87 Cruises
| Where: | Caribbean - Easte | Nights: | Any Length |
| When: | Any Month | Line: | Windstar Cruises |
| From: | Any Port | Ship: | Any Ship |
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: 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: 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: 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: 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, 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: Sun, Nov 15, 2026 from San Juan
Ends: Sun, Nov 22, 2026 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: 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:
