10 reviews | Mar 08, 2025 | Windstar | Wind Star | Central America | Puerto Caldera | Bridgetown | 18 Nights | Balboa / Fuerte Amador | Bridgetown | Cartagena | Colón | Golfo Dulce | Isla Parida | Kralendijk | Mayreau | Oranjestad | Puerto Caldera | Quepos | Santa Marta | St. George's | Willemstad | $5,299 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 | | Onboard Credit! |
24 reviews | Jul 28, 2024 | Windstar | Wind Surf | Mediterranean | Barcelona | Lisbon | 8 Nights | Almeria, Spain | Barcelona | Cádiz | Cartagena | Gibraltar | Lisbon | Málaga | Palma de Mallorca | $2,699 Up To $300 Onboard Credit | | |
24 reviews | Nov 01, 2024 | Windstar | Wind Surf | Mediterranean | Barcelona | Lisbon | 8 Nights | Almeria, Spain | Barcelona | Cádiz | Cartagena | Gibraltar | Lisbon | Málaga | Palma de Mallorca | $3,999 Up To $500 Onboard Credit | | Onboard Credit! |
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24 reviews | Jan 18, 2025 | 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 | $4,599 Up To $500 Onboard Credit | | Onboard Credit! |
24 reviews | Feb 22, 2025 | 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 | $4,399 Up To $500 Onboard Credit | | Onboard Credit! |
24 reviews | Apr 08, 2025 | Windstar | Wind Surf | Caribbean | Lisbon | Barcelona | 8 Nights | Almeria, Spain | Barcelona | Cádiz | Cartagena | Gibraltar | Lisbon | LISBON, Portugal | Málaga | Palma de Mallorca | $6,499 Up To $750 Onboard Credit | | Onboard Credit! |
24 reviews | Jul 27, 2025 | Windstar | Wind Surf | Mediterranean | Barcelona | Lisbon | 8 Nights | Almeria, Spain | Barcelona | Cádiz | Cartagena | Gibraltar | Lisbon | Málaga | Palma de Mallorca | $3,499 Up To $500 Onboard Credit | | |
24 reviews | Jul 31, 2025 | Windstar | Wind Surf | Caribbean | Lisbon | Barcelona | 8 Nights | Almeria, Spain | Barcelona | Cádiz | Cartagena | Gibraltar | Lisbon | LISBON, Portugal | Málaga | Palma de Mallorca | $5,599 Up To $750 Onboard Credit | | Onboard Credit! |
24 reviews | Nov 10, 2025 | Windstar | Wind Surf | Mediterranean | Barcelona | Lisbon | 8 Nights | Almeria, Spain | Barcelona | Cádiz | Cartagena | Gibraltar | Lisbon | Málaga | Palma de Mallorca | $2,999 Up To $300 Onboard Credit | | Onboard Credit! |
24 reviews | Dec 02, 2025 | Windstar | Wind Surf | Caribbean | Philipsburg | Philipsburg | 12 Nights | Basseterre | Charlestown | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Roseau | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $3,399 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 | Dec 07, 2025 | 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 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Dec 14, 2025 | 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 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Dec 14, 2025 | 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 | $3,999 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Dec 21, 2025 | Windstar | Wind Surf | Caribbean | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,699 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Dec 21, 2025 | 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 | $4,299 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Dec 28, 2025 | 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 | $2,699 Up To $300 Onboard Credit | | |
24 reviews | Jan 04, 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 | $2,499 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Jan 04, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Bridgetown | 14 Nights | Basseterre | Bridgetown | Deshaies | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Little Bay | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $3,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |