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) |
2 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/243.jpg.webp) | Jul 04, 2024 | Windstar | Star Breeze | Tahiti | Papeete | Papeete | 14 Nights | Bora Bora | Fakarava | Moorea | Motu Mahaea (Tahaa) | Omoa, Fatu Hiva, Marquesas | Papeete | Rangiroa | $6,099 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) | Sep 06, 2024 | Windstar | Star Pride | USA - New England | Reykjavik | Montreal | 14 Nights | Bonne Bay / Woody Point | Havre | Montreal | Nanortalik | Narsaq | Prince Christian Sound | Qaqortoq | Quebec City | Reykjavik | St. Anthony | $7,289 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
2 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/243.jpg.webp) | Sep 26, 2024 | Windstar | Star Breeze | Tahiti | Papeete | Papeete | 14 Nights | Bora Bora | Fakarava | Moorea | Motu Mahaea (Tahaa) | Omoa, Fatu Hiva, Marquesas | Papeete | Rangiroa | $6,099 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
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10 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/121.jpg.webp) | Oct 12, 2024 | Windstar | Wind Star | Mediterranean | Athens (Piraeus) | Barcelona | 14 Nights | Athens, Greece | Barcelona | Bastia | Calvi | Gythion | Mahon | Messina (Taormina) | Monemvasia | Palma de Mallorca | Ponza | Portoferraio | Rome | Sorrento | $6,419 Up To $750 Onboard Credit | | |
11 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/120.jpg.webp) | Oct 20, 2024 | Windstar | Wind Spirit | Mediterranean | Athens (Piraeus) | Barcelona | 14 Nights | Athens, Greece | Barcelona | Bastia | Calvi | Gythion | Mahon | Messina (Taormina) | Monemvasia | Palma de Mallorca | Ponza | Portoferraio | Rome | Sorrento | $4,499 Up To $500 Onboard Credit | | Onboard Credit! |
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/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) | 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) |
11 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/120.jpg.webp) | Dec 07, 2024 | 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 | $4,799 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Itineraires_Map/130350__202301191121__.jpg.webp) | Dec 14, 2024 | 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 | $4,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
10 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Itineraires_Map/130352__202301191115__.jpg.webp) | Dec 14, 2024 | Windstar | Wind Star | Central America | Colon | Puerto Caldera | 14 Nights | Bahia Herradura | Balboa / Fuerte Amador | Colón | Corinto | Golfo Dulce | Isla Parida | Playa Flamingo | Playas del Coco | Puerto Caldera | Quepos | San Juan del Sur | $5,099 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 14, 2024 | 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 | $4,999 Up To $750 Onboard Credit | | Onboard Credit! |
10 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Itineraires_Map/130356__202301191109__.jpg.webp) | Dec 21, 2024 | Windstar | Wind Star | Central America | Puerto Caldera | Colon | 14 Nights | Bahia Herradura | Balboa / Fuerte Amador | Colón | Corinto | Golfo Dulce | Isla Parida | Playa Flamingo | Playas del Coco | Puerto Caldera | Quepos | San Juan del Sur | $6,599 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
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 | | Onboard Credit! |
11 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/120.jpg.webp) | Dec 21, 2024 | 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 | $4,699 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Itineraires_Map/130362__202301191120__.jpg.webp) | Dec 28, 2024 | Windstar | Star Pride | Caribbean - Southern | Balboa | Bridgetown | 14 Nights | Balboa / Fuerte Amador | Bocas del Toro | Bridgetown | Cartagena | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | San Blas | Santa Marta | Soufriere | Willemstad | $4,999 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
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! |