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Cruises in January 2026


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34 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 18, 2026

(Sunday)

7 Night Jewels of the Windward Islands Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Bridgetown, Barbados
Ends: Bridgetown, Barbados
Ports of Call:
Bridgetown, Anse Mitan, Castries, Pigeon Island, Bequia, Mayreau, St George's, Bridgetown

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)
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Jan 25, 2026

(Sunday)

7 Night Windward Ways and Tobago Cays Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Bridgetown, Barbados
Ends: Oranjestad, Aruba
Ports of Call:
Bridgetown, Man of War Bay, Mayreau, Soufriere , Bonaire, Willemstad (Curacao), Oranjestad

7 Nights


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Lowest from

$2,699

per person
(double occupancy)
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Jan 08, 2026

(Thursday)

7 Night Dreams of Tahiti Cruise

Star Breeze
Windstar Cruises
4.2 based on 5 ratings
Starts: Papeete, French Polynesia
Ends: Papeete, French Polynesia
Ports of Call:
Papeete, Moorea, Raiatea, Motu Mahaea Tahaa Island French Polynesia France, Bora Bora, Huahine...

7 Nights


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Lowest from

$2,699

per person
(double occupancy)
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Feb 01, 2026

(Sunday)

8 Night In the Wake of the Spanish Armadas Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Oranjestad, Aruba
Ends: Colon, Panama
Ports of Call:
Oranjestad, Santa Marta, Cartagena, Bocas Del Toro, Colon

8 Nights


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Lowest from

$3,199

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 29, 2026

(Thursday)

10 Night Canary Islands Idyll Cruise

Wind Star
Windstar Cruises
4.2 based on 5 ratings
Starts: Santa Cruz de Tenerife, Spain
Ends: Santa Cruz de Tenerife, Spain
Ports of Call:
Santa Cruz de Tenerife, San Sebastian de la Gomera, Santa Cruz de la Palma, Madeira, Lanzarote...

10 Nights


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Lowest from

$3,499

per person
(double occupancy)
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Jan 19, 2026

(Monday)

10 Night Canary Islands Idyll Cruise

Wind Star
Windstar Cruises
4.2 based on 5 ratings
Starts: Santa Cruz de Tenerife, Spain
Ends: Santa Cruz de Tenerife, Spain
Ports of Call:
Santa Cruz de Tenerife, San Sebastian de la Gomera, Santa Cruz de la Palma, Madeira, Lanzarote...

10 Nights


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Lowest from

$3,499

per person
(double occupancy)
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Jan 09, 2026

(Friday)

10 Night Canary Islands Idyll Cruise

Wind Star
Windstar Cruises
4.2 based on 5 ratings
Starts: Santa Cruz de Tenerife, Spain
Ends: Santa Cruz de Tenerife, Spain
Ports of Call:
Santa Cruz de Tenerife, San Sebastian de la Gomera, Santa Cruz de la Palma, Madeira, Lanzarote...

10 Nights


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Lowest from

$3,899

per person
(double occupancy)
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Jan 18, 2026

(Sunday)

14 Night Star Collector Captivating Caribbean Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Bridgetown, Barbados
Ends: Oranjestad, Aruba
Ports of Call:
Bridgetown, Anse Mitan, Castries, Pigeon Island, Bequia, Mayreau, St George's, Bridgetown...

14 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 25, 2026

(Sunday)

15 Night Star Collector Windward Islands and Spanish New World Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Bridgetown, Barbados
Ends: Colon, Panama
Ports of Call:
Bridgetown, Man of War Bay, Mayreau, Soufriere , Bonaire, Willemstad (Curacao), Oranjestad...

15 Nights


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Lowest from

$4,699

per person
(double occupancy)
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Jan 07, 2026

(Wednesday)

11 Night Marvels of Ecuador Peru and the Panama Canal Cruise

Star Pride
Windstar Cruises
Starts: Callao, Peru
Ends: Colon, Panama
Ports of Call:
Callao, Salavery, Machala, Guayaquil, Manta, Cruising the Panama Canal, Colon

11 Nights


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Lowest from

$4,699

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 01, 2026

(Sunday)

16 Night Star Collector Natural History Meets Ancient Mystery Latin America and Beyond Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Oranjestad, Aruba
Ends: Cozumel, Mexico
Ports of Call:
Oranjestad, Santa Marta, Cartagena, Bocas Del Toro, Colon, Bocas Del Toro, San Andres Island...

16 Nights


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Lowest from

$5,099

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)

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 29, 2026

(Thursday)

7 Night Dreams of Tahiti Cruise

Star Breeze
Windstar Cruises
4.2 based on 5 ratings
Starts: Papeete, French Polynesia
Ends: Papeete, French Polynesia
Ports of Call:
Papeete, Moorea, Raiatea, Motu Mahaea Tahaa Island French Polynesia France, Bora Bora, Huahine...

7 Nights


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Lowest from

$8,169

per person
(double occupancy)
Learn More

Jan 29, 2026

(Thursday)

11 Night Marvels of Ecuador Peru and the Panama Canal Cruise

Star Pride
Windstar Cruises
Starts: Callao, Peru
Ends: Colon, Panama
Ports of Call:
Callao, Salavery, Machala, Guayaquil, Manta, Cruising the Panama Canal, Colon

11 Nights


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Lowest from

$8,399

per person
(double occupancy)
Learn More

Jan 18, 2026

(Sunday)

11 Night Marvels of Ecuador Peru and the Panama Canal Cruise

Star Pride
Windstar Cruises
Starts: Colon, Panama
Ends: Callao, Peru
Ports of Call:
Colon, Cruising the Panama Canal, Manta, Guayaquil, Machala, Salavery, Callao

11 Nights


Add to Favorites
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Lowest from

$8,399

per person
(double occupancy)
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