163 Cruises
| Where: | Caribbean | Nights: | Any Length |
| When: | Any Month | Line: | Windstar Cruises |
| From: | Any Port | Ship: | Any Ship |
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, Mar 28, 2026 from Bridgetown
Ends: Mon, Apr 13, 2026 in Malaga
Cruise Ports: Bridgetown, Tangier, Malaga
Starts: Sun, Mar 22, 2026 from Bridgetown
Ends: Tue, Apr 7, 2026 in Amsterdam
Cruise Ports: Bridgetown, Lisbon, Amsterdam
Bonus Offer:
Starts: Mon, Mar 6, 2028 from Oranjestad
Ends: Mon, Mar 13, 2028 in San Juan
Cruise Ports: Oranjestad, Willemstad (Curacao), Bonaire, Gustavia St. Barts, Great Harbour, Prickly Pear British Virgin Islands, San Juan
Bonus Offer:
Starts: Mon, Dec 6, 2027 from Lisbon
Ends: Mon, Dec 20, 2027 in San Juan
Cruise Ports: Lisbon, Madeira, Great Harbour, San Juan
Starts: Mon, Jan 3, 2028 from Philipsburg (St. Maarten)
Ends: Sun, Jan 9, 2028 in Philipsburg (St. Maarten)
Cruise Ports: Philipsburg (St. Maarten), Road Bay, Gustavia St. Barts, Great Harbour, Prickly Pear British Virgin Islands, Sopers Hole, Philipsburg (St. Maarten)
Bonus Offer:
Starts: Fri, Nov 5, 2027 from Lisbon
Ends: Sat, Nov 20, 2027 in Philipsburg (St. Maarten)
Cruise Ports: Lisbon, Madeira, Great Harbour, Philipsburg (St. Maarten)
Bonus Offer:
Starts: Sun, Mar 19, 2028 from Philipsburg (St. Maarten)
Ends: Mon, Apr 3, 2028 in Lisbon
Cruise Ports: Philipsburg (St. Maarten), Horta, Ponta Delgada, Lisbon
Bonus Offer:
Starts: Mon, Nov 29, 2027 from San Juan
Ends: Mon, Dec 6, 2027 in Colon
Cruise Ports: San Juan, Catalina Island, Santo Domingo, Cartagena, San Blas Islands, Colon
Bonus Offer:
Starts: Mon, Feb 28, 2028 from San Juan
Ends: Tue, Mar 14, 2028 in Lisbon
Cruise Ports: San Juan, Agadir, Casablanca, Lisbon
Starts: Sun, Dec 12, 2027 from Philipsburg (St. Maarten)
Ends: Sun, Dec 19, 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, Nov 28, 2027 from Philipsburg (St. Maarten)
Ends: Sun, Dec 5, 2027 in Philipsburg (St. Maarten)
Cruise Ports: Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Iles des Saintes, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten)
Starts: Mon, Nov 15, 2027 from San Juan
Ends: Mon, Nov 22, 2027 in San Juan
Cruise Ports: San Juan, Cruz Bay, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten), Great Harbour, Prickly Pear British Virgin Islands, San Juan
Bonus Offer:
Starts: Mon, Nov 1, 2027 from San Juan
Ends: Mon, Nov 8, 2027 in San Juan
Cruise Ports: San Juan, Cruz Bay, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten), Great Harbour, Prickly Pear British Virgin Islands, San Juan
Starts: Sun, Dec 5, 2027 from Philipsburg (St. Maarten)
Ends: Sun, Dec 12, 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: 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: Mon, Nov 8, 2027 from San Juan
Ends: Mon, Nov 15, 2027 in San Juan
Cruise Ports: San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan
Starts: Mon, Nov 22, 2027 from San Juan
Ends: Mon, Nov 29, 2027 in San Juan
Cruise Ports: San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan
Starts: Sun, Jan 16, 2028 from Philipsburg (St. Maarten)
Ends: Sun, Jan 23, 2028 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)
Bonus Offer:
Starts: Sun, Jan 30, 2028 from Philipsburg (St. Maarten)
Ends: Sun, Feb 6, 2028 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:
