24 reviews | Feb 17, 2026 | Windstar | Wind Surf | Caribbean | Cozumel | Philipsburg | 18 Nights | Basseterre | Cayman Brac | Charlestown | Cozumel | Grand Cayman | Gustavia | Jost Van Dyke, Great Harbour | La Romana | Les Saintes | Pigeon Island | Port Antonio | Roseau | Santo Domingo | St. Maarten | Virgin Gorda / Prickly Pear | $4,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
5 reviews | Feb 20, 2026 | Windstar | Star Legend | Caribbean | Rome | Barcelona | 16 Nights | Barcelona | Cartagena | Genoa, Italy | Gibraltar | Livorno | Málaga | Nice | Palma de Mallorca | Rome | Valencia | $5,299 Up To $750 Onboard Credit | | |
11 reviews | Feb 21, 2026 | Windstar | Wind Spirit | Caribbean | Philipsburg | Bridgetown | 21 Nights | Anse Mitan | Basseterre | Bridgetown | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $6,099 Up To $750 Onboard Credit | | |
15 reviews | Feb 26, 2026 | Windstar | Star Pride | 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 | | Suite! |
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5 reviews | Feb 27, 2026 | Windstar | Star Legend | Caribbean | Barcelona | Rome | 16 Nights | Barcelona | Cartagena | Genoa, Italy | Gibraltar | Livorno | Málaga | Nice | Palma de Mallorca | Rome | Valencia | $5,299 Up To $750 Onboard Credit | | Suite! |
11 reviews | Feb 28, 2026 | Windstar | Wind Spirit | Caribbean | Philipsburg | Bridgetown | 14 Nights | Anse Mitan | Basseterre | Bridgetown | Gustavia | Les Saintes | Little Bay | Pigeon Island | Roseau | St. Maarten | $3,999 Up To $500 Onboard Credit | | Onboard Credit! |
11 reviews | Mar 07, 2026 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bridgetown | Les Saintes | Little Bay | Pigeon Island | Roseau | $2,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Mar 07, 2026 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 14 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Kingstown | Les Saintes | Little Bay | Mayreau | Pigeon Island | Roseau | St. George's | The Pitons | $4,099 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | Mar 14, 2026 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 14 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Kingstown | Les Saintes | Little Bay | Mayreau | Pigeon Island | Roseau | St. George's | The Pitons | $4,099 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
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 | | Onboard Credit! |
11 reviews | Nov 18, 2025 | Windstar | Wind Spirit | Caribbean - Southern | Bridgetown | Colon | 11 Nights | Bequia | Bridgetown | Cartagena | Colón | Kralendijk | Mayreau | Oranjestad | St. George's | Willemstad | $3,499 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
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 | | |
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! |
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 | | Onboard Credit! |
5 reviews | Nov 07, 2025 | Windstar | Star Legend | Mediterranean | Barcelona | Malaga | 7 Nights | Barcelona | Cartagena | Gibraltar | Málaga | Palma de Mallorca | Valencia | $2,699 Up To $300 Onboard Credit | | Suite! |
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 | | |
5 reviews | Dec 13, 2025 | Windstar | Star Legend | Mediterranean | Malaga | Barcelona | 7 Nights | Barcelona | Cartagena | Gibraltar | Málaga | Palma de Mallorca | Valencia | $3,099 Up To $500 Onboard Credit | | Suite! |
5 reviews | Dec 13, 2025 | Windstar | Star Legend | Mediterranean | Malaga | Venice | 22 Nights | Barcelona | Cartagena | Dubrovnik | Genoa, Italy | Gibraltar | Livorno | Málaga | Messina (Taormina) | Naples | Nice | Palma de Mallorca | Rome | Valencia | Venice | Zadar | $8,299 Up To $1000 Onboard Credit | | Suite! |
5 reviews | Jan 04, 2026 | Windstar | Star Legend | Mediterranean | Venice | Barcelona | 24 Nights | Barcelona | Cartagena | Dubrovnik | Genoa, Italy | Gibraltar | Livorno | Málaga | Messina (Taormina) | Naples | Nice | Palma de Mallorca | Rome | Valencia | Venice | Zadar | $7,999 Up To $1000 Onboard Credit | | Suite! |