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Showing 21 - 40 Cruises

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Sail Date	Cruise Line	Ship	Destination	Departs	Length	Price	You Save	Discounts
24 reviews	14 night Star Collector Voyages (Caribbean Explorations 14D PH1-PH1 (Feb 22 2025))	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	$4,399 Up To $500 Onboard Credit View Cruise Get FREE Quote		View Itinerary	Get FREE Quote
24 reviews	14 night Star Collector Voyages (Caribbean Explorations 14D PH1-PH1 (Mar 8 2025))	Mar 08, 2025	Windstar	Wind Surf	Caribbean - Eastern	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	$4,799 Shipboard Credit Per Person ($100) View Cruise Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
24 reviews	7 night Caribbean (Beach Fun & Sun: A Remote Caribbean Getaway 7D PH1-PH1 (Mar 8 2025))	Mar 08, 2025	Windstar	Wind Surf	Caribbean - Eastern	Philipsburg	Philipsburg	7 Nights	Falmouth Harbour \| Gustavia \| Jost Van Dyke, Great Harbour \| Road Bay \| Soper's Hole \| St. Maarten \| Virgin Gorda	$2,999 Shipboard Credit Per Person ($100) View Cruise Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
24 reviews	14 night Star Collector Voyages (Caribbean Explorations 14D PH1-PH1 (Mar 15 2025))	Mar 15, 2025	Windstar	Wind Surf	Caribbean - Eastern	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	$4,799 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	7 night Caribbean (Classic Caribbean 7D PH1-PH1 (Mar 15 2025))	Mar 15, 2025	Windstar	Wind Surf	Caribbean - Eastern	Philipsburg	Philipsburg	7 Nights	Basseterre \| Charlestown \| Gustavia \| Les Saintes \| Pigeon Island \| Roseau \| St. Maarten	$2,999 Up To $300 Onboard Credit Welcome Reception Exclusive Amenity Distinctive Host View Cruise Get FREE Quote	*Distinctive Voyage	View Itinerary	Get FREE Quote
24 reviews	7 night Caribbean (Beach Fun & Sun: A Remote Caribbean Getaway 7D PH1-PH1 (Mar 22 2025))	Mar 22, 2025	Windstar	Wind Surf	Caribbean - Eastern	Philipsburg	Philipsburg	7 Nights	Falmouth Harbour \| Gustavia \| Jost Van Dyke, Great Harbour \| Road Bay \| Soper's Hole \| St. Maarten \| Virgin Gorda	$2,999 Up To $300 Onboard Credit View Cruise Get FREE Quote	Onboard Credit!	View Itinerary	Get FREE Quote
24 reviews	8 night Cruise Tours (Portuguese Passages & Spanish Shorelines: A Cruise Tour 8D LIS-BCN (Apr 12 2025))	Apr 08, 2025	Windstar	Wind Surf	Caribbean	Lisbon	Barcelona	8 Nights	Almeria, Spain \| Barcelona \| Cádiz \| Cartagena \| Gibraltar \| Lisbon \| LISBON, Portugal \| Málaga \| Palma de Mallorca	$6,499 Up To $750 Onboard Credit View Cruise Get FREE Quote		View Itinerary	Get FREE Quote
24 reviews	8 night Mediterranean (Spanish Symphony 8D BCN-LIS (Jul 27 2025))	Jul 27, 2025	Windstar	Wind Surf	Mediterranean	Barcelona	Lisbon	8 Nights	Almeria, Spain \| Barcelona \| Cádiz \| Cartagena \| Gibraltar \| Lisbon \| Málaga \| Palma de Mallorca	$3,599 Up To $500 Onboard Credit View Cruise Get FREE Quote	Onboard Credit!	View Itinerary	Get FREE Quote
24 reviews	8 night Cruise Tours (Portuguese Passages & Spanish Shorelines: A Cruise Tour 8D LIS-BCN (Aug 4 2025))	Jul 31, 2025	Windstar	Wind Surf	Caribbean	Lisbon	Barcelona	8 Nights	Almeria, Spain \| Barcelona \| Cádiz \| Cartagena \| Gibraltar \| Lisbon \| LISBON, Portugal \| Málaga \| Palma de Mallorca	$5,699 Up To $750 Onboard Credit View Cruise Get FREE Quote		View Itinerary	Get FREE Quote
24 reviews	8 night Mediterranean (Spanish Symphony 8D BCN-LIS (Nov 10 2025))	Nov 10, 2025	Windstar	Wind Surf	Mediterranean	Barcelona	Lisbon	8 Nights	Almeria, Spain \| Barcelona \| Cádiz \| Cartagena \| Gibraltar \| Lisbon \| Málaga \| Palma de Mallorca	$3,199 Up To $500 Onboard Credit View Cruise Get FREE Quote	Onboard Credit!	View Itinerary	Get FREE Quote
24 reviews	19 night Star Collector Voyages (Hearty Ports & Rum Punches - A Transatlantic Crossing 19D LIS-PH1 (Nov 18 2025))	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	$3,599 Shipboard Credit Per Person ($100) View Cruise Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
24 reviews	12 night Star Collector Voyages (Ivory Beaches & Sapphire Seas of the Caribbean 12D PH1-PH1 (Dec 2 2025))	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	$3,399 Shipboard Credit Per Person ($100) View Cruise Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
24 reviews	5 night Caribbean (Barefoot Break in the British Virgin Islands 5D PH1-PH1 (Dec 2 2025))	Dec 02, 2025	Windstar	Wind Surf	Caribbean	Philipsburg	Philipsburg	5 Nights	Gustavia \| Jost Van Dyke, Great Harbour \| Soper's Hole \| St. Maarten \| Virgin Gorda / Prickly Pear	$1,999 Shipboard Credit Per Person ($100) View Cruise Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
24 reviews	7 night Caribbean (Classic Caribbean 7D PH1-PH1 (Dec 7 2025))	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 Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
24 reviews	14 night Star Collector Voyages (Caribbean Explorations 14D PH1-PH1 (Dec 7 2025))	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 Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
24 reviews	7 night Caribbean (Beach Fun & Sun: A Remote Caribbean Getaway 7D PH1-PH1 (Dec 14 2025))	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 Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
24 reviews	14 night Star Collector Voyages (Caribbean Explorations 14D PH1-PH1 (Dec 14 2025))	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 Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
24 reviews	7 night Caribbean (Classic Caribbean 7D PH1-PH1 (Dec 21 2025))	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 Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
24 reviews	14 night Star Collector Voyages (Caribbean Explorations 14D PH1-PH1 (Dec 21 2025))	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 Get FREE Quote	Shipboard Credit Per Person ($100)	View Itinerary	Get FREE Quote
24 reviews	7 night Caribbean (Beach Fun & Sun: A Remote Caribbean Getaway 7D PH1-PH1 (Dec 28 2025))	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 Get FREE Quote	Onboard Credit!	View Itinerary	Get FREE Quote

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Your Caribbean - All Results