10 reviews | Apr 27, 2024 | Windstar | Wind Star | Greek Isles | Civitavecchia | Athens (Piraeus) | 7 Nights | Athens, Greece | Gythion | Messina (Taormina) | Monemvasia | Ponza | Rome | Sorrento | $1,899 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | May 05, 2024 | Windstar | Wind Spirit | Greek Isles | Civitavecchia | Athens (Piraeus) | 7 Nights | Athens, Greece | Gythion | Messina (Taormina) | Monemvasia | Ponza | Rome | Sorrento | $2,099 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
10 reviews | Jan 11, 2025 | Windstar | Wind Star | Central America | Puerto Caldera | Puerto Caldera | 7 Nights | Bahia Herradura | Corinto | Playa Flamingo | Playas del Coco | Puerto Caldera | Quepos | San Juan del Sur | $2,199 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Jan 25, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,199 Up To $250 Onboard Credit | | |
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10 reviews | Feb 15, 2025 | Windstar | Wind Star | Central America | Puerto Caldera | Puerto Caldera | 7 Nights | Bahia Herradura | Corinto | Playa Flamingo | Playas del Coco | Puerto Caldera | Quepos | San Juan del Sur | $2,199 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Feb 22, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,199 Up To $250 Onboard Credit | | Onboard Credit! |
24 reviews | Mar 01, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,199 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Mar 08, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda | $2,199 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Mar 15, 2025 | Windstar | Star Pride | South America | Oranjestad | Bridgetown | 7 Nights | Balboa / Fuerte Amador | Bocas del Toro | Cartagena | Oranjestad | San Blas | Santa Marta | $2,299 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Mar 22, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda | $2,299 Up To $250 Onboard Credit | | |
15 reviews | Mar 22, 2025 | Windstar | Star Pride | Caribbean | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bridgetown | Les Saintes | Little Bay | Pigeon Island | Roseau | $2,299 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Mar 29, 2025 | Windstar | Star Pride | Caribbean | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Mayreau | Pigeon Island | St. George's | The Pitons | $2,299 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Dec 07, 2025 | Windstar | Wind Surf | Caribbean | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,299 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Feb 28, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,299 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Mar 21, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,299 Up To $250 Onboard Credit | | |
24 reviews | Jan 04, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,399 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Jan 04, 2025 | Windstar | Wind Spirit | Caribbean - Southern | Bridgetown | Bridgetown | 7 Nights | Bequia | Bridgetown | Castries | Kingstown | Mayreau | Pigeon Island | St. George's | The Pitons | $2,399 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Jan 25, 2025 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bridgetown | Les Saintes | Little Bay | Pigeon Island | Roseau | $2,399 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Feb 01, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda | $2,399 Up To $250 Onboard Credit | | |
11 reviews | Feb 01, 2025 | Windstar | Wind Spirit | Caribbean - Southern | Bridgetown | Bridgetown | 7 Nights | Bequia | Bridgetown | Castries | Kingstown | Mayreau | Pigeon Island | St. George's | The Pitons | $2,399 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |