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Cruises from Philipsburg (St. Maarten) in January 2026


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26 Matched Sailings
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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, Little Bay, Gustavia St. Barts, Deshaies, Roseau...

7 Nights


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Lowest from

$2,299

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)
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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, Virgin Gorda...

7 Nights


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Lowest from

$3,299

per person
(double occupancy)
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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


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Lowest from

$3,499

per person
(double occupancy)
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Jan 18, 2026

(Sunday)

7 Night Philipsburg to San Juan Cruise

Seadream II
Sea Dream Yacht Club
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: San Juan, Puerto Rico
Ports of Call:
Philipsburg (St. Maarten), Falmouth Harbour, Charlestown, Terre de Haut, Saba, Gustavia St. Barts...

7 Nights


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Lowest from

$3,999

per person
(double occupancy)
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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


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Lowest from

$4,099

per person
(double occupancy)
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Jan 31, 2026

(Saturday)

7 Night Yachtsmans Caribbean Cruise

Seabourn Ovation
Seabourn Cruises
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Bridgetown, Barbados
Ports of Call:
Philipsburg (St. Maarten), Frenchman's Cay, Carambola Beach, Saint-Pierre Martinique France...
Special Promotions

7 Nights


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Lowest from

$4,299

per person
(double occupancy)
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Jan 17, 2026

(Saturday)

7 Night Yachtsmans Caribbean Cruise

Seabourn Ovation
Seabourn Cruises
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Bridgetown, Barbados
Ports of Call:
Philipsburg (St. Maarten), Frenchman's Cay, Carambola Beach, Saint-Pierre Martinique France...
Special Promotions

7 Nights


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Lowest from

$4,299

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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Jan 11, 2026

(Sunday)

14 Night Star Collector Antilles Adventures 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, Little Bay, Gustavia St. Barts, Deshaies, Roseau...

14 Nights


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Lowest from

$5,399

per person
(double occupancy)
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Jan 04, 2026

(Sunday)

14 Night Star Collector Leeward and Windward Caribbean Havens 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), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Virgin Gorda...

14 Nights


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Lowest from

$5,399

per person
(double occupancy)
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Jan 04, 2026

(Sunday)

21 Night Star Collector A Lesser Antilles Odyssey 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), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour, Virgin Gorda...

21 Nights


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Lowest from

$5,599

per person
(double occupancy)
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Jan 04, 2026

(Sunday)

7 Night Philipsburg to Philipsburg Cruise

Silver Shadow
Silversea Cruises
4.3 based on 19 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), St John's, St Thomas, Little Bay, Castries, Mayreau, Iles des Saintes...

7 Nights


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Lowest from

$6,100

per person
(double occupancy)
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Jan 11, 2026

(Sunday)

7 Night Philipsburg to Philipsburg Cruise

Silver Shadow
Silversea Cruises
4.3 based on 19 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), St John's, St Thomas, Little Bay, Castries, Mayreau, Iles des Saintes...

7 Nights


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Lowest from

$6,100

per person
(double occupancy)
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Jan 18, 2026

(Sunday)

7 Night Philipsburg to Bridgetown Cruise

Silver Shadow
Silversea Cruises
4.3 based on 19 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Bridgetown, Barbados
Ports of Call:
Philipsburg (St. Maarten), St John, Gustavia St. Barts, Roseau, St George's, Trois Ilets...

7 Nights


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Lowest from

$6,100

per person
(double occupancy)
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Jan 17, 2026

(Saturday)

14 Night Gems of the Caribbean Cruise

Seabourn Ovation
Seabourn Cruises
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Frenchman's Cay, Carambola Beach, Saint-Pierre Martinique France...
Special Promotions

14 Nights


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Lowest from

$7,499

per person
(double occupancy)
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Jan 04, 2026

(Sunday)

28 Night Star Collector The Best of the Windward and Leeward Isles Cruise

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

28 Nights


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Lowest from

$7,799

per person
(double occupancy)
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Jan 31, 2026

(Saturday)

14 Night Yachtsmans Island Jewels Cruise

Seabourn Ovation
Seabourn Cruises
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Bridgetown, Barbados
Ports of Call:
Philipsburg (St. Maarten), Frenchman's Cay, Carambola Beach, Saint-Pierre Martinique France...
Special Promotions

14 Nights


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Lowest from

$7,999

per person
(double occupancy)
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Jan 04, 2026

(Sunday)

55 Night Star Collector Grand Caribbean Adventure 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...

55 Nights


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Lowest from

$14,999

per person
(double occupancy)
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Jan 10, 2026

(Saturday)

7 Night Leeward Islands Cruise

Star Flyer
Star Clipper Cruises
3.6 based on 5 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), St John's, Cabrits, Terre de Haut, Deshaies, Falmouth Harbour...

7 Nights


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Jan 03, 2026

(Saturday)

7 Night Treasure Islands Cruise

Star Flyer
Star Clipper Cruises
3.6 based on 5 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Road Bay, White Bay, Sopers Hole, Cruising Sir Francis Drake Channel...

7 Nights


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Jan 17, 2026

(Saturday)

7 Night Treasure Islands Cruise

Star Flyer
Star Clipper Cruises
3.6 based on 5 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Road Bay, White Bay, Sopers Hole, Cruising Sir Francis Drake Channel...

7 Nights


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Jan 11, 2026

(Sunday)

14 Night Philipsburg to Bridgetown Cruise

Silver Shadow
Silversea Cruises
4.3 based on 19 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Bridgetown, Barbados
Ports of Call:
Philipsburg (St. Maarten), St John's, St Thomas, Little Bay, Castries, Mayreau, Iles des Saintes...

14 Nights


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Jan 31, 2026

(Saturday)

7 Night Treasure Islands Cruise

Star Flyer
Star Clipper Cruises
3.6 based on 5 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Road Bay, White Bay, Sopers Hole, Cruising Sir Francis Drake Channel...

7 Nights


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