181 Cruises
Where: | Caribbean | Nights: | Any Length |
When: | Any Month | Line: | Windstar Cruises |
From: | Any Port | Ship: | Any Ship |
Windstar Cruises
Starts: Tue, Dec 2, 2025 from Philipsburg (St. Maarten)
Ends: Sun, Dec 7, 2025 in Philipsburg (St. Maarten)
Cruise Ports: Philipsburg (St. Maarten), Sopers Hole, Great Harbour, Virgin Gorda, Gustavia St. Barts, Philipsburg (St. Maarten)
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Windstar Cruises
Starts: Sat, Jan 25, 2025 from Fuerte Amador
Ends: Sat, Feb 1, 2025 in Oranjestad
Cruise Ports: Fuerte Amador, Cruising the Panama Canal, Bocas Del Toro, San Blas Islands, Cartagena, Oranjestad
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Windstar Cruises
Starts: Sun, Dec 7, 2025 from Philipsburg (St. Maarten)
Ends: Sun, Dec 14, 2025 in Philipsburg (St. Maarten)
Cruise Ports: Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten)
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Windstar Cruises
Starts: Sat, Feb 28, 2026 from Philipsburg (St. Maarten)
Ends: Sat, Mar 7, 2026 in Philipsburg (St. Maarten)
Cruise Ports: Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten)
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Windstar Cruises
Starts: Sat, Mar 21, 2026 from Philipsburg (St. Maarten)
Ends: Sat, Mar 28, 2026 in Philipsburg (St. Maarten)
Cruise Ports: Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Iles des Saintes, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten)
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Windstar Cruises
Starts: Sat, Mar 28, 2026 from Philipsburg (St. Maarten)
Ends: Sat, Apr 4, 2026 in Philipsburg (St. Maarten)
Cruise Ports: Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Virgin Gorda, Gustavia St. Barts, Philipsburg (St. Maarten)
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Windstar Cruises
Starts: Sat, Feb 28, 2026 from Philipsburg (St. Maarten)
Ends: Sat, Mar 7, 2026 in Bridgetown
Cruise Ports: Philipsburg (St. Maarten), Basseterre, Gustavia St. Barts, Little Bay, Iles des Saintes, Roseau, Pigeon Island, Bridgetown
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Windstar Cruises
Starts: Sat, Mar 7, 2026 from Philipsburg (St. Maarten)
Ends: Sat, Mar 14, 2026 in Philipsburg (St. Maarten)
Cruise Ports: Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Virgin Gorda, Gustavia St. Barts, Philipsburg (St. Maarten)
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Windstar Cruises
Starts: Sat, Mar 14, 2026 from Philipsburg (St. Maarten)
Ends: Sat, Mar 21, 2026 in Philipsburg (St. Maarten)
Cruise Ports: Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Virgin Gorda, Gustavia St. Barts, Philipsburg (St. Maarten)
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Windstar Cruises
Starts: Sun, Dec 14, 2025 from Philipsburg (St. Maarten)
Ends: Sun, Dec 21, 2025 in Philipsburg (St. Maarten)
Cruise Ports: Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Virgin Gorda, Gustavia St. Barts, Philipsburg (St. Maarten)
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Windstar Cruises
Starts: Sat, Mar 29, 2025 from Bridgetown
Ends: Sat, Apr 5, 2025 in Bridgetown
Cruise Ports: Bridgetown, Pigeon Island, Castries, The Pitons, Anse Mitan, Mayreau, St George's, Bequia, Bridgetown
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Windstar Cruises
Starts: Sat, Feb 22, 2025 from Bridgetown
Ends: Sun, Mar 9, 2025 in Lisbon
Cruise Ports: Bridgetown, Lisbon
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Windstar Cruises
Starts: Wed, Mar 26, 2025 from Bridgetown
Ends: Thu, Apr 10, 2025 in Lisbon
Cruise Ports: Bridgetown, Lisbon
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Windstar Cruises
Starts: Sat, Apr 5, 2025 from Bridgetown
Ends: Tue, Apr 15, 2025 in Santa Cruz de Tenerife
Cruise Ports: Bridgetown, Santa Cruz de Tenerife
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Windstar Cruises
Starts: Tue, Nov 4, 2025 from Lisbon
Ends: Tue, Nov 18, 2025 in Bridgetown
Cruise Ports: Lisbon, Bridgetown
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Windstar Cruises
Starts: Wed, Nov 13, 2024 from Lisbon
Ends: Wed, Nov 27, 2024 in Bridgetown
Cruise Ports: Lisbon, Bridgetown
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Windstar Cruises
Starts: Sun, Nov 3, 2024 from San Juan
Ends: Sat, Nov 9, 2024 in San Juan
Cruise Ports: San Juan, Sint Maarten, Charlestown, Gustavia St. Barts, Great Harbour, Virgin Gorda, San Juan
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Windstar Cruises
Starts: Sat, Nov 16, 2024 from San Juan
Ends: Sat, Nov 23, 2024 in San Juan
Cruise Ports: San Juan, Charlotte Amalie (St Thomas), Sint Maarten, Gustavia St. Barts, Basseterre, Great Harbour, Virgin Gorda, San Juan
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Windstar Cruises
Starts: Sat, Nov 23, 2024 from San Juan
Ends: Sat, Nov 30, 2024 in San Juan
Cruise Ports: San Juan, St George's, Bequia, Pigeon Island, Iles des Saintes, Philipsburg (St. Maarten), San Juan
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Windstar Cruises
Starts: Sat, Dec 7, 2024 from San Juan
Ends: Sat, Dec 14, 2024 in Bridgetown
Cruise Ports: San Juan, Charlotte Amalie (St Thomas), Gustavia St. Barts, Basseterre, Roseau, Pigeon Island, St George's, Bridgetown
Bonus Offer: