Windstar Cruises to Caribbean - Southern 2023/2024
Save up to 75% on Windstar cruises
As a large-scale seller of Windstar Cruises to Caribbean - Southern 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 | |
---|---|---|---|---|---|---|---|---|---|
24 reviews ![]() | Mar 25, 2023 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $1,799 Up To $200 Onboard Credit | Onboard Credit! |
12 reviews ![]() | Nov 04, 2023 | Windstar | Star Pride | Philipsburg | Bridgetown | 14 Nights | 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 | $3,999 Up To $500 Onboard Credit | |
12 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 | $5,999 Up To $750 Onboard Credit | |
12 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 | $7,899 Up To $1000 Onboard Credit | Suite! |
12 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 | $10,499 Up To $1000 Onboard Credit | |
12 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 | $3,999 Up To $500 Onboard Credit | Suite! |
12 reviews ![]() | Nov 11, 2023 | Windstar | Star Pride | Philipsburg | Bridgetown | 7 Nights | Basseterre | Bridgetown | Gustavia | Les Saintes | Little Bay | Pigeon Island | Roseau | St. Maarten | $2,499 Up To $250 Onboard Credit | Suite! |
12 reviews ![]() | Nov 18, 2023 | Windstar | Star Pride | Bridgetown | Oranjestad | 14 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | Pigeon Island | Soufriere | St. George's | The Pitons | Willemstad | $3,899 Up To $500 Onboard Credit | Suite! |
12 reviews ![]() | Nov 18, 2023 | Windstar | Star Pride | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Mayreau | Pigeon Island | St. George's | The Pitons | $2,499 Up To $250 Onboard Credit | Suite! |
12 reviews ![]() | Nov 25, 2023 | Windstar | Star Pride | 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 | $3,999 Up To $500 Onboard Credit | |
12 reviews ![]() | Nov 25, 2023 | Windstar | Star Pride | Bridgetown | Oranjestad | 7 Nights | Bridgetown | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | Soufriere | Willemstad | $2,399 Up To $250 Onboard Credit | |
12 reviews ![]() | Dec 02, 2023 | Windstar | Star Pride | Oranjestad | Balboa | 7 Nights | Balboa / Fuerte Amador | Bocas del Toro | Cartagena | Oranjestad | San Blas | Santa Marta | $2,599 Up To $300 Onboard Credit | |
10 reviews ![]() | Dec 05, 2023 | Windstar | Wind Star | Lisbon | Bridgetown | 14 Nights | Bridgetown | Lisbon | $2,199 Up To $250 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 | $2,199 Up To $250 Onboard Credit | |
12 reviews ![]() | Dec 09, 2023 | Windstar | Star Pride | Balboa | Oranjestad | 7 Nights | Balboa / Fuerte Amador | Bocas del Toro | Cartagena | Oranjestad | San Blas | Santa Marta | $2,499 Up To $250 Onboard Credit | Suite! |
12 reviews ![]() | Dec 09, 2023 | Windstar | Star Pride | Balboa | Bridgetown | 13 Nights | Balboa / Fuerte Amador | Bocas del Toro | Bridgetown | Cartagena | Kralendijk | Mayreau | Oranjestad | Panama Canal | San Blas | Santa Marta | Soufriere | Willemstad | $3,899 Up To $500 Onboard Credit | Suite! |
12 reviews ![]() | Dec 16, 2023 | Windstar | Star Pride | Oranjestad | Bridgetown | 6 Nights | Bridgetown | Kralendijk | Mayreau | Oranjestad | Soufriere | Willemstad | $2,399 Up To $250 Onboard Credit | |
10 reviews ![]() | Dec 19, 2023 | Windstar | Wind Star | Bridgetown | Puerto Caldera | 18 Nights | Balboa / Fuerte Amador | Bequia | Bridgetown | Cartagena | Colón | Golfo Dulce | Isla Parida | Kralendijk | Mayreau | Oranjestad | Puerto Caldera | Quepos | St. George's | Willemstad | $4,799 Up To $500 Onboard Credit | Onboard Credit! |
10 reviews ![]() | Dec 19, 2023 | Windstar | Wind Star | Bridgetown | Colon | 11 Nights | Bequia | Bridgetown | Cartagena | Colón | Kralendijk | Mayreau | Oranjestad | St. George's | Willemstad | $3,399 Up To $500 Onboard Credit | Onboard Credit! |
12 reviews ![]() | Dec 22, 2023 | Windstar | Star Pride | Bridgetown | Oranjestad | 8 Nights | Bridgetown | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | Soufriere | St. George's | Willemstad | $2,899 Up To $300 Onboard Credit |
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