24 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | 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 | | |
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) | Oct 23, 2024 | Windstar | Star Pride | Caribbean | Boston | San Juan | 11 Nights | Basseterre | Boston | Gustavia | Hamilton | San Juan | St. George's | Virgin Gorda | $2,899 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 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 | | |
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15 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/233.jpg.webp) | Nov 03, 2024 | Windstar | Star Pride | Caribbean - Eastern | San Juan | San Juan | 13 Nights | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | San Juan | St. George's | St. Maarten | Virgin Gorda | $4,749 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) | Nov 03, 2024 | Windstar | Star Pride | Caribbean - Eastern | San Juan | San Juan | 6 Nights | Gustavia | Jost Van Dyke, Great Harbour | Little Bay | San Juan | St. Maarten | Virgin Gorda | $2,599 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) | Nov 09, 2024 | Windstar | Star Pride | Caribbean - Eastern | San Juan | San Juan | 7 Nights | Bequia | Les Saintes | Pigeon Island | San Juan | St. George's | St. Maarten | $3,199 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) | Nov 09, 2024 | Windstar | Star Pride | Caribbean | San Juan | San Juan | 14 Nights | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | San Juan | St. George's | St. Maarten | St. Thomas | Virgin Gorda / Prickly Pear | $4,749 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) | 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) |
15 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Itineraires_Map/130338__202301191125__.jpg.webp) | Nov 16, 2024 | Windstar | Star Pride | Caribbean - Eastern | San Juan | San Juan | 14 Nights | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | San Juan | St. George's | St. Maarten | St. Thomas | Virgin Gorda | $4,199 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) | Nov 16, 2024 | Windstar | Star Pride | Caribbean - Eastern | San Juan | San Juan | 7 Nights | Gustavia | Jost Van Dyke, Great Harbour | Little Bay | San Juan | St. Maarten | St. Thomas | Virgin Gorda | $2,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
10 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/121.jpg.webp) | 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) |
15 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Itineraires_Map/130342__202301191124__.jpg.webp) | Nov 23, 2024 | Windstar | Star Pride | Caribbean - Eastern | San Juan | San Juan | 14 Nights | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | San Juan | St. George's | St. Maarten | St. Thomas | Virgin Gorda | $4,449 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) | Nov 23, 2024 | Windstar | Star Pride | Caribbean - Eastern | San Juan | San Juan | 7 Nights | Bequia | Les Saintes | Pigeon Island | San Juan | St. George's | St. Maarten | $2,399 Up To $250 Onboard Credit | | Suite! |
11 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/120.jpg.webp) | Nov 27, 2024 | Windstar | Wind Spirit | Caribbean | Bridgetown | Bridgetown | 10 Nights | Bridgetown | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | Soper's Hole | Virgin Gorda / Prickly Pear | $3,699 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) | Nov 30, 2024 | Windstar | Star Pride | Caribbean - Eastern | San Juan | San Juan | 7 Nights | Gustavia | Jost Van Dyke, Great Harbour | Little Bay | San Juan | St. Maarten | St. Thomas | Virgin Gorda | $2,999 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
10 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/121.jpg.webp) | Dec 03, 2024 | 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) | $5,199 Up To $750 Onboard Credit | | Onboard Credit! |
15 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/233.jpg.webp) | Dec 07, 2024 | Windstar | Star Pride | Caribbean - Eastern | San Juan | Bridgetown | 7 Nights | Bridgetown | Gustavia | Little Bay | Pigeon Island | Roseau | San Juan | St. George's | St. Thomas | $2,599 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) | 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 ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/233.jpg.webp) | Dec 07, 2024 | Windstar | Star Pride | Caribbean | San Juan | Oranjestad | 14 Nights | Bridgetown | Gustavia | Kralendijk | Little Bay | Man-O-War Bay | Mayreau | Oranjestad | Pigeon Island | Roseau | San Juan | Soufriere | St. George's | St. Thomas | Willemstad | $4,199 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |