MAARTEN; PHILIPSBURG, ST. MAARTEN
DepartingInteriorOceanviewBalconySuite
Jan 2, 2027-$2,131-$2,971
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
Jan 10, 2027-$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: 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 Central America & Panama Canal Cruise from Colon, Panama
7 Night Central America & Panama Canal Cruise from Colon, Panama
Windstar Cruises 3tar Legend
Departure Port: Colon, Panama
OCG Class
Luxury
Cruises to: FUERTE AMADOR, PANAMA CITY; FUERTE AMADOR, PANAMA CITY; QUEPOS, MANUEL ANTONIO NATL PK; PUERTO CALDERA, SAN JOSE'
DepartingInteriorOceanviewBalconySuite
Jan 19, 2027Contact cruise line for pricing & availability
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