8 reviews | Dec 21, 2024 | Star Clippers | Star Flyer | Caribbean | Philipsburg | Philipsburg | 7 Nights | Basseterre, St. Kitts (morning) | Gustavia, St. Barts | Philipsburg, St. Maarten | Road Bay, Anguilla | Sopers Hole - Tortola, British Virgin Islands (BVI) | South Friars Bay - Beach, St. Kitts (afternoon) | Spanish Town - Virgin Gorda, British Virgin Islands (B.V.I) | White Bay, Jost van Dyke (B.V.I.) | $1,640 Up To $200 Onboard Credit | | Rebate! |
8 reviews | Dec 20, 2025 | Star Clippers | Star Flyer | Caribbean | Philipsburg | Philipsburg | 7 Nights | Basseterre, St. Kitts (morning) | Gustavia, St. Barts | Philipsburg, St. Maarten | Road Bay, Anguilla | Sopers Hole - Tortola, British Virgin Islands (BVI) | South Friars Bay - Beach, St. Kitts (afternoon) | Spanish Town - Virgin Gorda, British Virgin Islands (B.V.I) | White Bay, Jost van Dyke (B.V.I.) | $1,730 Up To $250 Onboard Credit | | Rebate! |
5 reviews | 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 | $6,100 Up To $750 Onboard Credit | | |
5 reviews | 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 | $6,100 Up To $750 Onboard Credit | | Balcony! |
Need Help Planning A Cruise?
Our cruise experts can help you:
- Find the best discounts
- Hold a cabin for 24 hours for free
- Receive personalized recommendations
- Book handicap accessible cabins
|
5 reviews | Jan 18, 2026 | Silversea | Silver Shadow | Caribbean | Philipsburg | Bridgetown | 7 Nights | Gustavia, Saint Barthélemy | Philipsburg, St. Maarten | Roseau, Dominica | St. John, Virgin Islands | $6,100 Up To $750 Onboard Credit | | |
5 reviews | 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 | $5,900 Up To $750 Onboard Credit | | Balcony! |
5 reviews | Feb 26, 2026 | Silversea | Silver Shadow | Caribbean | Philipsburg | Bridgetown | 7 Nights | Gustavia, Saint Barthélemy | Philipsburg, St. Maarten | Roseau, Dominica | St. John, Virgin Islands | $5,900 Shipboard Credit Per Person ($300) | | Shipboard Credit Per Person ($300) |
24 reviews | 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) | | Shipboard Credit Per Person ($100) |
24 reviews | 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) | | Shipboard Credit Per Person ($100) |
24 reviews | 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) | | Shipboard Credit Per Person ($100) |
24 reviews | 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 | | |
24 reviews | Jan 04, 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 | $2,499 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
24 reviews | Jan 11, 2026 | Windstar | Wind Surf | Caribbean | Philipsburg | Bridgetown | 7 Nights | Basseterre | Bridgetown | Deshaies | Gustavia | Little Bay | Pigeon Island | Roseau | St. Maarten | $2,499 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
11 reviews | 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 | | Onboard Credit! |
11 reviews | 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) | | Shipboard Credit Per Person ($100) |
11 reviews | 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 | | Onboard Credit! |
11 reviews | 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 | | Onboard Credit! |
11 reviews | 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) | | Shipboard Credit Per Person ($100) |
11 reviews | 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 | | Onboard Credit! |
24 reviews | 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) | | Shipboard Credit Per Person ($100) |