Windstar Cruises to Caribbean - Southern 2024/2025
Save up to 80% on Windstar cruises
As a large-scale seller of Windstar Cruises to Caribbean - Southern 2024/2025, 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 80% 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 | ||||
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16 reviews | 14 night Star Collector Voyages (Lovely Leewards (Nov 16 2024)) | Nov 16, 2024 | Windstar | Star Pride | San Juan | San Juan | 14 Nights | Basseterre | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Philipsburg, St. Maarten | Pigeon Island | San Juan | St. George's | St. Thomas | $6,408 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
11 reviews | 11 night Caribbean (Colombian & Southern Caribbean Coastlines (Nov 19 2024)) | Nov 19, 2024 | Windstar | Wind Star | Bridgetown | Colon | 11 Nights | Bequia | Bridgetown | Cartagena | Colón | Kralendijk | Mayreau | Oranjestad | St. George's | Willemstad | $2,700 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
16 reviews | 14 night Star Collector Voyages (Lovely Leewards (Nov 23 2024)) | Nov 23, 2024 | Windstar | Star Pride | San Juan | San Juan | 14 Nights | Basseterre | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Philipsburg, St. Maarten | Pigeon Island | San Juan | St. George's | St. Thomas | $5,208 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
16 reviews | 7 night Caribbean (Windward Islands Surf & Sunsets (Nov 23 2024)) | Nov 23, 2024 | Windstar | Star Pride | San Juan | San Juan | 7 Nights | Bequia | Les Saintes | Philipsburg, St. Maarten | Pigeon Island | San Juan | St. George's | $2,118 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
11 reviews | 10 night Caribbean (Hidden Treasures of the Lesser Antilles (Nov 27 2024)) | Nov 27, 2024 | Windstar | Wind Spirit | Bridgetown | Bridgetown | 10 Nights | Basseterre | Bridgetown | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Soper's Hole | $4,077 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
16 reviews | 7 night Caribbean (San Juan & the Virgin Islands (Nov 30 2024)) | Nov 30, 2024 | Windstar | Star Pride | San Juan | San Juan | 7 Nights | Basseterre | Gustavia | Jost Van Dyke, Great Harbour | Philipsburg, St. Maarten | San Juan | St. Thomas | $3,368 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
16 reviews | 14 night Star Collector Voyages (White Sands of the Windwards (Dec 7 2024)) | Dec 07, 2024 | Windstar | Star Pride | San Juan | Oranjestad | 14 Nights | Basseterre | Bridgetown | Gustavia | Man-O-War Bay | Mayreau | Oranjestad | Pigeon Island | Roseau | San Juan | Soufriere | St. George's | St. Thomas | Willemstad | $3,930 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
16 reviews | 7 night Caribbean (Winter Antilles Escape (Dec 7 2024)) | Dec 07, 2024 | Windstar | Star Pride | San Juan | Bridgetown | 7 Nights | Basseterre | Bridgetown | Gustavia | Pigeon Island | Roseau | San Juan | St. George's | St. Thomas | $2,200 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
11 reviews | 14 night Star Collector Voyages (Windward Treasures: An Antilles Odyssey (Dec 7 2024)) | Dec 07, 2024 | Windstar | Wind Spirit | Bridgetown | Bridgetown | 14 Nights | Anse Mitan | Basseterre | Bequia | Bridgetown | Castries | Kingstown | Les Saintes | Mayreau | Pigeon Island | Roseau | St. George's | The Pitons | $4,468 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
11 reviews | 7 night Caribbean (Jewels of the Windward Islands (Dec 7 2024)) | Dec 07, 2024 | Windstar | Wind Spirit | Bridgetown | Bridgetown | 7 Nights | Bequia | Bridgetown | Castries | Kingstown | Mayreau | Pigeon Island | St. George's | The Pitons | $2,651 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
16 reviews | 14 night Star Collector Voyages (Windward Islands & Spanish New World (Dec 14 2024)) | Dec 14, 2024 | Windstar | Star Pride | Bridgetown | Fuerte Amador | 14 Nights | Bocas del Toro | Bridgetown | Cartagena | Man-O-War Bay | Mayreau | Oranjestad | San Blas | Soufriere | St. George's | Willemstad | $5,085 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
16 reviews | 7 night Caribbean (Windward Ways & Tobago Cays (Dec 14 2024)) | Dec 14, 2024 | Windstar | Star Pride | Bridgetown | Oranjestad | 7 Nights | Bridgetown | Man-O-War Bay | Mayreau | Oranjestad | Soufriere | St. George's | Willemstad | $2,098 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
11 reviews | 14 night Star Collector Voyages (Windward Treasures: An Antilles Odyssey (Dec 14 2024)) | Dec 14, 2024 | Windstar | Wind Spirit | Bridgetown | Bridgetown | 14 Nights | Anse Mitan | Basseterre | Bequia | Bridgetown | Castries | Kingstown | Les Saintes | Mayreau | Pigeon Island | Roseau | St. George's | The Pitons | $5,068 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
11 reviews | 7 night Caribbean (Windward Island Delights (Dec 14 2024)) | Dec 14, 2024 | Windstar | Wind Spirit | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Basseterre | Bridgetown | Les Saintes | Pigeon Island | Roseau | $2,310 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
11 reviews | 7 night Caribbean (Jewels of the Windward Islands (Dec 21 2024)) | Dec 21, 2024 | Windstar | Wind Spirit | Bridgetown | Bridgetown | 7 Nights | Bequia | Bridgetown | Castries | Kingstown | Mayreau | Pigeon Island | St. George's | The Pitons | $3,151 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
25 reviews | 14 night Star Collector Voyages (Caribbean Explorations (Dec 21 2024)) | Dec 21, 2024 | Windstar | Wind Surf | Philipsburg | Philipsburg | 14 Nights | $6,769 Up To $750 Onboard Credit | View Itinerary | Get FREE Quote | ||
16 reviews | 7 night Caribbean (Windward Ways & Tobago Cays (Jan 4 2025)) | Jan 04, 2025 | Windstar | Star Pride | Oranjestad | Bridgetown | 7 Nights | Bridgetown | Man-O-War Bay | Mayreau | Oranjestad | Soufriere | St. George's | Willemstad | $2,696 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
25 reviews | 14 night Star Collector Voyages (Caribbean Explorations (Jan 4 2025)) | Jan 04, 2025 | Windstar | Wind Surf | Philipsburg | Philipsburg | 14 Nights | Basseterre | Charlestown | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Philipsburg, St. Maarten | Pigeon Island | Road Bay | Roseau | Soper's Hole | $4,439 Up To $500 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
11 reviews | 14 night Star Collector Voyages (Windward Treasures: An Antilles Odyssey (Jan 4 2025)) | Jan 04, 2025 | Windstar | Wind Spirit | Bridgetown | Bridgetown | 14 Nights | Anse Mitan | Basseterre | Bequia | Bridgetown | Castries | Kingstown | Les Saintes | Mayreau | Pigeon Island | Roseau | St. George's | The Pitons | $5,068 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
11 reviews | 7 night Caribbean (Jewels of the Windward Islands (Jan 4 2025)) | Jan 04, 2025 | Windstar | Wind Spirit | Bridgetown | Bridgetown | 7 Nights | Bequia | Bridgetown | Castries | Kingstown | Mayreau | Pigeon Island | St. George's | The Pitons | $2,450 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
Departure Ports
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