Your Caribbean - All Results
Your Caribbean - All Results
Sail Date | Cruise Line | Ship | Destination | Departs | Length | Price | You Save | Discounts | ||||
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24 reviews | 14 night Star Collector Voyages (Caribbean Explorations 14D PH1-PH1 (Feb 28 2026)) | Feb 28, 2026 | Windstar | Wind Surf | 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) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
11 reviews | 7 night Caribbean (Jewels of Windward Islands 7D BGI-BGI (Mar 7 2026)) | Mar 07, 2026 | Windstar | Wind Spirit | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bridgetown | Les Saintes | Little Bay | Pigeon Island | Roseau | $2,599 Shipboard Credit Per Person ($100) | 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 | 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) | 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 7 2026)) | Mar 07, 2026 | Windstar | Wind Surf | 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 Up To $250 Onboard Credit | Onboard Credit! | 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 | 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) | 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 | Bridgetown | Bridgetown | 7 Nights | Bequia | Bridgetown | Castries | Kingstown | Mayreau | Pigeon Island | St. George's | The Pitons | $2,599 Shipboard Credit Per Person ($100) | 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 14 2026)) | Mar 14, 2026 | Windstar | Wind Surf | 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) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
24 reviews | 14 night Star Collector Voyages (Caribbean Explorations 14D PH1-PH1 (Mar 14 2026)) | Mar 14, 2026 | Windstar | Wind Surf | 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 | Onboard Credit! | 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 | Bridgetown | Bridgetown | 7 Nights | Anse Mitan | Bridgetown | Les Saintes | Little Bay | Pigeon Island | Roseau | $2,599 Up To $300 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
24 reviews | 7 night Caribbean (Classic Caribbean 7D PH1-PH1 (Mar 21 2026)) | Mar 21, 2026 | Windstar | Wind Surf | Philipsburg | Philipsburg | 7 Nights | Basseterre | Charlestown | Gustavia | Les Saintes | Pigeon Island | Roseau | St. Maarten | $2,299 Up To $250 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
24 reviews | 14 night Star Collector Voyages (Caribbean Explorations 14D PH1-PH1 (Mar 21 2026)) | Mar 21, 2026 | Windstar | Wind Surf | 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 | Onboard Credit! | View Itinerary | Get FREE Quote |
24 reviews | 7 night Caribbean (Beach Fun & Sun: A Remote Caribbean Getaway 7D PH1-PH1 (Mar 28 2026)) | Mar 28, 2026 | Windstar | Wind Surf | 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 Up To $250 Onboard Credit | Onboard Credit! | View Itinerary | Get FREE Quote |
15 reviews | 13 night Star Collector Voyages (Lovely Leewards 13D SJU-SJU (Nov 3 2024)) | Nov 03, 2024 | Windstar | Star Pride | San Juan | San Juan | 13 Nights | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | San Juan | St. George's | St. Maarten | Virgin Gorda | $4,749 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
15 reviews | 6 night Caribbean (San Juan & the Virgin Islands 6D SJU-SJU (Nov 3 2024)) | Nov 03, 2024 | Windstar | Star Pride | San Juan | San Juan | 6 Nights | Gustavia | Jost Van Dyke, Great Harbour | Little Bay | San Juan | St. Maarten | Virgin Gorda | $2,599 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
15 reviews | 7 night Caribbean (Windward Islands Surf & Sunsets 7D SJU-SJU (Nov 9 2024)) | Nov 09, 2024 | Windstar | Star Pride | San Juan | San Juan | 7 Nights | Bequia | Les Saintes | Pigeon Island | San Juan | St. George's | St. Maarten | $3,199 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
15 reviews | 14 night Star Collector Voyages (Lovely Leewards 14D SJU-SJU (Nov 16 2024)) | Nov 16, 2024 | Windstar | Star Pride | San Juan | San Juan | 14 Nights | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | San Juan | St. George's | St. Maarten | St. Thomas | Virgin Gorda | $4,399 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
15 reviews | 7 night Caribbean (San Juan & the Virgin Islands 7D SJU-SJU (Nov 16 2024)) | Nov 16, 2024 | Windstar | Star Pride | San Juan | San Juan | 7 Nights | Gustavia | Jost Van Dyke, Great Harbour | Little Bay | San Juan | St. Maarten | St. Thomas | Virgin Gorda | $2,599 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
15 reviews | 14 night Star Collector Voyages (Lovely Leewards 14D SJU-SJU (Nov 23 2024)) | Nov 23, 2024 | Windstar | Star Pride | San Juan | San Juan | 14 Nights | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | San Juan | St. George's | St. Maarten | St. Thomas | Virgin Gorda | $4,449 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
15 reviews | 7 night Caribbean (Windward Islands Surf & Sunsets 7D SJU-SJU (Nov 23 2024)) | Nov 23, 2024 | Windstar | Star Pride | San Juan | San Juan | 7 Nights | Bequia | Les Saintes | Pigeon Island | San Juan | St. George's | St. Maarten | $2,749 Up To $300 Onboard Credit | Suite! | View Itinerary | Get FREE Quote |
15 reviews | 7 night Caribbean (San Juan & the Virgin Islands 7D SJU-SJU (Nov 30 2024)) | Nov 30, 2024 | Windstar | Star Pride | San Juan | San Juan | 7 Nights | Gustavia | Jost Van Dyke, Great Harbour | Little Bay | San Juan | St. Maarten | St. Thomas | Virgin Gorda | $2,999 Shipboard Credit Per Person ($100) | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
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