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Cruises from San Juan


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44 Matched Sailings
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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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$1,854

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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$2,730

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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$2,730

per person
(double occupancy)
Includes taxes & fees
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Nov 29, 2026

(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, Cruz Bay, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten), Great Harbour...

7 Nights


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$2,762

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

(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, Cruz Bay, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten), Great Harbour...

7 Nights


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$2,762

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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$2,930

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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$2,930

per person
(double occupancy)
Includes taxes & fees
Learn More

Nov 15, 2026

(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, Cruz Bay, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten), Great Harbour...

7 Nights


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$2,962

per person
(double occupancy)
Includes taxes & fees
Learn More

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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$3,330

per person
(double occupancy)
Includes taxes & fees
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Jan 10, 2027

(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, Cruz Bay, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten), Great Harbour...

7 Nights


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$3,462

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

(Monday)

7 Night New World Caribbean Trio Cruise

Star Seeker
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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$3,726

per person
(double occupancy)
Includes taxes & fees
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Dec 07, 2025

(Sunday)

13 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, Santo Domingo, Cartagena, San Blas Islands, Colon, Cruising the Panama Canal...
Special Promotions

13 Nights


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$3,752

per person
(double occupancy)
Includes taxes & fees
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Oct 28, 2026

(Wednesday)

11 Night Masterpieces at Sea Gems of the Leeward Islands Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, Cruz Bay, Gustavia St. Barts, Basseterre, Falmouth Harbour, Iles des Saintes...

11 Nights


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$3,757

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

(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, Cruz Bay, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten), Great Harbour...

7 Nights


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$3,862

per person
(double occupancy)
Includes taxes & fees
Learn More

Nov 29, 2026

(Sunday)

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, Cruz Bay, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten), Great Harbour...
Special Promotions

14 Nights


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$4,393

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

(Sunday)

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, Mayreau, Iles des Saintes, Marigot, San Juan, Cruz Bay...
Special Promotions

14 Nights


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$4,393

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

(Sunday)

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, Cruz Bay, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten), Great Harbour...
Special Promotions

14 Nights


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$4,493

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

(Sunday)

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, Mayreau, Iles des Saintes, Marigot, San Juan, Cruz Bay...
Special Promotions

14 Nights


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$4,593

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

(Sunday)

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, Mayreau, Iles des Saintes, Marigot, San Juan, Cruz Bay, Basseterre...
Special Promotions

14 Nights


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$4,693

per person
(double occupancy)
Includes taxes & fees
Learn More

Nov 15, 2026

(Sunday)

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, Cruz Bay, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten), Great Harbour...
Special Promotions

14 Nights


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$4,693

per person
(double occupancy)
Includes taxes & fees
Learn More

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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$5,033

per person
(double occupancy)
Includes taxes & fees
Learn More

Jan 30, 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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$5,127

per person
(double occupancy)
Includes taxes & fees
Learn More

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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$5,136

per person
(double occupancy)
Includes taxes & fees
Learn More

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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$5,227

per person
(double occupancy)
Includes taxes & fees
Learn More

Mar 06, 2026

(Friday)

7 Night San Juan and the Virgin Islands Cruise

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

7 Nights


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from

$5,362

per person
(double occupancy)
Includes taxes & fees
Learn More



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