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Cruises from San Juan


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31 Matched Sailings
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Priced from

Nov 03, 2024

(Sunday)

6 Night San Juan and the Virgin Islands Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, Philipsburg (St. Maarten), Charlestown, Gustavia St. Barts, Great Harbour...

6 Nights


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Lowest from

$2,499

per person
(double occupancy)
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Nov 16, 2024

(Saturday)

7 Night San Juan and the Virgin Islands Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, Charlotte Amalie (St Thomas), Philipsburg (St. Maarten), Gustavia St. Barts, Basseterre...

7 Nights


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Lowest from

$2,499

per person
(double occupancy)
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Nov 23, 2024

(Saturday)

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, Pigeon Island, Iles des Saintes, Philipsburg (St. Maarten), San Juan

7 Nights


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Lowest from

$2,499

per person
(double occupancy)
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Dec 07, 2024

(Saturday)

7 Night Winter Antilles Escape Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: Bridgetown, Barbados
Ports of Call:
San Juan, Charlotte Amalie (St Thomas), Gustavia St. Barts, Basseterre, Roseau, Pigeon Island...

7 Nights


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Lowest from

$2,499

per person
(double occupancy)
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Oct 26, 2025

(Sunday)

7 Night San Juan and the Virgin Islands Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten), Great Harbour...

7 Nights


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Lowest from

$2,599

per person
(double occupancy)
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Nov 02, 2025

(Sunday)

7 Night San Juan and the Virgin Islands Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten), Great Harbour...

7 Nights


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Lowest from

$2,599

per person
(double occupancy)
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Nov 09, 2025

(Sunday)

7 Night San Juan and the Virgin Islands Cruise

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

7 Nights


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Lowest from

$2,599

per person
(double occupancy)
Learn More

Nov 16, 2025

(Sunday)

7 Night San Juan and the Virgin Islands Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten), Great Harbour...

7 Nights


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Lowest from

$2,599

per person
(double occupancy)
Learn More

Nov 23, 2025

(Sunday)

7 Night San Juan and the Virgin Islands Cruise

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

7 Nights


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Lowest from

$2,599

per person
(double occupancy)
Learn More

Nov 30, 2025

(Sunday)

7 Night San Juan and the Virgin Islands Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten), Great Harbour...

7 Nights


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Lowest from

$2,599

per person
(double occupancy)
Learn More

Nov 30, 2024

(Saturday)

7 Night San Juan and the Virgin Islands Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, Charlotte Amalie (St Thomas), Philipsburg (St. Maarten), Basseterre, Gustavia St. Barts...

7 Nights


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Lowest from

$2,699

per person
(double occupancy)
Learn More

Dec 07, 2025

(Sunday)

6 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, Santo Domingo, Cartagena, San Blas Islands, Colon

6 Nights


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Lowest from

$2,799

per person
(double occupancy)
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Nov 09, 2024

(Saturday)

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, Pigeon Island, Iles des Saintes, Philipsburg (St. Maarten), San Juan

7 Nights


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Lowest from

$2,899

per person
(double occupancy)
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Nov 23, 2024

(Saturday)

14 Night Star Collector Lovely Leewards Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, St George's, Bequia, Pigeon Island, Iles des Saintes, Philipsburg (St. Maarten), San Juan...

14 Nights


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Lowest from

$3,999

per person
(double occupancy)
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Nov 16, 2024

(Saturday)

14 Night Star Collector Lovely Leewards Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, Charlotte Amalie (St Thomas), Philipsburg (St. Maarten), Gustavia St. Barts, Basseterre...

14 Nights


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Lowest from

$3,999

per person
(double occupancy)
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Dec 07, 2024

(Saturday)

14 Night Star Collector White Sands of the Windward Islands Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: Oranjestad, Aruba
Ports of Call:
San Juan, Charlotte Amalie (St Thomas), Gustavia St. Barts, Basseterre, Roseau, Pigeon Island...

14 Nights


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Lowest from

$3,999

per person
(double occupancy)
Learn More

Nov 09, 2024

(Saturday)

14 Night Star Collector Lovely Leewards Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, St George's, Bequia, Pigeon Island, Iles des Saintes, Philipsburg (St. Maarten), San Juan...

14 Nights


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Lowest from

$4,299

per person
(double occupancy)
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Nov 03, 2024

(Sunday)

13 Night Star Collector Lovely Leewards Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, Philipsburg (St. Maarten), Charlestown, Gustavia St. Barts, Great Harbour...

13 Nights


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Lowest from

$4,299

per person
(double occupancy)
Learn More

Nov 01, 2025

(Saturday)

14 Night Star Collector Lovely Leewards Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, St John, Philipsburg (St. Maarten), Basseterre, Gustavia St. Barts, Great Harbour...

14 Nights


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Lowest from

$4,499

per person
(double occupancy)
Learn More

Nov 08, 2025

(Saturday)

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, Pigeon Island, Iles des Saintes, Philipsburg (St. Maarten), San Juan

7 Nights


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Pricing On
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Nov 08, 2025

(Saturday)

14 Night Star Collector Lovely Leewards Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, St George's, Bequia, Pigeon Island, Iles des Saintes, Philipsburg (St. Maarten), San Juan...

14 Nights


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Nov 01, 2025

(Saturday)

7 Night San Juan and the Virgin Islands Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, St John, Philipsburg (St. Maarten), Basseterre, Gustavia St. Barts, Great Harbour...

7 Nights


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Dec 06, 2025

(Saturday)

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

7 Nights


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Dec 06, 2025

(Saturday)

14 Night Star Collector Coffee Canal and Callaloo Central America Colombia and the Caribbean Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: Puerto Caldera, Costa Rica
Ports of Call:
San Juan, Catalina Island, Santo Domingo, Cartagena, San Blas Islands, Colon...

14 Nights


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Nov 29, 2025

(Saturday)

7 Night San Juan and the Virgin Islands Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, St John, Philipsburg (St. Maarten), Basseterre, Gustavia St. Barts, Great Harbour...

7 Nights


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