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Cruises from San Juan


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33 Matched Sailings
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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, Mayreau, Iles des Saintes, Marigot, San Juan

7 Nights


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$3,323

per person
(double occupancy)
Includes taxes & fees
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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, Mayreau, Iles des Saintes, Marigot, San Juan

7 Nights


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$3,323

per person
(double occupancy)
Includes taxes & fees
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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, Cruz Bay, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten), Great Harbour...

7 Nights


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$3,355

per person
(double occupancy)
Includes taxes & fees
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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, Cruz Bay, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten), Great Harbour...

7 Nights


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$3,355

per person
(double occupancy)
Includes taxes & fees
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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, Cruz Bay, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten), Great Harbour...

7 Nights


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$3,355

per person
(double occupancy)
Includes taxes & fees
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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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$3,429

per person
(double occupancy)
Includes taxes & fees
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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, Cruz Bay, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten), Great Harbour...

7 Nights


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$3,555

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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$3,726

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

Feb 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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$3,755

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, Soufriere , Bequia, Mayreau, San Juan

7 Nights


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$3,829

per person
(double occupancy)
Includes taxes & fees
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Feb 20, 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, Philipsburg (St. Maarten), Gustavia St. Barts, Great Harbour...

7 Nights


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$3,855

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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$3,919

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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$4,020

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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$4,020

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

Jan 23, 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

$4,055

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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$4,755

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

Mar 27, 2026

(Friday)

10 Night Gems of the Leeward Islands Cruise

Star Seeker
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, Cruz Bay, St John's, Iles des Saintes, Pigeon Island, St George's, Gustavia St. Barts...

10 Nights


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$5,047

per person
(double occupancy)
Includes taxes & fees
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Nov 09, 2025

(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...

14 Nights


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$5,579

per person
(double occupancy)
Includes taxes & fees
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Nov 16, 2025

(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...

14 Nights


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$5,579

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

Nov 23, 2025

(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...

14 Nights


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$5,579

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

Nov 02, 2025

(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...

14 Nights


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$6,079

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

Feb 20, 2026

(Friday)

14 Night Star Collector Lovely Leewards Cruise

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

14 Nights


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$6,685

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

Jan 30, 2026

(Friday)

14 Night Star Collector Lovely Leewards 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, Cruz Bay, Basseterre...

14 Nights


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from

$6,776

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

Feb 06, 2026

(Friday)

14 Night Star Collector Lovely Leewards 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...

14 Nights


Add to Favorites
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from

$6,776

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

Feb 13, 2026

(Friday)

14 Night Star Collector Lovely Leewards 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, Cruz Bay, Basseterre...

14 Nights


Add to Favorites
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from

$6,876

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



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