Your Caribbean - Southern Results
Your Caribbean - Southern Results
Sail Date | Cruise Line | Ship | Destination | Departs | Length | Price | You Save | Discounts | |
---|---|---|---|---|---|---|---|---|---|
24 reviews | Dec 07, 2025 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,299 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
24 reviews | Dec 14, 2025 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $2,399 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
24 reviews | Dec 21, 2025 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,699 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
24 reviews | Dec 28, 2025 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $2,699 Up To $300 Onboard Credit | |
24 reviews | Jan 04, 2026 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $2,499 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
24 reviews | Jan 11, 2026 | Windstar | Wind Surf | Philipsburg | Bridgetown | 7 Nights | Basseterre | Bridgetown | Deshaies | Gustavia | Little Bay | Pigeon Island | Roseau | St. Maarten | $2,499 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
24 reviews | Jan 18, 2026 | Windstar | Wind Surf | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Mayreau | Pigeon Island | St. George's | $2,499 Up To $250 Onboard Credit | Onboard Credit! |
24 reviews | Jan 25, 2026 | Windstar | Wind Surf | Bridgetown | Oranjestad | 7 Nights | Bridgetown | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | Soufriere | Willemstad | $2,699 Up To $300 Onboard Credit | Onboard Credit! |
24 reviews | Feb 28, 2026 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,299 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
24 reviews | Feb 01, 2026 | Windstar | Wind Surf | Oranjestad | Colon | 8 Nights | Bocas del Toro | Cartagena | Colón | Oranjestad | Santa Marta | $3,199 Up To $500 Onboard Credit | |
24 reviews | Dec 02, 2025 | Windstar | Wind Surf | Philipsburg | Philipsburg | 12 Nights | Basseterre | Charlestown | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Pigeon Island | Roseau | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $3,399 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
24 reviews | Jan 18, 2025 | 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 / Prickly Pear | $4,599 Up To $500 Onboard Credit | |
24 reviews | Feb 22, 2025 | 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 / Prickly Pear | $4,399 Up To $500 Onboard Credit | |
24 reviews | Dec 07, 2025 | 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 / Prickly Pear | $3,699 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
24 reviews | Dec 14, 2025 | 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 / Prickly Pear | $3,999 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
24 reviews | Dec 21, 2025 | 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 / Prickly Pear | $4,299 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
24 reviews | Jan 04, 2026 | Windstar | Wind Surf | Philipsburg | Bridgetown | 14 Nights | Basseterre | Bridgetown | Deshaies | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Little Bay | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $3,799 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
24 reviews | Jan 11, 2026 | Windstar | Wind Surf | Philipsburg | Bridgetown | 14 Nights | Anse Mitan | Basseterre | Bequia | Bridgetown | Castries | Deshaies | Gustavia | Little Bay | Mayreau | Pigeon Island | Roseau | St. George's | St. Maarten | $3,999 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
24 reviews | Jan 18, 2026 | Windstar | Wind Surf | Bridgetown | Oranjestad | 14 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Kralendijk | Man-O-War Bay | Mayreau | Oranjestad | Pigeon Island | Soufriere | St. George's | Willemstad | $4,099 Up To $500 Onboard Credit | Onboard Credit! |
24 reviews | Feb 28, 2026 | 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 / Prickly Pear | $3,699 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
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