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45 Matched Sailings

Departing	Itinerary and Ship	Length	Save to Favorites	Priced from
Nov 29, 2027 (Monday) Other Dates	7 Night The Spanish Main Rise of the New World Cruise Star Pride Windstar Cruises Starts: San Juan, Puerto Rico Ends: Colon, Panama Ports of Call: San Juan, Catalina Island, Santo Domingo, Cartagena, San Blas Islands, Colon (see itinerary) Special Promotions $300 Reduced Deposit Free All-Inclusive Package	7 Nights	Add to Favorites Compare Favorites	from $2,416 per person (double occupancy) Includes taxes & fees Learn More
Jan 03, 2028 (Monday) Other Dates	7 Night Costa Rica and Panama Canal Cruise Star Pride Windstar Cruises Starts: Colon, Panama Ends: Puerto Caldera, Costa Rica Ports of Call: Colon, Cruising the Panama Canal, Fuerte Amador, Isla Parida, Golfo Dulce, Quepos, Puerto Caldera (see itinerary)	7 Nights	Add to Favorites Compare Favorites	from $2,878 per person (double occupancy) Includes taxes & fees Learn More
Feb 07, 2028 (Monday) Other Dates	7 Night Costa Rica and Panama Canal Cruise Star Pride Windstar Cruises Starts: Puerto Caldera, Costa Rica Ends: Colon, Panama Ports of Call: Puerto Caldera, Golfo Dulce, Quepos, Isla Parida, Fuerte Amador, Cruising the Panama Canal, Colon (see itinerary)	7 Nights	Add to Favorites Compare Favorites	from $2,948 per person (double occupancy) Includes taxes & fees Learn More
Dec 20, 2027 (Monday) Other Dates	7 Night Costa Rica and Panama Canal Cruise Star Pride Windstar Cruises Starts: Colon, Panama Ends: Puerto Caldera, Costa Rica Ports of Call: Colon, Cruising the Panama Canal, Fuerte Amador, Isla Parida, Golfo Dulce, Quepos, Puerto Caldera (see itinerary) Special Promotions $300 Reduced Deposit Free All-Inclusive Package The Signature Collection - A Hosted Sailing	7 Nights	Add to Favorites Compare Favorites	from $2,948 per person (double occupancy) Includes taxes & fees Learn More
Jan 24, 2028 (Monday) Other Dates	7 Night Costa Rica and Panama Canal Cruise Star Pride Windstar Cruises Starts: Puerto Caldera, Costa Rica Ends: Colon, Panama Ports of Call: Puerto Caldera, Golfo Dulce, Quepos, Isla Parida, Fuerte Amador, Cruising the Panama Canal, Colon (see itinerary)	7 Nights	Add to Favorites Compare Favorites	from $2,983 per person (double occupancy) Includes taxes & fees Learn More
Jan 31, 2028 (Monday) Other Dates	7 Night Costa Rica and Panama Canal Cruise Star Pride Windstar Cruises Starts: Colon, Panama Ends: Puerto Caldera, Costa Rica Ports of Call: Colon, Cruising the Panama Canal, Fuerte Amador, Isla Parida, Golfo Dulce, Quepos, Puerto Caldera (see itinerary) The Signature Collection - Exclusive Amenities	7 Nights	Add to Favorites Compare Favorites	from $2,983 per person (double occupancy) Includes taxes & fees Learn More
Dec 20, 2026 (Sunday) Other Dates	8 Night Naturally Costa Rica Cruise Star Legend Windstar Cruises Starts: Fuerte Amador, Panama Ends: Puerto Caldera, Costa Rica Ports of Call: Fuerte Amador, Isla Parida, Golfo Dulce, Quepos, Punta Leona, Curu Reserve, Playa Flamingo... (see itinerary)	8 Nights	Add to Favorites Compare Favorites	from $3,004 per person (double occupancy) Includes taxes & fees Learn More
Dec 13, 2027 (Monday) Other Dates	7 Night Costa Rica and Panama Canal Cruise Star Pride Windstar Cruises Starts: Puerto Caldera, Costa Rica Ends: Colon, Panama Ports of Call: Puerto Caldera, Golfo Dulce, Quepos, Isla Parida, Fuerte Amador, Cruising the Panama Canal, Colon (see itinerary) Special Promotions $300 Reduced Deposit Free All-Inclusive Package The Signature Collection - Exclusive Amenities	7 Nights	Add to Favorites Compare Favorites	from $3,088 per person (double occupancy) Includes taxes & fees Learn More
Dec 27, 2027 (Monday) Other Dates	7 Night Costa Rica and Panama Canal Cruise Star Pride Windstar Cruises Starts: Puerto Caldera, Costa Rica Ends: Colon, Panama Ports of Call: Puerto Caldera, Golfo Dulce, Quepos, Isla Parida, Fuerte Amador, Cruising the Panama Canal, Colon (see itinerary) Special Promotions $300 Reduced Deposit Free All-Inclusive Package	7 Nights	Add to Favorites Compare Favorites	from $3,123 per person (double occupancy) Includes taxes & fees Learn More
Jan 26, 2027 (Tuesday) Other Dates	7 Night Costa Rica and Panama Canal Cruise Star Legend Windstar Cruises Starts: Puerto Caldera, Costa Rica Ends: Colon, Panama Ports of Call: Puerto Caldera, Quepos, Golfo Dulce, Isla Parida, Fuerte Amador, Cruising the Panama Canal, Colon (see itinerary) Special Promotions $300 Reduced Deposit Free All-Inclusive Package	7 Nights	Add to Favorites Compare Favorites	from $3,236 per person (double occupancy) Includes taxes & fees Learn More
Jan 05, 2027 (Tuesday) Other Dates	7 Night Costa Rica and Panama Canal Cruise Star Legend Windstar Cruises Starts: Colon, Panama Ends: Puerto Caldera, Costa Rica Ports of Call: Colon, Cruising the Panama Canal, Fuerte Amador, Isla Parida, Golfo Dulce, Quepos, Puerto Caldera (see itinerary) Special Promotions Solo Traveler Offer $300 Reduced Deposit Free All-Inclusive Package	7 Nights	Add to Favorites Compare Favorites	from $3,236 per person (double occupancy) Includes taxes & fees Learn More
Jan 12, 2027 (Tuesday) Other Dates	7 Night Costa Rica and Panama Canal Cruise Star Legend Windstar Cruises Starts: Puerto Caldera, Costa Rica Ends: Colon, Panama Ports of Call: Puerto Caldera, Quepos, Golfo Dulce, Isla Parida, Fuerte Amador, Cruising the Panama Canal, Colon (see itinerary) Special Promotions $300 Reduced Deposit Free All-Inclusive Package The Signature Collection - Exclusive Amenities	7 Nights	Add to Favorites Compare Favorites	from $3,236 per person (double occupancy) Includes taxes & fees Learn More
Jan 19, 2027 (Tuesday) Other Dates	7 Night Costa Rica and Panama Canal Cruise Star Legend Windstar Cruises Starts: Colon, Panama Ends: Puerto Caldera, Costa Rica Ports of Call: Colon, Cruising the Panama Canal, Fuerte Amador, Isla Parida, Golfo Dulce, Quepos, Puerto Caldera (see itinerary) Special Promotions $300 Reduced Deposit Free All-Inclusive Package	7 Nights	Add to Favorites Compare Favorites	from $3,236 per person (double occupancy) Includes taxes & fees Learn More
Jan 17, 2028 (Monday) Other Dates	7 Night Costa Rica and Panama Canal Cruise Star Pride Windstar Cruises Starts: Colon, Panama Ends: Puerto Caldera, Costa Rica Ports of Call: Colon, Cruising the Panama Canal, Fuerte Amador, Isla Parida, Golfo Dulce, Quepos, Puerto Caldera (see itinerary) The Signature Collection - Exclusive Amenities	7 Nights	Add to Favorites Compare Favorites	from $3,263 per person (double occupancy) Includes taxes & fees Learn More
Feb 09, 2027 (Tuesday) Other Dates	7 Night Naturally Costa Rica Cruise Star Legend Windstar Cruises Starts: Puerto Caldera, Costa Rica Ends: Fuerte Amador, Panama Ports of Call: Puerto Caldera, Playa Flamingo, Punta Leona, Quepos, Golfo Dulce, Isla Parida, Fuerte Amador (see itinerary) Special Promotions Solo Traveler Offer $300 Reduced Deposit Free All-Inclusive Package The Signature Collection - Exclusive Amenities	7 Nights	Add to Favorites Compare Favorites	from $3,344 per person (double occupancy) Includes taxes & fees Learn More
Feb 21, 2028 (Monday) Other Dates	7 Night Naturally Costa Rica Cruise Star Pride Windstar Cruises Starts: Puerto Caldera, Costa Rica Ends: Fuerte Amador, Panama Ports of Call: Puerto Caldera, Playa Flamingo, Punta Leona, Quepos, Golfo Dulce, Isla Parida, Fuerte Amador (see itinerary) The Signature Collection - Exclusive Amenities	7 Nights	Add to Favorites Compare Favorites	from $3,352 per person (double occupancy) Includes taxes & fees Learn More
Feb 02, 2027 (Tuesday) Other Dates	7 Night Costa Rica and Panama Canal Cruise Star Legend Windstar Cruises Starts: Colon, Panama Ends: Puerto Caldera, Costa Rica Ports of Call: Colon, Cruising the Panama Canal, Fuerte Amador, Isla Parida, Golfo Dulce, Quepos, Puerto Caldera (see itinerary) Special Promotions $300 Reduced Deposit Free All-Inclusive Package	7 Nights	Add to Favorites Compare Favorites	from $3,446 per person (double occupancy) Includes taxes & fees Learn More
Jan 02, 2027 (Saturday) Other Dates	7 Night Costa Rica and Panama Canal Cruise Wind Star Windstar Cruises Starts: Colon, Panama Ends: Puerto Caldera, Costa Rica Ports of Call: Colon, Cruising the Panama Canal, Fuerte Amador, Isla Parida, Golfo Dulce, Quepos, Puerto Caldera (see itinerary) Special Promotions Solo Traveler Offer $300 Reduced Deposit Free All-Inclusive Package	7 Nights	Add to Favorites Compare Favorites	from $3,575 per person (double occupancy) Includes taxes & fees Learn More
Dec 28, 2026 (Monday) Other Dates	8 Night Costa Rica and Panama Canal Cruise Star Legend Windstar Cruises Starts: Puerto Caldera, Costa Rica Ends: Colon, Panama Ports of Call: Puerto Caldera, Punta Leona, Quepos, Golfo Dulce, Fuerte Amador, Cruising the Panama Canal... (see itinerary) Special Promotions Solo Traveler Offer	8 Nights	Add to Favorites Compare Favorites	from $3,596 per person (double occupancy) Includes taxes & fees Learn More
Dec 12, 2026 (Saturday) Other Dates	8 Night Panama Canal Cartagena San Blas Islands and More Cruise Star Legend Windstar Cruises Starts: Oranjestad, Aruba Ends: Fuerte Amador, Panama Ports of Call: Oranjestad, Cartagena, Bocas Del Toro, San Blas Islands, Cruising the Panama Canal, Fuerte Amador (see itinerary)	8 Nights	Add to Favorites Compare Favorites	from $3,612 per person (double occupancy) Includes taxes & fees Learn More
Feb 14, 2028 (Monday) Other Dates	7 Night Costa Rica and Panama Canal Cruise Star Pride Windstar Cruises Starts: Colon, Panama Ends: Puerto Caldera, Costa Rica Ports of Call: Colon, Cruising the Panama Canal, Fuerte Amador, Isla Parida, Golfo Dulce, Quepos, Puerto Caldera (see itinerary)	7 Nights	Add to Favorites Compare Favorites	from $3,613 per person (double occupancy) Includes taxes & fees Learn More
Jan 10, 2028 (Monday) Other Dates	7 Night Costa Rica and Panama Canal Cruise Star Pride Windstar Cruises Starts: Puerto Caldera, Costa Rica Ends: Colon, Panama Ports of Call: Puerto Caldera, Golfo Dulce, Quepos, Isla Parida, Fuerte Amador, Cruising the Panama Canal, Colon (see itinerary)	7 Nights	Add to Favorites Compare Favorites	from $3,718 per person (double occupancy) Includes taxes & fees Learn More
Dec 06, 2027 (Monday) Other Dates	7 Night Costa Rica and Panama Canal Cruise Star Pride Windstar Cruises Starts: Colon, Panama Ends: Puerto Caldera, Costa Rica Ports of Call: Colon, Cruising the Panama Canal, Fuerte Amador, Isla Parida, Golfo Dulce, Quepos, Puerto Caldera (see itinerary) Special Promotions $300 Reduced Deposit Free All-Inclusive Package The Signature Collection - Exclusive Amenities	7 Nights	Add to Favorites Compare Favorites	from $3,788 per person (double occupancy) Includes taxes & fees Learn More
Dec 19, 2026 (Saturday) Other Dates	7 Night Costa Rica and Panama Canal Cruise Wind Star Windstar Cruises Starts: Colon, Panama Ends: Puerto Caldera, Costa Rica Ports of Call: Colon, Cruising the Panama Canal, Fuerte Amador, Isla Parida, Golfo Dulce, Quepos, Puerto Caldera (see itinerary) Special Promotions Solo Traveler Offer The Signature Collection - Exclusive Amenities	7 Nights	Add to Favorites Compare Favorites	from $3,855 per person (double occupancy) Includes taxes & fees Learn More
Dec 12, 2026 (Saturday) Other Dates	7 Night Costa Rica and Panama Canal Cruise Wind Star Windstar Cruises Starts: Puerto Caldera, Costa Rica Ends: Colon, Panama Ports of Call: Puerto Caldera, Quepos, Golfo Dulce, Isla Parida, Fuerte Amador, Cruising the Panama Canal, Colon (see itinerary) Special Promotions Solo Traveler Offer The Signature Collection - Exclusive Amenities	7 Nights	Add to Favorites Compare Favorites	from $3,890 per person (double occupancy) Includes taxes & fees Learn More