112 Cruises
| Where: | Caribbean | Nights: | Any Length |
| When: | Any Month | Line: | Windstar Cruises |
| From: | Any Port | Ship: | Any Ship |
Starts: Mon, Mar 9, 2026 from Colon
Ends: Sun, Mar 15, 2026 in Oranjestad
Cruise Ports: Colon, Bocas Del Toro, San Blas Islands, Cartagena, Oranjestad
Bonus Offer:
Starts: Sun, Mar 15, 2026 from Oranjestad
Ends: Sun, Mar 22, 2026 in Bridgetown
Cruise Ports: Oranjestad, Bonaire, Kingstown, The Pitons, Bequia, Mayreau, Scarborough, Bridgetown
Bonus Offer:
Starts: Tue, Oct 20, 2026 from Boston
Ends: Wed, Oct 28, 2026 in San Juan
Cruise Ports: Boston, Hamilton, St George, San Juan
Bonus Offer:
Starts: Sat, Mar 6, 2027 from Philipsburg (St. Maarten)
Ends: Sat, Mar 13, 2027 in Philipsburg (St. Maarten)
Cruise Ports: Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)
Bonus Offer:
Starts: Mon, Feb 9, 2026 from Colon
Ends: Tue, Feb 17, 2026 in Cozumel
Cruise Ports: Colon, Bocas Del Toro, San Andres Island, Roatan, Belize City, Costa Maya, Cozumel
Bonus Offer:
Starts: Sun, Dec 6, 2026 from San Juan
Ends: Sun, Dec 13, 2026 in San Juan
Cruise Ports: San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan
Bonus Offer:
Starts: Fri, Nov 27, 2026 from Bridgetown
Ends: Fri, Dec 4, 2026 in Bridgetown
Cruise Ports: Bridgetown, Anse Mitan, Pigeon Island, Castries, The Pitons, Mayreau, St George's, Bequia, Bridgetown
Bonus Offer:
Starts: Sat, Feb 20, 2027 from Philipsburg (St. Maarten)
Ends: Sat, Feb 27, 2027 in Philipsburg (St. Maarten)
Cruise Ports: Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)
Bonus Offer:
Starts: Sat, Mar 20, 2027 from Philipsburg (St. Maarten)
Ends: Sat, Mar 27, 2027 in Philipsburg (St. Maarten)
Cruise Ports: Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)
Bonus Offer:
Starts: Sat, Jan 23, 2027 from Philipsburg (St. Maarten)
Ends: Sat, Jan 30, 2027 in Philipsburg (St. Maarten)
Cruise Ports: Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)
Bonus Offer:
Starts: Sun, Dec 13, 2026 from San Juan
Ends: Sun, Dec 20, 2026 in San Juan
Cruise Ports: San Juan, Cruz Bay, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten), Great Harbour, Prickly Pear British Virgin Islands, San Juan
Bonus Offer:
Starts: Sun, Nov 29, 2026 from San Juan
Ends: Sun, Dec 6, 2026 in San Juan
Cruise Ports: San Juan, Cruz Bay, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten), Great Harbour, Prickly Pear British Virgin Islands, San Juan
Bonus Offer:
Starts: Sat, Jan 2, 2027 from Philipsburg (St. Maarten)
Ends: Sat, Jan 9, 2027 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)
Bonus Offer:
Starts: Sat, Apr 4, 2026 from Philipsburg (St. Maarten)
Ends: Sat, Apr 18, 2026 in Lisbon
Cruise Ports: Philipsburg (St. Maarten), Ponta Delgada, Lisbon
Bonus Offer:
Starts: Sat, Dec 5, 2026 from Lisbon
Ends: Sat, Dec 19, 2026 in Philipsburg (St. Maarten)
Cruise Ports: Lisbon, St John's, Philipsburg (St. Maarten)
Bonus Offer:
Starts: Sat, Feb 6, 2027 from Philipsburg (St. Maarten)
Ends: Sat, Feb 13, 2027 in Philipsburg (St. Maarten)
Cruise Ports: Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)
Bonus Offer:
Starts: Sat, Jan 30, 2027 from Philipsburg (St. Maarten)
Ends: Sat, Feb 6, 2027 in Philipsburg (St. Maarten)
Cruise Ports: Philipsburg (St. Maarten), Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Falmouth Harbour, Philipsburg (St. Maarten)
Bonus Offer:
Starts: Sat, Feb 13, 2027 from Philipsburg (St. Maarten)
Ends: Sat, Feb 20, 2027 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)
Bonus Offer:
Starts: Sat, Feb 27, 2027 from Philipsburg (St. Maarten)
Ends: Sat, Mar 6, 2027 in Philipsburg (St. Maarten)
Cruise Ports: Philipsburg (St. Maarten), Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Gustavia St. Barts, Road Bay, Falmouth Harbour, Philipsburg (St. Maarten)
Bonus Offer:
Starts: Sat, Mar 13, 2027 from Philipsburg (St. Maarten)
Ends: Sat, Mar 20, 2027 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)
Bonus Offer:
