Your Caribbean - All Results
Your Caribbean - All Results
Sail Date | Cruise Line | Ship | Destination | Departs | Length | Price | You Save | Discounts | |||
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24 reviews | Jan 18, 2026 | Windstar | Wind Surf | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bequia | Bridgetown | Castries | Mayreau | Pigeon Island | St. George's | $2,699 Up To $300 Onboard Credit | View Itinerary | Get FREE Quote | |
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! | View Itinerary | Get FREE Quote |
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) | View Itinerary | Get FREE Quote |
24 reviews | Mar 07, 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 | $999,999 Up To $1000 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
24 reviews | Mar 14, 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 | $2,399 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
24 reviews | Mar 21, 2026 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,299 Up To $250 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
24 reviews | Mar 28, 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 | $2,399 Up To $250 Onboard Credit | View Itinerary | Get FREE Quote | |
24 reviews | Jul 28, 2024 | Windstar | Wind Surf | Barcelona | Lisbon | 8 Nights | Almeria, Spain | Barcelona | Cádiz | Cartagena | Gibraltar | Lisbon | Málaga | Palma de Mallorca | $3,859 Up To $500 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
24 reviews | Nov 01, 2024 | Windstar | Wind Surf | Barcelona | Lisbon | 8 Nights | Almeria, Spain | Barcelona | Cádiz | Cartagena | Gibraltar | Lisbon | Málaga | Palma de Mallorca | $3,999 Up To $500 Onboard Credit | View Itinerary | Get FREE Quote | |
24 reviews | Apr 08, 2025 | Windstar | Wind Surf | Lisbon | Barcelona | 8 Nights | Almeria, Spain | Barcelona | Cádiz | Cartagena | Gibraltar | Lisbon | LISBON, Portugal | Málaga | Palma de Mallorca | $6,499 Up To $750 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
24 reviews | Jul 27, 2025 | Windstar | Wind Surf | Barcelona | Lisbon | 8 Nights | Almeria, Spain | Barcelona | Cádiz | Cartagena | Gibraltar | Lisbon | Málaga | Palma de Mallorca | $3,599 Up To $500 Onboard Credit | View Itinerary | Get FREE Quote | |
24 reviews | Jul 31, 2025 | Windstar | Wind Surf | Lisbon | Barcelona | 8 Nights | Almeria, Spain | Barcelona | Cádiz | Cartagena | Gibraltar | Lisbon | LISBON, Portugal | Málaga | Palma de Mallorca | $5,699 Up To $750 Onboard Credit | View Itinerary | Get FREE Quote | |
24 reviews | Nov 10, 2025 | Windstar | Wind Surf | Barcelona | Lisbon | 8 Nights | Almeria, Spain | Barcelona | Cádiz | Cartagena | Gibraltar | Lisbon | Málaga | Palma de Mallorca | $3,199 Up To $500 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
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 | Onboard Credit! | View Itinerary | Get FREE Quote |
24 reviews | Feb 09, 2026 | Windstar | Wind Surf | Colon | Cozumel | 8 Nights | Belize City | Bocas del Toro | Colón | Costa Maya | Cozumel | Isla San Andres | Roatan | $3,199 Up To $500 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
24 reviews | Feb 17, 2026 | Windstar | Wind Surf | Cozumel | Philipsburg | 11 Nights | Cayman Brac | Cozumel | Grand Cayman | Jost Van Dyke, Great Harbour | La Romana | Port Antonio | Santo Domingo | St. Maarten | Virgin Gorda / Prickly Pear | $3,799 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
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) | View Itinerary | Get FREE Quote |
24 reviews | Dec 21, 2024 | 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 | $5,699 Up To $750 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
24 reviews | Dec 28, 2024 | 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 | $5,699 Up To $750 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
24 reviews | Jan 04, 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 | $4,799 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
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