24 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | Mar 28, 2026 | 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 Up To $250 Onboard Credit | | | View Itinerary | Get FREE Quote |
5 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/129.jpg.webp) | Jan 04, 2026 | Silversea | Silver Shadow | Caribbean | Philipsburg | Philipsburg | 7 Nights | Les Saintes, Guadeloupe | Little Bay, Montserrat, Montserrat | Philipsburg, St. Maarten | St. Johns, Antigua | St. Thomas, Virgin Islands | $5,700 Up To $750 Onboard Credit | | Balcony! | View Itinerary | Get FREE Quote |
5 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/129.jpg.webp) | Jan 11, 2026 | Silversea | Silver Shadow | Caribbean | Philipsburg | Philipsburg | 7 Nights | Les Saintes, Guadeloupe | Little Bay, Montserrat, Montserrat | Philipsburg, St. Maarten | St. Johns, Antigua | St. Thomas, Virgin Islands | $5,700 Up To $750 Onboard Credit | | | View Itinerary | Get FREE Quote |
5 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/129.jpg.webp) | Jan 18, 2026 | Silversea | Silver Shadow | Caribbean | Philipsburg | Bridgetown | 7 Nights | Bridgetown | Gustavia, Saint Barthélemy | Kingstown, St. Vincent | Philipsburg, St. Maarten | Roseau, Dominica | St. John, Virgin Islands | $5,700 Up To $750 Onboard Credit | | Balcony! | View Itinerary | Get FREE Quote |
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5 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/129.jpg.webp) | Feb 19, 2026 | Silversea | Silver Shadow | Caribbean | Philipsburg | Philipsburg | 7 Nights | Les Saintes, Guadeloupe | Little Bay, Montserrat, Montserrat | Philipsburg, St. Maarten | St. Johns, Antigua | St. Thomas, Virgin Islands | $5,500 Up To $750 Onboard Credit | | | View Itinerary | Get FREE Quote |
5 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/129.jpg.webp) | Feb 26, 2026 | Silversea | Silver Shadow | Caribbean | Philipsburg | Bridgetown | 7 Nights | Bridgetown | Gustavia, Saint Barthélemy | Kingstown, St. Vincent | Philipsburg, St. Maarten | Roseau, Dominica | St. John, Virgin Islands | $5,500 Shipboard Credit Per Person ($300) | | Shipboard Credit Per Person ($300) | View Itinerary | Get FREE Quote |
11 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/120.jpg.webp) | 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) | | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
24 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | 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) | | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
9 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/286__201704130803__.jpg.webp) | Jan 11, 2025 | Seabourn | Ovation | Caribbean | Philipsburg | Philipsburg | 14 Nights | Antigua | Bridgetown, Barbados | Fort-De-France, Martinique | Jost Van Dyke, B.V.I. | Philipsburg, St. Maarten | Port Elizabeth, Bequia | St. Lucia | $7,059 Up To $750 Onboard Credit Welcome Reception Exclusive Amenity Distinctive Host | | *Distinctive Voyage | View Itinerary | Get FREE Quote |
9 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/286__201704130803__.jpg.webp) | Feb 22, 2025 | Seabourn | Ovation | Caribbean | Philipsburg | Philipsburg | 14 Nights | Antigua | Bridgetown, Barbados | Fort-De-France, Martinique | Jost Van Dyke, B.V.I. | Philipsburg, St. Maarten | Port Elizabeth, Bequia | St. Lucia | $7,549 Up To $1000 Onboard Credit Welcome Reception Exclusive Amenity Distinctive Host | | *Distinctive Voyage | View Itinerary | Get FREE Quote |
9 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/286__201704130803__.jpg.webp) | Jan 17, 2026 | Seabourn | Ovation | Caribbean | Philipsburg | Philipsburg | 14 Nights | Antigua | Bridgetown, Barbados | Jost Van Dyke, B.V.I. | Philipsburg, St. Maarten | Port Elizabeth, Bequia | Saint Pierre et Miquelon, France | St. Lucia | $6,689 Up To $750 Onboard Credit | | | View Itinerary | Get FREE Quote |
9 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/286__201704130803__.jpg.webp) | Jan 31, 2026 | Seabourn | Ovation | Caribbean | Philipsburg | Bridgetown | 14 Nights | Bridgetown, Barbados | Philipsburg, St. Maarten | Port Elizabeth, Bequia | Rodney Bay, Saint Lucia | Roseau, Dominica | Saint Pierre et Miquelon, France | $6,709 Up To $750 Onboard Credit | | Suite! | View Itinerary | Get FREE Quote |
9 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/286__201704130803__.jpg.webp) | Feb 21, 2026 | Seabourn | Ovation | Caribbean | Philipsburg | Philipsburg | 14 Nights | Antigua | Bridgetown, Barbados | Jost Van Dyke, B.V.I. | Philipsburg, St. Maarten | Port Elizabeth, Bequia | Saint Pierre et Miquelon, France | St. Lucia | $6,689 Up To $750 Onboard Credit | | | View Itinerary | Get FREE Quote |
9 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/286__201704130803__.jpg.webp) | Mar 07, 2026 | Seabourn | Ovation | Caribbean | Philipsburg | Bridgetown | 14 Nights | Bridgetown, Barbados | Philipsburg, St. Maarten | Port Elizabeth, Bequia | Rodney Bay, Saint Lucia | Roseau, Dominica | Saint Pierre et Miquelon, France | $6,709 Up To $750 Onboard Credit | | | View Itinerary | Get FREE Quote |
24 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | Jan 18, 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 | $4,799 Up To $500 Onboard Credit | | Onboard Credit! | View Itinerary | Get FREE Quote |
24 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | 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 Itinerary | Get FREE Quote |
24 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | 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) | | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
24 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | 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) | | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
24 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | 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) | | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |
24 reviews ![Itinerary Map/Ship Image](https://img.affordabletours.com/AffordableCruisesWeb/Ship/230x_/122.jpg.webp) | Jan 04, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Bridgetown | 14 Nights | Basseterre | Bridgetown | Deshaies | Falmouth Harbour | Gustavia | Jost Van Dyke, Great Harbour | Little Bay | Pigeon Island | Road Bay | Roseau | Soper's Hole | St. Maarten | Virgin Gorda / Prickly Pear | $4,099 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) | View Itinerary | Get FREE Quote |