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Showing 41 - 60 Cruises

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Sail Date	Cruise Line	Ship	Destination	Departs	Length	Price	You Save	Discounts
24 reviews	Nov 18, 2025	Windstar	Wind Surf	Transatlantic	Lisbon	Philipsburg	19 Nights	Gustavia \| Jost Van Dyke, Great Harbour \| Lisbon \| Soper's Hole \| St. Maarten \| Virgin Gorda / Prickly Pear	$3,499 Shipboard Credit Per Person ($100) View Cruise	Shipboard Credit Per Person ($100)
15 reviews	Nov 30, 2025	Windstar	Star Pride	Caribbean	San Juan	San Juan	7 Nights	Basseterre \| Gustavia \| Jost Van Dyke, Great Harbour \| San Juan \| St. Maarten \| Virgin Gorda / Prickly Pear	$2,899 Up To $300 Onboard Credit View Cruise	Suite!
24 reviews	Dec 02, 2025	Windstar	Wind Surf	Caribbean	Philipsburg	Philipsburg	12 Nights	Basseterre \| Charlestown \| Gustavia \| Jost Van Dyke, Great Harbour \| Les Saintes \| Pigeon Island \| Roseau \| Soper's Hole \| St. Maarten \| Virgin Gorda / Prickly Pear	$3,299 Shipboard Credit Per Person ($100) View Cruise	Shipboard Credit Per Person ($100)
24 reviews	Dec 07, 2025	Windstar	Wind Surf	Caribbean	Philipsburg	Philipsburg	14 Nights	Basseterre \| Charlestown \| Falmouth Harbour \| Gustavia \| Jost Van Dyke, Great Harbour \| Les Saintes \| Pigeon Island \| Road Bay \| Roseau \| Soper's Hole \| St. Maarten \| Virgin Gorda / Prickly Pear	$3,699 Shipboard Credit Per Person ($100) View Cruise	Shipboard Credit Per Person ($100)
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15 reviews	Dec 07, 2025	Windstar	Star Pride	Caribbean	San Juan	Colon	6 Nights	Cartagena \| Colón \| San Blas \| San Juan \| Santo Domingo	$2,899 Up To $300 Onboard Credit View Cruise
24 reviews	Dec 14, 2025	Windstar	Wind Surf	Caribbean	Philipsburg	Philipsburg	14 Nights	Basseterre \| Charlestown \| Falmouth Harbour \| Gustavia \| Jost Van Dyke, Great Harbour \| Les Saintes \| Pigeon Island \| Road Bay \| Roseau \| Soper's Hole \| St. Maarten \| Virgin Gorda / Prickly Pear	$3,999 Shipboard Credit Per Person ($100) View Cruise	Shipboard Credit Per Person ($100)
24 reviews	Dec 21, 2025	Windstar	Wind Surf	Caribbean	Philipsburg	Philipsburg	14 Nights	Basseterre \| Charlestown \| Falmouth Harbour \| Gustavia \| Jost Van Dyke, Great Harbour \| Les Saintes \| Pigeon Island \| Road Bay \| Roseau \| Soper's Hole \| St. Maarten \| Virgin Gorda / Prickly Pear	$4,299 Shipboard Credit Per Person ($100) View Cruise	Shipboard Credit Per Person ($100)
24 reviews	Jan 04, 2026	Windstar	Wind Surf	Caribbean	Philipsburg	Bridgetown	14 Nights	Basseterre \| Bridgetown \| Deshaies \| Falmouth Harbour \| Gustavia \| Jost Van Dyke, Great Harbour \| Little Bay \| Pigeon Island \| Road Bay \| Roseau \| Soper's Hole \| St. Maarten \| Virgin Gorda / Prickly Pear	$3,799 Shipboard Credit Per Person ($100) View Cruise	Shipboard Credit Per Person ($100)
24 reviews	Jan 04, 2026	Windstar	Wind Surf	Caribbean	Philipsburg	Bridgetown	21 Nights	Anse Mitan \| Basseterre \| Bequia \| Bridgetown \| Castries \| Deshaies \| Falmouth Harbour \| Gustavia \| Jost Van Dyke, Great Harbour \| Little Bay \| Mayreau \| Pigeon Island \| Road Bay \| Roseau \| Soper's Hole \| St. George's \| St. Maarten \| Virgin Gorda / Prickly Pear	$5,999 Up To $750 Onboard Credit View Cruise
24 reviews	Jan 04, 2026	Windstar	Wind Surf	Caribbean	Philipsburg	Philipsburg	55 Nights	Anse Mitan \| Basseterre \| Belize City \| Bequia \| Bocas del Toro \| Bridgetown \| Cartagena \| Castries \| Cayman Brac \| Colón \| Costa Maya \| Cozumel \| Deshaies \| Falmouth Harbour \| Grand Cayman \| Gustavia \| Isla San Andres \| Jost Van Dyke, Great Harbour \| Kralendijk \| La Romana \| Little Bay \| Man-O-War Bay \| Mayreau \| Oranjestad \| Pigeon Island \| Port Antonio \| Road Bay \| Roatan \| Roseau \| Santa Marta \| Santo Domingo \| Soper's Hole \| Soufriere \| St. George's \| St. Maarten \| Virgin Gorda / Prickly Pear \| Willemstad	$15,599 Up To $1000 Onboard Credit View Cruise
24 reviews	Jan 04, 2026	Windstar	Wind Surf	Caribbean	Philipsburg	Oranjestad	28 Nights	Anse Mitan \| Basseterre \| Bequia \| Bridgetown \| Castries \| Deshaies \| Falmouth Harbour \| Gustavia \| Jost Van Dyke, Great Harbour \| Kralendijk \| Little Bay \| Man-O-War Bay \| Mayreau \| Oranjestad \| Pigeon Island \| Road Bay \| Roseau \| Soper's Hole \| Soufriere \| St. George's \| St. Maarten \| Virgin Gorda / Prickly Pear \| Willemstad	$7,899 Up To $1000 Onboard Credit View Cruise
11 reviews	Jan 14, 2026	Windstar	Wind Spirit	Caribbean	Philipsburg	Philipsburg	17 Nights	Anse Mitan \| Bequia \| Castries \| Falmouth Harbour \| Gustavia \| Jost Van Dyke, Great Harbour \| Les Saintes \| Little Bay \| Mayreau \| Road Bay \| Roseau \| Soper's Hole \| St. George's \| St. Maarten \| Virgin Gorda / Prickly Pear	$4,799 Shipboard Credit Per Person ($100) View Cruise	Shipboard Credit Per Person ($100)
11 reviews	Jan 31, 2026	Windstar	Wind Spirit	Caribbean	Philipsburg	Philipsburg	14 Nights	Basseterre \| Charlestown \| Falmouth Harbour \| Gustavia \| Jost Van Dyke, Great Harbour \| Les Saintes \| Pigeon Island \| Road Bay \| Roseau \| Soper's Hole \| St. Maarten \| Virgin Gorda / Prickly Pear	$4,099 Shipboard Credit Per Person ($100) View Cruise	Shipboard Credit Per Person ($100)
11 reviews	Feb 07, 2026	Windstar	Wind Spirit	Caribbean	Philipsburg	Philipsburg	14 Nights	Basseterre \| Charlestown \| Falmouth Harbour \| Gustavia \| Jost Van Dyke, Great Harbour \| Les Saintes \| Pigeon Island \| Road Bay \| Roseau \| Soper's Hole \| St. Maarten \| Virgin Gorda / Prickly Pear	$4,099 Up To $500 Onboard Credit View Cruise	Onboard Credit!
24 reviews	Feb 09, 2026	Windstar	Wind Surf	Caribbean	Colon	Philipsburg	19 Nights	Belize City \| Bocas del Toro \| Cayman Brac \| Colón \| Costa Maya \| Cozumel \| Grand Cayman \| Isla San Andres \| Jost Van Dyke, Great Harbour \| La Romana \| Port Antonio \| Roatan \| Santo Domingo \| St. Maarten \| Virgin Gorda / Prickly Pear	$5,599 Up To $750 Onboard Credit View Cruise	Onboard Credit!
24 reviews	Feb 17, 2026	Windstar	Wind Surf	Caribbean	Cozumel	Philipsburg	11 Nights	Cayman Brac \| Cozumel \| Grand Cayman \| Jost Van Dyke, Great Harbour \| La Romana \| Port Antonio \| Santo Domingo \| St. Maarten \| Virgin Gorda / Prickly Pear	$3,799 Shipboard Credit Per Person ($100) View Cruise	Shipboard Credit Per Person ($100)
24 reviews	Feb 17, 2026	Windstar	Wind Surf	Caribbean	Cozumel	Philipsburg	18 Nights	Basseterre \| Cayman Brac \| Charlestown \| Cozumel \| Grand Cayman \| Gustavia \| Jost Van Dyke, Great Harbour \| La Romana \| Les Saintes \| Pigeon Island \| Port Antonio \| Roseau \| Santo Domingo \| St. Maarten \| Virgin Gorda / Prickly Pear	$4,799 Shipboard Credit Per Person ($100) View Cruise	Shipboard Credit Per Person ($100)
11 reviews	Feb 21, 2026	Windstar	Wind Spirit	Caribbean	Philipsburg	Bridgetown	14 Nights	Basseterre \| Bridgetown \| Falmouth Harbour \| Gustavia \| Jost Van Dyke, Great Harbour \| Les Saintes \| Little Bay \| Pigeon Island \| Road Bay \| Roseau \| Soper's Hole \| St. Maarten \| Virgin Gorda / Prickly Pear	$3,999 Shipboard Credit Per Person ($100) View Cruise	Shipboard Credit Per Person ($100)
11 reviews	Feb 21, 2026	Windstar	Wind Spirit	Caribbean	Philipsburg	Bridgetown	21 Nights	Anse Mitan \| Basseterre \| Bridgetown \| Falmouth Harbour \| Gustavia \| Jost Van Dyke, Great Harbour \| Les Saintes \| Little Bay \| Pigeon Island \| Road Bay \| Roseau \| Soper's Hole \| St. Maarten \| Virgin Gorda / Prickly Pear	$6,099 Up To $750 Onboard Credit View Cruise	Onboard Credit!
24 reviews	Feb 28, 2026	Windstar	Wind Surf	Caribbean	Philipsburg	Philipsburg	14 Nights	Basseterre \| Charlestown \| Falmouth Harbour \| Gustavia \| Jost Van Dyke, Great Harbour \| Les Saintes \| Pigeon Island \| Road Bay \| Roseau \| Soper's Hole \| St. Maarten \| Virgin Gorda / Prickly Pear	$3,699 Shipboard Credit Per Person ($100) View Cruise	Shipboard Credit Per Person ($100)

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