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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, Virgin Gorda, Gustavia St. Barts...

5 Nights


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Lowest from

$1,899

per person
(double occupancy)
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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, Sint Maarten, Charlestown, Gustavia St. Barts, Great Harbour, Virgin Gorda, San Juan

6 Nights


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Lowest from

$1,999

per person
(double occupancy)
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Jan 02, 2025

(Thursday)

14 Night Ocean Crossing Cruise

Star Breeze
Windstar Cruises
4.2 based on 5 ratings
Starts: Papeete, French Polynesia
Ends: Puerto Caldera, Costa Rica
Ports of Call:
Papeete, Puerto Caldera

14 Nights


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Lowest from

$1,999

per person
(double occupancy)
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Feb 02, 2025

(Sunday)

14 Night Ocean Crossing Cruise

Star Breeze
Windstar Cruises
4.2 based on 5 ratings
Starts: Puerto Caldera, Costa Rica
Ends: Papeete, French Polynesia
Ports of Call:
Puerto Caldera, Papeete

14 Nights


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Lowest from

$1,999

per person
(double occupancy)
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Feb 01, 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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Lowest from

$2,199

per person
(double occupancy)
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Feb 08, 2025

(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, Iles des Saintes, Basseterre...

7 Nights


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Lowest from

$2,199

per person
(double occupancy)
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Feb 08, 2025

(Saturday)

7 Night 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, Pigeon Island, Bridgetown

7 Nights


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Lowest from

$2,199

per person
(double occupancy)
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Jan 25, 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, Road Bay, Sopers Hole, Great Harbour, Virgin Gorda...

7 Nights


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Lowest from

$2,199

per person
(double occupancy)
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Jan 25, 2025

(Saturday)

7 Night Windward Islands Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Bridgetown, Barbados
Ends: Bridgetown, Barbados
Ports of Call:
Bridgetown, St John's, Roseau, Iles des Saintes, Anse Mitan, Pigeon Island, Bridgetown

7 Nights


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Lowest from

$2,199

per person
(double occupancy)
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Feb 01, 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, Road Bay, Sopers Hole, Great Harbour, Virgin Gorda...

7 Nights


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Lowest from

$2,199

per person
(double occupancy)
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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, Virgin Gorda, Sopers Hole...

7 Nights


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Lowest from

$2,199

per person
(double occupancy)
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Feb 15, 2025

(Saturday)

7 Night Naturally Costa Rica Cruise

Wind Star
Windstar Cruises
4.2 based on 5 ratings
Starts: Puerto Caldera, Costa Rica
Ends: Puerto Caldera, Costa Rica
Ports of Call:
Puerto Caldera, Playa Flamingo, Corinto, San Juan del Sur, Playas del Coco, Herradura, Quepos...

7 Nights


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Lowest from

$2,199

per person
(double occupancy)
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Feb 15, 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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Lowest from

$2,199

per person
(double occupancy)
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Feb 22, 2025

(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, Iles des Saintes, Basseterre...

7 Nights


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Lowest from

$2,199

per person
(double occupancy)
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Mar 01, 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, Road Bay, Sopers Hole, Great Harbour, Virgin Gorda...

7 Nights


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Lowest from

$2,199

per person
(double occupancy)
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Mar 08, 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, Road Bay, Sopers Hole, Great Harbour, Virgin Gorda...

7 Nights


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Lowest from

$2,199

per person
(double occupancy)
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Mar 15, 2025

(Saturday)

7 Night James Beard Foundation Windward Ways and Tobago Cays Cruise

Star Pride
Windstar Cruises
Starts: Oranjestad, Aruba
Ends: Bridgetown, Barbados
Ports of Call:
Oranjestad, Willemstad (Curacao), Bonaire, Soufriere , Mayreau, Man of War Bay, Bridgetown
Theme Cruise

7 Nights


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Lowest from

$2,199

per person
(double occupancy)
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Mar 15, 2025

(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, Iles des Saintes, Basseterre...

7 Nights


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Lowest from

$2,199

per person
(double occupancy)
Learn More

Mar 22, 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, Road Bay, Sopers Hole, Great Harbour, Virgin Gorda...

7 Nights


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Lowest from

$2,199

per person
(double occupancy)
Learn More

Jan 04, 2025

(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, Iles des Saintes...

7 Nights


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Lowest from

$2,199

per person
(double occupancy)
Learn More

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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Lowest from

$2,199

per person
(double occupancy)
Learn More

Jan 11, 2025

(Saturday)

7 Night 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, Pigeon Island, Bridgetown

7 Nights


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Lowest from

$2,199

per person
(double occupancy)
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Jan 11, 2025

(Saturday)

7 Night Naturally Costa Rica Cruise

Wind Star
Windstar Cruises
4.2 based on 5 ratings
Starts: Puerto Caldera, Costa Rica
Ends: Puerto Caldera, Costa Rica
Ports of Call:
Puerto Caldera, Playa Flamingo, Corinto, San Juan del Sur, Playas del Coco, Herradura, Quepos...

7 Nights


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Lowest from

$2,199

per person
(double occupancy)
Learn More

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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Compare Favorites
Lowest from

$2,199

per person
(double occupancy)
Learn More

Jan 11, 2025

(Saturday)

7 Night Windward Ways and Tobago Cays Cruise

Star Pride
Windstar Cruises
Starts: Bridgetown, Barbados
Ends: Oranjestad, Aruba
Ports of Call:
Bridgetown, Man of War Bay, Mayreau, Soufriere , Willemstad (Curacao), Bonaire, Oranjestad

7 Nights


Add to Favorites
Compare Favorites
Lowest from

$2,199

per person
(double occupancy)
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