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Your Caribbean - Western Results

Showing 21 - 40 Cruises

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Sail Date	Cruise Line	Ship	Destination	Departs	Length	Price	You Save	Discounts
24 reviews	Jan 18, 2026	Windstar	Wind Surf	Caribbean	Bridgetown	Oranjestad	14 Nights	Anse Mitan \| Bequia \| Bridgetown \| Castries \| Kralendijk \| Man-O-War Bay \| Mayreau \| Oranjestad \| Pigeon Island \| Soufriere \| St. George's \| Willemstad	$4,099 Up To $500 Onboard Credit View Cruise
24 reviews	Jan 25, 2026	Windstar	Wind Surf	World Cruise	Bridgetown	Colon	15 Nights	Bocas del Toro \| Bridgetown \| Cartagena \| Colón \| Kralendijk \| Man-O-War Bay \| Mayreau \| Oranjestad \| Santa Marta \| Soufriere \| Willemstad	$4,699 Up To $500 Onboard Credit View Cruise	Onboard Credit!
11 reviews	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	Shipboard Credit Per Person ($100)
11 reviews	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	Shipboard Credit Per Person ($100)
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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 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	Dec 14, 2024	Windstar	Wind Star	Caribbean	Colon	Puerto Caldera	11 Nights	Balboa / Fuerte Amador \| Colón \| Golfo Dulce \| Isla Parida \| La Fortuna (Arenal), Costa Rica \| Panama Canal \| Puerto Caldera \| Quepos \| Santa Elena (Monteverde)	$5,199 Up To $750 Onboard Credit View Cruise	Onboard Credit!
11 reviews	Nov 29, 2025	Windstar	Wind Spirit	Caribbean	Colon	Puerto Caldera	11 Nights	Balboa / Fuerte Amador \| Colón \| Golfo Dulce \| Isla Parida \| La Fortuna (Arenal), Costa Rica \| Panama Canal \| Puerto Caldera \| Quepos \| Santa Elena (Monteverde)	$5,399 Shipboard Credit Per Person ($100) View Cruise	Shipboard Credit Per Person ($100)
15 reviews	Dec 13, 2025	Windstar	Star Pride	Caribbean	Colon	Puerto Caldera	11 Nights	Balboa / Fuerte Amador \| Colón \| Golfo Dulce \| Isla Parida \| La Fortuna (Arenal), Costa Rica \| Panama Canal \| Puerto Caldera \| Quepos \| Santa Elena (Monteverde)	$4,899 Shipboard Credit Per Person ($100) View Cruise	Shipboard Credit Per Person ($100)
24 reviews	Feb 09, 2026	Windstar	Wind Surf	Mexico	Colon	Cozumel	8 Nights	Belize City \| Bocas del Toro \| Colón \| Costa Maya \| Cozumel \| Isla San Andres \| Roatan	$3,199 Up To $500 Onboard Credit View Cruise	Onboard Credit!
24 reviews	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	Onboard Credit!
15 reviews	Feb 09, 2026	Windstar	Star Pride	Caribbean	Colon	Puerto Caldera	11 Nights	Balboa / Fuerte Amador \| Colón \| Golfo Dulce \| Isla Parida \| La Fortuna (Arenal), Costa Rica \| Panama Canal \| Puerto Caldera \| Quepos \| Santa Elena (Monteverde)	$5,499 Up To $750 Onboard Credit View Cruise	Suite!
15 reviews	Feb 23, 2026	Windstar	Star Pride	Caribbean	Colon	Puerto Caldera	11 Nights	Balboa / Fuerte Amador \| Colón \| Golfo Dulce \| Isla Parida \| La Fortuna (Arenal), Costa Rica \| Panama Canal \| Puerto Caldera \| Quepos \| Santa Elena (Monteverde)	$5,099 Up To $750 Onboard Credit View Cruise	Suite!
24 reviews	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	Shipboard Credit Per Person ($100)
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)
15 reviews	Jan 29, 2026	Windstar	Star Pride	Panama Canal	Lima	Puerto Caldera	18 Nights	Balboa / Fuerte Amador \| Colón \| Golfo Dulce \| Guayaquil, Ecuador \| Isla Parida \| Lima, Peru \| Manta, Equador \| Panama Canal \| Puerto Caldera \| Quepos \| Trujillo, Peru	$6,399 Up To $750 Onboard Credit View Cruise
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 04, 2026	Windstar	Wind Surf	Caribbean	Philipsburg	Bridgetown	21 Nights	Anse Mitan \| Basseterre \| Bequia \| Bridgetown \| Castries \| Deshaies \| Falmouth Harbour \| Gustavia \| Jost Van Dyke, Great Harbour \| Little Bay \| Mayreau \| Pigeon Island \| Road Bay \| Roseau \| Soper's Hole \| St. George's \| St. Maarten \| Virgin Gorda / Prickly Pear	$5,999 Up To $750 Onboard Credit View Cruise
24 reviews	Jan 04, 2026	Windstar	Wind Surf	Caribbean	Philipsburg	Oranjestad	28 Nights	Anse Mitan \| Basseterre \| Bequia \| Bridgetown \| Castries \| Deshaies \| Falmouth Harbour \| Gustavia \| Jost Van Dyke, Great Harbour \| Kralendijk \| Little Bay \| Man-O-War Bay \| Mayreau \| Oranjestad \| Pigeon Island \| Road Bay \| Roseau \| Soper's Hole \| Soufriere \| St. George's \| St. Maarten \| Virgin Gorda / Prickly Pear \| Willemstad	$7,899 Up To $1000 Onboard Credit View Cruise

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Your Caribbean - Western Results