Windstar's 2025-2026 Itineraries
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5-night Barefoot Break in the British Virgin Islands
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:$2,1507-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:$2,3517-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 Beach Fun & Sun: A Remote Caribbean Getaway
Dec 14, 2025 Aboard Wind Surf St. Maarten (Philipsburg), Falmouth Harbour,...St. Maarten (Philipsburg), Falmouth Harbour, Antigua, Road Bay, Sopers Hole, Tortola, Jost Van Dyke, Jost Van Dyke,... pricing from:$2,4677-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 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:$2,5517-night Beach Fun & Sun: A Remote Caribbean Getaway
Jan 4, 2026 Aboard Wind Surf St. Maarten (Philipsburg), Falmouth Harbour,...St. Maarten (Philipsburg), Falmouth Harbour, Antigua, Road Bay, Sopers Hole, Tortola, Jost Van Dyke, Jost Van Dyke,... pricing from:$2,6107-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 Beach Fun & Sun: A Remote Caribbean Getway
Feb 21, 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:$2,6607-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:$2,6607-night Beach Fun & Sun: A Remote Caribbean Getway
Feb 14, 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:$2,6607-night Dreams of Tahiti
Mar 5, 2026 Aboard Star Breeze Papeete, Papeete, Moorea, Raiatea, Raiatea,...Papeete, Papeete, Moorea, Raiatea, Raiatea, Taha'a Motu Mahana, Bora Bora, Bora Bora, Huahine, Papeete pricing from:$2,7157-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:$2,7517-night Beach Fun & Sun: A Remote Caribbean Getaway
Dec 28, 2025 Aboard Wind Surf St. Maarten (Philipsburg), Falmouth Harbour,...St. Maarten (Philipsburg), Falmouth Harbour, Antigua, Road Bay, Sopers Hole, Tortola, Jost Van Dyke, Jost Van Dyke,... pricing from:$2,7677-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:$2,9407-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:$2,9697-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:$3,1577-night Dreams of Tahiti
Apr 16, 2026 Aboard Star Breeze Papeete, Papeete, Moorea, Raiatea, Raiatea,...Papeete, Papeete, Moorea, Raiatea, Raiatea, Taha'a Motu Mahana, Bora Bora, Bora Bora, Huahine, Papeete pricing from:$3,2127-night Dreams of Tahiti Cruise
Dec 4, 2025 Aboard Star Breeze Papeete, Papeete, Moorea, Raiatea, Raiatea,...Papeete, Papeete, Moorea, Raiatea, Raiatea, Taha'a Motu Mahana, Bora Bora, Bora Bora, Huahine, Papeete pricing from:$3,2157-night Dreams of Tahiti Cruise
Dec 11, 2025 Aboard Star Breeze Papeete, Papeete, Moorea, Raiatea, Raiatea,...Papeete, Papeete, Moorea, Raiatea, Raiatea, Taha'a Motu Mahana, Bora Bora, Bora Bora, Huahine, Papeete pricing from:$3,215
showing 1 - 20 of 76 matching results
Terms and Conditions: Fares/rates are per person, based on double occupancy for select sail and travel dates; are capacity controlled and subject to availability at time booking and may be pulled without notice. We reserve the right to correct errors. Information and pricing is subject to change without notice. While we do our very best to ensure that information and pricing appearing in this website is complete and accurate, we cannot be responsible for incomplete and inaccurate representations, which may or may not be under our control. In the event of a pricing error, misrepresentation or omission, we reserve the right to adjust the pricing or make any other corrections.