Windstar's 2025-2026 Itineraries
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showing 1 - 20 of 68 matching results
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7-night Classic Caribbean
Dec 7, 2025 Aboard Wind Surf St. Maarten (Philipsburg), Charlestown, Roseau,...St. Maarten (Philipsburg), Charlestown, Roseau, Dominica, Pigeon Island, St. Lucia, Iles des Saintes, Gustavia,... pricing from:$2,3517-night Classic Caribbean
Mar 21, 2026 Aboard Wind Surf St. Maarten (Philipsburg), Charlestown, Roseau,...St. Maarten (Philipsburg), Charlestown, Roseau, Dominica, Pigeon Island, St. Lucia, Iles des Saintes, Gustavia,... pricing from:$2,4517-night Lush & Lovely Islands of the Lesser Antilles
Feb 28, 2026 Aboard Wind Spirit St. Maarten (Philipsburg), Basseterre, St. Kitts,...St. Maarten (Philipsburg), Basseterre, St. Kitts, Gustavia, Little Bay, Iles des Saintes, Roseau, Dominica, Pigeon... pricing from:$2,5207-night Jewels of the Windward Islands
Mar 21, 2026 Aboard Wind Spirit Bridgetown (Barbados), Little Bay, Iles des...Bridgetown (Barbados), Little Bay, Iles des Saintes, Roseau, Dominica, Anse Mitan, Pigeon Island, St. Lucia, Bridgetown... pricing from:$2,6167-night Classic Caribbean
Feb 28, 2026 Aboard Wind Surf St. Maarten (Philipsburg), Charlestown, Roseau,...St. Maarten (Philipsburg), Charlestown, Roseau, Dominica, Pigeon Island, St. Lucia, Iles des Saintes, Gustavia,... pricing from:$2,6517-night Classic Caribbean
Feb 7, 2026 Aboard Wind Spirit St. Maarten (Philipsburg), Charleston, SC,...St. Maarten (Philipsburg), Charleston, SC, Roseau, Dominica, Pigeon Island, St. Lucia, Iles des Saintes, Gustavia,... pricing from:$2,7177-night Beach Fun & Sun: A Remote Caribbean Getway
Jan 24, 2026 Aboard Wind Spirit St. Maarten (Philipsburg), Sopers Hole, Tortola,...St. Maarten (Philipsburg), Sopers Hole, Tortola, Jost Van Dyke, Jost Van Dyke, Virgin Gorda ,... pricing from:$2,7607-night Dreams of Tahiti Cruise
Dec 4, 2025 Aboard Star Breeze Papeete, Moorea, Raiatea, Raiatea, Taha'a, Bora...Papeete, Moorea, Raiatea, Raiatea, Taha'a, Bora Bora, Bora Bora, Huahine, Papeete pricing from:$2,9157-night Dreams of Tahiti Cruise
Dec 11, 2025 Aboard Star Breeze Papeete, Moorea, Raiatea, Raiatea, Taha'a, Bora...Papeete, Moorea, Raiatea, Raiatea, Taha'a, Bora Bora, Bora Bora, Huahine, Papeete pricing from:$2,9157-night Classic Caribbean
Dec 21, 2025 Aboard Wind Surf St. Maarten (Philipsburg), Charlestown, Roseau,...St. Maarten (Philipsburg), Charlestown, Roseau, Dominica, Pigeon Island, St. Lucia, Iles des Saintes, Gustavia,... pricing from:$2,9517-night Costa Rica & Panama Canal
Dec 6, 2025 Aboard Wind Spirit Puerto Caldera (Puntarenas), Quepos, Golfo Dulce...Puerto Caldera (Puntarenas), Quepos, Golfo Dulce (Puerto Jimenez), Isla Parida, Balboa, Panama Canal, Colon (Panama) pricing from:$3,1697-night Dreams of Tahiti Cruise
Jan 8, 2026 Aboard Star Breeze Papeete, Moorea, Raiatea, Raiatea, Taha'a, Bora...Papeete, Moorea, Raiatea, Raiatea, Taha'a, Bora Bora, Bora Bora, Huahine, Papeete, Papeete pricing from:$3,3157-night Costa Rica and Panama Canal
Feb 23, 2026 Aboard Star Pride Colon (Panama), Panama Canal, Balboa, Balboa,...Colon (Panama), Panama Canal, Balboa, Balboa, Isla Parida, Golfo Dulce (Puerto Jimenez), Quepos, Puntarenas pricing from:$3,3577-night Costa Rica and Panama Canal
Feb 16, 2026 Aboard Star Pride Puntarenas, Quepos, Golfo Dulce (Puerto Jimenez),...Puntarenas, Quepos, Golfo Dulce (Puerto Jimenez), Isla Parida, Balboa, Panama Canal, Colon (Panama) pricing from:$3,3577-night Costa Rica and Panama Canal
Mar 2, 2026 Aboard Star Pride Puntarenas, Quepos, Golfo Dulce (Puerto Jimenez),...Puntarenas, Quepos, Golfo Dulce (Puerto Jimenez), Isla Parida, Balboa, Panama Canal, Colon (Panama) pricing from:$3,35712-night Star Collector: Ivory Beaches & Sapphire Seas of the Caribbean
Dec 2, 2025 Aboard Wind Surf St. Maarten (Philipsburg), Sopers Hole, Tortola,...St. Maarten (Philipsburg), Sopers Hole, Tortola, Jost Van Dyke, Jost Van Dyke, Virgin Gorda ,... pricing from:$3,50210-night Canary Island Idyll
Jan 19, 2026 Aboard Wind Star Santa Cruz de Tenerife, La Gomera, Santa Cruz de...Santa Cruz de Tenerife, La Gomera, Santa Cruz de La Palma, Funchal (Madeira), Portugal, Funchal (Madeira), Portugal,... pricing from:$3,51910-night Canary Island Idyll
Jan 29, 2026 Aboard Wind Star Santa Cruz de Tenerife, La Gomera, Santa Cruz de...Santa Cruz de Tenerife, La Gomera, Santa Cruz de La Palma, Funchal (Madeira), Portugal, Funchal (Madeira), Portugal,... pricing from:$3,51910-night Canary Island Idyll
Feb 8, 2026 Aboard Wind Star Santa Cruz de Tenerife, La Gomera, Santa Cruz de...Santa Cruz de Tenerife, La Gomera, Santa Cruz de La Palma, Funchal (Madeira), Portugal, Funchal (Madeira), Portugal,... pricing from:$3,51910-night Canary Island Idyll
Feb 18, 2026 Aboard Wind Star Santa Cruz de Tenerife, La Gomera, Santa Cruz de...Santa Cruz de Tenerife, La Gomera, Santa Cruz de La Palma, Funchal (Madeira), Portugal, Funchal (Madeira), Portugal,... pricing from:$3,519
showing 1 - 20 of 68 matching results
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