1 reviews | Nov 22, 2025 | Virgin Voyages | Valiant Lady | Caribbean | San Juan | San Juan | 10 Nights | Basseterre, St. Kitts & Nevis, Saint Kitts and Nevis | Bridgetown, Barbados, Barbados | Castries, St. Lucia, Saint Lucia | Fort-de-France, Martinique, Martinique | Philipsburg, Sint Maarten (Dutch part) | Road Town, Tortola, BVI, Virgin Islands, British | San Juan, Puerto Rico | St. John's, Antigua, Antigua and Barbuda | $3,770 Up To $500 Onboard Credit | | Onboard Credit! |
1 reviews | Dec 13, 2025 | Virgin Voyages | Valiant Lady | Caribbean | San Juan | San Juan | 7 Nights | Basseterre, St. Kitts & Nevis, Saint Kitts and Nevis | Bridgetown, Barbados, Barbados | Castries, St. Lucia, Saint Lucia | Philipsburg, Sint Maarten (Dutch part) | Roseau, Dominica | San Juan, Puerto Rico | $2,438 Up To $500 Onboard Credit | | Onboard Credit! |
1 reviews | Dec 20, 2025 | Virgin Voyages | Valiant Lady | Caribbean | San Juan | San Juan | 7 Nights | Miami, Florida, USA | Puerto Plata, Dominican Republic | San Juan, Puerto Rico | The Beach Club at Bimini, Bahamas | $2,926 Up To $500 Onboard Credit | | Onboard Credit! |
1 reviews | Dec 27, 2025 | Virgin Voyages | Valiant Lady | Caribbean | San Juan | San Juan | 7 Nights | Basseterre, St. Kitts & Nevis, Saint Kitts and Nevis | Bridgetown, Barbados, Barbados | Castries, St. Lucia, Saint Lucia | Frederiksted, St. Croix | Philipsburg, Sint Maarten (Dutch part) | San Juan, Puerto Rico | $3,738 Up To $500 Onboard Credit | | |
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1 reviews | Jan 31, 2026 | Virgin Voyages | Valiant Lady | Caribbean | San Juan | San Juan | 10 Nights | Basseterre, St. Kitts & Nevis, Saint Kitts and Nevis | Bridgetown, Barbados, Barbados | Castries, St. Lucia, Saint Lucia | Fort-de-France, Martinique, Martinique | Kingstown, Saint Vincent and the Grenadines | Philipsburg, Sint Maarten (Dutch part) | San Juan, Puerto Rico | St. John's, Antigua, Antigua and Barbuda | $3,608 Up To $500 Onboard Credit | | Onboard Credit! |
1 reviews | Mar 14, 2026 | Virgin Voyages | Valiant Lady | Caribbean | San Juan | San Juan | 7 Nights | Basseterre, St. Kitts & Nevis, Saint Kitts and Nevis | Fort-de-France, Martinique, Martinique | Oranjestad, Aruba, Aruba | San Juan, Puerto Rico | Willemstad, Curacao, Curaçao | $2,600 Up To $500 Onboard Credit | | Onboard Credit! |
1 reviews | Mar 21, 2026 | Virgin Voyages | Valiant Lady | Caribbean | San Juan | San Juan | 7 Nights | Bridgetown, Barbados, Barbados | Castries, St. Lucia, Saint Lucia | Philipsburg, Sint Maarten (Dutch part) | Road Town, Tortola, BVI, Virgin Islands, British | San Juan, Puerto Rico | St. John's, Antigua, Antigua and Barbuda | $2,600 Up To $500 Onboard Credit | | Onboard Credit! |
15 reviews | Nov 09, 2024 | Windstar | Star Pride | Caribbean | 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 / Prickly Pear | $4,749 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Dec 07, 2024 | Windstar | Star Pride | Caribbean | San Juan | Oranjestad | 14 Nights | Bridgetown | Gustavia | Kralendijk | Little Bay | Man-O-War Bay | Mayreau | Oranjestad | Pigeon Island | Roseau | San Juan | Soufriere | St. George's | St. Thomas | Willemstad | $4,199 Shipboard Credit Per Person ($100) | | Shipboard Credit Per Person ($100) |
15 reviews | Oct 26, 2025 | Windstar | Star Pride | Caribbean | San Juan | San Juan | 7 Nights | Basseterre | Gustavia | Jost Van Dyke, Great Harbour | San Juan | St. Maarten | Virgin Gorda / Prickly Pear | $2,699 Up To $300 Onboard Credit | | Suite! |
15 reviews | Nov 02, 2025 | Windstar | Star Pride | Caribbean | San Juan | San Juan | 7 Nights | Basseterre | Gustavia | Jost Van Dyke, Great Harbour | San Juan | St. Maarten | Virgin Gorda / Prickly Pear | $2,699 Up To $300 Onboard Credit | | Suite! |
15 reviews | Nov 09, 2025 | Windstar | Star Pride | Caribbean | San Juan | San Juan | 7 Nights | Bequia | Les Saintes | Marigot, St. Martin | Pigeon Island | San Juan | St. George's | $2,699 Up To $300 Onboard Credit | | Suite! |
15 reviews | Nov 16, 2025 | Windstar | Star Pride | Caribbean | San Juan | San Juan | 7 Nights | Basseterre | Gustavia | Jost Van Dyke, Great Harbour | San Juan | St. Maarten | Virgin Gorda / Prickly Pear | $2,699 Up To $300 Onboard Credit | | Suite! |
15 reviews | Nov 23, 2025 | Windstar | Star Pride | Caribbean | San Juan | San Juan | 7 Nights | Bequia | Les Saintes | Marigot, St. Martin | Pigeon Island | San Juan | St. George's | $2,699 Up To $300 Onboard Credit | | Suite! |
15 reviews | Nov 30, 2025 | Windstar | Star Pride | Caribbean | San Juan | San Juan | 7 Nights | Basseterre | Gustavia | Jost Van Dyke, Great Harbour | San Juan | St. Maarten | Virgin Gorda / Prickly Pear | $2,699 Up To $300 Onboard Credit | | |
15 reviews | Dec 07, 2025 | Windstar | Star Pride | Caribbean | San Juan | Colon | 6 Nights | Cartagena | Colón | San Blas | San Juan | Santo Domingo | $2,899 Up To $300 Onboard Credit | | |
36 reviews | Jan 03, 2025 | Regent | Seven Seas Navigator | Caribbean | San Juan | San Juan | 10 Nights | Basseterre | Fort De France | Gustavia | Kingstown | Pointe A Pitre | Roseau | San Juan | St. George's | St. John's | From: $15,998 $5,099You Save: $10,899 Up To $750 Onboard Credit | 68% | |
36 reviews | Jan 13, 2025 | Regent | Seven Seas Navigator | Caribbean | San Juan | San Juan | 7 Nights | Castries | Charlotte Amalie | Gustavia | Philipsburg | Roseau | San Juan | St. John's | From: $12,898 $4,037You Save: $8,861 Up To $500 Onboard Credit | 68% | |
36 reviews | Jan 20, 2025 | Regent | Seven Seas Navigator | Caribbean | San Juan | San Juan | 10 Nights | Basseterre | Fort De France | Gustavia | Kingstown | Pointe A Pitre | Roseau | San Juan | St. George's | St. John's | From: $15,998 $5,099You Save: $10,899 Up To $750 Onboard Credit Welcome Reception Exclusive Amenity Distinctive Host | 68% | *Distinctive Voyage |
36 reviews | Jan 30, 2025 | Regent | Seven Seas Navigator | Caribbean | San Juan | San Juan | 7 Nights | Castries | Charlotte Amalie | Frederiksted | Gustavia | Roseau | San Juan | St. John's | From: $11,998 $3,599You Save: $8,399 Up To $500 Onboard Credit | 70% | Suite! |