38 Cruises
| Where: | Any Destination | Nights: | Any Length |
| When: | Any Month | Line: | Windstar Cruises |
| From: | San Juan | Ship: | Any Ship |
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: 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: Sun, Nov 22, 2026 from San Juan
Ends: Sun, Nov 29, 2026 in San Juan
Cruise Ports: San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan
Bonus Offer:
Starts: Sun, Nov 8, 2026 from San Juan
Ends: Sun, Nov 15, 2026 in San Juan
Cruise Ports: San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan
Bonus Offer:
Starts: Sun, Dec 20, 2026 from San Juan
Ends: Sun, Dec 27, 2026 in San Juan
Cruise Ports: San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan
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: Sun, Jan 3, 2027 from San Juan
Ends: Sun, Jan 10, 2027 in San Juan
Cruise Ports: San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan
Starts: Sun, Jan 10, 2027 from San Juan
Ends: Sun, Jan 17, 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: Wed, Oct 28, 2026 from San Juan
Ends: Sun, Nov 8, 2026 in San Juan
Cruise Ports: San Juan, Cruz Bay, Gustavia St. Barts, Basseterre, Falmouth Harbour, Iles des Saintes, Pigeon Island, St George's, Great Harbour, Prickly Pear British Virgin Islands, San Juan
Bonus Offer:
Starts: Sun, Dec 27, 2026 from San Juan
Ends: Sun, Jan 3, 2027 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: 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
Bonus Offer:
Starts: Sun, Dec 6, 2026 from San Juan
Ends: Sun, Dec 20, 2026 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
Bonus Offer:
Starts: Sun, Nov 29, 2026 from San Juan
Ends: Sun, Dec 13, 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, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan
Bonus Offer:
Starts: Sun, Nov 22, 2026 from San Juan
Ends: Sun, Dec 6, 2026 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
Bonus Offer:
Starts: Sun, Dec 13, 2026 from San Juan
Ends: Sun, Dec 27, 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, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan
Bonus Offer:
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
Bonus Offer:
Starts: Sun, Nov 15, 2026 from San Juan
Ends: Sun, Nov 29, 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, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan
Bonus Offer:
Starts: Sun, Nov 8, 2026 from San Juan
Ends: Sun, Nov 22, 2026 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
Bonus Offer:
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, Mayreau, Bequia, Soufriere , San Juan
Bonus Offer:
