11 reviews | Mar 21, 2026 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bridgetown | Les Saintes | Little Bay | Pigeon Island | Roseau | $2,599 Up To $300 Onboard Credit | | |
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 | Mar 21, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Philipsburg | 14 Nights | Basseterre | Charlestown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $3,699 Up To $500 Onboard Credit | | |
24 reviews | Mar 28, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $2,399 Up To $250 Onboard Credit | | |
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10 reviews | Nov 19, 2024 | Windstar | Wind Star | Caribbean - Southern | Bridgetown | Colon | 11 Nights | Bequia | Bridgetown | Cartagena | Colón | Kralendijk | Mayreau | Oranjestad | St. George's | Willemstad | $3,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Dec 07, 2024 | Windstar | Wind Spirit | Caribbean - Southern | Bridgetown | Bridgetown | 7 Nights | Bequia | Bridgetown | Castries | Kingstown | Mayreau | Pigeon Island | St. George's | The Pitons | $2,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Dec 14, 2024 | Windstar | Star Pride | Caribbean - Southern | Bridgetown | Balboa | 14 Nights | Balboa / Fuerte Amador | Bocas del Toro | Bridgetown | Cartagena | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | San Blas | Santa Marta | Soufriere | Willemstad | $4,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Dec 14, 2024 | Windstar | Star Pride | Caribbean - Southern | Bridgetown | Oranjestad | 7 Nights | Bridgetown | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | Soufriere | Willemstad | $2,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Dec 21, 2024 | Windstar | Wind Spirit | Caribbean - Southern | Bridgetown | Bridgetown | 7 Nights | Bequia | Bridgetown | Castries | Kingstown | Mayreau | Pigeon Island | St. George's | The Pitons | $2,899 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Dec 28, 2024 | Windstar | Star Pride | Caribbean - Southern | Balboa | Bridgetown | 14 Nights | Balboa / Fuerte Amador | Bocas del Toro | Bridgetown | Cartagena | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | San Blas | Santa Marta | Soufriere | Willemstad | $4,999 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Jan 04, 2025 | Windstar | Star Pride | Caribbean - Southern | Oranjestad | Bridgetown | 7 Nights | Bridgetown | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | Soufriere | Willemstad | $2,699 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 | $2,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Jan 11, 2025 | Windstar | Star Pride | Caribbean - Southern | Bridgetown | Balboa | 14 Nights | Balboa / Fuerte Amador | Bocas del Toro | Bridgetown | Cartagena | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | San Blas | Santa Marta | Soufriere | Willemstad | $4,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Jan 11, 2025 | Windstar | Star Pride | Caribbean - Southern | Bridgetown | Oranjestad | 7 Nights | Bridgetown | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | Soufriere | Willemstad | $2,999 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Jan 18, 2025 | Windstar | Wind Spirit | Caribbean - Southern | Bridgetown | Bridgetown | 7 Nights | Bequia | Bridgetown | Castries | Kingstown | Mayreau | Pigeon Island | St. George's | The Pitons | $2,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
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 | $2,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Feb 15, 2025 | Windstar | Wind Spirit | Caribbean - Southern | Bridgetown | Bridgetown | 7 Nights | Bequia | Bridgetown | Castries | Kingstown | Mayreau | Pigeon Island | St. George's | The Pitons | $2,699 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Feb 22, 2025 | Windstar | Star Pride | Caribbean - Southern | Bridgetown | Balboa | 14 Nights | Balboa / Fuerte Amador | Bocas del Toro | Bridgetown | Cartagena | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | San Blas | Santa Marta | Soufriere | Willemstad | $4,299 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Feb 22, 2025 | Windstar | Star Pride | Caribbean - Southern | Bridgetown | Oranjestad | 7 Nights | Bridgetown | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | Soufriere | Willemstad | $2,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
10 reviews | Mar 15, 2025 | Windstar | Wind Star | Caribbean - Southern | Colon | Bridgetown | 11 Nights | Bridgetown | Cartagena | Colón | Kralendijk | Mayreau | Oranjestad | Santa Marta | St. George's | Willemstad | $3,399 Up To $500 Onboard Credit | | |