Your Caribbean - Southern Results
Your Caribbean - Southern Results
Sail Date | Cruise Line | Ship | Destination | Departs | Length | Price | You Save | Discounts | |
---|---|---|---|---|---|---|---|---|---|
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 | 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 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 04, 2026 | Windstar | Wind Surf | Philipsburg | Bridgetown | 21 Nights | Anse Mitan | Basseterre | Bequia | Bridgetown | Castries | Deshaies | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Little Bay | Mayreau | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. George's | St. Maarten | Virgin Gorda / Prickly Pear | $5,999 Up To $750 Onboard Credit | Onboard Credit! |
24 reviews | Jan 04, 2026 | Windstar | Wind Surf | Philipsburg | Oranjestad | 28 Nights | Anse Mitan | Basseterre | Bequia | Bridgetown | Castries | Deshaies | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Kralendijk | Little Bay | Man-O-War Bay | Mayreau | Oranjestad | Pigeon Island | Road Bay | Roseau | Soper's Hole | Soufriere | St. George's | St. Maarten | Virgin Gorda / Prickly Pear | Willemstad | $7,899 Up To $1000 Onboard Credit | |
24 reviews | Jan 04, 2026 | Windstar | Wind Surf | Philipsburg | Philipsburg | 55 Nights | Anse Mitan | Basseterre | Belize City | Bequia | Bocas del Toro | Bridgetown | Cartagena | Castries | Cayman Brac | Colón | Costa Maya | Cozumel | Deshaies | Falmouth Harbour | Grand Cayman | Gustavia | Isla San Andres | Jost Van Dyke, Great Harbour | Kralendijk | La Romana | Little Bay | Man-O-War Bay | Mayreau | Oranjestad | Pigeon Island | Port Antonio | Road Bay | Roatan | Roseau | Santa Marta | Santo Domingo | Soper's Hole | Soufriere | St. George's | St. Maarten | Virgin Gorda / Prickly Pear | Willemstad | $16,599 Up To $1000 Onboard Credit | Onboard Credit! |
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 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) |
11 reviews | Jan 14, 2026 | Windstar | Wind Spirit | Philipsburg | Philipsburg | 17 Nights | Anse Mitan | Bequia | Castries | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Mayreau | Road Bay | Roseau | Soper's Hole | St. George's | St. Maarten | Virgin Gorda / Prickly Pear | $4,799 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
11 reviews | Jan 14, 2026 | Windstar | Wind Spirit | Philipsburg | Philipsburg | 10 Nights | Anse Mitan | Bequia | Castries | Gustavia | Les Saintes | Little Bay | Mayreau | Roseau | St. George's | St. Maarten | $3,499 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
11 reviews | Jan 24, 2026 | Windstar | Wind Spirit | 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 Up To $250 Onboard Credit | |
11 reviews | Jan 31, 2026 | Windstar | Wind Spirit | 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) |
11 reviews | Jan 31, 2026 | Windstar | Wind Spirit | 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 | $4,099 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
11 reviews | Feb 07, 2026 | Windstar | Wind Spirit | 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 | $4,099 Up To $500 Onboard Credit | Onboard Credit! |
11 reviews | Feb 07, 2026 | Windstar | Wind Spirit | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,599 Up To $300 Onboard Credit | Onboard Credit! |
11 reviews | Feb 14, 2026 | Windstar | Wind Spirit | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $2,599 Up To $300 Onboard Credit | |
11 reviews | Feb 21, 2026 | Windstar | Wind Spirit | 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 / Prickly Pear | $3,999 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
11 reviews | Feb 21, 2026 | Windstar | Wind Spirit | Philipsburg | Philipsburg | 7 Nights | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Road Bay | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $2,599 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) |
11 reviews | Feb 21, 2026 | Windstar | Wind Spirit | Philipsburg | Bridgetown | 21 Nights | Anse Mitan | 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 / Prickly Pear | $6,099 Up To $750 Onboard Credit | Onboard Credit! |
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