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Showing 61 - 80 Cruises

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Sail Date	Cruise Line	Ship	Destination	Departs	Length	Price	You Save	Discounts
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
24 reviews	7 night Caribbean (Windward Ways & Tobago Cays 7D BGI-ORJ (Jan 25 2026))	Jan 25, 2026	Windstar	Wind Surf	Caribbean	Bridgetown	Oranjestad	7 Nights	Bridgetown \| Kralendijk \| Man-O-War Bay \| Mayreau \| Oranjestad \| Soufriere \| Willemstad	$2,699 Up To $300 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
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24 reviews	8 night Caribbean (In the Wake of the Spanish Armadas 8D ORJ-ONX (Feb 1 2026))	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 Get FREE Quote	Onboard Credit!	View Itinerary	Get FREE Quote
24 reviews	16 night Star Collector Voyages (Natural History Meets Ancient Mystery: Latin America & Beyond 16D ORJ-CZM (Feb 1 2026))	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 Get FREE Quote		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	Onboard Credit!	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
24 reviews	19 night Star Collector Voyages (Caribbean Cultures: Latin America & the Greater Antilles 19D ONX-PH1 (Feb 9 2026))	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 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		View Itinerary	Get FREE Quote
24 reviews	11 night Caribbean (Stars of the Greater Antilles 11D CZM-PH1 (Feb 17 2026))	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 Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
24 reviews	18 night Star Collector Voyages (Deep Dive into the Blue: Underwater Worlds of the Caribbean 18D CZM-PH1 (Feb 17 2026))	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 Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
5 reviews	16 night Star Collector Voyages (*NEW Winter & Spain & Rivieras 16D CVV-BCN (Feb 20 2026))	Feb 20, 2026	Windstar	Star Legend	Caribbean	Rome	Barcelona	16 Nights	Barcelona \| Cartagena \| Genoa, Italy \| Gibraltar \| Livorno \| Málaga \| Nice \| Palma de Mallorca \| Rome \| Valencia	$5,299 Up To $750 Onboard Credit View Cruise Get FREE Quote	Suite!	View Itinerary	Get FREE Quote
11 reviews	14 night Star Collector Voyages (Leeward & Windward Caribbean Havens 14D PH1-BGI (Feb 21 2026))	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 Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
11 reviews	7 night Caribbean (Beach Fun & Sun: A Remote Caribbean Getaway 7D PH1-PH1 (Feb 21 2026))	Feb 21, 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 Shipboard Credit Per Person ($100) View Cruise Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
11 reviews	21 night Star Collector Voyages (A Lesser Antilles Odyssey 21D PH1-BGI (Feb 21 2026))	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 Get FREE Quote		View Itinerary	Get FREE Quote
5 reviews	16 night Star Collector Voyages (*NEW Winter & Spain & Rivieras 16D BCN-CVV (Feb 27 2026))	Feb 27, 2026	Windstar	Star Legend	Caribbean	Barcelona	Rome	16 Nights	Barcelona \| Cartagena \| Genoa, Italy \| Gibraltar \| Livorno \| Málaga \| Nice \| Palma de Mallorca \| Rome \| Valencia	$5,299 Up To $750 Onboard Credit View Cruise Get FREE Quote		View Itinerary	Get FREE Quote
11 reviews	7 night Caribbean (Lush & Lovely Islands of the Lesser Antilles 7D PH1-BGI (Feb 28 2026))	Feb 28, 2026	Windstar	Wind Spirit	Caribbean	Philipsburg	Bridgetown	7 Nights	Basseterre \| Bridgetown \| Gustavia \| Les Saintes \| Little Bay \| Pigeon Island \| Roseau \| St. Maarten	$2,399 Up To $250 Onboard Credit View Cruise Get FREE Quote		View Itinerary	Get FREE Quote
11 reviews	14 night Star Collector Voyages (Antilles Adventures 14D PH1-BGI (Feb 28 2026))	Feb 28, 2026	Windstar	Wind Spirit	Caribbean	Philipsburg	Bridgetown	14 Nights	Anse Mitan \| Basseterre \| Bridgetown \| Gustavia \| Les Saintes \| Little Bay \| Pigeon Island \| Roseau \| St. Maarten	$3,999 Up To $500 Onboard Credit View Cruise Get FREE Quote	Onboard Credit!	View Itinerary	Get FREE Quote
24 reviews	7 night Caribbean (Classic Caribbean 7D PH1-PH1 (Feb 28 2026))	Feb 28, 2026	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 Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote

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Your Caribbean - All Results