As a large-scale seller of Windstar Cruises to Caribbean - Eastern 2023/2024, we are able to offer you unbeatable prices and unparalleled value. With cruise line volume buys plus our low everyday prices you can save up to 75% versus the brochure price! Once you have found the discounted Windstar cruise of your choice, please call our cruise consultants to book your vacation and save money with our first-rate personalized service! Book your Windstar cruise today with AffordableTours.com, your discounted cruise headquarters.
| Sail Date | Cruise Line | Ship | Destination | Departs | Length | Price | You Save | Discounts | |
|---|---|---|---|---|---|---|---|---|---|
15 reviews  | Oct 26, 2023 | Windstar | Star Pride | Boston | Philipsburg | 9 Nights | Boston | Gustavia | Hamilton | St. George's | St. Maarten | $1,599 Up To $200 Onboard Credit | |
15 reviews | Nov 04, 2023 | Windstar | Star Pride | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda | $1,599 Up To $200 Onboard Credit | Suite! |
15 reviews | Nov 04, 2023 | Windstar | Star Pride | Philipsburg | Bridgetown | 21 Nights | Anse Mitan | Basseterre | Bequia | Bridgetown | Castries | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Mayreau | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. George's | St. Maarten | The Pitons | Virgin Gorda | $5,199 Up To $750 Onboard Credit | |
15 reviews | Nov 04, 2023 | Windstar | Star Pride | Philipsburg | Oranjestad | 28 Nights | Anse Mitan | Basseterre | Bequia | Bridgetown | Castries | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Kralendijk | Les Saintes | Little Bay | Man-O-War Bay | Mayreau | Oranjestad | Pigeon Island | Road Bay | Roseau | Soper's Hole | Soufriere | St. George's | St. Maarten | The Pitons | Virgin Gorda | Willemstad | $8,699 Up To $1000 Onboard Credit | Suite! |
15 reviews | Nov 04, 2023 | Windstar | Star Pride | Philipsburg | Balboa | 35 Nights | Anse Mitan | Balboa / Fuerte Amador | Basseterre | Bequia | Bocas del Toro | Bridgetown | Cartagena | Castries | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Kralendijk | Les Saintes | Little Bay | Man-O-War Bay | Mayreau | Oranjestad | Panama Canal | Pigeon Island | Road Bay | Roseau | San Blas | Santa Marta | Soper's Hole | Soufriere | St. George's | St. Maarten | The Pitons | Virgin Gorda | Willemstad | $10,799 Up To $1000 Onboard Credit | |
15 reviews | Nov 11, 2023 | Windstar | Star Pride | Philipsburg | Bridgetown | 14 Nights | Anse Mitan | Basseterre | Bequia | Bridgetown | Castries | Gustavia | Les Saintes | Little Bay | Mayreau | Pigeon Island | Roseau | St. George's | St. Maarten | The Pitons | $2,699 Up To $300 Onboard Credit | Suite! |
15 reviews | Nov 11, 2023 | Windstar | Star Pride | Philipsburg | Bridgetown | 7 Nights | Basseterre | Bridgetown | Gustavia | Les Saintes | Little Bay | Pigeon Island | Roseau | St. Maarten | $1,599 Up To $200 Onboard Credit | |
24 reviews  | Nov 26, 2023 | Windstar | Wind Surf | Lisbon | Philipsburg | 13 Nights | Lisbon | St. Maarten | $1,499 Up To $150 Onboard Credit | Onboard Credit! |
24 reviews | Dec 09, 2023 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $1,999 Up To $200 Onboard Credit | |
24 reviews | Dec 09, 2023 | Windstar | Wind Surf | 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 | $3,699 Up To $500 Onboard Credit | |
24 reviews | Dec 16, 2023 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda | $1,999 Up To $200 Onboard Credit | Onboard Credit! |
24 reviews | Dec 16, 2023 | Windstar | Wind Surf | 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 Up To $500 Onboard Credit | Onboard Credit! |
24 reviews | Dec 23, 2023 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,699 Up To $300 Onboard Credit | Onboard Credit! |
24 reviews | Dec 23, 2023 | Windstar | Wind Surf | 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 | $4,799 Up To $500 Onboard Credit | Onboard Credit! |
24 reviews | Dec 30, 2023 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda | $2,699 Up To $300 Onboard Credit | |
24 reviews | Dec 30, 2023 | Windstar | Wind Surf | 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 | $4,399 Up To $500 Onboard Credit | |
24 reviews | Jan 06, 2024 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,499 Up To $250 Onboard Credit | |
24 reviews | Jan 06, 2024 | Windstar | Wind Surf | 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 Up To $500 Onboard Credit | Onboard Credit! |
24 reviews | Jan 13, 2024 | Windstar | Wind Surf | 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 | Onboard Credit! |
24 reviews | Jan 13, 2024 | Windstar | Wind Surf | 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 | $4,499 Up To $500 Onboard Credit | |
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