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Jan 18, 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 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 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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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 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)
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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 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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Dec 14, 2024

(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)
Learn More

Dec 07, 2024

(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)

15 Night Ocean Crossing Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Bridgetown, Barbados
Ends: Lisbon, Portugal
Ports of Call:
Bridgetown, Lisbon

15 Nights


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Lowest from

$2,399

per person
(double occupancy)
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Feb 28, 2026

(Saturday)

7 Night Lush and Lovely Islands of the Lesser Antilles Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Bridgetown, Barbados
Ports of Call:
Philipsburg (St. Maarten), Basseterre, Gustavia St. Barts, Little Bay, Iles des Saintes, Roseau...

7 Nights


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Lowest from

$2,399

per person
(double occupancy)
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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), Sopers Hole, Great Harbour, Virgin Gorda, Gustavia St. Barts, Road Bay...

7 Nights


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Lowest from

$2,499

per person
(double occupancy)
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Jan 31, 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), Sopers Hole, Great Harbour, Virgin Gorda, Gustavia St. Barts, Road Bay...

7 Nights


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Lowest from

$2,499

per person
(double occupancy)
Learn More

Nov 04, 2025

(Tuesday)

14 Night Ocean Crossing Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Lisbon, Portugal
Ends: Bridgetown, Barbados
Ports of Call:
Lisbon, Bridgetown

14 Nights


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Lowest from

$2,499

per person
(double occupancy)
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Nov 13, 2024

(Wednesday)

14 Night Ocean Crossing Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Lisbon, Portugal
Ends: Bridgetown, Barbados
Ports of Call:
Lisbon, Bridgetown

14 Nights


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Lowest from

$2,499

per person
(double occupancy)
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Dec 21, 2024

(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

$2,599

per person
(double occupancy)
Learn More

Mar 07, 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, Little Bay, Iles des Saintes, Roseau, Anse Mitan, Pigeon Island, Bridgetown

7 Nights


Add to Favorites
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Lowest from

$2,599

per person
(double occupancy)
Learn More

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, Little Bay, Iles des Saintes, Roseau, Anse Mitan, Pigeon Island, Bridgetown

7 Nights


Add to Favorites
Compare Favorites
Lowest from

$2,599

per person
(double occupancy)
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), Sopers Hole, Great Harbour, Virgin Gorda, Gustavia St. Barts, Road Bay...

7 Nights


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Lowest from

$2,599

per person
(double occupancy)
Learn More

Feb 07, 2026

(Saturday)

7 Night Classic Caribbean 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), Charlestown, Roseau, Pigeon Island, Iles des Saintes...

7 Nights


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Lowest from

$2,599

per person
(double occupancy)
Learn More

Dec 28, 2024

(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, Castries, Anse Mitan, Pigeon Island, Bridgetown

7 Nights


Add to Favorites
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Lowest from

$2,599

per person
(double occupancy)
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), Sopers Hole, Great Harbour, Virgin Gorda, Gustavia St. Barts, Road Bay...

7 Nights


Add to Favorites
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Lowest from

$2,599

per person
(double occupancy)
Learn More

Mar 14, 2026

(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, Pigeon Island, Castries, The Pitons, Kingstown, Mayreau, St George's, Bequia, Bridgetown

7 Nights


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Lowest from

$2,599

per person
(double occupancy)
Learn More

Nov 27, 2024

(Wednesday)

10 Night Hidden Treasures of the Lesser Antilles Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Bridgetown, Barbados
Ends: Bridgetown, Barbados
Ports of Call:
Bridgetown, Basseterre, Gustavia St. Barts, Sopers Hole, Great Harbour, Virgin Gorda...

10 Nights


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Lowest from

$2,899

per person
(double occupancy)
Learn More

Nov 18, 2025

(Tuesday)

11 Night Colombian and Southern Caribbean Coastlines Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Bridgetown, Barbados
Ends: Colon, Panama
Ports of Call:
Bridgetown, Bequia, Mayreau, St George's, Bonaire, Willemstad (Curacao), Oranjestad, Cartagena...

11 Nights


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Lowest from

$3,199

per person
(double occupancy)
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Jan 25, 2025

(Saturday)

14 Night Star Collector Windward Treasures An Antilles Odyssey 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...

14 Nights


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Lowest from

$3,499

per person
(double occupancy)
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Feb 08, 2025

(Saturday)

14 Night Star Collector Windward Treasures An Antilles Odyssey 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...

14 Nights


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Lowest from

$3,499

per person
(double occupancy)
Learn More

Jan 14, 2026

(Wednesday)

10 Night Blue Waters of the Leeward Islands 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), Basseterre, Roseau, Castries, Bequia, St George's, Mayreau, Anse Mitan...

10 Nights


Add to Favorites
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Lowest from

$3,499

per person
(double occupancy)
Learn More

Jan 11, 2025

(Saturday)

14 Night Star Collector Windward Treasures An Antilles Odyssey 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...

14 Nights


Add to Favorites
Compare Favorites
Lowest from

$3,499

per person
(double occupancy)
Learn More

Jan 04, 2025

(Saturday)

14 Night Star Collector Windward Treasures An Antilles Odyssey 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...

14 Nights


Add to Favorites
Compare Favorites
Lowest from

$3,499

per person
(double occupancy)
Learn More

Dec 07, 2024

(Saturday)

14 Night Star Collector Windward Treasures An Antilles Odyssey 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...

14 Nights


Add to Favorites
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Lowest from

$3,499

per person
(double occupancy)
Learn More

Feb 01, 2025

(Saturday)

14 Night Star Collector Windward Treasures An Antilles Odyssey 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...

14 Nights


Add to Favorites
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Lowest from

$3,499

per person
(double occupancy)
Learn More

Jan 18, 2025

(Saturday)

14 Night Star Collector Windward Treasures An Antilles Odyssey 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...

14 Nights


Add to Favorites
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Lowest from

$3,499

per person
(double occupancy)
Learn More

Dec 28, 2024

(Saturday)

14 Night Star Collector Windward Treasures An Antilles Odyssey 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, Castries, Anse Mitan, Pigeon Island, Bridgetown, Pigeon Island...

14 Nights


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Lowest from

$3,799

per person
(double occupancy)
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Dec 14, 2024

(Saturday)

14 Night Star Collector Windward Treasures An Antilles Odyssey 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...

14 Nights


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Lowest from

$3,799

per person
(double occupancy)
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Feb 21, 2026

(Saturday)

14 Night Star Collector Leeward and Windward Caribbean Havens Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Bridgetown, Barbados
Ports of Call:
Philipsburg (St. Maarten), Sopers Hole, Great Harbour, Virgin Gorda, Gustavia St. Barts, Road Bay...

14 Nights


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Lowest from

$3,999

per person
(double occupancy)
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Feb 28, 2026

(Saturday)

14 Night Star Collector Antilles Adventures Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Bridgetown, Barbados
Ports of Call:
Philipsburg (St. Maarten), Basseterre, Gustavia St. Barts, Little Bay, Iles des Saintes, Roseau...

14 Nights


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Lowest from

$3,999

per person
(double occupancy)
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Feb 07, 2026

(Saturday)

14 Night Star Collector Caribbean Explorations 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), Charlestown, Roseau, Pigeon Island, Iles des Saintes...

14 Nights


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Lowest from

$4,099

per person
(double occupancy)
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Mar 07, 2026

(Saturday)

14 Night Star Collector Blue Seas 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, Little Bay, Iles des Saintes, Roseau, Anse Mitan, Pigeon Island, Bridgetown...

14 Nights


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Lowest from

$4,099

per person
(double occupancy)
Learn More

Dec 21, 2024

(Saturday)

14 Night Star Collector Windward Treasures An Antilles Odyssey 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...

14 Nights


Add to Favorites
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Lowest from

$4,099

per person
(double occupancy)
Learn More

Jan 31, 2026

(Saturday)

14 Night Star Collector Caribbean Explorations 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), Sopers Hole, Great Harbour, Virgin Gorda, Gustavia St. Barts, Road Bay...

14 Nights


Add to Favorites
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Lowest from

$4,099

per person
(double occupancy)
Learn More

Mar 14, 2026

(Saturday)

14 Night Star Collector Blue Seas 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...

14 Nights


Add to Favorites
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Lowest from

$4,099

per person
(double occupancy)
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Jan 14, 2026

(Wednesday)

17 Night Star Collector Hidden Gems of the Caribbean 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), Basseterre, Roseau, Castries, Bequia, St George's, Mayreau, Anse Mitan...

17 Nights


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Lowest from

$4,799

per person
(double occupancy)
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Feb 21, 2026

(Saturday)

21 Night Star Collector A Lesser Antilles Odyssey Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Bridgetown, Barbados
Ports of Call:
Philipsburg (St. Maarten), Sopers Hole, Great Harbour, Virgin Gorda, Gustavia St. Barts, Road Bay...

21 Nights


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Lowest from

$6,099

per person
(double occupancy)
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Nov 18, 2025

(Tuesday)

18 Night Star Collector Reefs and Rainforests the Caribbean Colombia Panama and Costa Rica via the Panama Canal Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Bridgetown, Barbados
Ends: Puerto Caldera, Costa Rica
Ports of Call:
Bridgetown, Bequia, Mayreau, St George's, Bonaire, Willemstad (Curacao), Oranjestad, Cartagena...

18 Nights


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Lowest from

$6,199

per person
(double occupancy)
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Feb 21, 2026

(Saturday)

28 Night Star Collector Grand Caribbean Adventure Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Bridgetown, Barbados
Ports of Call:
Philipsburg (St. Maarten), Sopers Hole, Great Harbour, Virgin Gorda, Gustavia St. Barts, Road Bay...

28 Nights


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Lowest from

$8,099

per person
(double occupancy)
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Dec 20, 2025

(Saturday)

18 Night Star Collector Reefs and Rainforests the Caribbean Colombia Panama and Costa Rica via the Panama Canal Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Puerto Caldera, Costa Rica
Ends: Bridgetown, Barbados
Ports of Call:
Puerto Caldera, Quepos, Golfo Dulce, Isla Parida, Fuerte Amador, Cruising the Panama Canal, Colon...

18 Nights


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Dec 27, 2025

(Saturday)

11 Night Colombian and Southern Caribbean Coastlines Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Colon, Panama
Ends: Bridgetown, Barbados
Ports of Call:
Colon, Cartagena, Santa Marta, Oranjestad, Willemstad (Curacao), Bonaire, St George's, Mayreau...

11 Nights


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Dec 27, 2025

(Saturday)

18 Night Star Collector Lesser Antilles and Colombian Hideaways Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Colon, Panama
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Colon, Cartagena, Santa Marta, Oranjestad, Willemstad (Curacao), Bonaire, St George's, Mayreau...

18 Nights


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Jan 07, 2026

(Wednesday)

7 Night Lush and Lovely Islands of the Lesser Antilles Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Bridgetown, Barbados
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Bridgetown, Roseau, Pigeon Island, Iles des Saintes, Little Bay, Gustavia St. Barts, Basseterre...

7 Nights


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