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Showing 21 - 40 Cruises

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Sail Date	Cruise Line	Ship	Destination	Departs	Length	Price	You Save	Discounts
11 reviews	7 night Caribbean (Windward Island Delights 7D BGI-BGI (Feb 8 2025))	Feb 08, 2025	Windstar	Wind Spirit	Caribbean	Bridgetown	Bridgetown	7 Nights	Anse Mitan \| Bridgetown \| Les Saintes \| Little Bay \| Pigeon Island \| Roseau	$2,999 Shipboard Credit Per Person ($100) View Cruise Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
11 reviews	7 night Caribbean (Jewels of the Windward Islands 7D BGI-BGI (Feb 15 2025))	Feb 15, 2025	Windstar	Wind Spirit	Caribbean - Southern	Bridgetown	Bridgetown	7 Nights	Bequia \| Bridgetown \| Castries \| Kingstown \| Mayreau \| Pigeon Island \| St. George's \| The Pitons	$2,999 Shipboard Credit Per Person ($100) View Cruise Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
11 reviews	18 night Star Collector Voyages (Reefs & Rainforests: The Caribbean, Colombia, Panama & Costa Rica via the Panama Canal 18D BGI-PTC (Nov 18 2025))	Nov 18, 2025	Windstar	Wind Spirit	Caribbean	Bridgetown	Puerto Caldera	18 Nights	Balboa / Fuerte Amador \| Bequia \| Bridgetown \| Cartagena \| Colón \| Golfo Dulce \| Isla Parida \| Kralendijk \| Mayreau \| Oranjestad \| Panama Canal \| Puerto Caldera \| Quepos \| St. George's \| Willemstad	$5,499 Shipboard Credit Per Person ($100) View Cruise Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
11 reviews	11 night Caribbean (Colombian & Southern Caribbean Coastlines 11D BGI-ONX (Nov 18 2025))	Nov 18, 2025	Windstar	Wind Spirit	Caribbean - Southern	Bridgetown	Colon	11 Nights	Bequia \| Bridgetown \| Cartagena \| Colón \| Kralendijk \| Mayreau \| Oranjestad \| St. George's \| Willemstad	$3,599 Shipboard Credit Per Person ($100) View Cruise Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
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11 reviews	7 night Caribbean (Jewels of Windward Islands 7D BGI-BGI (Mar 7 2026))	Mar 07, 2026	Windstar	Wind Spirit	Caribbean	Bridgetown	Bridgetown	7 Nights	Anse Mitan \| Bridgetown \| Les Saintes \| Little Bay \| Pigeon Island \| Roseau	$2,599 Shipboard Credit Per Person ($100) View Cruise Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
11 reviews	14 night Star Collector Voyages (Captivating Caribbean 14D BGI-BGI (Mar 7 2026))	Mar 07, 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 Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
11 reviews	14 night Star Collector Voyages (Captivating Caribbean 14D BGI-BGI (Mar 14 2026))	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 Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
11 reviews	7 night Caribbean (Windward Island Delights 7D BGI-BGI (Mar 14 2026))	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 Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
11 reviews	7 night Caribbean (Jewels of Windward Islands 7D BGI-BGI (Mar 21 2026))	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 Get FREE Quote	Onboard Credit!	View Itinerary	Get FREE Quote
11 reviews	14 night Ocean Crossings	Nov 13, 2024	Windstar	Wind Spirit	Transatlantic	Lisbon	Bridgetown	14 Nights	Bridgetown \| Lisbon	$2,799 Shipboard Credit Per Person ($100) View Cruise Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
11 reviews	9 night Mediterranean (Treasures of Southern Spain & Morocco 9D LIS-BCN (Apr 6 2025))	Apr 06, 2025	Windstar	Wind Spirit	Mediterranean	Lisbon	Barcelona	9 Nights	Barcelona \| Cartagena \| Lisbon \| Málaga \| Palma de Mallorca \| Tangier \| Tarragona \| Valencia	$3,299 Up To $500 Onboard Credit View Cruise Get FREE Quote		View Itinerary	Get FREE Quote
11 reviews	14 night Ocean Crossings	Nov 04, 2025	Windstar	Wind Spirit	Transatlantic	Lisbon	Bridgetown	14 Nights	Bridgetown \| Lisbon	$2,499 Shipboard Credit Per Person ($100) View Cruise Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
11 reviews	17 night Star Collector Voyages (A Leeward Island Loop 17D PH1-PH1 (Jan 14 2026))	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 Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
11 reviews	10 night Caribbean (Blue Waters of the Leeward Islands PH1-PH1 (Jan 14 2026))	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 Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
11 reviews	7 night Caribbean (Classic Caribbean 7D PH1-PH1 (Jan 24 2026))	Jan 24, 2026	Windstar	Wind Spirit	Caribbean	Philipsburg	Philipsburg	7 Nights	Falmouth Harbour \| Gustavia \| Jost Van Dyke, Great Harbour \| Road Bay \| Soper's Hole \| St. Maarten \| Virgin Gorda / Prickly Pear	$2,499 Up To $250 Onboard Credit View Cruise Get FREE Quote		View Itinerary	Get FREE Quote
11 reviews	7 night Caribbean (Beach Fun & Sun: A Remote Caribbean Getaway 7D PH1-PH1 (Jan 31 2026))	Jan 31, 2026	Windstar	Wind Spirit	Caribbean	Philipsburg	Philipsburg	7 Nights	Falmouth Harbour \| Gustavia \| Jost Van Dyke, Great Harbour \| Road Bay \| Soper's Hole \| St. Maarten \| Virgin Gorda / Prickly Pear	$2,499 Shipboard Credit Per Person ($100) View Cruise Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
11 reviews	14 night Star Collector Voyages (Caribbean Explorations 14D PH1-PH1 (Jan 31 2026))	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 Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
11 reviews	14 night Star Collector Voyages (Caribbean Explorations 14D PH1-PH1 (Feb 7 2026))	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 Get FREE Quote		View Itinerary	Get FREE Quote
11 reviews	7 night Caribbean (Classic Caribbean 7D PH1-PH1 (Feb 7 2026))	Feb 07, 2026	Windstar	Wind Spirit	Caribbean	Philipsburg	Philipsburg	7 Nights	Basseterre \| Charlestown \| Gustavia \| Les Saintes \| Pigeon Island \| Roseau \| St. Maarten	$2,599 Up To $300 Onboard Credit View Cruise Get FREE Quote	Onboard Credit!	View Itinerary	Get FREE Quote
11 reviews	7 night Caribbean (Beach Fun & Sun: A Remote Caribbean Getaway 7D PH1-PH1 (Feb 14 2026))	Feb 14, 2026	Windstar	Wind Spirit	Caribbean	Philipsburg	Philipsburg	7 Nights	Falmouth Harbour \| Gustavia \| Jost Van Dyke, Great Harbour \| Road Bay \| Soper's Hole \| St. Maarten \| Virgin Gorda / Prickly Pear	$2,599 Up To $300 Onboard Credit View Cruise Get FREE Quote	Onboard Credit!	View Itinerary	Get FREE Quote

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Your Caribbean - All Results