33 Cruises
| Where: | Any Destination | Nights: | Any Length |
| When: | Any Month | Line: | Windstar Cruises |
| From: | San Juan | Ship: | Any Ship |
Starts: Sun, Nov 9, 2025 from San Juan
Ends: Sun, Nov 16, 2025 in San Juan
Cruise Ports: San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan
Starts: Sun, Nov 23, 2025 from San Juan
Ends: Sun, Nov 30, 2025 in San Juan
Cruise Ports: San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan
Starts: Sun, Nov 16, 2025 from San Juan
Ends: Sun, Nov 23, 2025 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, Oct 26, 2025 from San Juan
Ends: Sun, Nov 2, 2025 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, Nov 30, 2025 from San Juan
Ends: Sun, Dec 7, 2025 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
Starts: Sun, Dec 7, 2025 from San Juan
Ends: Sat, Dec 13, 2025 in Colon
Cruise Ports: San Juan, Santo Domingo, Cartagena, San Blas Islands, Colon
Starts: Sun, Nov 2, 2025 from San Juan
Ends: Sun, Nov 9, 2025 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: Fri, Mar 13, 2026 from San Juan
Ends: Fri, Mar 20, 2026 in San Juan
Cruise Ports: San Juan, Marigot, Iles des Saintes, Mayreau, Bequia, Pigeon Island, The Pitons, San Juan
Starts: Fri, Feb 6, 2026 from San Juan
Ends: Fri, Feb 13, 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
Starts: Fri, Feb 27, 2026 from San Juan
Ends: Fri, Mar 6, 2026 in San Juan
Cruise Ports: San Juan, Philipsburg (St. Maarten), Iles des Saintes, Soufriere , Bequia, Mayreau, San Juan
Starts: Fri, Feb 20, 2026 from San Juan
Ends: Fri, Feb 27, 2026 in San Juan
Cruise Ports: San Juan, Cruz Bay, Basseterre, Philipsburg (St. Maarten), Gustavia St. Barts, Great Harbour, Prickly Pear British Virgin Islands, San Juan
Starts: Mon, Apr 6, 2026 from San Juan
Ends: Mon, Apr 13, 2026 in Colon
Cruise Ports: San Juan, Catalina Island, Santo Domingo, Cartagena, San Blas Islands, Colon
Starts: Fri, Feb 13, 2026 from San Juan
Ends: Fri, Feb 20, 2026 in San Juan
Cruise Ports: San Juan, Bequia, Mayreau, Soufriere , Iles des Saintes, Marigot, San Juan
Starts: Fri, Jan 30, 2026 from San Juan
Ends: Fri, Feb 6, 2026 in San Juan
Cruise Ports: San Juan, Bequia, Mayreau, Soufriere , Iles des Saintes, Marigot, San Juan
Starts: Fri, Jan 23, 2026 from San Juan
Ends: Fri, Jan 30, 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
Starts: Fri, Mar 6, 2026 from San Juan
Ends: Fri, Mar 13, 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
Starts: Fri, Mar 27, 2026 from San Juan
Ends: Mon, Apr 6, 2026 in San Juan
Cruise Ports: San Juan, Cruz Bay, St John's, Iles des Saintes, Pigeon Island, St George's, Gustavia St. Barts, Great Harbour, Prickly Pear British Virgin Islands, San Juan
Starts: Sun, Nov 9, 2025 from San Juan
Ends: Sun, Nov 23, 2025 in San Juan
Cruise Ports: San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan, Cruz Bay, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten), Great Harbour, Prickly Pear British Virgin Islands, San Juan
Starts: Sun, Nov 16, 2025 from San Juan
Ends: Sun, Nov 30, 2025 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, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan
Starts: Sun, Nov 23, 2025 from San Juan
Ends: Sun, Dec 7, 2025 in San Juan
Cruise Ports: San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan, Cruz Bay, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten), Great Harbour, Prickly Pear British Virgin Islands, San Juan
