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Priced from

Mar 09, 2026

(Monday)

6 Night Panamas Pristine Caribbean Cruise

Star Pride
Windstar Cruises
Starts: Colon, Panama
Ends: Oranjestad, Aruba
Ports of Call:
Colon, Bocas Del Toro, San Blas Islands, Cartagena, Oranjestad

6 Nights


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$2,338

per person
(double occupancy)
Includes taxes & fees
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Mar 15, 2026

(Sunday)

7 Night Windward Ways and Tobago Cays Cruise

Star Pride
Windstar Cruises
Starts: Oranjestad, Aruba
Ends: Bridgetown, Barbados
Ports of Call:
Oranjestad, Bonaire, Kingstown, The Pitons, Bequia, Mayreau, Scarborough, Bridgetown

7 Nights


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$2,399

per person
(double occupancy)
Includes taxes & fees
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Dec 06, 2026

(Sunday)

7 Night Windward Islands Surf and Sunsets Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan

7 Nights


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$3,130

per person
(double occupancy)
Includes taxes & fees
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Nov 27, 2026

(Friday)

7 Night Jewels of the Windward Islands Cruise

Star Legend
Windstar Cruises
Starts: Bridgetown, Barbados
Ends: Bridgetown, Barbados
Ports of Call:
Bridgetown, Anse Mitan, Pigeon Island, Castries, The Pitons, Mayreau, St George's, Bequia...

7 Nights


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$3,138

per person
(double occupancy)
Includes taxes & fees
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Dec 20, 2026

(Sunday)

7 Night Windward Islands Surf and Sunsets Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan

7 Nights


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$3,330

per person
(double occupancy)
Includes taxes & fees
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Nov 08, 2026

(Sunday)

7 Night Windward Islands Surf and Sunsets Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan

7 Nights


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$3,330

per person
(double occupancy)
Includes taxes & fees
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Nov 22, 2026

(Sunday)

7 Night Windward Islands Surf and Sunsets Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan

7 Nights


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$3,330

per person
(double occupancy)
Includes taxes & fees
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Dec 12, 2026

(Saturday)

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

8 Nights


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$3,465

per person
(double occupancy)
Includes taxes & fees
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Feb 16, 2027

(Tuesday)

6 Night Panama Canal Cartagena San Blas Islands and More Cruise

Star Legend
Windstar Cruises
Starts: Fuerte Amador, Panama
Ends: Oranjestad, Aruba
Ports of Call:
Fuerte Amador, Cruising the Panama Canal, Bocas Del Toro, San Blas Islands, Cartagena, Oranjestad

6 Nights


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$3,465

per person
(double occupancy)
Includes taxes & fees
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Dec 04, 2026

(Friday)

8 Night Windward Ways and Tobago Cays Cruise

Star Legend
Windstar Cruises
Starts: Bridgetown, Barbados
Ends: Oranjestad, Aruba
Ports of Call:
Bridgetown, Rodney Bay, The Pitons, Scarborough, Bequia, Mayreau, Bonaire, Willemstad (Curacao)...

8 Nights


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$3,519

per person
(double occupancy)
Includes taxes & fees
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Mar 22, 2026

(Sunday)

16 Night Ocean Crossing Cruise

Star Pride
Windstar Cruises
Starts: Bridgetown, Barbados
Ends: Amsterdam, Netherlands
Ports of Call:
Bridgetown, Lisbon, Amsterdam

16 Nights


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$3,714

per person
(double occupancy)
Includes taxes & fees
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Nov 10, 2026

(Tuesday)

14 Night Knot Your Average Crossing Cruise

Wind Star
Windstar Cruises
Starts: Lisbon, Portugal
Ends: Bridgetown, Barbados
Ports of Call:
Lisbon, Bridgetown

14 Nights


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$3,725

per person
(double occupancy)
Includes taxes & fees
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Jan 03, 2027

(Sunday)

7 Night Windward Islands Surf and Sunsets Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan

7 Nights


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$4,030

per person
(double occupancy)
Includes taxes & fees
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Dec 12, 2026

(Saturday)

16 Night Star Collector Latin America Explorer Cruise

Star Legend
Windstar Cruises
Starts: Oranjestad, Aruba
Ends: Puerto Caldera, Costa Rica
Ports of Call:
Oranjestad, Cartagena, Bocas Del Toro, San Blas Islands, Cruising the Panama Canal, Fuerte Amador...

16 Nights


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$5,227

per person
(double occupancy)
Includes taxes & fees
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Nov 24, 2026

(Tuesday)

11 Night Colombian and Southern Caribbean Coastlines Cruise

Wind Star
Windstar Cruises
Starts: Bridgetown, Barbados
Ends: Colon, Panama
Ports of Call:
Bridgetown, Bequia, St George's, Bonaire, Willemstad (Curacao), Oranjestad, Cartagena...

11 Nights


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$5,530

per person
(double occupancy)
Includes taxes & fees
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Nov 27, 2026

(Friday)

15 Night Star Collector Captivating Caribbean Cruise

Star Legend
Windstar Cruises
Starts: Bridgetown, Barbados
Ends: Oranjestad, Aruba
Ports of Call:
Bridgetown, Anse Mitan, Pigeon Island, Castries, The Pitons, Mayreau, St George's, Bequia...

15 Nights


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$5,658

per person
(double occupancy)
Includes taxes & fees
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Dec 04, 2026

(Friday)

16 Night Star Collector Windward Islands and Spanish New World Cruise

Star Legend
Windstar Cruises
Starts: Bridgetown, Barbados
Ends: Fuerte Amador, Panama
Ports of Call:
Bridgetown, Rodney Bay, The Pitons, Scarborough, Bequia, Mayreau, Bonaire, Willemstad (Curacao)...

16 Nights


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$5,711

per person
(double occupancy)
Includes taxes & fees
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Mar 13, 2026

(Friday)

7 Night Windward Islands Surf and Sunsets Cruise

Star Seeker
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, Marigot, Iles des Saintes, Mayreau, Bequia, Pigeon Island, The Pitons, San Juan

7 Nights


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$5,733

per person
(double occupancy)
Includes taxes & fees
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Feb 27, 2026

(Friday)

7 Night Windward Islands Surf and Sunsets Cruise

Star Seeker
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, Philipsburg (St. Maarten), Iles des Saintes, Mayreau, Bequia, Soufriere , San Juan

7 Nights


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$5,836

per person
(double occupancy)
Includes taxes & fees
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Feb 13, 2026

(Friday)

7 Night Windward Islands Surf and Sunsets Cruise

Star Seeker
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, Bequia, Mayreau, Soufriere , Iles des Saintes, Marigot, San Juan

7 Nights


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$5,927

per person
(double occupancy)
Includes taxes & fees
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Feb 16, 2027

(Tuesday)

14 Night Star Collector Windward Islands and Spanish New World Cruise

Star Legend
Windstar Cruises
Starts: Fuerte Amador, Panama
Ends: Bridgetown, Barbados
Ports of Call:
Fuerte Amador, Cruising the Panama Canal, Bocas Del Toro, San Blas Islands, Cartagena, Oranjestad...

14 Nights


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$5,985

per person
(double occupancy)
Includes taxes & fees
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Nov 24, 2026

(Tuesday)

18 Night Star Collector Reefs and Rainforests the Caribbean Colombia Panama and Costa Rica via the Panama Canal Cruise

Wind Star
Windstar Cruises
Starts: Bridgetown, Barbados
Ends: Puerto Caldera, Costa Rica
Ports of Call:
Bridgetown, Bequia, St George's, Bonaire, Willemstad (Curacao), Oranjestad, Cartagena...

18 Nights


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$15,500

per person
(double occupancy)
Includes taxes & fees
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Nov 10, 2026

(Tuesday)

25 Night Star Collector Southern Caribbean Thanksgiving Jubilee Cruise

Wind Star
Windstar Cruises
Starts: Lisbon, Portugal
Ends: Colon, Panama
Ports of Call:
Lisbon, Bridgetown, Bequia, St George's, Bonaire, Willemstad (Curacao), Oranjestad, Cartagena...

25 Nights


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Oct 19, 2026

(Monday)

70 Night Star Collector Grand Mediterranean and Latin America Adventure Cruise

Star Legend
Windstar Cruises
Starts: Istanbul, Turkey
Ends: Puerto Caldera, Costa Rica
Ports of Call:
Istanbul, Myrina, Mykonos, Kusadasi (Ephesus), Bodrum, Santorini, Itea, Cruising the Corinth Canal...

70 Nights


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Mar 15, 2026

(Sunday)

13 Night Star Collector Blue Seas of the Windward Islands Cruise

Wind Spirit
Windstar Cruises
Starts: Bridgetown, Barbados
Ends: Bridgetown, Barbados
Ports of Call:
Bridgetown, Tobago Cays, Pigeon Island, Castries, The Pitons, Mayreau, Bequia, Bridgetown...

13 Nights


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