142 Cruises
| Where: | Caribbean | Nights: | Any Length |
| When: | Any Month | Line: | Windstar Cruises |
| From: | Any Port | Ship: | Any Ship |
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, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten)
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
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, Mayreau, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)
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, Mayreau, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)
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
Starts: Sat, Jan 4, 2025 from Bridgetown
Ends: Sat, Jan 11, 2025 in Bridgetown
Cruise Ports: Bridgetown, Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St George's, Bequia, Bridgetown
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, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten)
Starts: Sat, Mar 28, 2026 from Philipsburg (St. Maarten)
Ends: Sat, Apr 4, 2026 in Philipsburg (St. Maarten)
Cruise Ports: Philipsburg (St. Maarten), St John's, Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten)
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, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten)
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, Deshaies, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)
Starts: Sat, Feb 1, 2025 from Oranjestad
Ends: Sat, Feb 8, 2025 in Fuerte Amador
Cruise Ports: Oranjestad, Cartagena, San Blas Islands, Bocas Del Toro, Cruising the Panama Canal, Fuerte Amador
Starts: Sun, Jan 4, 2026 from Philipsburg (St. Maarten)
Ends: Sun, Jan 11, 2026 in Philipsburg (St. Maarten)
Cruise Ports: Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten)
Starts: Sat, Mar 21, 2026 from Bridgetown
Ends: Sat, Mar 28, 2026 in Bridgetown
Cruise Ports: Bridgetown, Basseterre, Iles des Saintes, Roseau, Anse Mitan, Mayreau, Bridgetown
Starts: Sat, Feb 15, 2025 from Philipsburg (St. Maarten)
Ends: Sat, Feb 22, 2025 in Philipsburg (St. Maarten)
Cruise Ports: Philipsburg (St. Maarten), Falmouth Harbour, Great Harbour, Prickly Pear British Virgin Islands, Sopers Hole, Gustavia St. Barts, Road Bay, Philipsburg (St. Maarten)
Starts: Sat, Jan 11, 2025 from Philipsburg (St. Maarten)
Ends: Sat, Jan 18, 2025 in Philipsburg (St. Maarten)
Cruise Ports: Philipsburg (St. Maarten), Falmouth Harbour, Gustavia St. Barts, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Road Bay, Philipsburg (St. Maarten)
Starts: Sun, Nov 9, 2025 from San Juan
Ends: Sun, Nov 16, 2025 in San Juan
Cruise Ports: San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan
Starts: Sun, Nov 23, 2025 from San Juan
Ends: Sun, Nov 30, 2025 in San Juan
Cruise Ports: San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan
Starts: Sun, Jan 11, 2026 from Philipsburg (St. Maarten)
Ends: Sun, Jan 18, 2026 in Bridgetown
Cruise Ports: Philipsburg (St. Maarten), Basseterre, Gustavia St. Barts, St John's, Iles des Saintes, Pigeon Island, Kingstown, Bridgetown
Starts: Sat, Jan 24, 2026 from Philipsburg (St. Maarten)
Ends: Sat, Jan 31, 2026 in Philipsburg (St. Maarten)
Cruise Ports: Philipsburg (St. Maarten), St John's, Road Bay, Prickly Pear British Virgin Islands, Sopers Hole, Great Harbour, Gustavia St. Barts, Philipsburg (St. Maarten)
Starts: Sat, Feb 14, 2026 from Philipsburg (St. Maarten)
Ends: Sat, Feb 21, 2026 in Philipsburg (St. Maarten)
Cruise Ports: Philipsburg (St. Maarten), St John's, Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten)
