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Your Caribbean - Southern Results

Showing 41 - 60 Cruises

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Sail Date	Cruise Line	Ship	Destination	Departs	Length	Price	You Save	Discounts
11 reviews	Mar 14, 2026	Windstar	Wind Spirit	Caribbean	Bridgetown	Bridgetown	14 Nights	Anse Mitan \| Bequia \| Bridgetown \| Castries \| Kingstown \| Les Saintes \| Little Bay \| Mayreau \| Pigeon Island \| Roseau \| St. George's \| The Pitons	$4,099 Shipboard Credit Per Person ($100) View Cruise	Shipboard Credit Per Person ($100)
11 reviews	Mar 14, 2026	Windstar	Wind Spirit	Caribbean	Bridgetown	Bridgetown	7 Nights	Bequia \| Bridgetown \| Castries \| Kingstown \| Mayreau \| Pigeon Island \| St. George's \| The Pitons	$2,599 Shipboard Credit Per Person ($100) View Cruise	Shipboard Credit Per Person ($100)
11 reviews	Mar 21, 2026	Windstar	Wind Spirit	Caribbean	Bridgetown	Bridgetown	7 Nights	Anse Mitan \| Bridgetown \| Les Saintes \| Little Bay \| Pigeon Island \| Roseau	$2,599 Up To $300 Onboard Credit View Cruise	Onboard Credit!
10 reviews	Mar 15, 2025	Windstar	Wind Star	Caribbean - Southern	Colon	Bridgetown	11 Nights	Bridgetown \| Cartagena \| Colón \| Kralendijk \| Mayreau \| Oranjestad \| Santa Marta \| St. George's \| Willemstad	$3,299 Up To $500 Onboard Credit View Cruise	Onboard Credit!
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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	Nov 13, 2024	Windstar	Wind Spirit	Transatlantic	Lisbon	Bridgetown	14 Nights	Bridgetown \| Lisbon	$2,499 Shipboard Credit Per Person ($100) View Cruise	Shipboard Credit Per Person ($100)
11 reviews	Nov 04, 2025	Windstar	Wind Spirit	Transatlantic	Lisbon	Bridgetown	14 Nights	Bridgetown \| Lisbon	$2,499 Shipboard Credit Per Person ($100) View Cruise	Shipboard Credit Per Person ($100)
15 reviews	Jan 04, 2025	Windstar	Star Pride	Caribbean - Southern	Oranjestad	Bridgetown	7 Nights	Bridgetown \| Kralendijk \| Man-O-War Bay \| Mayreau \| Oranjestad \| Soufriere \| Willemstad	$2,499 Shipboard Credit Per Person ($100) View Cruise	Shipboard Credit Per Person ($100)
24 reviews	Feb 01, 2026	Windstar	Wind Surf	Caribbean	Oranjestad	Colon	8 Nights	Bocas del Toro \| Cartagena \| Colón \| Oranjestad \| Santa Marta	$3,199 Up To $500 Onboard Credit View Cruise	Onboard Credit!
24 reviews	Feb 01, 2026	Windstar	Wind Surf	Caribbean	Oranjestad	Cozumel	16 Nights	Belize City \| Bocas del Toro \| Cartagena \| Colón \| Costa Maya \| Cozumel \| Isla San Andres \| Oranjestad \| Roatan \| Santa Marta	$5,099 Up To $750 Onboard Credit View Cruise
24 reviews	Jan 18, 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	$4,499 Up To $500 Onboard Credit View Cruise	Onboard Credit!
24 reviews	Feb 22, 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 Up To $500 Onboard Credit View Cruise	Onboard Credit!
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	7 Nights	Basseterre \| Charlestown \| Gustavia \| Les Saintes \| Pigeon Island \| Roseau \| St. Maarten	$2,299 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)
24 reviews	Dec 14, 2025	Windstar	Wind Surf	Caribbean	Philipsburg	Philipsburg	7 Nights	Falmouth Harbour \| Gustavia \| Jost Van Dyke, Great Harbour \| Road Bay \| Soper's Hole \| St. Maarten \| Virgin Gorda / Prickly Pear	$2,399 Shipboard Credit Per Person ($100) View Cruise	Shipboard Credit Per Person ($100)
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	7 Nights	Basseterre \| Charlestown \| Gustavia \| Les Saintes \| Pigeon Island \| Roseau \| St. Maarten	$2,699 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	Dec 28, 2025	Windstar	Wind Surf	Caribbean	Philipsburg	Philipsburg	7 Nights	Falmouth Harbour \| Gustavia \| Jost Van Dyke, Great Harbour \| Road Bay \| Soper's Hole \| St. Maarten \| Virgin Gorda / Prickly Pear	$2,699 Up To $300 Onboard Credit View Cruise	Onboard Credit!

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