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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	Dec 21, 2024	Windstar	Wind Spirit	Caribbean - Southern	Bridgetown	Bridgetown	7 Nights	Bequia \| Bridgetown \| Castries \| Kingstown \| Mayreau \| Pigeon Island \| St. George's \| The Pitons	$2,899 Shipboard Credit Per Person ($100) View Cruise	Shipboard Credit Per Person ($100)
15 reviews	Oct 26, 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!
15 reviews	Nov 02, 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
15 reviews	Nov 16, 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!
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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
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
15 reviews	Nov 09, 2025	Windstar	Star Pride	Caribbean	San Juan	San Juan	7 Nights	Bequia \| Les Saintes \| Marigot, St. Martin \| Pigeon Island \| San Juan \| St. George's	$2,999 Up To $300 Onboard Credit View Cruise	Suite!
15 reviews	Nov 23, 2025	Windstar	Star Pride	Caribbean	San Juan	San Juan	7 Nights	Bequia \| Les Saintes \| Marigot, St. Martin \| Pigeon Island \| San Juan \| St. George's	$2,999 Up To $300 Onboard Credit View Cruise	Suite!
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!
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
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)
11 reviews	Nov 18, 2025	Windstar	Wind Spirit	Caribbean - Southern	Bridgetown	Colon	11 Nights	Bequia \| Bridgetown \| Cartagena \| Colón \| Kralendijk \| Mayreau \| Oranjestad \| St. George's \| Willemstad	$3,499 Shipboard Credit Per Person ($100) View Cruise	Shipboard Credit Per Person ($100)
11 reviews	Jan 14, 2026	Windstar	Wind Spirit	Caribbean	Philipsburg	Philipsburg	10 Nights	Anse Mitan \| Bequia \| Castries \| Gustavia \| Les Saintes \| Little Bay \| Mayreau \| Roseau \| St. George's \| St. Maarten	$3,499 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	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)
24 reviews	Mar 14, 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 Up To $500 Onboard Credit View Cruise	Onboard Credit!
24 reviews	Mar 21, 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 Up To $500 Onboard Credit View Cruise
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)
10 reviews	Nov 19, 2024	Windstar	Wind Star	Caribbean - Southern	Bridgetown	Colon	11 Nights	Bequia \| Bridgetown \| Cartagena \| Colón \| Kralendijk \| Mayreau \| Oranjestad \| St. George's \| Willemstad	$3,999 Shipboard Credit Per Person ($100) View Cruise	Shipboard Credit Per Person ($100)
11 reviews	Dec 07, 2024	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	$3,999 Shipboard Credit Per Person ($100) View Cruise	Shipboard Credit Per Person ($100)

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Your Caribbean - Southern Results