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Dec 02, 2025

(Tuesday)

5 Night Barefoot Break in the British Virgin Islands Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands...

5 Nights


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$2,645

per person
(double occupancy)
Includes taxes & fees
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Mar 29, 2025

(Saturday)

7 Night Jewels of the Windward Islands Cruise

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

7 Nights


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$2,940

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

(Sunday)

7 Night Classic Caribbean Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre...

7 Nights


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$3,044

per person
(double occupancy)
Includes taxes & fees
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Mar 21, 2026

(Saturday)

7 Night Classic Caribbean Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre...

7 Nights


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$3,044

per person
(double occupancy)
Includes taxes & fees
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Jan 25, 2025

(Saturday)

7 Night Panama Canal Cartagena San Blas Islands and More Cruise

Star Pride
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

7 Nights


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$3,138

per person
(double occupancy)
Includes taxes & fees
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Jan 04, 2025

(Saturday)

7 Night Jewels of the Windward Islands Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Bridgetown, Barbados
Ends: Bridgetown, Barbados
Ports of Call:
Bridgetown, Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St George's, Bequia, Bridgetown

7 Nights


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$3,143

per person
(double occupancy)
Includes taxes & fees
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Mar 14, 2026

(Saturday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour...

7 Nights


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$3,160

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

(Saturday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), St John's, Road Bay, Sopers Hole, Great Harbour...

7 Nights


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$3,160

per person
(double occupancy)
Includes taxes & fees
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Dec 14, 2025

(Sunday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour...

7 Nights


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$3,160

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

(Saturday)

7 Night Classic Caribbean Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Deshaies, Basseterre...

7 Nights


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$3,244

per person
(double occupancy)
Includes taxes & fees
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Feb 01, 2025

(Saturday)

7 Night Panama Canal Cartagena San Blas Islands and More Cruise

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

7 Nights


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$3,298

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

(Sunday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour...

7 Nights


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$3,303

per person
(double occupancy)
Includes taxes & fees
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Mar 21, 2026

(Saturday)

7 Night Jewels of the Windward Islands Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Bridgetown, Barbados
Ends: Bridgetown, Barbados
Ports of Call:
Bridgetown, Basseterre, Iles des Saintes, Roseau, Anse Mitan, Mayreau, Bridgetown

7 Nights


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$3,309

per person
(double occupancy)
Includes taxes & fees
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Feb 15, 2025

(Saturday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Falmouth Harbour, Great Harbour, Prickly Pear British Virgin Islands...

7 Nights


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$3,319

per person
(double occupancy)
Includes taxes & fees
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Jan 11, 2025

(Saturday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Falmouth Harbour, Gustavia St. Barts, Sopers Hole, Great Harbour...

7 Nights


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$3,319

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 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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Jan 11, 2026

(Sunday)

7 Night Lush and Lovely Islands of the Lesser Antilles Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Bridgetown, Barbados
Ports of Call:
Philipsburg (St. Maarten), Basseterre, Gustavia St. Barts, St John's, Iles des Saintes...

7 Nights


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$3,329

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

Jan 24, 2026

(Saturday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), St John's, Road Bay, Prickly Pear British Virgin Islands, Sopers Hole...

7 Nights


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$3,353

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

Feb 14, 2026

(Saturday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), St John's, Road Bay, Sopers Hole, Great Harbour...

7 Nights


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from

$3,353

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

Feb 21, 2026

(Saturday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), St John's, Road Bay, Prickly Pear British Virgin Islands, Sopers Hole...

7 Nights


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from

$3,353

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

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
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, 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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Apr 05, 2025

(Saturday)

10 Night Ocean Crossing Cruise

Star Pride
Windstar Cruises
Starts: Bridgetown, Barbados
Ends: Santa Cruz de Tenerife, Spain
Ports of Call:
Bridgetown, Santa Cruz de Tenerife

10 Nights


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$3,394

per person
(double occupancy)
Includes taxes & fees
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