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Cruises from San Juan


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Nov 29, 2027

(Monday)

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
Special Promotions

7 Nights


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$2,835

per person
(double occupancy)
Includes taxes & fees
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Feb 28, 2028

(Monday)

15 Night Ocean Crossing Cruise

Star Legend
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: Lisbon, Portugal
Ports of Call:
San Juan, Agadir, Casablanca, Lisbon

15 Nights


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$2,839

per person
(double occupancy)
Includes taxes & fees
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Nov 01, 2027

(Monday)

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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$2,862

per person
(double occupancy)
Includes taxes & fees
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Nov 15, 2027

(Monday)

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...
Special Promotions

7 Nights


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$2,862

per person
(double occupancy)
Includes taxes & fees
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Nov 08, 2027

(Monday)

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, 2027

(Monday)

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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Jan 10, 2028

(Monday)

7 Night Windward Islands Surf and Sunsets Cruise

Star Legend
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
Special Promotions

7 Nights


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$3,030

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

Jan 24, 2028

(Monday)

7 Night Windward Islands Surf and Sunsets Cruise

Star Legend
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
Special Promotions

7 Nights


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$3,030

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

Mar 13, 2028

(Monday)

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
Special Promotions

7 Nights


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$3,030

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

Mar 27, 2028

(Monday)

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
Special Promotions

7 Nights


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from

$3,030

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

Feb 07, 2028

(Monday)

7 Night Windward Islands Surf and Sunsets Cruise

Star Legend
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
Special Promotions

7 Nights


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$3,030

per person
(double occupancy)
Includes taxes & fees
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Feb 21, 2028

(Monday)

7 Night Windward Islands Surf and Sunsets Cruise

Star Legend
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
Special Promotions

7 Nights


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$3,030

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

Apr 03, 2028

(Monday)

16 Night Ocean Crossing Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: Amsterdam, Netherlands
Ports of Call:
San Juan, Lisbon, Brest, Amsterdam

16 Nights


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$3,039

per person
(double occupancy)
Includes taxes & fees
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Mar 20, 2028

(Monday)

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...
Special Promotions

7 Nights


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$3,062

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

Feb 14, 2028

(Monday)

7 Night San Juan and the Virgin Islands Cruise

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

7 Nights


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from

$3,062

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

Jan 31, 2028

(Monday)

7 Night San Juan and the Virgin Islands Cruise

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

7 Nights


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from

$3,062

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

Jan 17, 2028

(Monday)

7 Night San Juan and the Virgin Islands Cruise

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

7 Nights


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from

$3,062

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

Jan 03, 2028

(Monday)

7 Night San Juan and the Virgin Islands Cruise

Star Legend
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

7 Nights


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from

$3,062

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

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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$3,162

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

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, Deshaies, Marigot, San Juan

7 Nights


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$3,230

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

Dec 27, 2027

(Monday)

7 Night Windward Islands Surf and Sunsets Cruise

Star Legend
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
Special Promotions

7 Nights


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from

$3,230

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

Dec 20, 2027

(Monday)

7 Night San Juan and the Virgin Islands Cruise

Star Legend
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

7 Nights


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from

$3,262

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

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


Add to Favorites
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from

$3,262

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

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, Deshaies, Marigot, San Juan

7 Nights


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from

$3,330

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

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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from

$3,330

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



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