50 Cruises
| Where: | Caribbean - South | Nights: | Any Length |
| When: | Any Month | Line: | Windstar Cruises |
| From: | Any Port | Ship: | Any Ship |
Starts: Tue, Nov 24, 2026 from Bridgetown
Ends: Sat, Dec 12, 2026 in Puerto Caldera
Cruise Ports: Bridgetown, Bequia, St George's, Bonaire, Willemstad (Curacao), Oranjestad, Cartagena, San Blas Islands, Colon, Cruising the Panama Canal, Fuerte Amador, Isla Parida, Puerto Jimenez, Quepos, Puerto Caldera
Bonus Offer:
Starts: Fri, Dec 4, 2026 from Bridgetown
Ends: Sun, Dec 20, 2026 in Fuerte Amador
Cruise Ports: Bridgetown, Rodney Bay, The Pitons, Scarborough, Bequia, Mayreau, Bonaire, Willemstad (Curacao), Oranjestad, Cartagena, Bocas Del Toro, San Blas Islands, Cruising the Panama Canal, Fuerte Amador
Starts: Tue, Feb 16, 2027 from Fuerte Amador
Ends: Tue, Mar 2, 2027 in Bridgetown
Cruise Ports: Fuerte Amador, Cruising the Panama Canal, Bocas Del Toro, San Blas Islands, Cartagena, Oranjestad, Willemstad (Curacao), Bonaire, St George's, Rodney Bay, The Pitons, Mayreau, Bequia, Bridgetown
Starts: Sat, Mar 21, 2026 from Bridgetown
Ends: Sun, Apr 12, 2026 in Lisbon
Cruise Ports: Bridgetown, Basseterre, Iles des Saintes, Roseau, Fort de France, Mayreau, Bridgetown, Lisbon
Bonus Offer:
Starts: Sun, Mar 22, 2026 from Bridgetown
Ends: Tue, Apr 7, 2026 in Amsterdam
Cruise Ports: Bridgetown, Lisbon, Amsterdam
Starts: Sat, Mar 28, 2026 from Bridgetown
Ends: Sun, Apr 12, 2026 in Lisbon
Cruise Ports: Bridgetown, Lisbon
Starts: Mon, Oct 19, 2026 from Istanbul
Ends: Mon, Dec 28, 2026 in Puerto Caldera
Cruise Ports: Istanbul, Myrina, Mykonos, Kusadasi (Ephesus), Bodrum, Santorini, Itea, Cruising the Corinth Canal, Athens (Port of Piraeus), Cruising the Corinth Canal, Itea, Corfu, Argostoli, Messina, Trapani, Cagliari, Barcelona, To Be Announced, Malaga, Tangier, Casablanca, Madeira, Bridgetown, Anse Mitan, Pige
Starts: Tue, Nov 10, 2026 from Lisbon
Ends: Sat, Dec 5, 2026 in Colon
Cruise Ports: Lisbon, Bridgetown, Bequia, St George's, Bonaire, Willemstad (Curacao), Oranjestad, Cartagena, San Blas Islands, Colon
Bonus Offer:
Starts: Tue, Nov 10, 2026 from Lisbon
Ends: Tue, Nov 24, 2026 in Bridgetown
Cruise Ports: Lisbon, Bridgetown
Starts: Sun, Jan 4, 2026 from Philipsburg (St. Maarten)
Ends: Sat, Feb 28, 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), Basseterre, Gustavia St. Barts, St John's, Iles des Saintes, Roseau, Mayreau, Bridgetown, Anse Mitan, Castries, Pigeon Island, Beq
Starts: Sat, Dec 13, 2025 from Colon
Ends: Sat, Dec 20, 2025 in Oranjestad
Cruise Ports: Colon, San Blas Islands, Cartagena, Oranjestad
Starts: Sat, Dec 20, 2025 from Oranjestad
Ends: Sun, Dec 28, 2025 in Bridgetown
Cruise Ports: Oranjestad, Willemstad (Curacao), Bonaire, St George's, Mayreau, Bequia, Bridgetown
Starts: Sat, Dec 20, 2025 from Oranjestad
Ends: Sun, Jan 4, 2026 in Bridgetown
Cruise Ports: Oranjestad, Willemstad (Curacao), Bonaire, St George's, Mayreau, Bequia, Bridgetown, Basseterre, Iles des Saintes, Roseau, Mayreau, Fort de France, Bridgetown
Starts: Sun, Dec 28, 2025 from Bridgetown
Ends: Sun, Jan 4, 2026 in Bridgetown
Cruise Ports: Bridgetown, Basseterre, Iles des Saintes, Roseau, Mayreau, Fort de France, Bridgetown
Starts: Sun, Jan 4, 2026 from Philipsburg (St. Maarten)
Ends: Sun, Feb 1, 2026 in Oranjestad
Cruise Ports: Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten), Basseterre, Gustavia St. Barts, St John's, Iles des Saintes, Roseau, Mayreau, Bridgetown, Anse Mitan, Castries, Pigeon Island, Beq
Starts: Sun, Jan 4, 2026 from Philipsburg (St. Maarten)
Ends: Sun, Jan 25, 2026 in Bridgetown
Cruise Ports: Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Philipsburg (St. Maarten), Basseterre, Gustavia St. Barts, St John's, Iles des Saintes, Roseau, Mayreau, Bridgetown, Anse Mitan, Castries, Pigeon Island, Beq
Starts: Sun, Jan 11, 2026 from Philipsburg (St. Maarten)
Ends: Sun, Jan 25, 2026 in Bridgetown
Cruise Ports: Philipsburg (St. Maarten), Basseterre, Gustavia St. Barts, St John's, Iles des Saintes, Roseau, Mayreau, Bridgetown, Anse Mitan, Castries, Pigeon Island, Bequia, Mayreau, St George's, Bridgetown
Starts: Sat, Jan 17, 2026 from Oranjestad
Ends: Sun, Jan 25, 2026 in Fuerte Amador
Cruise Ports: Oranjestad, Cartagena, Bocas Del Toro, San Blas Islands, Cruising the Panama Canal, Fuerte Amador
Starts: Sun, Jan 18, 2026 from Bridgetown
Ends: Sun, Feb 1, 2026 in Oranjestad
Cruise Ports: Bridgetown, Anse Mitan, Castries, Pigeon Island, Bequia, Mayreau, St George's, Bridgetown, Bequia, Mayreau, Soufriere , Bonaire, Willemstad (Curacao), Oranjestad
Bonus Offer:
Starts: Sun, Jan 18, 2026 from Bridgetown
Ends: Sun, Jan 25, 2026 in Bridgetown
Cruise Ports: Bridgetown, Anse Mitan, Castries, Pigeon Island, Bequia, Mayreau, St George's, Bridgetown
