49 Cruises
| Where: | Any Destination | Nights: | Any Length |
| When: | Any Month | Line: | Windstar Cruises |
| From: | Philipsburg (St. | Ship: | Any Ship |
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: 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, 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, 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: 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, 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, 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:
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, 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)
Bonus Offer:
Starts: Sat, Jan 9, 2027 from Philipsburg (St. Maarten)
Ends: Sat, Jan 16, 2027 in Philipsburg (St. Maarten)
Cruise Ports: Philipsburg (St. Maarten), Charlestown, Iles des Saintes, Mayreau, Roseau, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten)
Bonus Offer:
Starts: Sat, Dec 26, 2026 from Philipsburg (St. Maarten)
Ends: Sat, Jan 2, 2027 in Philipsburg (St. Maarten)
Cruise Ports: Philipsburg (St. Maarten), Gustavia St. Barts, Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre, Philipsburg (St. Maarten)
Bonus Offer:
Starts: Sat, Dec 19, 2026 from Philipsburg (St. Maarten)
Ends: Sat, Dec 26, 2026 in Philipsburg (St. Maarten)
Cruise Ports: Philipsburg (St. Maarten), Gustavia St. Barts, Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands, Philipsburg (St. Maarten)
Bonus Offer:
Starts: Sat, Jan 16, 2027 from Philipsburg (St. Maarten)
Ends: Sat, Jan 23, 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, 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)
Bonus Offer:
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)
Bonus Offer:
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, Prickly Pear British Virgin Islands, Sopers Hole, Great Harbour, Gustavia St. Barts, Philipsburg (St. Maarten)
Bonus Offer:
Starts: Sat, Mar 27, 2027 from Philipsburg (St. Maarten)
Ends: Sun, Apr 11, 2027 in Lisbon
Cruise Ports: Philipsburg (St. Maarten), Madeira, PORTO SANTO, Lisbon
Bonus Offer:
