24 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | 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) |
15 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/233.jpg.webp) | Jan 29, 2026 | Windstar | Star Pride | Panama Canal | Lima | Puerto Caldera | 18 Nights | Balboa / Fuerte Amador | Colón | Golfo Dulce | Guayaquil, Ecuador | Isla Parida | Lima, Peru | Manta, Equador | Panama Canal | Puerto Caldera | Quepos | Trujillo, Peru | $6,399 Up To $750 Onboard Credit | | |
11 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/120.jpg.webp) | Nov 13, 2024 | Windstar | Wind Spirit | Transatlantic | Lisbon | Bridgetown | 14 Nights | Bridgetown | Lisbon | $2,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/120.jpg.webp) | Apr 06, 2025 | Windstar | Wind Spirit | Mediterranean | Lisbon | Barcelona | 9 Nights | Barcelona | Cartagena | Lisbon | Málaga | Palma de Mallorca | Tangier | Tarragona | Valencia | $3,299 Up To $500 Onboard Credit | | |
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24 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | 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 ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | 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! |
11 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/120.jpg.webp) | Nov 04, 2025 | Windstar | Wind Spirit | Transatlantic | Lisbon | Bridgetown | 14 Nights | Bridgetown | Lisbon | $2,499 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | Nov 18, 2025 | Windstar | Wind Surf | Transatlantic | Lisbon | Philipsburg | 19 Nights | Gustavia | Jost Van Dyke, Great Harbour | Lisbon | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $3,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
5 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/244.jpg.webp) | 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 | | |
5 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/244.jpg.webp) | Dec 13, 2025 | Windstar | Star Legend | Caribbean | Malaga | Rome | 14 Nights | Barcelona | Cartagena | Genoa, Italy | Gibraltar | Livorno | Málaga | Nice | Palma de Mallorca | Rome | Valencia | $5,299 Up To $750 Onboard Credit | | Suite! |
5 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/244.jpg.webp) | 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! |
15 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/233.jpg.webp) | Oct 12, 2024 | Windstar | Star Pride | Canada | Montreal | San Juan | 22 Nights | Bar Harbor | Basseterre | Boston | Cap aux Meules | Gaspe | Gustavia | Halifax | Hamilton | Louisbourg | Lunenburg | Montreal | Portland | Quebec City | San Juan | St. George's | Virgin Gorda | $6,929 Up To $750 Onboard Credit | | Suite! |
15 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/233.jpg.webp) | 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) |
24 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | Feb 01, 2026 | Windstar | Wind Surf | Caribbean | Oranjestad | Colon | 8 Nights | Bocas del Toro | Cartagena | Colón | Oranjestad | Santa Marta | $3,199 Up To $500 Onboard Credit | | |
24 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | Feb 01, 2026 | Windstar | Wind Surf | Caribbean | Oranjestad | Cozumel | 16 Nights | Belize City | Bocas del Toro | Cartagena | Colón | Costa Maya | Cozumel | Isla San Andres | Oranjestad | Roatan | Santa Marta | $5,099 Up To $750 Onboard Credit | | |
24 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Itineraires_Map/130358__202301191054__.jpg.webp) | Dec 21, 2024 | 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 | $5,199 Up To $750 Onboard Credit | | |
24 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | Dec 21, 2024 | Windstar | Wind Surf | Caribbean - Eastern | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,999 Up To $300 Onboard Credit | | Onboard Credit! |
24 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Itineraires_Map/130365__202301191053__.jpg.webp) | Dec 28, 2024 | 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 | $5,199 Up To $750 Onboard Credit | | Onboard Credit! |
24 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | Dec 28, 2024 | 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 | $3,499 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Itineraires_Map/130372__202301191050__.jpg.webp) | Jan 04, 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 | $4,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |