Windstar Cruises from San Juan, Puerto Rico 2025/2026
Save up to 80% on Windstar cruises
As a large-scale seller of Windstar Cruises from San Juan, Puerto Rico 2025/2026, 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.
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- Choose from 1000+ Windstar Cruises
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| Sail Date | Cruise Line | Ship | Destination | Departs | Length | Price | You Save | Discounts | ||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|
16 reviews  | 7 night Caribbean (San Juan & the Virgin Islands (Oct 26 2025)) | Oct 26, 2025 | Windstar | Star Pride | San Juan | San Juan | 7 Nights | Basseterre | CRUZ BAY, ST. JOHN, Virgin Islands (U.S.) | Gustavia | Jost Van Dyke, Great Harbour | Philipsburg, St. Maarten | San Juan | $2,762 Up To $300 Onboard Credit | Suite! | View Itinerary | Get FREE Quote |
16 reviews | 7 night Caribbean (San Juan & the Virgin Islands (Nov 2 2025)) | Nov 02, 2025 | Windstar | Star Pride | San Juan | San Juan | 7 Nights | Basseterre | CRUZ BAY, ST. JOHN, Virgin Islands (U.S.) | Gustavia | Jost Van Dyke, Great Harbour | Philipsburg, St. Maarten | San Juan | $2,962 Up To $300 Onboard Credit | View Itinerary | Get FREE Quote | |
16 reviews | 14 night Star Collector Voyages (Lovely Leewards (Nov 2 2025)) | Nov 02, 2025 | Windstar | Star Pride | San Juan | San Juan | 14 Nights | Basseterre | Bequia | CRUZ BAY, ST. JOHN, Virgin Islands (U.S.) | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Marigot, St. Martin | Philipsburg, St. Maarten | Pigeon Island | San Juan | St. George's | $4,893 Up To $500 Onboard Credit | View Itinerary | Get FREE Quote | |
16 reviews | 7 night Caribbean (San Juan & the Virgin Islands (Nov 9 2025)) | Nov 09, 2025 | Windstar | Star Pride | San Juan | San Juan | 7 Nights | Bequia | Les Saintes | Marigot, St. Martin | Pigeon Island | San Juan | St. George's | $2,730 Shipboard Credit Per Person ($150) | Shipboard Credit Per Person ($150) | View Itinerary | Get FREE Quote |
16 reviews | 14 night Star Collector Voyages (Lovely Leewards (Nov 9 2025)) | Nov 09, 2025 | Windstar | Star Pride | San Juan | San Juan | 14 Nights | Basseterre | Bequia | CRUZ BAY, ST. JOHN, Virgin Islands (U.S.) | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Marigot, St. Martin | Philipsburg, St. Maarten | Pigeon Island | San Juan | St. George's | $4,393 Shipboard Credit Per Person ($150) | Shipboard Credit Per Person ($150) | View Itinerary | Get FREE Quote |
16 reviews | 7 night Caribbean (San Juan & the Virgin Islands (Nov 16 2025)) | Nov 16, 2025 | Windstar | Star Pride | San Juan | San Juan | 7 Nights | Basseterre | CRUZ BAY, ST. JOHN, Virgin Islands (U.S.) | Gustavia | Jost Van Dyke, Great Harbour | Philipsburg, St. Maarten | San Juan | $2,762 Shipboard Credit Per Person ($150) | Shipboard Credit Per Person ($150) | View Itinerary | Get FREE Quote |
16 reviews | 14 night Star Collector Voyages (Lovely Leewards (Nov 16 2025)) | Nov 16, 2025 | Windstar | Star Pride | San Juan | San Juan | 14 Nights | Basseterre | Bequia | CRUZ BAY, ST. JOHN, Virgin Islands (U.S.) | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Marigot, St. Martin | Philipsburg, St. Maarten | Pigeon Island | San Juan | St. George's | $4,393 Shipboard Credit Per Person ($150) | Shipboard Credit Per Person ($150) | View Itinerary | Get FREE Quote |
16 reviews | 7 night Caribbean (San Juan & the Virgin Islands (Nov 23 2025)) | Nov 23, 2025 | Windstar | Star Pride | San Juan | San Juan | 7 Nights | Bequia | Les Saintes | Marigot, St. Martin | Pigeon Island | San Juan | St. George's | $2,730 Shipboard Credit Per Person ($150) | Shipboard Credit Per Person ($150) | View Itinerary | Get FREE Quote |
16 reviews | 14 night Star Collector Voyages (Lovely Leewards (Nov 23 2025)) | Nov 23, 2025 | Windstar | Star Pride | San Juan | San Juan | 14 Nights | Basseterre | Bequia | CRUZ BAY, ST. JOHN, Virgin Islands (U.S.) | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Marigot, St. Martin | Philipsburg, St. Maarten | Pigeon Island | San Juan | St. George's | $4,393 Shipboard Credit Per Person ($150) | Shipboard Credit Per Person ($150) | View Itinerary | Get FREE Quote |
16 reviews | 7 night Caribbean (San Juan & the Virgin Islands (Nov 30 2025)) | Nov 30, 2025 | Windstar | Star Pride | San Juan | San Juan | 7 Nights | Basseterre | CRUZ BAY, ST. JOHN, Virgin Islands (U.S.) | Gustavia | Jost Van Dyke, Great Harbour | Philipsburg, St. Maarten | San Juan | $2,762 Shipboard Credit Per Person ($150) | Shipboard Credit Per Person ($150) | View Itinerary | Get FREE Quote |
16 reviews | 6 night Caribbean (The Spanish Main: Rise of the New World (Dec 7 2025)) | Dec 07, 2025 | Windstar | Star Pride | San Juan | Colon | 6 Nights | Cartagena | Colón | San Blas | San Juan | Santo Domingo | $2,935 Shipboard Credit Per Person ($150) | Shipboard Credit Per Person ($150) | View Itinerary | Get FREE Quote |
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