24 reviews | Feb 15, 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 | $2,699 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) |
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24 reviews | Feb 22, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,599 Up To $300 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 | | |
10 reviews | Mar 04, 2025 | Windstar | Wind Star | Caribbean | Puerto Caldera | Colon | 7 Nights | Balboa / Fuerte Amador | Colón | Golfo Dulce | Isla Parida | La Fortuna (Arenal), Costa Rica | Panama Canal | Puerto Caldera | PUERTO CALDERA, SAN JOSE, Costa Rica | Quepos | SAN JOSE, Costa Rica | Santa Elena (Monteverde) | $5,499 Up To $750 Onboard Credit | | |
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) |
24 reviews | Mar 08, 2025 | Windstar | Wind Surf | Caribbean - Eastern | 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 | $4,299 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 | $2,699 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Mar 08, 2025 | Windstar | Star Pride | World Cruise | Balboa | Bridgetown | 14 Nights | Balboa / Fuerte Amador | Bocas del Toro | Bridgetown | Cartagena | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | Panama Canal | San Blas | Santa Marta | Soufriere | Willemstad | $4,299 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 | Mar 15, 2025 | Windstar | Wind Surf | Caribbean - Eastern | 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 | $4,199 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Mar 15, 2025 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,699 Up To $300 Onboard Credit Welcome Reception Exclusive Amenity Distinctive Host | | *Distinctive Voyage |
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 | $2,599 Up To $300 Onboard Credit | | |
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 | $2,499 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
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 | $6,299 Up To $750 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! |
15 reviews | Oct 26, 2025 | Windstar | Star Pride | Caribbean | San Juan | San Juan | 7 Nights | Basseterre | Gustavia | Jost Van Dyke, Great Harbour | San Juan | St. Maarten | Virgin Gorda / Prickly Pear | $2,699 Up To $300 Onboard Credit | | Suite! |
5 reviews | Oct 30, 2025 | Windstar | Star Legend | Greek Isles | Athens (Piraeus) | Malaga | 15 Nights | Argostoli | Athens, Greece | Barcelona | Cagliari | Cartagena | Corfu | Corinth Canal | Delphi | Gibraltar | Málaga | Messina (Taormina) | Palma de Mallorca | Trapani | Valencia | $5,599 Up To $750 Onboard Credit | | |